All Good Things Come to an End (Thankfully) by Matthew Cook

Before I get into what I want to talk about with project management this month, I want to share some of my recent experiences. Have you guys ever seen those Venn Diagrams about life? They always include some version of family, work, and sleep; telling you to pick two. See below. 


I used to think these were super funny and accurate, and then I realized something. My life has been brutally way outside of that trichotomy. 


For months I’ve been bouncing around between different facets of my life, trying to do everything at once. Thankfully, that’s ending in just over a week when I finally finish my MBA. 

I’ve been blessed with amazing family, friends, and clients who have stuck with me and supported my decision to work and attend school, both full time. I want to take a second to publicly tell all of you, I can never thank you people enough for the encouragement and support you’ve given me over the past 19 months. Every kind word has meant more than you can know. It feels like it’s been so long since Steph and I took a huge leap of faith; tearing me away from easy employment and tossing me into the freelance and higher education worlds. I’ve never looked back, and I’ve never regretted it.

Ultimately, I praise God for strength and His blessing. I’m super pumped about having that silly work, family, and sleep Venn Diagram represent my life really soon. 

MBA: conquered (in a few days).

I Spoke at Clemson Today by Matthew Cook

Speaking at Clemson to the MBAe students today was great. We had some awesome conversation about freelancers in the web industry, how to be a good client, and the process of engaging and executing on web projects. Big thanks to the participants (especially Stefan). I’ve included a link to the pdf I used below.

Download or view the PDF on Scribd

I referenced some resources in the PDF. Find those below.




A List Apart


Brooklyn Beta



Finally, I listed some example web sites that I personally like a lot.

IWC (beautiful large-ish site)

Fork CMS (cool and simple example of responsive)

Wilderness Downtown (getting old, but still cool)

Speek (example of a startup in process)

Be a Hero, Save a Project by Matthew Cook

Update: .Net ended up posting my comments. Here’s the link if you’re interested; I’m one of many responses.

I figured I’d head this post with a photo of my most recent home office inspiration. Master Chief rocks. I need to write about Halo sometime. Nerdcore.

Anyways, I recently put together a little opinion about the place of project management in the web world and sent it in to a magazine. I don’t know if it will get published, but I’ll post it here as well. Hope it’s at least entertaining. I wrote it while sitting in Dulles trying to recover from a crazy day.

Project managers often cause more harm than good. I work independently as a freelance project manager for exactly that reason.

I think project managers tend to take roles that they shouldn’t for multiple reasons, the project is dragging, team leads are unavailable, budget is running out, you name it. The pressure to control variables that destroy projects can turn them into power-sucking monsters. I’m hearing Harvey Dent right now, “You either die a hero or live long enough to see yourself become the villain”. A wise friend once summed up an experience by saying that as a PM if a project fails, it’s his fault; if it succeeds it’s the team’s success. Sometimes that means as project managers we have to be “the hero that [the team] deserves, but not the one [they] need right now”. I hope you’re catching all of the super hero references. PM’s should be exactly that, super heroes. 

At SuperFriendly we’ve structured project management to defeat apathy and the forces of evil. Conventional project management puts up barriers, resists non-conformity, and strains the creative process. I think almost every designer can relate to the swoop and poop. A PM swoops in, tosses out several minutes of earth shattering changes or constraints, then flies off to some meeting. The project team has clean up the mess and carry on. This tends to happen when dollars are king and PMs are inept at controlling and foreseeing problems. There is an ever present pressure to supply a service or product for the most amount of money in the least amount of time. The result is usually mediocrity. What a team really needs is the project’s ultimate advocate. 

I put the project first and I don’t BS anyone.

I make it very clear to all stakeholders that I advocate each project I put my name to. I have what feels like a million little things I do to keep that a reality, but it can be boiled down to several simple principles. Fight for quality, stand up for the team, tell the truth, and put on my cape–being willing to pay the ultimate price to save the project. Living by this code keeps me from manipulating, shifting blame, caving for extra margin, failing to plan, or being a miserable person to work with. I facilitate, I don’t mandate. I converse, I don’t coerce. I hope for the best and plan for the worst. 

Take one of my recent projects for example. The client needed a ton of work but we knew they wouldn’t be keen on how much it would cost. I spent two weeks building their trust in my team, drawing up schedules and deliverables, and figuring pricing to make sure I’d hit a margin. I made it clear to the client that I wouldn’t bid to their budget and told them the exact truth about what we could do and why they needed us. We won the job.  Since then we’ve kicked off, pivoted for their needs, planned to our strengths, told them the difficult truths about their current performance, and made extra trips to visit; all while we’ve maintained their trust and our ability to meet deadlines while augmenting the project to fit their exact needs. We’re not sticking them on details and we’re not cheapening our work. We’ve worked to facilitate their needs within the constraints that we set together. It doesn’t always happen this way, but when things do get ugly, clients know exactly where I stand: right beside the project, fighting to maintain success.

Project management is rife with problems because the opportunity to be a bad human for the sake of earning some extra dollars is ever present. Ultimately, a PM needs to be a solid person. It’s not impossible, but it’s sometimes hard. My advice is to work hard, stand up for the project, and wear a cape (sometimes).

Sharing a Project in Process by Matthew Cook

Really cool stuff is going down.

