Why I love being part of a company over being a freelancer

Over the course of 10 years in the workforce, I’ve been a freelancer for 9 years, and I’ve been an employee for 5 years. These are some of my reflections, and why I prefer being part of a company at this stage of my life to being self-employed.

In the spring of 2004, I was about to graduate with a marketing degree and needed a 3 credit elective to keep my full-time status to be eligible for my scholarship that semester. So naturally I took a fashion design course thinking, “hey at least I will get to draw some, and maybe meet some nice girls.”

Though I was only one of two male students, there were no coed relationships that resulted from the class. I did, however, get to draw a ton. I even got to design my own [somewhat ghetto] clothing line, and managed to impress my professor enough for her to ask if I was interested in making a connection with someone she knew who was starting a new clothing line and needed a t-shirt designer.

It ended up being my first foray into the world of freelance graphic design, and helped me realize that perhaps the degree I had just earned wasn’t exactly the direction I wanted to pursue.

My freelancer chapter

I kept doing the freelance design thing on the side while working other jobs full or part time, until eventually I found myself a year into an admissions (i.e. phone sales) job at the Art Institute Online, and very dissatisfied. So I quit my job, my wife cashed out her very small retirement savings account, and I pursued a full-time freelance career as hard as I could.

Over the following two years I made freelance my full-time work. It was hard. Learning to work with clients was challenging, learning to manage a business was challenging, and learning to promote myself and network with potential clients was challenging. I made just under $10K over two years of contract work, which — even for Lebanon, PA—was a pittance.

What I did gain a lot of was knowledge, and experience. I worked with a variety of clients (mostly in the nonprofit sector), and I ventured past graphic design into web design, and eventually into front-end development as well. I put my advertising/public relations education to work as the foundation for my design consulting, and I learned how to self-start and how to work from home.

Being a full-time freelancer was far from lucrative, but it was a valuable education.

My in-house chapter

Eventually, because I was earning so little from my freelance work – and because we had our first child on the way – I took my first in-house job as a designer at a really amazing NGO where I did very rewarding work, and worked with some really amazing people.

After nearly three years at CURE, I left and joined a team of JavaScript engineers at a front-end consulting company where I worked with more very brilliant people. I was a visual design engineer, and I primarily wrote HMTL and CSS for some really cool responsive projects. I worked with world class developers, and again I learned and grew more than I expected. However, at appendTo, because I was primarily writing code, I was missing one of the things that I loved the most: design.

Years earlier while I was trying to make it as a freelancer, I had picked up the habit of kickstarting little side projects as a way to earn extra income, and as a venue to practice whatever new skills I was learning at the time (at first just HTML and CSS, later Wordpress php development, etc.). While at appendTo the lack of design tasks for me to work on only fueled my side project fire. Remote Jobs and Dev Tees are just two of the things I worked on in my spare time (only the later is still alive today) to help satiate my need for a creative outlet.

I also continued to do freelance work while at CURE and appendTo to support my growing family.

Eventually, even with side projects, I realized I needed to be in an atmosphere where design was just as core to my job as development, or even more so. I also deeply longed to be back in a product environment where – just as during my time at CURE – I could contribute meaningfully to the direction of a product over time, something sorely lacking in the consulting arena as a) consultants are typically just hired guns who are executing on an already decided upon strategy, and b) consultants tend to move from project to project several times throughout the year.

In the spring of 2013 I began seeking a new home where I could work for a product focused company, and exercise my design skills. After a few months of searching and exploring opportunities, I was hired at GitHub.

At GitHub I’ve had the privilege of being part of an amazing team of brilliant people, and contribute meaningfully to a product I use every day. And for the first time in my life, I earn enough from my full-time job that I don’t have a need to take on contract work in my spare time, which leaves me free to run a side project, and contribute to an open source project or two.

Both creatives and engineers seem to be drawn to environments where free thinking is encouraged, flexibility is inherent, and taking ownership is highly rewarded—all of which can be found by contractors.

But, while I loved the freedom and independence of being a freelancer in my earlier years, being part of a company has turned out to be even more rewarding in those areas than I ever expected.

What I’ve learned about being solo versus being an employee

I spent a total of 9 years being a freelancer, and 5 years being an employee, with 4 years of overlap between the two, and I’ve reflected a lot on the differences between being solo versus being part of a company.

Obviously, there are pros and cons to both, and one person’s pro is another person’s con. But, I’d like to share what I’ve learned from my experience.


