7 Ways to Protect the Freelance Life by Matthew Cook

I once heard that over 90% of US drivers think they have above average driving skills. Turns out, that’s pretty much true and the phenomena is called Illusory Superiority. We tend to be the first ones to excuse our faults and believe in ourselves. This is a good thing, but freelancers don’t have the luxury of wearing rose colored glasses. We have to find ways to measurably protect ourselves from our shortcomings, not just feel good.

While there are some really good resources out there that can inform you how to saveanalyze or fine-tune your performance, price your work, and get started, they don’t give you a lot of perspective from the trenches. That’s what I want to share: 7 ways to protect the freelance life–advice from the battlefield

  1. Choose a weekly or bi-weekly “salary” and budget your life around that income. It doesn’t matter if you run a family budget or shoot from the hip with monthly expenses. The big dark line to draw is living below your means. It doesn’t matter if you just received a $10,000 check. Don’t break the income rules you set. If you can’t be disciplined with spending in your personal life, you’re going to have even bigger problems trying to run a freelance business.
  2. Determine how much risk you’re comfortable with and find ways to mitigate it. I’m not very risk averse, but my wife is. Long ago I realized that I would be a 1-2 client freelancer with a side project or two. I can’t handle more–my roots go too deep with the friends I work along side. That means my biggest risk is losing a client. You can verbally agree with your partners as to what you will and won’t do when a relationship breaks down, but the reality is that you need to plan for a sudden cut in work and income. For me that means having a buffer account of $20,000 that I pay my personal salary from. All the checks get deposited there, and I pay my salary from there. It took a long time to hit that mark and discipline to not dip into it when things were easy, but it pays off during months of unpaid work or when I lose a job. I’ve even set up action points by dollar thresholds. If that account gets down to $10k, my wife and I have agreed that I have to start looking for traditional employment. Talk about motivation to keep the dream alive!
  3. Identify risks to your freelance business and plan around them. All businesses have cycles. Take the time to research the cycle for your industry and for your clients. Know when target clients will be looking to spend and know when they’re slow. You will get fired by someone at some point. Nobody starts a project expecting to burn bridges. It’s up to you to protect yourself and people contracting for or with you. Tie money out to money in. If you have contractors, write into your agreements with them that you’ll pay them when you get paid–then everyone push to keep the client happy together. Last thing, know your pipeline (or at least guesstimate it). How long does it take you to get a client from the first contact to the first check in your hands. Most freelancers under-estimate this. I used to say 2-3 weeks. It’s actually around 45-60 days. Signatures don’t count. Signed contracts don’t pay bills.
  4. Always have an exit strategy. I hate this one. I don’t want to work with other people or other companies let alone have a W-2 job. If I did, I’d be doing that, not contracting. You have to be willing to embrace the possibility that you’ll fail while also acting as if you won’t. For me this means making local industry friends, attending conferences, and talking to potential future clients–even when things are going great. This also means figuring out what a good client looks like. Good clients pay well and pay on time. Your best clients do that while also letting you do good work. Don’t get trapped by promises of better work or larger budgets. Cash flow is one of your biggest guarantees against failure. If your clients are threatening your cash flow, they’re threatening your ability to even be in business. 
  5. Save for taxes. You don’t want to get behind with the IRS. Get a good accountant and learn a little bit about tax code; at least know where you fall in the tax brackets. This will help you know what your maximum Federal tax liability is. Most people will remind you that taxes aren’t withheld by an employer, but what you may not know is that your employer actually pays some of your taxes. Employers pay matching amounts of your Medicare and Social Security when you have a W-2 job. When you’re self employed, you pay both portions. That’s right, you pay more taxes when you’re self employed–and you may be required to make quarterly tax payments. However, there are other things you can take advantage of such as a home office and a host of other tax write-offs. Again, get a good accountant. Save for taxes. 
  6. Save for yourself. American’s think they’re too broke to save. In most cases, that’s ridiculous. Take your future financial well-being seriously. You need to save for your own retirement, kids, cars, emergencies, homes, business assets, vacations, toys, and many many other things. You won’t have an employer-matched 401k, a company car, or an IT allowance. Save in bite-sizes (or byte-sizes–tech puns!). Utilize something like CapitalOne360 where you can have multiple cash accounts for free under one login with easy transfers. Only you can make yourself spend wisely.
  7. Run away often and make sure you have a plan for burnout. Plan time away and be real about the self-imposed constraint of being unavailable. You don’t have an office that opens and closes, and you don’t have a boss forcing you to attend meetings. Get used to saying “Sorry, I’m unavailable at 3p PT (6p ET)…” or “I’ll be away from December 21-25…”. Learn how much effort is too much and know what types of activities rejuvenate you. My wife and I run off to my conferences together or buy extra plane tickets and hotel nights for business trips. I write when I’m burned out, and I know making home espresso and running regularly help me manage stress and frustration. Reach out to friends and learn how to be open about your struggles.

Freelancing isn’t easy. It costs more money and effort than you imagine it will, and your failures hurt far deeper and longer than you most likely anticipate. Learning how to protect yourself is important if you want to make freelance a career choice and not just something that happens to you. I’ve been fired (multiple times), lost dream projects, and undergone months of unpaid work. I’ve also delivered great things, worked with amazing companies and friends; and freelanced my way through grad school, buying a house, and having a kid. The trick is knowing your limits and finding ways to support and protect yourself. 

The Only Way to Lose is to Play the Game by Matthew Cook

I produced a pitch for a potential client and we won the pitch but lost the project. 

The funny thing is that nobody won. That thought and all of it’s puns smacked me like a ton of bricks. For four weeks I competed on the basis of a Request for Proposal (RFP) issued by a potential client. That’s a ton of work, I undertook:

  • Six phone calls with the client. Four included some of my team members.
  • Building a hand-picked team of contractors. I intentionally tried to limit their involvement, but it still took two major brainstorming sessions for our team, plus pitch content from each of them.
  • Positioning my team against 10 other studios. Most were small, one was internationally recognized.
  • Construction of a pitch document. I concepted and outlined a pitch document. After 7 major versions we had a finished 25 page PDF.
  • Sending approximately 80 emails in total related to the project and an unknown amount of texts, Slack messages, and back-channeling.
  • Creating three versions of a project plan that spanned over five months and three distinct web properties.
  • Constructing an on-site presentation with my project lead who facilitated an in-person meeting in collaboration with me.
  • Travel. We purchased two plane tickets, lodging, and meals. We also spent two full days on this presentation away from our desks, let alone the time lost to preparing the initial pitch.

My team beat out eight of the eleven other studios to make it to the final round. After the on-site presentation we were fairly confident we had it in the bag. A week later, the client emailed and informed us that the budget was being drastically reduced and the work reconsidered.

After putting eleven studios through an RFP process and spending copious hours of their own team’s time, the client pulled the project and paid nobody. The sheer quantity of man hours wasted across all teams is staggering. In all meanings of the statement, 

Nobody won.

You’d think I’d know better. The last RFP I responded to (although I didn’t produce the pitch), my team won. Again, poignantly successful approach and execution. The client informed us we won. Celebrations! Over the weeks following, the client went dark. The project never happened.

That’s right. The last two RFPs I’ve been on, my team has won over the hearts and minds of the client but the project hasn’t happened. What gives?

There are a lot of causes that could be behind this. I work on hollywood model teams with highly qualified individuals. We’re small and cheaper than your typical high-powered studios, but costly as far as contractors go. Maybe we attract clients who are already overly budget conscious and prone to cold feet. 

Perhaps our pitches inspire teams to do the work themselves. After all, if a group of 4-5 guys and gals can do it, why can’t they? I don’t have a large enough sample size to guess accurately, and the clients don’t seem to be interested in giving feedback on the pitches although I explicitly ask.

Pitches are lost all the time, and there’s a wealth of resources on how to avoid the critical path to losing. A large loss percentage isn’t surprising.

What’s surprising is winning but not winning.

I think this is increasingly unique to teams like mine. Clients either hire us without bothering to go through qualification, or they are overly cautious because they’re not sure they can truly handle a relationship. That’s quite the spectrum of confidence and willingness to risk funds. So how do we deal with this conundrum? There are a few tactics I want to try on future RFPs. The first is this email reply:

Thanks for sending us your RFP, we are honored you thought of us and don’t take your interest lightly. Regrettably, we’re unable to commit time to an unpaid pitch because we’re a small team that takes on only a few projects at a time under very high-touch relationships. If you’re open to speaking with us outside the RFP process or considering a small fee for our time, we’re eager to hear more. Are you available to speak with me sometime over the next few days?

I don’t know how this email will be received, but for the sake of my teams, I’m ready to try it out.

The second tactic is insisting on a paid discovery prior to a fully scoped project. I’ve had success with this recently. Scope a full approach but only pitch a discovery valued at about 15-20% of the total project. This gives the client a test drive and lets you sell to their best interest: smaller timeframe and cost for a set of deliverables that can be used by any team that the client chooses for the final vendor—even if it’s not you. This isn’t a new tactic. You can even rename discovery to better suit the perception you want to build. How about evaluation?

The third tactic is insisting on meeting final stakeholders and receiving explicit written confirmation that my team’s projected budget is within an acceptable range. I’m even considering requiring the client to furnish 2 references. The balance of power is slightly shifted for highly talented web teams. At least for now, clients seem to need us more than we need them–I want to take advantage of that balance to mitigate lost time, money, and empathy. It’s not an ego thing, it’s just good sense. If selling in the world of hollywood model web work really is like dating, why is it so one-sided? 

I still think RFP’s can be valuable. Jamie or Matthew can tell you I’m always trying to make clients into better storytellers. An RFP can be a powerful tool in telling the story of a project. What I’m starting to lean toward is not only hijacking the RFP process to change the conversation, but also occasionally flipping the process back onto the client. How about we start making clients go through a PFR…a…Proposal Fitness Requirement process?

Get Your Digital Project Management Out Of My Digital Production by Matthew Cook

Digital Project Managers and Producers get a hard rap sometimes because we deserve it.

Let’s be clear right off the bat about the difference between a Digital Producer and a Digital Project Manager (DPM). They are different, don’t listen to the “we all make stuff happen” moniker that seems to get tossed around everywhere. A rose is a rose, but in this case we’re not talking about a single role by two names. We’re talking about two different perspectives and directions of effort with overlapping skill sets. There’s no explicit definition that everyone seems to agree on, so here’s mine.

Digital Project Manager - Concepts, drafts, scopes, and manages process toward end deliverables. Facilitates clear communication across platforms and skill sets. Coordinates stages of effort and tracks progress.
Digital Producer - Concepts, drafts, scopes, and facilitates creation of a specific set of deliverables. Speaks to the rightness and fit of specific work toward specific end goals. Builds perception of value in her team and their collective output.

Dig in a little deeper, you say? Well ok then.