I’m on a project right now with SuperFriendly; we’re going to tear the entire thing open and put it up on the internet as it happens. This includes meeting details, conversations, builds in process, notes, and even some files. It will all happen via posts like this online across multiple sites. I couldn’t be more excited. Let’s dig in. 

A number of weeks ago SuperFriendly and Dan Mall received an email from Reading is Fundamental (RIF), they were interested in updating their website. I’ll admit, I didn’t know much of RIF before the email conversations started flowing, so I dug into the internet to learn more. I found this, this, and this. I was sold.

We took RIF through our normal process for new clients. After introductions we asked a good bit of questions via email (some hard and some easy), which set the tone for our first call really well and got the broad strokes of what our relationship could look like down in writing. Our first call was surprisingly awesome. Those guys just make you wish you could high five people through the phone. Stepping back from that call, and one follow-up, we had most of the information we needed to start crafting a project and process. I ran through multiple sets of numbers and several months worth of calendar while Dan started talking to some SuperFriends (enter Noah Stokes and Kevin Hoffman). Dan also threw Josh Luciano in at this point. He’d been crushing his work recently and needed something more worthy of his time and talent. 

We came back to RIF with three different ballpark prices and structures, hammered through some more details on what the project needed to cover and wrapped up our preliminary conversations with a fully drafted statement of work and schedule. 

Since signing stuff and passing some money, we’ve had multiple group calls, a full day kickoff in Washington DC, and a good bit of brainstorming. I can’t take you back in time and put you in a chair during those events, but I can share some of my favorite notes coming out of those meetings.

Quotes direct from RIF about what success looks like for them personally:

  • “Really good communication”.
  • “Don’t forget we’re a non-profit”.
  • Hitting the mark on “time and budget”.
  • “My fear is [website] support”, speaking of what SuperFriendly builds and how we follow through.
  • “Everybody gets to go home at 5:30”, speaking about how effective SuperFriendly is at making this project work and not creating problems.

I think the best warning RIF issued to us was when they said they would love to see the website “drive the organization” in donations and brand presence. Shows the mentality they’re entering this project with.

I also think the best compliment they paid us was when they said “you guys, even in thinking, are going above and beyond”. Wow, big statement to live up to!

I love writing down quotes. It shows the honest opinion of our client at any given point, and gives us a great way to measure our success. If they’re still worried about a certain point, or we start slipping on one of their personal success factors, we’re doing something wrong. It’s black and white.

A few more notes I came away with that I want to share, not in order of importance:

  • We need to limit recommendations we make to RIF about social usage, and make sure those recommendations, if implemented, would be effective.
  • We should explore capitalizing on nostalgia (Owl Moon for me).
  • Site analytics and donation analytics are really important, and a good measure of whether we’re doing our job right.
  • We need to find ways to get rid of book data entry for RIF.
  • How can we know what people want to donate? That’s really powerful.

We built our SOW and kickoff meeting around the broad strokes and following details in the early calls, but a lot of our strategies and tactics also grow from situational details with the team, secondary objectives, and goals that we discover and set during kickoffs and brainstorming. 

I hope this is a healthy window into the beginning of our project. What I’m really trying to hit on is the assembly of cohesive plans and documentation based on information that comes from every direction in multiple places at multiple times. It’s really exciting to me to help engineer the compilation of everything needed to create success.

Looking forward to sharing more really soon! In the mean time, check out other perspectives on the beginning of this project from other team members who wrote some stuff:

Dan Mall - Head Honcho

Josh Luciano - Design Dude

Disrupting Models by Matthew Cook

I have a mohawk. Now, on to what I really want to talk about today.

I work out of a studio called CoWork Greenville; it’s a pretty awesome place. Every month we do something called Zero Day, a hiking metaphor. We all take the first Friday morning of the month, stop working, and meet up to talk about stuff that matters to us. 

This past Friday I presented an idea about a potentially disruptive model for my industry. I do a lot of work with SuperFriendly (run by Dan Mall) and I’ve been thinking about how to organize a group of awesome web people that lets everyone remain independent, make lots of money, and work on projects they love. Most of my inspiration comes from where I started as a Freelance Project Manager (let’s call this FPM) just over a year ago. 

Looking back, there are 4 common tracks that a FPM takes: they fail, get hired, take on tons of small clients to survive, or take on a few big clients. I’ll also admit that there are other possible directions to take, I just haven’t seen much else. See my little diagram below.

I’m on the few bigger clients path as a FPM. This gave me most of my inspiration for a new model idea. It’s very close to the structure of a legal practice (thanks David Haskins), but it’s also similar to a conglomerate, just made up of individuals. 

The idea is to take independent web professionals and put them under one brand to provide consistency, a cohesive presence, and a store-front for work and contracts. This also gives an entity to hold contracts with contractors for outsourced work. It’s much more than this, but you get the gist of it. Check out my second diagram to illustrate.

I haven’t gotten super far in my thinking about this model. I’m really looking for feedback from anyone willing to share. Below are my slides that I used to present at Zero Day. 

I’m not a huge fan of posting unfinished ideas, but I think it’s warranted this time. I know it feels awkward for some people to post in comments on blogs, but feel free. I’d love thoughts from anyone interested.

Like I said early on, my goal in writing is to post things that I’m going through in the hopes of spurring others to think outside the box while also refining my own ideas.