  1. Work/life balance — Has the opportunity to be a pro, but is most often a con. For every freelancer I’ve met, 9 out of 10 have a crappy work/life balance and will admit it. When you’re running your own gig, you gotta hustle. Like REALLY hustle.
  2. Money—Kind of a crapshoot, and is the topic of many a forum thread for freelancers. I’ve found that if you’re in the top 10% or 20% of professionals for your market, and live in the right region, the money can be amazing. Otherwise, prepare to stock up on Ramen noodles because there are no steady paychecks, only the ones you book for yourself.
  3. Creative freedom—Depends (on you and the client, mostly). If you demand creative freedom, and assert your competence, this can definitely be had. But I’ve found more often than not creative autonomy as a freelancer is a magical unicorn dangled like a carrot during the project/client courting phase, but dissolved at worst and maddeningly stymied at best in the actual client engagement.
  4. Daily schedule freedom—Also a crapshoot. While client needs often dictate the schedule of freelance professionals, the typical solo creative or developer does seem to have a lot more scheduling flexibility to work with than the average company employee on account of “business hours” and all that. Pfsh.
  5. Stress—Honestly depends on your scenario, and type of person you are. But there is certainly no lack of stress when you’re self-employed. You’ve got crazy clients from hell to deal with, money problems, self-promotion responsibilities, taxes to file, OH — and you need to learn that new piece of design software/javascript MVC framework by Monday. Did I mention you have no clue where your paycheck in two months is going to come from?
  6. Community—Depends primarily on two major factors: your ability to cultivate community around you or online, and the region where you live (which determines how hard/easy the former is). During my full-time freelancing years I lived in rural Pennsylvania, which was incredible isolating. So grossly generalizing I would say lack of community is a huge con for freelancers. It’s not always true, of course, but generally speaking. Also, anyone who disagrees and has more than 3K twitter followers has a skewed perspective. Just sayin.
  7. Clients/Stakeholders—Depends who you are working for, but there are some unique challenges to the stakeholders you have in a client setting. Sometimes your clients are amazing. And then there’s the other 90% of the time. I’m partly joking, but the reality is that as a freelancer you rarely have the opportunity to develop the level of trust, respect, rapport and relationships that you do when your stakeholders are fellow coworkers at the same organization.


  1. Work/life balance—Working for a company certainly doesn’t guarantee a more healthy work/life balance than being a freelancer. Much of this depends on your personality, and the demands of the company you work for, or role you play there. But personally I’ve found much greater opportunity for cultivating* a healthy work/life balance as an employee due largely to the burdens that a company will carry for you which otherwise you have to deal with on your own as a contractor (e.g. booking work, marketing and self-promotion, bookkeeping and other administration, communication with stakeholders, etc). *NOTE: the term “cultivating” used intentionally, as it always requires an intentional effort regardless of setting.
  2. Money—As noted above, this totally depends on your individual scenario. Personally, I’ve always found working for companies to be a fiscally far more stable venture than cowboying it.
  3. Creative freedom—Generally speaking, I’ve found far more creative freedom in the roles I’ve had at companies over contract positions. There are a lot of dynamics at play here, but I think much of it can be boiled down to the opportunity of in-house teams work with a product over time, which leaves a lot of room to earn the trust and respect of your team, often translating into greater ownership and freedom in working with the product/brand/application.
  4. Daily schedule freedom—This one completely depends on the company you work for. At GitHub, I actually have even more daily schedule freedom than even I did as a contractor, however I’d venture to say my experience is rare. In general, however, I think most contractors have the advantage here over company employees, as most companies still tend to require employees to work certain hours, etc.
  5. Stress—Again, this is dependent upon your scenario: the company you work for, and the type of person you are (i.e. how you deal with stress, how much responsibility you tend to seek out or take on, etc). While I’d really like to say working for a company is overall less stressful than working for yourself, it’s simply not accurate. Honestly, it’s usually just a different type of stress.
  6. Community—I will talk more about this in a moment, but for now let’s just say this is the most valuable aspect to me personally about being part of a company. I’ve found that the opportunity to be part of a community — to be part of a team — has been far greater at the companies I’ve worked for than in my experiences as a freelancer. Admittedly this is quite subjective to your circumstance, and perhaps even your personality type. But the community angle seems to be inherently built into companies, and fundamentally lacking as a freelancer
  7. Clients/Stakeholders—Often the tendency of freelance professionals is to really vilify the client/provider experience (I’m certainly guilty of this), and the resulting assumption is that in-house professionals are free from such negative experiences. The reality, of course, lies somewhere in between. We all have stakeholders to work with. In-house professionals typically have internal stakeholders to serve, whether a boss or manager, team in another department, or their company’s customers. What employees often do have going for them, though, is the same dynamic as expressed in my sentiments about creative freedom: the advantage of trust, respect, and relationships cultivated over time.
Building software as part of a great team isn’t everything. It’s just everything you are not, which makes all the difference. — @cravelight

For me personally

This week we at GitHub we shipped Enterprise 2.0. It’s a major milestone for our company, and a result of the cumulative efforts of a whole gaggle of GitHubbers. It’s one of the biggest product launches I’ve ever been a part of, and it’s a perfect example of why I love being part of a company.

There is something amazing about being part of something that is much larger than yourself, and contributing to a work that is much greater than your own individual contributions. As my friend Mark recently said, “Building software as part of a great team isn’t everything. It’s just everything you are not, which makes all the difference.”

It’s the same reason that as a person of faith I love being part of the larger family of people who follow Jesus. My faith is not just a personal experience, it’s a corporate experience where my story is a tiny part of a larger narrative over the course of history. It’s all about having a purpose greater than yourself, and it’s a core part of the experience of being human.

In my professional life, I’ve found that being part of a great company is a wonderful way to realize that same experience.

To be clear, it’s not that you cannot be part of something greater than yourself as a freelance or contract professional. You just maybe have to work a little harder at making that a reality, or shaping what that looks like.

But personally, I’ve found that rarely is my own work part of a greater, cohesive vision in the same way as I’ve found it to be when I’ve worked at organizations like GitHub and CURE International among amazing people, where my role – as needed and important as it may be – is just a small part in a symphony of collaborative effort.

For me, there is something deeply beautiful and fulfilling about being part of that type of harmony, and it makes all the difference.