A Digital Project Manager is a lens poised over a project. She brings focus, clarity, and awareness, but leaves material change to other members of the team. There’s a sort of disdain that often comes to these people. Always focusing on the shortfalls and issues without being the one who has to do the work to fix them. Other project management failures look like unexpected crunch time, lack of communication and understanding between any parties on the project, insufficient planning, failure to adapt plans, or losing clear sight of the quantifiable effort to complete the making of all the things.

DPMs fill a gap between goals of the business hired to do the work and the operation and smooth functioning of the team or studio of designers/developers. Their skills highlight cost (and profit), ensure timelines, allow for accurate higher level management control of the client relationship, and provide a mechanism for morphing and adapting effort on the project.

A Digital Producer is the tactician counterpart to a project lead such as a Design Director, Technical Director, or Creative Director. She’s the right hand. She guarantees completion at a specific level of quality and fitness through communication and learning/expertise; simultaneously in the weeds on problem issues yet accurately utilizing the entire breadth of skills and roles on the project. Producers are always leading the charge but never the subject matter expert. They get in over their heads, they’re messy, they’re barely good enough. Failure for this role looks like staying too topical on a project, disengaging from hard conversations, reluctance to find and clarify gray areas, and not building a sense of value in the client’s mind.

Digital Producers sit squarely in the middle between the project, the client, and the team. They’re the fastest learner in the room. They bring clarity to all parties and their business function is tied more to value than dollars. They ensure the client perceives the rightness of the project’s direction. In her role, she champions her team’s vision and expertise, her client’s needs, and the business’s need for profit and control—all simultaneously. She must play or solve for any missing part: code, UX, content strategy, or design as needed. The business is respected and reliably successful at delivering excellent solutions to clients’ needs because of the Digital Producer.

Both roles are very valuable to the business, the team, and the client. They’re also emphatically not mutually exclusive.

I work with companies structured in the Hollywood Model. We sometimes like to call it the Avengers Model. To carry that metaphor forward, if the project team is The Avengers, a DPM would be Coulson and a Digital Producer would be Nick Fury. Both are essential to the team, but neither can carry the weight that the Avengers inevitably must bear. They approach problems in a drastically different manner side-by-side. Ironically they’re also both easily defeated when they get isolated and in over their heads.

If DPMs and Digital Producers get a hard rap because they deserve it, they should also be championed when their projects are successful. 

But they rarely are, and in a way that’s really ok. There’s little to be gained from publicly extolling either of these roles along with the work that the team completed. Awards, portfolios, and best of breed websites rarely have much from a visuals aspect to point back to the DPM and Digital Producer. However, the client, the team, and the business have a lot to gain or lose based on these roles, and should value them extremely highly because they ultimately guarantee smooth team functioning and consistent performance; both of which highly affect prices, profits, reputation, and morale.

The result of our collective success as DPMs and Digital Producers is hard to quantify, but our failures are glaring. When communication falls through and the business loses a project, it’s easy and right to blame us. When a project is successful and wins awards for design and interaction, it’s easy and right to champion the business and the team; but often this seems to mean we get marginalized. When we’re buried or lost in a project and go AWOL, it’s easy and right to call us out.

So how do you properly champion these roles? Don’t conflate them and gauge their efficacy with a singular set of measures. Find ways to measure success unique to their disparate goals and emphases. Create mechanisms to champion and congratulate their contribution. Chances are, if your business is successful and growing, these people are a huge part of that consistent upward trend—even though you mostly notice them only when they aren’t performing at their best. Don’t simply concentrate on assessing failure and assigning blame. Recognize that organizations like .Net are wrong when they fail to acknowledge production and project management as key to good work and good projects in our industry. Realize that Digital Project Management and Production are functions that grew out of necessity, not classical education. Find smart ways to invest in and utilize us.

The Truths and Half Truths of Getting My MBA by Matthew Cook


There are multiple lies that higher education tells students today. The biggest of which seems to be what a college grad can expect to gain from their experience and expense. The cost of college has never been higher and students today keenly feel preyed upon by the institutions who educate them and the banks who saddle them with school debt. Despite a US economy that has generally recovered since 2009, the employment situation for US citizens is hardly bright and happy or clear.

The data supports what most Americans are starting to feel: college is not worth the money that we pay for it, especially when you consider the increasingly hollow promise of fulfilling and lucrative employment.

This feeling doesn’t just exist in collegiate America. For those of us who serially attempt to go above and beyond, graduate school and PHDs are a potential goal in life. They’re pretty to put on a wall and are sometimes a rubber stamp of demonstrated skill, but they also make promises for an even brighter and more fulfilling career (in addition to highly specialized learning).

A good measure of whether educational degrees are being utilized in careers is the rate of underemploymentForbes draws a handful of keen correlations between education level and underemployment. I’ll pull one statistic:

“A full 59% of those employed holding a masters degree were classified as underemployed… To further put things in perspective, the number of underemployed masters degree holders was more than the total number of masters degrees produced between 1998 and 2008 (5.75 million).”

Whoa. That number is worse than college degree holder underemployment

When I was looking for sources to cite I expected to find that 15%-25% of masters degree holders were underemployed and then I found these numbers based on US Bureau of Labor Statistics data. This is incredible, and goes to show that:

The tuition most graduate degree holders pay artificially supports an educational system that gives them little to no monetary benefit in return.

Credential inflation can be blamed partly for this phenomenon, but there’s a wider lesson to learn:

Potential students looking to get another degree need to carefully consider that degree’s value, both personally and professionally.

For example, let’s look at a Master of Business Administration (MBA) degree. My MBA. Two years ago I finished my academic journey at Clemson University. I began my studies in June, 2011 as a 24 year old finance grad with 2 years of small business experience. 18 months and $19,000 dollars later I was a freshly credentialed man, Matthew Cook BS, MBA, who was gainfully self employed. Fast forward to today and my perspective on the experience is starting to round out.

Considering the personal benefit of my MBA is best accomplished by weighing the promises that my institution made about the degree against what I actually experience today. Here’s what most MBA programs sell, mine included:

  • You’ll gain an indispensable network of colleagues which you can utilize to make lots of money in the future
  • It’s an invaluable learning experience
  • Career coaching and connection with potential employers will put you a step ahead of your non-MBA peers
  • Moving up in your career and getting that promotion that’s out of your reach is no longer a problem
  • You’ll get better at working in teams
  • You’ll get better at managing and leading, both soft and hard skills

While in the program, here’s what I found out:

  • Most of my classmates are hoping I’ll be part of the network that gets them money/jobs/promotions, but very few of them are interested in giving back to a network of colleagues
  • The academic environment in MBA school exists, but it’s generally more obligatory than involuntary
  • Career coaching from impersonal mentors at the institution feels like you’re being told to follow a prescribed path
  • Your classmates are frequently people trying to change their career or start their career rather than move up in their career
  • Scholastic teamwork, even at the graduate level, is closer to learning how to deal with teammates rather than learning how to be a good team as a group
  • Not everyone is suited to manage and/or lead

This was disheartening at times. Even though I considered my motives more pure than some (I don’t care to be an Enron-style greedy quantifying monster), I was finding that there was a disconnect between what the degree purported and what actually felt helpful. After about a year in the program I realized something. Even though a lot of the sellable benefits above turned out to feel like a sham, I was gaining other experiences that amounted to tectonic shifts in how I approach my job and career. Here are just a few:

  • I started to learn what I was actually bad at. In college and high school I could coast through almost any class, but MBA school made me face the music.
  • I learned what I was passionate about. I was in the right field, business, but sitting through my classes and rubbing shoulders with my classmates caused me to realize what really made me excited and energized.
  • I gained a healthy distrust for traditionally trusted institutions. MBA school impressed on me that honing and utilizing my own skills and employing them in a margin compensated environment was the safest career choice. 
  • My courses raised the bar. I gained more training across a multitude of topics that I use every day. From business law, to finance, to business innovation.
  • Scholastic credentials aren’t as important as being sharp and hungry. Nobody can fix a lack of true deep curiosity.

Getting my degree wasn’t so much gaining a credential as taking a $19,000 learning journey. I’ve spent much of my life’s time pursuing things to learn and developing my ability to learn. I’ve realized that a very potent skill for my chosen path is being the fastest learner in the room. I don’t think I would have realized that if it weren’t for my MBA studies, but I also don’t think I’d have taken the scholastic plunge if that’s what Clemson was selling.

What my graduate degree sold me and taught me wasn’t a lie, but it also wasn’t truth. The academic content ranged from useless to valuable, but the personal enlightenment was, for me, invaluable. So much of our culture is bent on quantifying education when sometimes results are by necessity very intimate and unquantifiable.

Nobody can tell you whether an academic journey is right for you, except you; and at the end of the day, you’re the one who is responsible to make it worth the effort and expense.

Pumpkins, the Stress of Independence, and Lessons from Bon Jovi by Matthew Cook

Shot through the heart, and you’re to blame, 

Stressin’, you give independence a bad name.

Ok, I know that’s a terrible misappropriation of Bon Jovi’s song, but hopefully you see my point. Let’s be honest and open up about freelance work life a bit. You can generally categorize self employed people into two groups. The first are motivated by the fact that there is always more to be done than can be accomplished. They accept that they will never accomplish everything and cope with focus and unearthing the best possibilities. They are the Explorers and will eventually burn out on a semi-predictable cycle as they deplete their ability to see through the fog. The second can’t handle uncertainty and the volume of demands for their time. This pushes them to accomplish super-human amounts of work. Completeness is their goal, and they’ll make the hard choices to ensure it’s accomplished. They hit impossible deadlines and expect the same from others. They are Gladiators, and are prone to exhaustion, panic, and paralysis—sometimes chronic.

Explorers are stressed by their dependence on constant discovery and curation. Gladiators are stressed by the need for order, resilience, and completion.

Bon Jovi helps me make a good point: Each of these types plays the game successfully, but the impossibility of sustaining long-term gives independence a bad name. I guess you could say independence isn’t a good partner to go steady with unless you’re constantly changing your relationship boundaries. 

There are two ways that I deal with this. One is to create a remote independent team structure for work life, the other is to do things like make coffee and cook pumpkins. Let’s dig into the fun one. Maybe I’ll talk about creating water cooler moments from 2000+ miles away another day.

I discovered a few years ago that I need a generative outlet to avoid the side effect of my Explorerness. Normal work life often leaves me feeling creatively quenched; over-extended. Some things regenerate as opposed to draining me: throwing on a pottery wheel, coffee, and video games to name a few. Throwing pottery is an impossibility for me at this point in life, video games take too much mental and time investment to keep up with, and coffee is perfect. I’ve found a lot of creative satisfaction in engineering a great cup of coffee. Selecting beans, roast, age, grind, prep method, etc. there’s a huge amount of influencers for a single cup. Manipulating all of those factors to create a great cup is fun and gives a new meaning to artisan coffee for me. It’s something I do for myself, and it’s something that’s privately enriching. 