Pick Projects Based on Trust Instead of Dollars by Matthew Cook


I’ve been thinking a lot recently about the role of a design partner as a strategic management consultant.

Many of the projects that I talk through with potential clients are presented as cut and dry. The conversation centers around needs and deliverables. They rarely pitch a project that includes thinking through uses of their design personnel, effective production processes, or how well their current operations as embodied in their web presence fits with higher company goals and values. Instead, you find these incongruous circumstances when you’re in photoshop during design round 3, completing stakeholder interviews during an IA exercise, or at a kickoff meeting having just received downpayment on your signed scope 2 days ago. When this happens you can do one of several things:

  1. Cry.
  2. Ignore it.
  3. Have a serious conversation with the client that usually involves asking for more money and time to do something that they feel very protective about.


This is nothing new. One of the reasons many studios and freelancers bill for “discovery” is exactly this. The standard fix to keep this from happening is anything but standard. Some studios fix this problem in their sales tactics. Others fix it by posting case studies that highlight the benefits outside of production or simple execution that they have provided to clients. Those ideas work, but they’re flawed. One is a potential barrier to the client (convince them of your consulting prowess) and the other is a text-based one way conversation. 

I argue that to get in position to provide strategic management consulting in addition to services as a designer, developer, etc. you have to be selective of your clients and tactically build trust in team leaders from the outset. Some potential clients should never make it past an email conversation with you; Old news. They may not fit your style or preferred process. Maybe they need a skill that you don’t enjoy providing. Maybe it’s as simple as not having the budget for what they’re asking for. These are all good reasons to decline work, but the most important reason to cut off a potential client is a lack of trust.

I think about this a lot. I’ve made it no secret that the reason I love my job is unequivocally the amazing people I work with. I have paramount respect for what the people in my industry are capable of doing. The most important thing I do is try to build client trust that mirrors my respect. Clients don’t have to feel the same way, but they need to understand the team they’re engaging is not simply a photoshop machine. It’s a widely experienced federation with an intimate understanding and intuition when it comes to implementation techniques to accomplish business goals.

I’ve found that this view of my team is best communicated by the way I treat them and talk about them in front of clients. I purposefully do little things that put us on the right path. I don’t respond to initial inquiries. The guy in the director role responds first and kindly hands their questions and goals over to me. After I take over I don’t stonewall, but I also don’t get everybody on phone calls at the drop of a hat. I dig in, ask the easy questions, and probe a little while helpfully teasing them with our past successes, excitement about certain types of work, and my personal opinion of how awesome my guys would be at doing their work. By the time everyone finally sees eachother on Skype the conversation isn’t about design rounds and content management systems as much as it is about whether the client thinks we’re the best fit. I set the client up to choose whether or not we’re worthy of their project, rather than how much money they’ll pay or what deliverables they want. 

If you can position your client to choose whether or not to trust you instead of whether or not to sign dollars, you’ll start each project in an awesome place. You’re set to ask the questions that your client is embarrassed to answer. He’ll feel ok telling you not only his business goals, but also his personal goals with the project. He’ll look to your team for validation of what he’s trying to do. He’ll want to know if you think he’s asking for the right thing and if they’re doing things the right way.


This is more than conversation tactics. It’s a way for managers and business minds to approach a business to business relationship as well as internal team dynamics. It means a lot of honesty and refusing to hard sell a client. Design teams need to understand that executing a project isn’t about who’s in charge, but about how to find and put out the best results. There are a lot of implications here on team dynamics and skill sets. Maybe I’ll hit that sometime soon.

So I had a Talk with Jamin Jantz by Matthew Cook

Fair warning, this post is really long, and dated several months. I sat down with Jamin Jantz, bought him a cheap sandwich, and picked his brain about project management for an hour. This was mostly for my own benefit covering a lot of my history and his, but I’ll put it here for anyone else interested. People keep asking me what I do and why I do it–here’s the long answer. Big thanks to Jamin for his time. Forgive our conversational language. My questions and comments are in bold. Some comments have been changed to protect the guilty.

What I would love to get out of this interview is info that made you successful as a freelance project manager and how that transition to Zaarly went down and whether that’s a typical, good, or only direction to go:

What are your projections for the web industry (Stable, declining, etc.) or even in our niche (startup web companies) and project management.

