Contracting One Year In

August 8, 2016

I took a leap of faith when I left my full-time gig to go it on my own, although, I really jumped in with a few other bright guys. We all onboarded at various times, but I was arguably the first (or second). The short of it is that I have no regrets about the lifestyle change and have learned a few valuable lessons along the way. In no particular order, here they are:

1. Perfect Setup

Along with being self-employed, I also spend the majority of working at in the bedroom (my co-work, co-habitate space). I have spent some time optimizing my work station to suit my work needs and improve my working posture. I opted for a motorized convertible desk from Ikea, dual monitors, a fatigue mat and a used Herman Miller Aeron chair. I’m extremely pleased with the setup (and the fact that my wife deals with a huge desk in the bedroom). Close by is my Lulzbot Taz6 3d printer for good measure. While 3d printing is not part of my daily duties, I run it in parallel sometimes and can keep a semi-watchful eye on things.

2. Family Time

I love being able to spend more time with my crew. Instead of (admittedly a very short) commute every day, I can spend those extra minutes with my wife and kids. If my wife is juggling too much at once with the little ones, I can pause my work to lend a hand. Coding at 11pm means I can take a beach break or go for a run in the middle of the day. The flexible schedule is a blessing (and a curse if not managed well). My biggest, unexpected consequence has been dealing with distractions at home: largely from the kids and the dog. My oldest is 4 years old and he’s finally starting to understand what “daddy working on the computer” actually means. My 1 year old looks like he’s escaped jail every time he enters the office. The dog on the other hand has no excuse and is the most high maintenance creature in the house. Fortunately, my wife understands if I have to lock the door or head to a coffee shop for a few hours to total concentration.

3. Benefiting

There is some cognitive overhead in dealing with an employee’s traditional benefits (subsidized health insurance, retirement accounts among others) and to be honest, I’ve been satisfied managing all of this on my own. I’ve setup my own IRA where I contribute on an as-needed basis into a wider range of investing options. Although the cost of health insurance hurts more, I at least have similar freedoms as investing in choosing what is important to my domestic situation.

4. Taking a break

Much of my time is billed on an hourly basis, so I quickly began thinking in the opportunity costs of not working. I began to get sucked into a working-overload state where each hour I could, I would spend on a particular project. The money does follow, but it also does not rule my life. My wife and I discussed what a general working day should look like and it has helped better compartmentalize my work/play balance. I work during a typical daytime schedule with the occasional errand or break and end my work day before 5pm. I may sneak back on after the kids go to bed, but it is usually for reading news or learning/honing a skill. Although improvements to finding the right balance are to be found, we’ve generally been happier with the balance. More time with the wife and kids is a blessing.

5. Learn, and Never Look Back

I have learned more in a year than at any other time or duration of my professional life. Every new project introduces a new technology or paradigm that I’m eager to grok. Some examples include production experience with Docker, PostgreSQL, CouchDB, Redis, AMQP, Sketch (the design tool) and React. Learning is a hobby and it mixes nicely with this lifestyle.

6. Mortgages

I had been living in my house for a year before I went self-employed, but a few months in, I got a call from our mortgage broker to refinance our home. Being that we had a few more years in our current digs, I jumped at the opportunity to get the process rolling. Nope! The process halted after I said the word ‘self-employed.’ I argued with the broker that I had almost doubled my previous salary, but that did not mean anything to him (although he congratulated me). Two years of reported self-employment income is likely needed for any mortgage loan. Lesson learned.


Being self-employed (and running a business) is hard work. Finding ways to balance that with family and hobbies puts the time management skills to the test. At one point, I was working on my master’s degree, but withdrew in order to not lose my sanity and family time. I’ve found that balance in most aspects of life is key and with this lifestyle, it is no different.