This fall, pumpkins have become my “new world” endeavor to maintain work drive. I still do the coffee thing, but I’m branching out. Every year my family goes to the Farmer’s Market an hour up the road toward Asheville, NC. We buy all sorts of fall foods, my joy is always in finding an excellent pumpkin for our fall pies and breads. I’ve gotten carried away.


Pumpkins can be enormously complex as an ingredient, just like coffee. The United States grows around 1.5 billion pounds of pumpkin each year (over 680M kg) across a purportedly unknown number of species in the Cucurbita Genus. It’s a relatively ambiguous Genus and the different species are difficult to classify given continual intermingling and domestication—no species is separated from others. The easiest way to differentiate them is by their five main categorical species: agryrosperma, ficifolia, maxima, moschata, and pepo. 

Adding to slight confusion, pumpkins are squashes, but not all squashes are pumpkins. Since both are the same Genus and flavors are similar, it’s widely overlooked in commercial and culinary context (chances are that your canned pumpkin has a good bit of non-pumpkin squash in it). Fun fact, a pumpkin is classified by botanists as a type of berry. I’ll wait here while you Google that.

These different factors are a gold mine for creative exercise since you can’t broadly prescribe recipes or cooking techniques to the ingredient since it varies by species.

So, as part of my creatively regenerating exercise I took a few notes on my pumpkins (and squashes) and offer you my findings from this year’s harvest. I selected 7 different species of Cucurbita. Yes, I mingled my squashes and pumpkins. Some of these are native to the Carolinas, and some are more global in origin:

  • Blue Hubbard
  • Butternut
  • Jarrahdale
  • Acorn
  • Cinderella
  • Candy Roaster
  • Fairytale
  • Kabocha

I decided to break all of these pumpkins down into a puree/paste. I don’t cook whole pieces of pumpkin regularly, but I do make pies, bread, cakes, etc. My method for prepping the pumpkin was as follows:

  • Clean exterior.
  • Scrape inside.
  • Cut into steam-able chunks
  • Steam until softened. I baked a few here and there.
  • Carve out the meat from the shell.
  • Blend the meat into a desired consistency.
  • Bag in two-cup portions for storage and use.

Here were my experiences with each:

Blue Hubbard

  • Very sweet and fragrant, even before cooking. 
  • Not a lot of meat on the shell.
  • A very wet pumpkin.
  • When cooked the skin looks like a waxy green toad.
  • Baked into a pie, it’s almost too sweet, I’m having to shorten sugar in my recipes with Blue Hubbard.


  • Soft and mild tasting/smelling. 
  • Came out so thick that I had difficulty blending it.
  • Extremely squashy smelling and tasting, not very sweet, but has a wonderful consistent creamy texture.


  • Ridiculously easy to cook and scrape.
  • Blended really smoothly, and came out as a thick paste. Creamy and yellow.
  • Smelled of melons when fresh, dulled when cooked.
  • Gets the most inappropriate comments due to it’s shape (thanks @joshuajantz and @wtflow).
  • Baked a pie with half Hubbard and half Butternut. Perfect flavor.

Candy Roaster

  • Really wet meat.
  • Skin pulverized while steaming. If you let it into your recipe, it bakes hard and ruins pies.
  • Comes out light orange. Almost the color of Mango. 
  • Maybe I should have baked this pumpkin. I grew up eating this, so I know how difficult it is to steam.
  • Still feels turgid even when cooked because it holds so much water. The most wet pumpkin I had. It sweat water the entire process, and I had to strain it before bagging because it was still so wet. 


  • Smelled like cantaloupe.
  • Came out BRIGHT orange.
  • Held a large amount of water, just not quite as much as a Candy Roaster.
  • Taste when steamed is light, creamy, and sweet. Not sure what I’ll make this into yet.


  • The most fragrant when I opened it up–the smell, even before cooking, filled my house. Insides looked like cotton candy.
  • Completely pulverized when steamed and turned a grayish green in some spots.
  • Tasted like a pumpkin, but a little more like a yellow summer squash than any other pumpkin I’ve tasted. I’m not very impressed. This will probably be made into a bread or a soup.

Jarrahdale (Australian)

  • One of two pumpkins I’m most unfamiliar with from this year.
  • Pretty doggone heavy, and really hard skin. Don’t cut yourself trying to carve this pumpkin open. 
  • The interior is just as rock hard. Beautiful deep orange flesh though. 
  • Took much longer to cook. Probably 2x as long as any other. 
  • Just like the Hubbard, it turned out looking like a waxy green toad. 
  • Turned out to be the most…chalky of all the pumpkins. Not a great amount of confidence in this gourd.
  • Made into a bread and a pie. Really good flavor (despite my misgivings)—heavy hints of honey.


  • This is the other pumpkin I was completely unfamiliar with.
  • Outer shell of the pumpkin was tough and took a lot of strength to cut through. 
  • Extremely dry, but that’s probably because it didn’t sit for a few weeks after harvesting. 
  • Pleasant pasty texture with a mild sweet flavor. Most similar to a sweet potato in texture. 
  • Soft homogenized orange color. 

That’s it for my pumpkin adventures so far. The more I take on small side endeavors like this, the more I realize how helpful they can be. I exhort you, find something to invest in personally. You’ll be surprised at how it influences your work life and family life. Whether running, coffee, or pumpkins, these passions can add a level of interest and richness that bleeds across borders in life—they make me a better person to work with. 

So as you eat some pumpkin pie this season (which is actually a pudding, not a pie if you read the definition of egg coagulations through heat pretty strictly), think about how you can add richness to your life and make yourself a sharper person to work with.

As a parting shot, here’s Bon Jovi being thankful. 

CoWork Greenville by Matthew Cook

Earlier this year I took to writing mini-manifestos as a method of formulating and solidifying my opinions. Like all good manifestos, many are crazed, flame-laced essays of doom, but invariably they end up uncovering a few gems that I feel I can latch onto, the rest is trash.

A few months ago I took on the yoke of general partner at CoWork Greenville with a few other talented folks. A lot has changed since then, and a lot hasn’t. I had some really strong opinions, and I made up others to test myself and my partners. Here’s where I started when I dove in:

CoWork has been through multiple reincarnations of itself, each of which has had it’s successes and failures. When we were small, it was tight knit but messy. When we were aspirational we made waves but never followed through. When we partnered up, we had momentum but felt like we sold our soul. Through each of these iterations our core never changed. We were purposeful, we were passionate, but we were also paradoxical. We think of ourselves as Henry V, but most often we are Hamlet.

I believe coworking was never meant to be like church, but that’s where it has often arrived for us—and a soulless instance of it at that. We pay our tithe, we rub shoulders with people who sit near us, identify ourselves by the passionate people we’re bent toward, sit under some preaching, and feel good about ourselves at the end of the day.

We shouldn’t be a crappy church, we should be Baby-Einstein-meets-The-Marines. Impressional. Missional. Sharp. Vindicated. Familial. And if we don’t know what we’re doing, we’ll figure it out with infinite pushups or puppet shows.

This passion and shared mindset doesn’t mean that there can’t be rank, reward, or responsibility. In fact it’s the opposite. To be all that we can be (see what I did there?!) those things are necessary. We need leaders, and leaders need followers. We should showcase success and help others as they struggle to emulate it. We should embrace the fact that we want to be profitable—darn it, we should we require that we’re profitable, and pay those people who pulled the weight to make it happen.

We’re not landlords, we’re the Mafia, and we’ll make you an offer you can’t refuse!

Figuring out where to go from where we’ve been isn’t simple, and there are very few organizations who do well what we’re setting out to accomplish. How do we blend community with smarts while being open about the fact that we’re in it to make money?

I think we have to center on what we do well. Like it or not, we’re borne of the internet, and we can’t lose our heritage in design and technical expertise. The silver lining is that the internet attracts. For better or worse design, development, and the overlapping skills that are essential to making awesome stuff online are sexy. We shouldn’t require CoWorkers to be internet savvy or industry participants. We should require that they’re impressional, missional, sharp…etc., while also seeing value and credibility in our design heart and soul. 

Again, we must be missional. CoWork has had a lot of rallying cries. Independence! Beer! Community! Entrepreneurship! Greenville! No Starbucks! None of these are valid. All of these are valid. We’ve missed the forest for the trees, and we have nobody to blame but ourselves. We’ve been carried by every wind and wave, but here’s the cool thing: that’s ok. Passion feeds expertise and freaking out breeds reinvention. The key is to communicate not what we fear or love, but why we fear or love it. We’ve written a Constitution without a Declaration of Independence. Why should anyone care what we’re doing if we don’t know why we’re doing it?

Profit should drive our choices and make everyone feel secure. There should always be a responsible party that anyone at CoWork, LLC or CoWorker, should be able to look at and say, “You had one job…”. Responsibility without reward is purgatory. Benevolence to our community without doctrine is heretical. B-corp, C-corp, S-corp, LLC, aside; however we choose to be formed or taxed, we should be held to the standard of profitability. This doesn’t mean we’re task masters or corporate leeches, but rather that we put our money where our mouth is. If we say we’re about community, where is our profit going? If we require responsibility, who’s getting paid for our success? If we’re out to build the next wave of web expertise, why are there kids in our city without summer jobs or internships (and for those who have them, why do they pay so little, if anything at all)?

Topics I never had time to flesh out:

  • We must be Community centered, but it can’t be forced. 
  • We have to give of our time without being assholes.
  • As owners, we need to be like-minded, but we don’t have to pretend we’re best friends.

Manifestos have been a really good exercise for me, and this was no different. I plan on doing an EOY post with new opinions and learnings on running a CoWorking space. I’ll link here when I do. Until then!

Steps 7-12: Selling and Qualifying Clients in the Hollywood Model by Matthew Cook

Over the past two weeks I started a run-through of selling and qualifying clients in the Hollywood Model on a step-by-step basis. This week I’ll wrap it up, but first, how about a recap?

In The Prequel I talked through some things that needed to be put on the table before digging into steps:

  1. The business model I work in is called the Hollywood Model.
  2. The process I’m outlining assumes sales are driven by reputation, referrals, and attraction.
  3. This process is designed for a two-man (or woman!) team.
  4. These steps are designed to qualify clients, not just sell them.
  5. A major goal in using these steps is to push potential clients that are a bad fit for you toward a “no”.
  6. I’ll be framing everything by how I work with Arbitrary

In Steps 1-6 I covered the first six steps (surprising, right?):

  1. The initial contact
  2. The handoff
  3. Producer contact
  4. Initial questions
  5. Initial call
  6. Project options & project net

Let’s get back to it, right in step.