Specifically to the niche of contract project management, this is a really fun and interesting topic because I think what you’re seeing on a broad level with individuals who are incredibly talented but have chosen to not work at an agency, (like a creative agency, advert agency, that kind of thing) but are out on their own and are still able to attract really high-dollar clients and work, is that this just speaks of a return to a craftsman-type marketplace and somewhat of a distrust of larger firms and more about a relational business (person to person) model. And technology is allowing people like that to still be able go after big projects as opposed to just subsist with local people and just do local jobs. Most of the people that I have worked with and known have a very very small percentage of their job is actually done locally, most of their work is done on a national or international level and that’s just powered by their ability to create a presence online and influence a broader industry outside of their city or state. Hand in hand with that, I think what is happening with the industry (if you want to call it that) of contract project management; it’s just developing. It’s catching up. I would venture to say it’s not even an industry yet. It’s being birthed right now in this time period. The past couple years has seen an explosion of people like Matthew Smith, pretty much half of the people at Brooklyn Beta are in that same scenario. And they’re getting to a point in their businesses (and this is where I think this industry is poised to explode with contract project management) because there hasn’t been a need for it. As these individuals have grown their business to a point, they’re at a crossroads, a number of them. Some of them work for agencies and are getting ready to make a leap out on to their own. They’re smart enough and bright enough to know that it’s just because they’re really talented and getting paid a lot of money at an agency–It’s not a one-to-one translation. When they go out on their own they’re not just immediately going to be able to run this amazing business. They know that they need help. So they’re looking for professional help. They’re hiring smart CPA consultants like Jason Blumer and they also need help on the day-to-day. Managing their clients managing their schedules and all the different moving pieces. Contractors if they have them. Then you have other ones, that started by them selves very small that just kind of scrapped their way to where they are now and are facing an option of either hiring and growing but they’re concerned about that because they don’t want to become an agency because of all the things they left agency world for–so they don’t necessarily know how to grow, or they also don’t want to work the rest of their lives exchanging one hour of their lives for a dollar. You can grow that but that’s a very slow slow growth and there’s a cap on what the market is going to pay you for one hour of your time unless you in the teeny-tiny percentage at the top where you can charge just a ridiculous amount of money but you’re still at the end of the day trading a finite amount of your time for dollars. That’s where I think our industry really has the ability to come in and help these talented craftsmen grow, because we can effectively come in and offer an alternative, a solution as opposed to the perpetuation of trading time for money or growing into an agency. We can offer the ability to stay small and stay agile and really lean and flexible, but also grow revenue and grow influence in the community by taking on larger projects. 

Let me go back really quickly to something you said in the middle of that. You had mentioned that there’s a trend for these highly skilled individuals to leave agencies. I just want to know your thoughts about why this is. Do you think this is a failure on the agency’s part? Do you think there is a going trend in the market place where freelancers have increased exposure, so they can be found easier so they don’t need the agency anymore? Or maybe there’s something else?

Yeah, I think there’s a couple of things. Agencies are a really easy place for people to start when they come out of school. Agencies tend to hire fast, and they hire young and it’s a great place to kind of cut your teeth. But if you look at a lot of the agencies around here I think that a lot of them are struggling to make the transition to truly a web-oriented marketplace. All of them (if they’ve been around for more than ten years) got their start in print and it’s a whole other ball game, web to print. And I think that a lot of them don’t know how to make that transition, so they simply fail in terms of truly competing. So if you’re a talented person who has made that transition or is making that transition and your agency isn’t keeping up with you, then you’re going to just naturally outpace your agency (that would be a failure on their part) so I do think that it’s much easier for an individual to build an  individual brand that is more influential and therefore doesn’t need the agency. And then I think part of it is just personality. Some people enjoy the safety and the (to some degree) repetition of an agency, and some people really enjoy and want to own and build something. This is not…all agencies are not evil some agencies do an excellent job of retaining great talent but I think they’re the exception rather than the rule.

Would you go as far as to say that the people leaving agencies are the best and brightest?

I would say that as a rule, yes. Because I think that the evidence in that is that if you look at the top leading web conferences and you look at all the keynote speakers, the lion’s share of those are not agency people. They are all individuals that own their own businesses and would be considered independent contractors and I think that’s where the proof is.

You kinda touched on this a little bit, but what would you say is a key challenge for this “birthing” industry? You mentioned that it’s new; it has not been around. Do you see any challenges beyond that, where the rubber meets the road, where there are big barriers?

Yeah, I think the biggest barrier is communicating value. What you’re doing is you’re going in and asking someone who has been running their business successfully, probably for several years and asking them to give up ___% of their income to you, and you have to sell them on the fact that by doing that they will not only make that money back, but be able to grow beyond that. It’s a cost-benefit for them. A lot of these people, most of these people are creative people and so they’re not necessarily wired to be thinking about those cost-benefit details. They kind of work off of, they have a really smart gut, hunch, whatever, and they’re naturally good at what they do, so if they’re smart bright people, they can build a pretty successful business without you but you have to come in at the right time when they see that they need something else, they need this other thing that will help them grow and you have to communicate that, and so the big challenge is understanding them as an individual; understanding how they think and process and communicate about these things and speaking to them in those terms. You can’t come in there with a sales pitch and just do a little song and dance. I think that’s one big barrier. And then just the reality of the newness of this, figuring out what works. You and I have talked about the challenges of doing this long distance and I’m dealing with that, and these are really big challenges and there’s not really a long history of saying “this works”. You have companies that are dispersed that have really strict processes, time tested processes. Not only that but working in a contractor role is a totally different ball game. So a lot of that is just trial and error and I think that is a big barrier; finding people who are willing to be guinea pigs and are willing to find this out with you and are excited about the opportunity to change the model and create a new way of doing business that has the potential to compete on the national and international level with the biggest agencies in the world and actually offer an alternative that offers a better product for a better price for the end consumer. 

Last question about our marketplace. I want to touch on the typical salaries, entry level through experienced. And then what are the opportunities for career growth. I think the direction I want to take this idea is, you talked about one of the biggest challenges is communicating value and I see there’s a little bit of strain between finding value and then communicating it, and then growing it. And that’s really what I want to touch on here. Nothing huge, but do you have any thoughts on how to find that value, communicate it, and then grow it?

I think questions to ask people…finding them is…I have been super blessed and lucky with CoWork. CoWork has just a ridiculously disproportionate level of talent versus other places. Not just in Greenville, but even around the country. I think finding a place like CoWork, like Studiomates up in NY, maybe like Citizen Space out in SF; coworking spaces that aren’t just simply where you share office space but actually where there is a community, because I think that’s really important because that’s what you’re trying to enter into and create. Finding something that already exists in that exists in that sense, even if someone isn’t doing what you’re doing, I think that’s the easiest way to create converts. One question that I ask potential clients, is to take a challenge and document, try to document for a week or two weeks the amount of non-billable crap that they do that wastes time where they’re not actually making dollars. Or maybe it’s just sitting down and thinking about it and talking about it. Just talking about that. That’s stuff that nobody in that position likes to do and they don’t do it well, so they probably just repress it. They don’t like to think about it. It’s easy for them to forget about it which makes it harder for you to actually quantify it. Another opportunity was just doing some contracting work. One of the ways I worked my way into a job was doing a consulting project where I actually did an analysis of the way they’re actually managing their projects. I was lucky there because they came to me and said, do this small contracting project. It was finite. I wasn’t thinking about it because I didn’t know this could exist as a long term relationship, and they didn’t know it existed, so I went in, I talked with them, I did interviews with them, I talked with their clients, sat down and put together some things and basically said this is what you’re doing now, this is why it’s terrible, this is the way I think you should do it, and two days later I was actually doing it for them. Two days later they hired me to start doing it, and that’s basically what started this. The growing the value thing I think is easy honestly. If I’m doing my job well, if you’re doing your job well, then they’re able to do more work, higher-dollar work which I think is more complex projects because you can manage them better, bring on contractors that you’re making money off their work. That, to me, just follows. Once you get them in the door and get them thinking about that, you’re just doing what any other business does. Just doing what grows their business which in turn grows your business and makes more money. 

Changing directions really fast, this is going to be a little about you. How did you get involved? You mentioned this already, but was that literally the first step? You weren’t even involved with CoWork at all when they said came to you?

It came through my brother, Jeremy. He had joined [CoWork Greenville] a few months before and I was out of work and doing contract work for Jeremy and a few other tiny things. So it came through a couple of connections. I was doing a little bit of work for Jason Blumer and I ran into him at Barley’s eating lunch with Matthew Smith. That was the first time I met Matthew, it was literally a “hi, hello, cool, nice to meet you” and then I met Jeremy and went to a get-together that Matthew had regarding CoWork when they were getting ready to get into their space. It was a couple of key interaction points and then my initial thoughts were more around doing writing and editing and content strategy for their clients, so I was looking to contract them and it wasn’t until Matthew posted a tweet saying “I’m looking for a contract project manager"… so really the idea is his as far as creating this whole thing, I would credit Matthew largely with that because I hadn’t even thought about it. I had been doing project management for 6 years. I mean I had been doing admin and blah blah blah for 6 years with previous employment but never had thought that it could exist in this area. So when he first put out this idea it turned on a light bulb in my head and so that’s when I contacted him and after talking with him we came up with this initial contract idea. Again, it was still very focused. There was no discussion or thought around long-term work. It wasn’t until after that and we started realizing how well we work together that we dove into that and it was basically figuring out, how I was going to get paid, and we basically tried something and tweaked it as we went along. 

Considering background, how people get into this position. It’s funny because the people that I have seen interest from (you, myself, and others) have all come from the exact same background for the most part with key changes. I was more on the finance side of it, another was more the creative side of it, and you were doing a little bit more of the creative side of it yourself, right?

What would you say that key background is?

Seeing the pain points of an agency. Working in an agency, seeing what doesn’t work, seeing what does work. Getting a high amount of respect for the kind of work that can be done well, and then coming out and being the problem solvers to help make it work and grow. 

Yes, I see three key things here. Two of those are personality and one of those is education. I think the number one skill that anybody in a role like this has is communication. You have to be a highly effective communicator. Primarily written communication, but also verbal. With that you have to have a highly analytical mind. You have to look at a problem, break it down, and figure out how you’re going to solve it. What steps, what phases, what resources you need (people or otherwise). I think the third (this is for me definitely true, I don’t know if you would say it’s true for you, or if others would either) but for me, I don’t consider myself a leader in the sense that I am the one that pursues being out front in front of a company; being the lead guy, the entrepreneur, the CEO, whatever. But one thing that I do instinctively is, I fill any gaps that exist, which goes hand-in-hand with the analytical problem solving personality. If there is a problem there is a hole that is not being filled or something is being done wrong and nobody is addressing it. So by my nature I gravitate toward that to fix it and figure out how to make it better. If something is going well then I’m like, fine I’ll leave it alone. I don’t feel like I need to have ownership over that. I would say that those are critical. I think that there are lots of other things that people can have but without those things I think that you’d be fairly crippled. I think all of those things can be learned. I’m always looking to improve communication because part of that is just getting to know people, figure out how they communicate, and then tailor your communication to meet their needs. And the analytical part is just continued growth. 

So! What did a typical day look like? 


What did you like, what did you hate, what did you think was most crucial?