Once we’ve figured out a few ways to approach the project and we’ve checked the viability of each to make money, we toss them into a [7] Bullet Email. We send the client an email with each of the two/three/four options fleshed out. Here’s the general content:

Hey Client (Jamie on cc),

As promised, we’ve put together a few options for you to look at which outline how we think Arbitrary could be a good fit for your team. Each of these proposes solutions for the needs we talked about. However, these aren’t final numbers or deliverables, rather it’s the first draft at a solution. We’d hate to end the conversation here based on price or anything we did or didn’t cover. Let’s be sure to set a time to chat this week. Let’s dig in!

Option A

  • Description
  • Team
  • Deliverables
  • Timeframe
  • Cost

Option Turtle*

  • Description
  • etc.


  • Description
  • etc.

That’s it for now! Again, we look forward to chatting through these and hearing your thoughts. What time works best for you this week? 


*If you’re confused about “option turtle” see last week

Usually after the bullet email, we wait. Some clients reply immediately, some take weeks. Following up is a delicate balance of pressure and cordiality, but the fact is that we lose more potential projects here than anywhere else, and that’s ok. If a client doesn’t fit with how you think about work or how much you are worth, it’s better to lose them here than have them fire you in a couple months and refuse to pay. 

If your client comes back with a positive response it’s time to [8] Contact Contractors. As mentioned last week, sometimes we do this earlier, or later, but now is the optimal time. We’ve given our potential client a set of approaches and they’re pretty happy with the overall idea of working with us even though we’ve said some hard things. This gives us solid basis to talk with our contractors, and if they’re interested and committed to the idea, we can talk about our potential team members with the client. 

Once we’re prepped to chat about our client’s reaction to the bullet email and we’ve contacted our project partners, it’s time for the [9] Full-Team Call. Jamie will make his debut here, and if we feel it’s appropriate we may add in a potential contractor or two (but usually not). On this call, the producer sets up the conversation, but takes a back seat when it comes to the meat of the interaction. For Arbitrary, this means the client usually comes prepared with thoughts for a single approach they like, a rough budget idea, and a potential start date. They feel like they lack a clear picture of what it’s like to interact with our expertise, but they understand how Arbitrary works. This is a perfect scenario. Jamie talks a lot–usually about projects similar to this one that we’ve done, why he’s excited about this potential client, what he thinks/feels about their competitors, and how excited he is to get underway when the client signs on. The main purpose for Arbitrary on this call is to create good feelings and remove barriers. The main purpose for the client is to verify that we’re reputable, and communicate their likes/dislikes in our options. 

The result of the full-team call is for us to go away and come back with a [10] Final Option. This is the easy part (usually). We make a few changes to cost, timeframe, or deliverables and send another email. We update our contractors, we double-check our schedules, and then wait for the client to say “yes”. Sometimes this takes another call or two, sometimes the client surprises us by saying “no”, but at this point we’re simply following up and making sure our client is equipped to make the decision. 

If the client gives the green light, we [11] Draw up the Statement of Work, and make sure everyone agrees. This usually takes a week or two to hash out complete terms.

After the SOW is agreed upon, we [12] Get Signatures and Payment, then start preparing for the kickoff where we lay the foundation for specific project interactions with the client. 

That’s it for selling and on-boarding! In wrapping up here, let’s run through a few weaknesses and strengths that I’ve observed and that I’m still playing with.


  • RFPs and Pitches. It’s really hard to create 70-page pitch documents and follow an RFP process with a two-person team. It takes copious amounts of time, the chances of winning are usually abnormally small, and the clients are usually abnormally difficult.
  • It’s High Effort. Selling projects takes time and discernment, and that means we’re not spending effort on other things. Neither Jamie nor I are truly, deeply passionate about sales; so this process can be taxing and we can get in over our heads before we realize it. We’re always talking about when the right time would be to bring on another person to help with sales. We aren’t at that point yet.
  • The Process is Centralized. This is a lot of information and tools to put into two guys’ heads. On top of the tools I’ve shared here, we craft emails, discuss potentials privately, draw up schedules for months in advance, create sales pipelines, maintain rolodexes, and find time to promote our work and write/speak. It’s a lot of work, and sometimes it can burn us out–especially when we lose a project we really wanted.
  • The Asshole Perception. When we make mistakes in this process, one of the most common side-effects is that our potential client thinks we’re total jerks who have an inflated sense of self-worth. Sometimes the line between “really valuable” and “totally full of it” is razor thin. We have to be perceptive, committed, and stable in front of our clients.


  • Removes the Budget Conversation. This process helps keep our clients mind on value, and turns budgets into a way for them to gauge the talent, involvement, and deliverables that they can afford. 
  • Preserves the Mystique. These steps keep us honest. We don’t over-commit our time or emotions, and we guard ourselves from doing free work. We also set up Jamie to look like a total wizard, and we build excitement and anticipation for a kickoff. 
  • Value Pricing and Small Teams. We avoid talking about our costs, and we build confidence in a small team of highly adaptive experts. This lets us work with friends and also point the client toward the work we think is best, not necessarily what they come looking for.
  • Flexibility and Lifestyle. This process allows us to approach many different kinds of work, rather than being pigeon-holed as a production partner or freelancer. It also allows us to adapt for personal life and plan crunch time. Nobody likes working weekends or missing vacation, and this process allows us to set client expectations for our availability and involvement. We know if we’re going to be busy, and we compensate for it. We plan for when we need time away, and we take it (most of the time).

I love talking about this stuff. As always, shoot an email over to mattecook(at)gmail.com if you’d like to chat more.

For more on how Jamie Kosoy and Arbitrary talk to to clients and run projects, you can harass Jamie on Twitter or find him in a classroom or at a conference in San Francisco. 

Steps 1-6: Selling and Qualifying Clients in the Hollywood Model by Matthew Cook

Last week in The Prequel I talked through an introduction to selling and qualifying given my experience over the past few years. Here’s a quick recap:

  1. The business model I work in is called the Hollywood Model.
  2. The process I’m outlining assumes sales are driven by reputation, referrals, and attraction.
  3. This process is designed for a two-man (or woman!) team.
  4. These steps are designed to qualify clients, not just sell them.
  5. A major goal in using these steps is to push potential clients that are a bad fit for you toward a “no”.
  6. I’ll be framing everything by how I work with Arbitrary

It’s time for steps 1-6 of 12, let’s continue! Everything starts with [1] The Initial Contact, when a person or company reaches out to Arbitrary. It may be a personal friend of Jamie’s, a larger agency, or an end client looking for a small team. We treat each potential in light of how they relate to us. It’s bad manners to reply to a friend like a stranger, and it’s uncomfortable when you’re too chummy with a big corporation.

After the potential client gets in touch, our first reply back is [2] The Handoff. Jamie replies with a personal note saying thanks, expressing interest, and passing the baton to me, the producer. The goal is to keep Jamie’s time sacred while also building trust in the producer role. Lots of potential clients are testing to see if Arbitrary is an actual company or just a front for Jamie’s contract work. The client should feel like they’re discovering the company structure and being given a personal contact, not like I’m the gatekeeper to Jamie.

Next comes the [3] Producer Contact. I step in, echo Jamie’s interest and appreciation, then start the conversation.

Immediately following are the [4] Initial Questions, a predetermined set of bullet questions that we change slightly each time we send them. Sometimes steps 3 and 4 are the same email, sometimes they’re separate. It depends on how detailed the client’s initial contact is. Was there an RFP? Do they sound like this is a big project for them? Did they ask lots of questions? I balance the formality of my reply with the formality of the inquiry while also creating the tone of Arbitrary’s communication. This is the first opportunity to display to the client how we’ll talk with them.

The initial questions we send can vary depending on the work, but more important than rewriting the questions, I let the client know that they’re templated. I say that I realize I’m asking them to do some homework which I assign to all potential clients, and tell them why: I want to help both of us make sure we’re the right fit for each other right out the gate. This alleviates my workload so that I’m not generating fresh questions for everyone who shows up, and it puts the client in a predetermined frame of mind. Here’s a paraphrased rundown of what we ask:

  • Can you recap what you’re looking to get done?
  • Have you started any of this work already?
  • Is there a hard deadline for completing this work? What drives that deadline?
  • What does your team look like, what roles do you have on staff?
  • How did you find us, and did did someone send you our way?
  • Are you talking to any other people about this project, and can you tell us who they are?
  • What is your budget for this project?
  • What specifically are you looking for us to accomplish on this project (as opposed to other teams your your internal team)?
  • Anything else?

Dan Mall has a great write-up about this step titled, Prequalifying Clients that I added a few thoughts to a while back. He’s been working on this step a lot longer than I have. It’s well worth reading.

If replies to the initial questions don’t throw up any show-stopping red flags, we move on to the [5] Initial Call. This is a call with only me–no Jamie. It’s important to draw that producer distinction and keep the client’s mind focused on how to set up the work and what they need to communicate. Throwing Jamie in at this point causes the client to feel like he’s just a freelancer (rather than team leader) and changes the topic of discussion from defining the work to testing out expertise, which is the first step toward free consulting. Again, let the client know it’s just them, anyone they feel like bringing, and the Producer. Also let them know the agenda, which almost never changes. It looks roughly like this:

  1. Tell us about your project. What are your hopes, dreams, and fears?
  2. I’ll ask you questions so that we can discuss details.
  3. I’ll tell you the story of Arbitrary; most importantly, why we do what we do, and why that makes us special.
  4. You can then ask me questions.
  5. Wrap up by talking about next steps.

If things went well and the opportunity still feels right, I take all of my findings to Jamie, and we start putting together [6a] Project Options and running them through a [6b] Project Net worksheet (see an example of that worksheet here). 

It’s paramount in this model that we pose multiple options for successfully completing the project. It builds confidence in our expertise, displays our comfort working with complex solutions, and up-ends the budget conversation. The real struggle here is offering multiple options that are truly different. We want to offer Option A and Option Turtle, not Option A and Option B. Clients are good at math. If I offer them incrementally additive options, they’ll subtract pieces they don’t want to pay for and calculate a price difference. I want them thinking about value. The value of the team, value that they put on the work to be done, and the value of one approach vs. another completely different one. This pushes them to think about what they truly want and can afford given the packages I communicate to them. 

The project net worksheet is our way of double checking ourselves. Because this process is set up to work in a value pricing approach, we can sometimes get lost in figuring out how much our services are worth in a given scenario. If we get lost, our client definitely will. These two spreadsheets give us a space for sketching out numbers. We can compare multiple options side-by-side and flesh out the final or preferred option. It’s a way to guess at components and estimate profitability; taking the things we want to do, and helping us think about the cost and income earning potential. This also gives us a jumping off point for thinking about the friends and contractors we’d want to bring on for the project. We talk to the team we want to hire early and intelligently. This is a good place to start looking at contractors, thinking about the roles and potential people to fill them.

That’s it for steps 1-6. If successful to this point, we’ve either pushed a client to realize they’re not right for us or we’ve sold them on the idea of Arbitrary and built confidence that we’ll return with the right project structure. 