Oh, dude there are no typical days. That’s like, the question I can never answer, even now, with my wife driving to work today she’s like, "So, what does today look like?” I’m like, I don’t know! I have no idea! I have things that I need to do, I have things on my list that I want to do, but at any point all of my plans could be derailed. Last week I revamped the entire week because our master repository blew up and we couldn’t ship anything. We couldn’t make any changes so I spent the whole week trying to fix that. I wasn’t writing any code, but I was talking to people, coordinating, finding out what to do, what options are there, blah blah blah blah blah. So I had a whole week that was lost. It’s just what you’ve got to do. For me, my number one goal is to move projects along smoothly toward the objectives that we’re trying to do. That could mean any number of things. It could mean having to sit down with someone or hop on the phone and be their personal counselor. They have things going on either work-wise or personal that are preventing them from  getting their objectives done. So I could just sit there and be like, “get it done”, or it might mean that I just need to sit down and talk with them and go grab coffee or hop on the phone and be like, what’s going on. It might mean jumping in and doing stuff. This is just a personal ability that I have with a writing background, it’s not my responsibility to write, I don’t always have time to write but sometimes it’s the most efficient thing for me to do is just grab a piece of the project and do it. So back to talents and skills, anybody who’s in this world, I would suggest you start learning design and front-end development and as much about the actual skills and talents you need to actually build a website because the more you know about those skills and how to use them the better asset you can. Even just being able to jump in and write some CSS or HTML is helpful. So, backing up to what my core responsibilities are. Internal communication around all of our projects. So that requires planning. I send out weekly updates to our founders and core team and basically give them a road map, where we’re going, what’s going on. And then I keep a humongously complicated master plan, I have a planning tool that I use that helps me know what’s going on and then basically that just means I’m following up and talking to people. And then from there, sometimes we spin out, we need to have a call. So I grab the people who need to be on there. So I need to know who’s doing what and who’s responsible for what so that if something comes up I know the stakeholders who need to be involved in that conversation. That goes back to internal communication being so, so critical.

You hinted around at something that made me think. You talk about the daily types of responsibilities you do and then the background we hit all around the bush on this one: what would a failure type of person for this position look like? We have the ideal picture of what a successful person would look like and the background they could come from, where they could go, and where they should be heading. What is the type of background that you would say, “you may be interested in this, don’t do it!”

Somebody who feels like they have to get a lot of credit for what they do to feel like they’re being successful. A project manager is kind of a sucky job in the sense that there’s not much gratification that happens. So, the way I stay really grounded and focused is if we’re getting our projects done and shipping; and before when I was doing this on an independent contractor role, if my clients are growing, and now if Zaarly is growing and things are going well, I know I’m doing my job right. Most other people aren’t necessarily going to see that. And so there are times, I’m thinking of several times where in one particular client call about a year ago, this was a particularly difficult client to work with just on a personal basis–probably one of my biggest challenges ever, he was the kind of person, his personality was like he was the type of person who had to be in charge and really had to…I think he had some issues with insecurity because when I talked with him one-on-one he was one person and when I talked with him when any of his team was in the room he was a completely different person and a far worse person. So there was one particular call where there was something wrong, and they were having problems so I interjected and said, here’s what I think we should do guys, we should do one, two, three. Laid it out in very simple steps a process that I thought would solve the problem and he jumps in immediately and is like, NO, and totally blew it apart and said, here’s what we should do–and he said the exact same thing. I’m not kidding you. Almost word for word. I wanted to reach through the phone and kick him in the throat, but I was like, you know what? Right now we need to solve the problem so I was like, “______ that is an awesome idea. I think we need to do that idea. Good Job.” And we were done. Afterwards I stood up and vented and ranted and raged, but that solved the problem. But at the end of the day it was about getting the client what he needed. And if that meant that he needed to think that he came up with that idea, great. And so a lot of this position, that’s where it goes back to psychology and really understanding the people you’re working with and the communication. So there are many times where it’s thankless, but having a perspective, being able to have a perspective of the big picture and the goals and that being enough to get you satisfied and really excited about what you do is critical. So if you’re an individual who has to continually be patted on the back in front of other people and have it said, this person did a really good job look at him look what he did, this is probably not a good field for you to be looking at getting into. 

Tangential, are you familiar with the concept of emotional intelligence?

Yeah, we talk about that a lot.

I’m just curious, if you were to put a rank say between one and ten, how important is emotional intelligence to what you are doing as a freelance project manager? The ability to know how you’re affecting people and control a relationship, not manipulating, but being completely clear and generating even down to the feelings what you’re trying to communicating to people. How important is that?

I would say incredibly high on a scale of one to ten; I’d say an eight or nine. That’s really just another way of saying when I say being a good communicator, that’s what you’re doing. Communication is number one, understand your audience. Everyone I work with, I talk with them differently. I communicate with them very differently. Some people I’m incredibly direct and I say, this is what we need to do, one, two, three. Other people I need to get them to think of it. And it’s more about, yeah, some people I need to be much more round about or some people I need to get them to think of it by asking them questions. And it’s not so much that they need to necessarily come up with the idea but I need to break down any potential barriers by asking 17 questions and then we get to the end and it’s, this is the only possible solution, and it’s like, good, we’ve accomplished it. It’s incredibly high. There are also times where I know that I should not have certain conversations or talk about certain topics because of what’s going on. If it’s a high-stress time don’t’ talk about X. Like, this is not a good time to bring this subject up because it’s a highly emotional subject or there are a lot of really strong opinions about this subject. So yeah, highly, highly important.