Without a clear picture of why we do what we do and the value we have to offer our clients, we have nothing to sell and steps 1-6 will feel hopeless and contrived. Starting the conversation can sometimes feel like grasping at straws, but the better we get at finding the right vision to communicate, the more we can refine how we sell it. 

Next week we’ll run through steps 7-12 and some things I’m still working on. As always, feel free to say hey in the meantime. 

The Prequel: Selling and Qualifying Clients in the Hollywood Model by Matthew Cook


I wrote up a blog post about the process I use for selling and qualifying clients as part of the teams I work with, but when it topped out around 3000 words I knew I needed to split it up. Over the next three weeks I’ll be posting three installments on this topic. Let’s dig in!

I’ve been refining how I approach and talk to clients over the past few years. As a producer on a two-man team I jump in at the beginning of new business conversations and I’m a big part of selling and qualifying.

The business model I work in is the Hollywood Model. I partner with a team lead to sell a project, find the best way to complete it, and then make it all come to fruition. Project to project a lot changes: we rarely build the same team, we fabricate a process from a common bag of elements, and we may have to learn a new tool or programming language to deliver the best results. As producer at Arbitrary I’ve been helping run sales and qualification for 13 months. And for the past three years up to this summer, I did the same with SuperFriendly.

Digging in with these companies and the different clients they attract has given me a lot of insight on steps and tactics. I’ve hopped on Hangouts to talk about responsive redesigns, di-electric mirrors, and custom CMS builds to name a few potentials. It can be crazy trying to get in front of the learning curve, let alone guide a conversation and communicate enough value to convince a client that they should hire us. What I want to talk through is the process that I’ve been working with to do just that!

I should cover a few things before we get too deep. First, it’s not completely correct to call this a sales process. Selling in this model is highly Driven by Reputation, Referrals, and Attraction, so this won’t work for everyone. For this to work you need a solid base of experience, and the portfolio and conversation skills to support it. You also need a strong network of friends in the industry who pass around work and regard you as a top-notch practitioner. If you don’t have this, there’s still a lot you can take away, but you’ll have a harder time finding clients to actually run this on, and you’ll have to do a little more convincing about your capability.

Second, this process is Designed for a Two Man (or Woman!) Team. It fits the way I work with my clients, but it can be adapted. I almost never follow every step exactly as listed, but all of the potential touch-points are here. As with most processes, things are rarely cut and dry. Sometimes knowing what buttons not to push is just as important as knowing the ones that we should push. I’ll frame everything by how Jamie Kosoy and I handle conversations with Arbitrary clients. 

Third, this process is Designed to Qualify Clients (as the title states), not just sell them. If you’re attempting to sign every potential that comes your way, this will seem very convoluted. In my experience, the process works great when we’re signing about 15%-20% of the projects that come our way. That means while walking through the steps, we should expect (or even shoot for) 80%-85% of our potential projects to fall through. So we keep a lookout for red flags, and we must be actively discerning if each client is best for us.

Fourth and finally, this process is Pushes to “No”. Optimally we are turning away very few potentials. Rather, potentials decide we’re not the best fit for them. This is important for two reasons: the drivers I talked about earlier (reputation, referrals, and attraction), and the fact that if we’re priced right, some people will find us too expensive.

If we tell a client no after they’ve been referred by a friend, we burn both the potential client and the person who referred them. Our friend may feel like we made him or her look bad, and the potential client feels like we were a bad referral. If we actively turn down a client who’s been keeping tabs on us, they may feel slighted because they’re a long-time fan of our work. When we turn them down, we possibly lose part of our following and someone who may have pointed others our way in the future. If we are able to guide the conversation so that the client feels like everyone is realizing we’re not best for each other, everyone wins.

On price, we should be looking for most clients to feel like we’re just right, or maybe a tad high. Their perception of value and how much we cost should match what we want them to pay, and how valuable we think we actually are (for more on how valuable you are, read this). This means the clients who undervalue our work will walk away if we’re priced correctly, and we’ll be left with those who have the correct appreciation for us and what we do.

So here’s where I’ve landed. This process that I’ll walk through over the coming weeks is my work in progress. A lot of it was built hand-in-hand with Jamie Kosoy and Dan Mall, and a lot of it is heavily centered on re-framing a traditional sales conversation. Next week I’ll walk through steps 1-6, and the following week I’ll wrap up with steps 7-12 and some observations I’m still noodling on. 

More soon.

Oral History of Designing and Building Things on the Internet by Matthew Cook


I’ve found the oral history of the broader web industry surprisingly important. There are entire eras of web history that are mostly superfluous now, except when it comes to context. While unearthing trends and best practices of days gone by, blog posts and ancient RSS feeds don’t really give the full picture. Oral history is important because it sets the base for reactionary progress and appropriate adherence to tried and true practices.

For instance, finding a definition for “bare URL” is easy enough, but getting the story on why “www.” exists and what we would do differently with web addresses today if we could start over is another thing entirely. The type of insight required to speak intelligently about something like that comes from perspective across skill sets and time, and is invaluable when reinventing how things work—especially when you apply it to a project at hand.

Oral history in our industry isn’t important because it’s better than written or video blogged contributions. It’s important because it’s fast, contextual, and (again) reactionary. Oral history has the blessing of being recalled situationally, not just by keyword or search rankings.

It also creates vision that connects dots, whether there are dots or not, with the advent of new technologies. It gives context to things like the Apple keynote this week. Who is Kevin Lynch and what’s so interesting about him demoing the Apple watch? Why does it matter that he was the CTO of Macromedia? Why are all of the old Flash guys like, “Nooooo Kevin!”?

We all have gaps in our understanding of the internet and how the world of the wider web works (see what I did there?). Take for example a team working together out of a small agency, shouldering the redesign of an animation heavy website. Fair warning, it’s story time:

The Art Director has been designing sites since the 90’s, the Senior Designer has been in the industry since 2007, and the intern on the project just dropped out of college last year in hopes of getting a job; this is her 3rd project. There are a lot of potential directions this team could take, and at a brainstorming session they look to the Art Director to set them down the right path. As she looks out at her team, the Art Director realizes the gaps in understanding.

Her Senior Designer is thinking about what this site will look like as a suite of experiences across multiple devices. He’s excited about the incremental changes between screen sizes and is noodling on break points and how each platform’s design can best suit a particular user.

Next, she remembers how her intern laughed nervously over lunch yesterday while telling her that she’s never even learned how to design for a non-responsive site, and she’s nervous about the process and deliverables involved in doing anything outside of her wheelhouse.

Finally, she recognizes she’s imagining what this site would have looked like in Flash, and her sense of best-of-breed practice tends to flow step-by-step from what was fresh when she first started to what is cutting edge today. She has solid basis for where her ideas are coming from, and she’s thinking with a high amount of originality.

This is a super simplistic scenario that leaves out a lot of things to consider, but there’s a powerful dynamic here, and we’re not even thinking about how the developers could and should fit into this conversation. Some Art Directors would just steamroll the design conversation at this point and send everyone scurrying after tossing together some inspiration and sending it to everyone. A much more helpful choice would be to give context to the project.

Imagine the Art Director talking about how she sees what designers used to accomplish with Flash as the foundation for a lot of current animation-heavy interactive design. She fleshes out design for multiple screen resolutions and the changes in design processes she’s experienced and invites her team to think about what the next step forward from current trendy designs could be. Instead of sending her team around the internet for other site designs they like, equipped only with a few loose concepts, she’s given them almost 20 years of design history condensed down over lunch. She just cherry-picked the most salient pieces of relevant information to add intent and clarity of purpose.

There’s a tremendous amount of power that guidance like this can hold when it’s specific to audience and context. This rehearsed oral history helps us know why to do or not do something. What to do can be shepherded after.

So be a historian, and be ready to dispense wisdom in a way that isn’t preachy or condescending. Good historians don’t use gibberish. They speak in layman’s terms and explain jargon. They speak to the level of their least educated listener, and they call out potential while inviting contribution and inclusion. They also don’t presume to know the only or even the best solution for a given problem, even though they’re seasoned problem-solvers. Instead they shoulder the burden of informing the group, adding perspective, and responsibly ensuring success.

I’ve been been blessed by people who have dispensed this context beautifully, and also been cursed by other’s who are misinformed, careless, or belligerent leaders.

The nature of the internet and the speed of it’s change tends to give us grizzled, bearded ancients and organizational oracles. It’s given us leaders who have lived through multiple dynasties of technology, and occasionally stalwarts who refuse to leave a dying technology. We’ve also gotten plenty of sunshine soldiers and snake oil salesmen who pedal manipulative practices or contrived temporary results. All of these groups thrive on either sharing their own perception, or the lack of other’s perspective.

So, take it from someone who wasn’t really aware of what it took to build things on the internet before iPhones existed: talking others through the highs and lows of the internet’s history is really important and helpful. Fill in gaps. Breathe life into an industry that a lot of times feels like it’s more interested in sparkle, fresh, simple, innovative, disruptive…etc. Contextualize what’s important. The history of the internet and it’s designs, technology, and content is well documented, but history isn’t just facts. It’s how they are arranged and the perspective you communicate them with.

Do/Don’t do this to make your clients/team value/undervalue you by Matthew Cook


I’ve discovered that I occasionally have lapses in aspects of my work life that passively communicate a great deal to the people around me. Whether that person is a client, partner, or even my wife, there are things that are much more apparent to those around me than they are to me.

I think this is a common problem. The things I fail to see in myself, I often see it in the people around me. I’m also quick to perceive an underlying cause. I can tell this is happening when thoughts start dawning on me like:

That last project was really taxing and we didn’t get to do anything fun, maybe that’s why everyone seems down.

Maybe he doesn’t care about this project/task anymore.

Something new would be better for all of us right now.

It struck me that while this is a great diagnostic habit between team members or in a relationship, this is really dangerous when it happens with a client. Where teams and spouses have a lot of motivation to come along side you, clients don’t necessarily. They may get scared. They may get dissatisfied. No client should ever feel like their project is overly taxing and un-fun. No client should feel like you don’t care. No client should start to feel like everyone on their project just needs something new. So here’s my list on how to avoid these feelings:


Make your value clear. Clients are very aware of your cost, stop talking about it. However, they will sometimes forget why you’re valuable and why you matter in the long run. Keep reminding them. Tell them with the quality of your work, but also tell them with your timeliness, interpersonal consideration, and how you structure your fees. Stop invoicing at random times when you aren’t clearly contributing to your project. Get crafty; show glimpses of your work when you invoice. Invoice a small initial payment then kill it in a kickoff meeting and follow up with an invoice for the first 50% of the project.

Over-communicate in times of uncertainty and crisis. This is well documented. Clients can tell when you go dark, and sometimes they aren’t the type to pipe up when something feels wrong.