We’re rounding things out here. Basically, the last topic that I want to cover is a little bit of application from your perspective on getting someone else started in the position that you were at. Some of the things that I want to know are; what do you think about my background for this? Another is, are there jobs similar to this or positions similar to this that you think are valid for pursuing? Not necessarily only for me but for people who are looking to get into this. So my next questions, they talk a lot about me, but I also want to cover what you think about other people who would be entering into this as well. To that, what would you recommend to me to get deeper into this type of work? Looking at you, you had your introductions and since then you have just tumbled down the rabbit hole and you are at Zaarly. How do you see that process going, how do you guide it, and what do you recommend for others?

I would actually add two more things to personality and background. I think that just a fast learner is really important. Everyone wants to think that they’re a fast learner, but most people aren’t necessarily. I like to put a fine point on it, an ability to live in an abstract world and still feel comfortable. One of the first calls with a client with Matthew, the client made a joke about “IE 6” and I didn’t get it. I just kinda laughed along and I felt really stupid. Really, really stupid. And I went and figured out what the joke was. So I mean, when I started, I was green. In the web industry specifically. I knew I had the personal talents to do the technical skills I needed to do to manage Matthew’s business, but I did not know the industry at all. So, there were many many times where I felt like I was totally just talking out my butt, and to a degree I was, but I had the confidence. I was living the abstractness. I could hear the client talking about things that I didn’t understand, but I could still get to the bottom of what needed to happen, and I could fill in the gaps later. So, being able to do that, some people are comfortable with that. I’m in the middle of that now. When I joined Zaarly, at that point I was very comfortable with web design and development, but software design is a whole other ballgame. I had no idea what was going on, and had to very quickly ramp up and I’m still in that phase. I think another aspect of that is a high tolerance for risk. Not just financial risk. You are building your own business and you are dealing with other individuals who may be considered risky; you’re not in an agency, you’re jumping in. Just learn about your industry. That’s one big thing, because if you have the certain personal talents and abilities and you’re wired in a way, then you’re going to figure out what that industry needs as you learn about it. I don’t have a lot of love for specific management methodology, software development. I think there’s value in understanding how they work, but I think that the web is changing so fast that any methodology is archaic the moment you start developing it. So, I try to keep myself familiarized and read up on all of those things and then try to pull the best possible ideas and then look at our team and customize it. Ongoing education is a given in any industry, but understanding what is going on and what’s being talked about is, I dunno. I guess understanding what’s going on. I think this idea of contract project management is applicable to other industries.

Last two questions, if someone is interested in getting into this, and being part of this, who do you recommend they talk to?


Are there people or positions similar enough to where given a perspective of what’s happening here, they can go and talk to someone, glean information, and apply it? Or do they really need to just sit down and talk with a designer/developer and see what they need?

I think both. I don’t want to be arrogant and say we’re the only ones doing it right. I learned a lot, a TON, living in agency world. I know you did too. I think a lot of what we learned came through seeing what was being done wrong and wanting to do it right. 


Especially in agency world being too restricting which is really primarily a leadership failure, not necessarily an agency failure, but still…there is definitely value to be learned there but there is also a risk in potentially getting caught in an outdated model or being pigeon-holed into one way of doing things. One of the biggest things that you see coming into this environment like CoWork and this industry of freelance project management is just how big of a thing it can be. And how big of an opportunity, it’s just really eye-opening. I think talking with creatives is helpful… man, this is just a hard question. A really hard question. I think I would say the next year is going to be really interesting, because the past year or two has just kick-started this as something that’s actually getting talked about in influential circles in the web, outside of CoWork. Primarily by Matthew. He’s kind of championed this idea, and then other people who maybe were doing similar things but didn’t realize the overlap. Again, it’s not something that CoWork has created and invented but there is starting to be some convergence on a bigger level. So, I had an opportunity to talk with one influential designer at Brooklyn Beta and we talked a lot about what I do and he shares a lot of similar ideals an goals and he’s a creative director. As we started getting some momentum in those different areas I think there will be more opportunity to connect and talk with people about this idea. I think some of it is just time. I really don’t know how to answer the question about what someone should do, because you could talk to creatives, but I would venture a guess to say that unless they’re in the top tier, meaning that they’re turning away a bunch of work and thinking a lot about how they should grow, probably a lot of them aren’t thinking about it. They can’t see a need for it, or they’re so narrowly focused on doing this for the rest of their life. Just, the trade-off of trading an hour of their life for a dollar is worth not having to work at an agency–“I guess I’ll just do this for the rest of my life. It’s hard but there’s payoffs so I’m ok with that.” Maybe they just haven’t been able to get a vision for what something else could be. I think I should preface this to say, not every contract independent designer/developer needs to build a business or has the ability to do that. I mean you need skills you need personality and things to do this. There are some people who are just always going to be an independent designer or developer and that’s what they need to do. Those are the skills that they have been given and developed, and trying to talk them into growing would be a disaster. Just like certain people shouldn’t start businesses, because that’s what you’re doing here.

Last question. Knowing what you do now, what happened, how it went; would you approach this position and your career in the same way? What would you do differently?

Like all the way back to when I left school?

Yeah, but at the same time…to clarify this question a little bit, I always say that I would never have landed CoWork if it hadn’t been that I landed somewhere else first. 