Go to the problem and be honest. You may be able to get away with lying to your client once and you may be able to avoid a problem by simply ignoring it, but those are scorched ground tactics and won’t be forgotten. Running toward conflicts and dealing with them strategically (and with pace) sets the stage for a solid open relationship. It also lets you do cool things like documenting issues and having a back-log to learn from or prove your value to your client.

Complain. You read that correctly, go complain more. Don’t whine, but sit back, be strategic and complain. Bring up the problems, bring up the weaknesses, then be the first one to propose the best solution.

Over deliver. Over deliver. Over deliver. Don’t just do what you say you will (which is hard enough for some of us who like to bite a lot off), but do it well, and do it better. Then do a little more.

Embrace ambiguity. Colin Shaw has a great article about this. If anyone lives and breathes in an ambiguous world it’s those of us who design and build things online. Your clients already don’t understand most of what you do, but that’s a strength. Sometimes we create things in spaces others don’t even know exist. We delight where something is boring. We make money grow on trees.


Work in a black box. Make it clear what you’re doing and why it matters. Trust is extremely important, and you can’t gain it or keep it if you’re not communicating.

Forget to congratulate your team and occasionally yourself. There’s a lot of power to telling your team and your client that they’re doing a great job. Don’t pander, but celebrate small successes and your adaptability when you turn a challenge into a success.

Hold back your dreams and aspirations. The why is sometimes just as important as the what. Dreaming out loud can be intoxicating for a team. Even if you’re the most junior member, making your passions known and displaying why it makes you such a good fit can be a powerful exercise in pulling client and team together.

Assume problems will blow over. Again, be the person who runs to the issues. Avoiding them leaves them out of your control and creates ambiguity–the bad kind. By taking on the hard stuff, you show that you’re committed and professional. You sweat the small stuff and respect the big stuff.

Let your client get away with not putting everything on the table. The sneaky thing about unspoken expectations is that they’re unspoken. Make it known you expect forthrightness and clarity. Have thick skin and take criticism as graciously as you take praise. Force a vision for the future to be put on the table. Be honest about what you’re going to do and expect the same from your clients.

Be comfortable. Death by a thousand paper cuts looks a lot like business as normal until you can’t stop the bleeding. Even good relationships and happy feelings need support. Create a list of assumptions you’re making about a project or client and then try to remember the last time you talked about them. Preempt the “we’re just good roommates” conversation and start building relationships.

Radio Free Europe by Matthew Cook


You can be hanged for visiting our site.

It’s not often I get to take on a project where the client lives in that context, but this is reality for Radio Free Europe. RFE delivers news and truth to some of the most information-starved countries and people groups in the world, and I can’t help but be impressed. We met with a small team in Prague; sometimes eight members, sometimes 15, but never a huge committee, and never with a hierarchical room of Directors and VPs. Everyone cares, nobody has just one purpose, and the atmosphere of actionable outcomes is tangible.

With content carrying this type of consequence, and the team being small and intent, there’s a crystal clarity to the goal of everything we plan to do in redesigning rferl.org.

Get the message out.

SuperFriendly is wading into a atomic design process with RFE, and we want to share the experience openly on responsivedesign.rferl.org.

The iterative process with SuperFriendly will flow roughly like this:

  1. Kickoff
  2. Design Direction through element collages
  3. Performance Budgeting
  4. Design Production
  5. Front End Development
  6. Handoff

From there RFE will carry on with integration, content migration, and using the elements we create together to build out websites for sister organizations.

It’s a big process, distributed team, and a weighty purpose. Look for more updates on the responsivedesign.rferl.org blog as we progress. Also see intro posts to this process from other SuperFriendly team members Tim Kadlec and Dan Mall.

If you’re interested you can also keep an eye on our twitter accounts as we progress. I’m sure we’ll be tossing out ideas and findings along the way.

Emotional Intelligence by Matthew Cook

Let’s talk about emotional intelligence (EI) for a few minutes.

Last month, The Atlantic published an article titled The Dark Side of Emotional Intelligence, Huffington Post published one by the same title in October, and Daniel Goleman published a short opinion, An Antidote to the Dark Side of Emotional Intelligence on LinkedIn just several weeks ago.

Quick note, Daniel Goleman is a well-known thought leader when it comes to EI since the publication of his book, Emotional Intelligence: Why It Can Matter More Than IQ.

The Atlantic’s point is simple, “Emotional intelligence is important, but the unbridled enthusiasm has obscured a dark side”. The writer, Adam Grant, goes on to define the dark side as manipulating someone to act against their own best interests”. Although the works he cites dig deep into the mechanisms behind EI and manipulation, the article seems content to wave a red flag and draw attention to the fact that abuse of EI exists and is quantifiably provable. 

The Huffington Post article has an even more simple point, “[higher] emotional intelligence – which is typically thought to be a boon to relationships and prosocial behavior – could also increase the ability to manipulate others.”

It’s a little weird that the concept of EI having a dark side is being posited as so ground-breaking. I guess having measures to compare emotional intelligence levels and finally being able to identify and record a person’s ability to use it manipulatively is new.

My goal isn’t to talk about the merits or shortfalls of these articles or the facts they unearth and regurgitate. I’m citing them to demonstrate the timeliness of the topic and show that manipulation utilizing EI is identifiable and mainstream–let’s take a second to reflect on this with what’s going on around us in our own industry. I want to talk through something more central to what we do and what I see when interacting with potential clients as a freelance producer. 

The majority of start-up owners I’ve talked to try to employ EI to the ends explicitly described as the “dark side” by The Atlantic, The Huffington Post, and Goleman. Sometimes it sounds like “Building this is the easy part. It’s a sure thing” and sometimes it sounds like “Nobody gives more than 5% equity. We’re giving 8%, and when this thing sells we’ll all be glad we put in the time”. It takes many forms and sounds completely different depending on who you are, but I see it way more frequently than I ever thought I would. I know this is a harsh accusation, and I know it’s not really a nice thing to say about people, but I think we should realize and think about it.

Not all of these guys and gals are out to hose us and make a million bucks, but they seem to think it’s acceptable and the modus operandi for our world. Entrepreneurs are used to telling stories, they’re used to bootstrapping, and they’re used to evangelizing. 

I think it was Guy Kawasaki who said something like, “Ideas are easy. Implementation is hard”. Entrepreneurs preach this when they talk to investors and are looking to prove their mettle, but we often hear the opposite from these same entrepreneurs when they’re trying to contract a team to build their idea: “Implementation is easy. Ideas are hard.”

I guess what I want to say is two-fold. First, watch out for the idea chaser. I’m not talking about John Nash a la A Beautiful Mind. I’m talking about patent trolls, charlatans, and people who at their core are oversold on themselves. Second, don’t be that entrepreneur. Our industry needs idea people and evangelists but we don’t need any more fluffy personalities, hollow projects that never pay (or launch), or men/women looking to build their fortune on the skulls of unassuming designers and developers.

I encourage you to be discerning and kindly oppose these people when they show up at your door or in your inbox. Be someone who shoots for fairness and builds an honest foundation for everyone you work with. 

My year in numbers and silly facts by Matthew Cook

A lot happened in 2013. Some I want to repeat, some I don’t, and plenty of new things I’d love to dig into for the first time in 2014. I think it’s good to share some of these and be transparent. Here goes:

  • Sent 24 invoices for my services.
  • Took 4.5 weeks of vacation.
  • Worked on 6 projects that launched and 9 that didn’t (or haven’t yet).
  • On those 15 total projects I had the privilege to work with around 36 unique teammates.
  • Changed my job title once.
  • Ran 330 miles including my first half marathon.
  • Attended 2 conferences.
  • Attended my first non-classical concert and it was awesome.
  • The range from “x” to “y” was my forecasted income for 2013, and y was greater than 1.75x. I ended the year at 1.3x (math!).
  • Changed my hair 6 times between 4 different styles.
  • Failed to go snowboarding at least once for the first time in 12 years.
  • Flew to NYC 4 times, took a bus to Boston 2 times, flew to Boston 1 time, flew to Seattle one time, and flew to Philadelphia one time.
  • Dogfish Head beers are the most frequently consumed beer in my apartment making up 17% of the 2013 total.

I hope your 2013 was phenomenal, and here’s to a year of growth and learning in 2014.


Conversation Strategy and Planning by Matthew Cook


I started thinking about writing an opinion piece on conversation planning a while back. After attending Brooklyn Beta and reading To Sell is Human by Dan Pink, I’m ready and even more galvanized than before. Let’s go.

Start actively participating in conversations. Failure to plan discourse is stupid. Blindly accepting what someone says is dangerous.

Research by the Carnegie Institute of Technology says that 85% of an individual’s financial success in life is attributable to human engineering–basically your personality and communication skills. Forbes wrote a good overview of CIT’s findings. Research like this (and many other sources) continues to point to what a lot of us innately know and see in our day to day lives: Intelligence isn’t as closely linked to our success as who we are and how we communicate is. 

If it’s widely understood that communication is so intimate with our success, why do we spend such little time preparing for it and carefully considering outcomes?

As a freelance Producer, I have a ridiculous goal when talking to clients: never meet a response that I didn’t already consider. It’s impossible to meet that goal, someone inevitably throws out something insane that I never thought of. The point of that high bar is not to gauge my success or failure, but rather to keep myself engaged. 

For us web industry folks, this comic by Matthew Inman nails our occasional feelings about client communication. The truly painful thing about the situation depicted here is how avoidable it is. As individuals or teams that create beautiful things that solve complex problems, we sometimes forget that our end purpose isn’t to create the perfect user experience or architect content in the most intuitive way, it’s to serve a client. You can build the most amazing thing ever, but if you can’t convince your client of its value, you’ve failed.

Willful resistance aside, It’s your fault when your client doesn’t see value in your work.

Continuing with the humor, remember this poem? Taylor Mali makes some great points about tone and conviction, and his feelings perfectly illustrate that you have to participate if you want your communication to be effective. Stop spectating your conversations or waiting for them to happen to you.

With SuperFriendly and Arbitrary (shoutout to my dudes Dan Mall and Jamie Kosoy) I precap, take notes, recap, and real-time strategize in almost every client conversation. I literally use two moleskin notebooks, textedit, Skype chat (private), and Skype chat (client) in addition to verbal conversation for almost every call. I’ve mapped out a way for myself to make note of things I find important and respond immediately or record them for strategizing later. Note taking isn’t about memorizing for a final exam. It’s about gathering specific thoughts and feelings at a specific time in a specific context. Not considering negotiation and verbal discourse, I’m equipping myself to communicate. I’m trying to catch all of the little pieces so that I can not only understand what’s being talked about, but also project possible outcomes and infect all of my conversations involving this client with an understanding that goes beyond bullet lists, action items, and knee-jerk reactions.

To round things out, consider this article from 2011 published on the Psychology Today website. Psychologist Mitchell Handelsman, Ph.D. is addressing multiple problems with the lecture format–one of which is:

“I tell my students that nobody will ever pay them to sit and listen, or to take notes. Even Roger Ebert doesn’t get paid to watch movies. Rather, he gets paid to think, analyze, critique, write, and communicate.”