So knowing what you know, what would you change, and what would you say was a necessary pain?

Yeah, um. I think that probably the one thing I would have changed is, there was a very critical moment… where we made a decision [at my previous employer]. I was informed of it but I don’t know that I had any influence whatsoever. When we started off we were like contractors. Basically everyone was paid off of a percentage, and it was a flawed model from the get-go. It was not financially viable at all, but it was still independent contractor set-up. I would have kept it that forever. That’s the one change that I would have done. That one model would have allowed for tweaking and changing in the future that would have saved the company. And that’s effectively on one level what’s happening with this sort of role. It’s allowing for that growth and contraction much more naturally and quickly and painlessly than if you’re an agency and you’re hiring and firing versus just saying yeah, don’t have a lot of work for you right now. 

Are you basically saying that the model we have here at CoWork is self curating whereas at your previous employer you were having a problem where, with everyone not being independent anymore, there started to be inequities between work being done and money coming in?

Oh yeah!

People were dragging down, people were being the champion and there was no way to cut the people that weren’t performing from the people who were being awesome.

To be fair, some of it wasn’t the need for curation, some of it was leadership. Hiring who we shouldn’t have hired and not being willing to fire when we needed to fire. But, if it had been contractor model, none of that would have mattered because it would have corrected itself. So, I think self-curation is part of it, I just think self-correction…um…I’m sure there’s a better term for that. The ability to scale and bring on 15 people to do a big animation project and then when that’s done be back down to basically now we have full-time work for 6 people. So, farming that out in that way. I don’t know that, as far as would I have still gone through the necessary pain. Um, maybe. I don’t know. Most of the necessary pain was seeing poor leadership decisions and  interpersonal problems that weren’t resolved. I think some of those still would have existed and manifested in different ways. Yeah, that would be the one big thing. It’s kind of, like you said, if you hand’t gone through some things that were difficult you wouldn’t have seen so clearly other things that you learned. So, I’m super thankful for all of that and it was really that, at the end of the day, my desire to fix things was my undoing at that previous employer, so without that I would never be where I am now, because I still believed in the dream–the ideals of that company, so if there was a way to stay there and if I had any faith at all that I could have helped that be fulfilled I would have stayed there.

Do you think at this point in the infancy at this position that a failure experience previous to getting into this is almost a requirement?

Probably. It goes back to the risk. At this point I think I would say I agree with that. A little different perspective would be that I think it takes the perfect combination of events in your life to be influential and successful in this industry right now. Which is a little broader than saying you have to have a failure because I think you could potentially get here another way but when I look back at how I got here it’s the craziest…there is no plan. I was here, and then I was here, and I was here, and I was here and then all these things happened and boom, I’m doing this. I can see how they’re all connected but there’s no possible way you could have gone after that without all of these things stringing together in like a crazy scenario

I’m almost wondering if we all just tumbled out of the tree the same way and hit the same branches on the way down. 

Yeah, I think so.

The idea that I’m struck with is that the web industry is changing so quickly and this position is being birthed by necessity, and so the types of people you are seeing arriving to this first are the ones that have all fallen through the same problems in the same industry circumstances, and landed in the same spot and said, I want to do this.

So really it’s like, yeah, if you were to put together a job description for it the requirements for the job would be: personality, the things we already talked about. Job experience would be a negative experience with a poor leader, a poorly run mismanaged business that you had the knowledge and skills and potential ability to fix, but were thwarted by the owner/manager/leader, which left you incredibly jaded and burned and looking for a better world and opportunity. Then, couple that with you have connection and opportunity to work with wildly talented people who are very self-aware of their own limits. Your clients have to know their limits. That’s the only way that this works. When you have those experiences coupled with those people who are talented and bringing in enough money and can justify in their own mind your expense because they know you can do things better than they can and help them get here when by themselves they would only get here, you have opportunity for growth. 

So I guess someone who comes in who doesn’t have to go through that failure experience in the first place is going to have to be someone who either learns or is taught the principles that we have gathered from those failures and knows how to act either by imitation or by being taught on the job the things that do work. Right now, since there is nobody else in that position the only way to learn is by pain.

And I can say, yeah, that doesn’t work and here’s why. I have five experiences with that being a terrible idea. I think that someone that wants to get into this industry comes in in some sort of an apprenticeship scenario where you can’t take on any more clients and so you’re in the same boat that you’re helping your clients get out of. You either need to hire full-time salary or contract–any potential ones of those could work, and then you grow and you’ve got this individual who’s managing these clients and you have heavy oversight and you pull back and now they have their little book of clients and you’re teaching them and managing them and you have a couple of core clients. That’s effectively the road I was on. The first goal was, I needed someone to take off the bottom third of what I’m doing. Which is stuff like writing up contracts and putting together proposals. A lot of that’s busy-work and then I could come in and provide the core, key information. And then eventually add verticals of clients in the sense of when they grow, and that could be replicated. And then you grow up and over and maybe focus on the core most important clients and oversee. It might be that someone who wants to get into this, we start offering classes. There’s actually discussion and training through the Johnson’s Pathwright. Next summer when Matthew and I do this presentation, hopefully if we do it right and it’s impactful it’s going to make some noise. Matthew actually has a second opportunity at a conference so, I think the next year is going to be an interesting year for this industry and we’re going to see what happens.