What I took from this article is that there’s definitely a place for one-way communication, but that place isn’t in a conference room with your client at a review milestone. No matter your role, your skill, or how smart you think feel, you need to be wrestling with both sides of these conversations. You may not get to respond immediately (or even ever), but you darn well should be ready.

Here’s a basic outline that I’ve started using when strategizing before hopping on a call with someone–specifically clients:

  1. Who am I talking with and why am I talking with them?
  2. What is this person bringing into this conversation that will affect how they view what I need to tell them?
  3. How can I earn this person’s trust and what do I not understand about them?
  4. How might they react when they hear what I’m about to tell them?

That’s it, and it’s super basic. These questions often lead to more questions for myself, those additional questions for myself often lead to more questions I’ll have for the client, and those questions often lead to conversation topics that I would have never prepared for if I hadn’t taken 10 minutes to devise a plan. 

We need to get more tactical in our conversations. We’re often surprised when a conversation ends up in a crazy place. You can never fully keep that from happening, but you can be ready and head off the big issues. 

Just Doing a Podcast by Matthew Cook


I was on a podcast today!

Big thanks to Jason Blumer, and Dan Mall for having me on as a guest co-host. If you missed the show you can find it (9/12/13) here. We talked with Dave Onkels about his company Dotvita and how he’s shifting strategy, balancing risk, and forging his own path in the web industry.

I’ll be returning to the Businessology Show for a second stint in a couple weeks. Super fun.

Woo Hoo!

Update: My second stint as cohost was yesterday. with Jason and Cameron Moll. Find that interview (9/26/13) here

Starting Your Own Business Without the Fanfare by Matthew Cook


I started this article on one of my recent trips to Charleston, SC. I’ve got several of these rambling personal blog posts stored up that I haven’t been publishing. I’ll start putting some of them up now and again. Keeping a good blend of casual thinking and professional thinking is my goal–so here we go.

Talking about starting your own company in tech is a hot topic right now. There’s a lot of excitement and jittery nerves around the start-up scene as we experience a bit of a tech boom here in The States. Lots of quoting Steve Jobs, and lots of dreaming big. It’s fun, it can be intoxicating, and (as is often stated) one in a million make it big. It’s fun to watch, it’s fun to read about, and how can you not like Steve if you’re young and love tech? I want to talk about those of us who live in this start-up world as individuals but aren’t really part of it. 

For all intensive purposes, I’m a business owner. I’m an independent contractor working as an LLC that I run all of my income and liability through–waiting for my paperwork on that LLC. I provide a service to clients that they need, I pay myself, and I cover 100% of my own taxes. However, I don’t have employees, I don’t have investors, I don’t have a product, and I don’t have wild ambitions for scale. There are lots of people who work this way, and I think we’re an over-marginalized piece of the tech start-up scene. We sort of fit into the Independent Small Business Owner category, but we also fit into the Independent Contractor category as well as the broader Entrepreneur moniker. 

We have all of the financial burdens that come with being in the start-up world, but none of the fanfare; sometimes it’s great, and sometimes it’s terrible. Forget investors, forget products, forget incubators, and forget imagining your company as the next Apple or Facebook. We’re gloriously and terribly alone except for the clients or fellow industry lone wolves we call friends. I like to make my own category for what we are.

We are the wheels in a lego box. You never know what you’re going to build when you pull out the huge bin of pieces, but wheels are a safe bet. After all, unless it’s a fort, you’re going to need to go somewhere, right? I like thinking of people like us as the unused building blocks of the start-up world that everyone needs.

Who we are and what we do are the individual pieces to larger teams that can make amazing things and go to amazing places. For now, I’ve chosen to stay small and touch as many things as I possibly can. I know great men and women who have decided to become a cornerstone in a larger structure, and I know some who are intentionally and chronically that lone set of wheels. 

For me, I know I can’t stay alone long term. At some future point I’ll either take a stab at building my own thing, or I’ll go W-2 (again). I’m looking at a BLS.gov graph that shows the success rate of small businesses by year. As it declines from 100% to around 20% over a 17 year span, I’m sitting here wondering how long my “business” will survive. I know it’s an imperfect comparison, assuming I’m not actually an accurate sample for that model, but it’s definitely a driver to be a building block or a set of wheels rather than a cog in the machine.  

Where I’ve landed for now is that I know I want to do my own thing. That means a lot of working with SuperFriendly while finding my way with Arbitrary and the odd side project. There’s a ton of power in staying independent, but I feel an impending sense of eventual marginalization. I can’t stay here forever or I’ll never accomplish anything bigger than what I can do alone. Eventually I want to either start my own thing for real with scale, fear, and huge potential; or I want to officially hitch my wagon to a business/product I believe in and can push forward.

Oh, final note. I changed my hairstyle again and started running

You Can’t Afford to be Employed by Matthew Cook


I’ve been noticing recently that freelancers around me seem to be disappearing. They’re taking jobs with cool startups, getting on board with agencies, or straight up getting hired by large corporations. Let me say something clearly.

There’s nothing wrong with being employed

…but I think talented people in our industry are selling out. Given the way the web industry and the US economy are right now, I say you can’t afford to be employed.

The US Bureau of Labor Statistics says growth in jobs for web graphic designers will increase at four times the national average in the coming years. At the same time, the studentscholarships.org database shows only a 3% unemployment rate for designers nationwide–compared to about 8% of the US population that is either unemployed or recently dropped out of the labor pool due to chronic unemployment. Combine this with the fact that a staggering 29% of broadly termed graphic designers are self employed, and you’ll see what most of us already know, web designers work so, dang, much. They also make over $43,000/year on average, so pay isn’t too terrible.

Another interesting thing I found, taking a full-time position simply because it offers steady income and some immediate safety is counterintuitive. The U.S. workforce is expected to be 40% contractor by 2020 according to a recent article on Quartz (and many other sources). Our workforce is currently at around 30% contractor by most estimations. You can’t think that finding a job or a startup to hook your wagon to will solve your career problems indefinitely. To quote another recent article,

This [shift in perspective] is not just a recession-induced thing… It reflects a long-term change in the economy. Since the 1980s, management’s philosophy has evolved to “look at work as projects.” Instead of keeping workers on staff to perform all tasks needed, they outsource them or hire consultants. 

If our economy is shifting toward contractors and teams of freelancers, why do so many of us insist on taking a job? Knowing that jobs currently exist in great number, shouldn’t we be encouraged to reach higher? If companies are shifting to contract relationships, why not meet them where they’re heading?

Web people, you are valuable and needed

Excellence in our industry is in high demand. As overworked young professionals, the allure of a stable job that offers benefits and the ability to stop working nights at home is powerful. The funny thing is that what we can earn in traditional employment pales in comparison to what we can earn in other forms of organization (intentionally vague here, stick with me). Save specific skill sets like iOS development or web development in securities and commodities contract intermediation (whoa there!), growth in our salaries is startlingly average. Add to that, our quality of life can be much greater outside of employment. Shift gears again for a second.

It’s time to get down to business

All of us need to stop hating on business. Seriously. I work in a coworking space, and most of the time when I talk about the business of what we do my compatriots’ eyes glaze over and they say something like “I’m glad there are people like you” or, “that’s not really my thing”. I understand that sentiment completely. However, I value what you do just as much as I value what I do. I value both of our skillsets because together they can make both you and I happy, successful, fulfilled at work, and loved by our clients. Stop looking down on being a businessman or businesswoman AND a designer, developer, or whatever you are.

Accenture recently did a study on contract workers. They describe the relationships we have with each other as a “supply chain of talent”. The most successful freelancers find out where they fit in a bigger process and take advantage of the value they create in order to pay themselves, do what they love, and/or do things like work at home while the kiddos are growing up. This puts businesses who work with web freelancers in a weird position. The internet is ablaze with articles and opinions about managing people like us and successfully outsourcing deliverables. Businesses have to manage you, usually at distance, and they’re terrible at it. They’re terrible at managing your talent, they’re terrible at approaching you, they’re terrible at on-boarding you, they’re terrible at feedback, and they live in a world of analytics but don’t know how to measure your progress and success.

You must be good at managing yourself and your client

If you’re going to be the one handling solutions to your client’s weaknesses in process and approach, you need their trust. Getting back to the idea of making more money, having a better quality of life, and working with people you want on projects you want; this trust comes in part from how you approach your clients. The efficacy of freelancers compounds when we band together, and so does our ability to command respect, larger projects, and money. There’s a lot of reward in shifting the freelance perception. Clients who trust you give you the ability to do what you do best in the way you need to do it, while charging a fair price. If you put some effort into creating trust, it will pay back in spades. 

There are a lot of ways to earn trust and in turn be awarded awesome projects, but I want to highlight one–I mentioned earlier that web professionals are in high demand. One way to effectively meet that demand and blow away your client’s perceptions is to group together as freelancers. Small communities like CoWork Greenville or companies like SuperFriendly are current illustrations of that power. Not only do we receive the benefit of working around awesome people, but we also have the added credibility of the roles represented around us. Pitching as a crack team of professionals assembled specifically for the needs of a given project is an attractive proposition.

As a freelance project manager I capitalize on this increased trust all the time. Clients tend to see me, if I’m alone, as a gatekeeper to what they want. I’m in the way. Clients also tend to see designers or developers as production skill that should be compensated at an hourly rate. When we’re together, they see a team that is worthy of pitching a full scope with value pricing. By grouping up we show them right out the gate that we will only assemble (and charge them for) relevant skills, that we know the roles we need, and that we believe ourselves capable of managing what we put our names to.  We’re no longer two guys and one gal working for $125 per hour; we’re a team of specialists tackling a website redesign and CMS build at a fixed bid of $__,___.__ for a planned duration; complete with schedules and Gantt charts as needed. We have the power to manage the project in the way that our expertise and experience tells us we should, rather than struggling to conform to a client’s notion of how the second website redesign they’ve ever attempted should proceed. 

I’m not saying you have the opportunity to hose your clients and get filthy rich. What I’m saying is that you will be able to reap the reward of taking more than just an hourly contractor role with your client. Your value increases if you can manage all of the pieces and shoulder the majority of the risk of failure rather than just filling one role. There’s no doubt you can make more money as a team, but there’s more to it. You can decide your schedule, and how much you should be paid to work 60 hours a week for two months (for example). You can decide if you want to travel to the client’s office regularly, and who else you want to work with. You get to set the tone of your relationship with the client as an equal rather than a subordinate. 

Set your sights higher

Why are we happy trying to work for Facebook or a top ad agency instead of meeting the industry where it needs us, educating ourselves, and forging our own way? There are a ton of valid career reasons to get hired or stay hired as opposed to going freelance, and I’m not too blind to admit it. However, that should be an educated choice, not a default.

It’s a great day to go disrupt our industry. Get going, and name your salary while you’re at it.


Special thanks: A lot of my final thoughts for this article were refined at An Event Apart in Seattle. This has been on my mind for a long time, but dunking myself in the talent, personalities, and perspectives at AEA forced a lot of clarity. Kudos to a great conference.

I Really Like this Game Called Halo by Matthew Cook


I think inspiration is really important, and I think it’s distinctly different from having passion. I can’t remember a time when I haven’t been driven and inspired. Maybe that’s just me, but having something pushing me from the inside always felt right. It was normal; being hungry for a challenge was normal. I don’t think it’s the same for everyone.

The first time I had a passion for something that I considered a potential career path was in high school. I always thought I’d make a good lawyer, writer, or businessman but I never seriously dug in. I loved logical debate, performing, writing, and engaging with people, so it made sense to me. Law and Order (and Sam Waterson) were awesome to me. My literature papers received praise from teachers. I was pretty good at administration and loved everything that came with being an elected officer in high school. The problem was that I couldn’t dig into the professions related to these passions—or I was freaked out that they were terrible career choices. I needed inspiration, but I was floundering.

Change of direction, I have a ridiculous imagination. It’s really easy for me to feel like I’m on Pandora when watching Avatar, I’m practically comatose if there’s a television in a room, and I can’t remember a time when I wasn’t creating my own little fantasy world as a kid. I’m sure you know someone like me.

Being an entertainment junky with a big imagination made me super interested in animation, video games, stories, and movies as a kid. That plus growing up in the 90’s meant I lived out my imagination partly in video games. My first video game system as a kid was a Nintendo Entertainment System (NES) that I bummed off of some friends when they upgraded to a Sega Genesis. I don’t think I could have been more enamored with it, and I beat every game my family owned except for Ninja Gaiden (darn you Tecmo). After a year with the NES I bought a Genesis for myself using Christmas money and discovered just how passionate I was about video games. I hated it; the experience was appalling. The controllers felt unwieldy and the games weren’t as much fun as Nintendo’s. I took it back the day after Christmas and bought a bug oven.

I played my NES all the way until the Nintendo 64 came out. By that point my affinity to games had persuaded my parents that they didn’t need to encourage my gaming by buying me new consoles. That’s when I met one of my lifelong friends, Seth. We had almost nothing in common except love of the N64, and he owned one. I think I spent more weekends with him than my family during late elementary school. I had more pizza, Mountain Dew, Goldeneye, and Mario Kart than any kid ever should. Even when my friends’ interest in the console started to wane, I was still in love with it. I always played the core games such as Super Smash Brothers, Mario Kart, and GoldenEye, but by junior high I had picked up a system of my own and started buying my own games. I played Diddy Kong Racing, Perfect Dark, Zelda Ocarina of Time, Rush, Starfox, Star Wars Episode 1 Racer, and many more. I was digging in. I was finding out what I liked and what I hated–don’t even ask me to play Super Mario 64.

Toward the end of my stint with the N64, I had an affair with the Playstation. I picked one up from my cousins when they moved on to the Playstation 2. They were generous; it came with three controllers (one great, one with sloppy sticks, and one broken), four games, one game guide, and two memory sticks. I played Tekken every once in a while just to mash buttons, and then I discovered Final Fantasy IX. It was awesome. I think I’ve beaten that game five times at around 70 hours a pop, and as I write this, I’m in the middle of it again on my PS3. Final Fantasy taught me something. I learned that whole worlds could exist within the confines of a game, and they could be viscerally intoxicating. Video games became a passion. Then Halo happened.

During the summer of 2002 my family went to Nags Head, NC for a week long beach vacation. Every evening I would sit downstairs with my cousins Dan and Will and play through the campaign of Halo Combat Evolved. I totally succumbed to its power. I fought the covenant. I had the chills for days after seeing The Flood for the first time. I was friends with Cortana. I became Master Chief. We beat the game by the end of the week, and I was hooked. As soon as I could scrape the money together, I bought an Xbox, Halo CE, and four controllers. It was my golden age of gaming, my renaissance, my new passion. I bought each Halo game after that on launch day, and they were pretty much all I played on Xbox. I trained my buddies on multiplayer, bought Xbox Live, made friends online, had LAN parties, joined Bungie.net, and generally did whatever I could to be part of anything Halo. Some of my best high school memories come from playing Halo with friends at 2am. I became part of the story of Halo, and it became part of me.

In 2005 I had to decide what I was going to be when I grew up. With all of my early life passions tied up in hobbies (or vices depending who you ask) like sports, animation, and video games, I fell back on what I thought I was naturally good at—those academic inclinations I mentioned earlier. I majored in Comprehensive Business Management during my first semester Freshman year, minoring in Creative Writing. It was terrible. Second semester I switched my major to Financial Management. Still terrible. Over the summer before my Sophomore year I decided to give in to my artistic and imaginative passions. I switched to Graphic Design and had one of the best experiences of my academic life. I pulled in good grades and loved absolutely everything—even painting. I finished that year supremely confused. I noticed that while I was above competent at design, inspiration to create unique work didn’t come quickly to me. I did well, but I was slow, and I wasn’t at the top of my class. Before my Junior year I made one final change to my collegiate concentration. I finished school with a major in Financial Management and a minor in Art. I realized that while I loved design and the studio environment, including everything that went into it, I didn’t want to produce with my artistic talent under the constraints of time and money. I couldn’t translate that passion into a career; I couldn’t sustain it. I told myself I respected it too much to become just another average guy. It was a hard choice, but leaving design gave meaning to my business studies. I became desperately interested in the business of design, illustration, and animation—from web design to animation and video games.

This is where everything comes together.

My passion for video games led me to love Halo, and Halo led me to pursue the business of design. I’d spent hours bouncing out of maps on Halo 2, which lead to hours of reading online about what causes those glitches. That in turn led me to read about how Bungie didn’t really have producers (or project managers if you please) for Halo 2—and the pain that it caused. From that point on I was all over project management and production for any type of creative studio. I read articles online, downloaded GDC talks, collected write-ups and presentations, and started looking for ways to plug my finance (and eventually MBA) skillset into the business of design. My passion for an awesome video game franchise developed into being consumed with making the creative process successful in a studio environment—which is what I get to do every day now with the best web designers and developers I know.

We’ll end the personal history there. My point is that inspiration is really important, but not in a gooey, feel-good kind of way. In short, not everyone is equipped to follow all of their passions in life, but inspiration can lead anyone to find new passions and achieve great things. Inspiration is something you find through passion, and it takes work to sustain it.

I love design, but I am not a good designer. I love illustration, but I can’t keep a consistent style with my drawings. I am enamored by beautiful and gripping video games, but there’s no way I could concept or code them.

Inspiration is that tricky blend of your passions and your skills. It’s something that can happen to you, but that you need to take control of. It should be harnessed and nurtured. In the business world, a popular topic to converse on is having the right people for the right jobs. Jim Collins (the writer of Good to Great) talks about having the right people on the bus and the wrong people off. One type of wrong person for any bus is someone that is super pumped about where he’s going, but has no idea where he’s supposed to sit; or worse, he’s sitting in someone else’s seat. Don’t be that person. I’ve been that person more than once, and it sucks.

I’ve by no means arrived at any form of perfection professionally, but I have come to the conclusion that I want to look for passion and help create inspiration. My challenge to you is to discover your passions. Figure out what really drives you as a person, and what can drive you as a professional. If you’re terrible at your passion, keep it as a hobby. If you’re great at it, feed it. Dream about it. Nurse that passion until you can find and create inspiration to do awesome stuff; work hard to find opportunities to take control of wherever it leads you.

If you’re already there, help other people find inspiration through their passions. We’re all willing to complain about how education needs to change, or say how much kids need great teachers and mentors. Be that teacher. Help turn passion into inspiration. Hand out opportunities.

*Disclosure: I owned and played many other gaming systems and games, some hand-held, others console and computer. If you’re interested in exactly how dorky I am, feel free to comment, email, or tweet at me and we can geek out over games. 

Being Intentional about Client Services by Matthew Cook


Client services can mentally, emotionally, and creatively destroy you. It’s not always easy, it can be hard, and you have to find a good way to deal with people and organizations. As much as we all wish we could make awesome stuff on the web and never have to deal with the people who are paying for it, our industry doesn’t work that way. Sure you can take a shot with your own start-up or side project, but most of us will still have to work with clients at the end of the day.

There aren’t really a ton of tools and techniques out there to help freelancers strategically pick the right clients. By the way, you should be picking clients just as much as they’re picking you. Some freelancers have more choices than others, but ultimately you should be choosing every single one. What I see happening is awesome web people don’t do a lot of thinking before they sign on with a client.

  • Why do you want to work with this client?
  • What do you want to accomplish with this client and this project?
  • What drives you toward the type of work this client offers?
  • What is the most important characteristic this client needs for this type of project?
  • Where do you want your work in general to take you?

If your first answer to each of those questions is some form of “more money”, you’re doing it wrong.

There’s a time and place to let money come first, but it shouldn’t be your universal answer. Anyone running any type of design gig should be able to effectively profile potentials and projects, set measurable strategic business goals, and be prepared for a personal post-project relationship assessment before ever accepting a client. You should be able to consider each client separately from the project they’re offering

Client qualification shouldn’t be synonymous to project qualification. Successes and failures are rarely caused by business justification, deliverables, timeframe, and money as long as you are setting up and executing your projects right. They’re caused by the people and impetuses behind each of those considerations.  Making sure your work, team, competencies, etc. fit what the client needs isn’t what I’m talking about. I’m talking about strategically steering the business of what you do; I’m talking about how to funnel your skills, interests, and inclinations into an intentional plan to take over your little corner of the world and win the hearts, trust, money, and acclaim of its inhabitants.

Many freelancers and small studios don’t consider the implications of working with who they work with. A lot of what comes forward in their thinking is simply “more”. More clients. More money. More awards. More opportunity to do and refine what I am good at. Figuring out a direction to take and exactly howto pursue it can be an arduous task. We can all solve this, and I think one piece of the solution could be client profiles.

Profiles are really cool. They’re simple, clarifying, and relatively easy to make and use as long as you have the information to make them accurately. To illustrate, consider user profiles for a website. For a negative example, think of racial profiling. See what I mean?

I haven’t figured out completely how I want to do this yet or what it will look like in order to be truly helpful and usable. Making a profile work in tandem with a playbook for approaching specific projects that come from different potential clients would be amazing. I see these profiles, even if they’re just for myself, as the first step in assembling a toolbox. Once I have the groundwork laid, I can start thinking about different areas such as contractor on-boarding for specific types of clients or projects, communication norms and peculiarities, process augmentations or no-no’s, etc.

Big picture, my hypothesis is that profiling each type of client who you want to work with (or who wants to work with you) will help you clarify how you’re accomplishing your goals, and what steps to take along the way.