Why Are You

I’m writing this from the wonderful, artful park a couple miles north of my house. It’s close enough that I could – and really should – spend a little bit of everyday here. Yet, this is the first time in more than a year I headed up here alone to work.

In college I knew at some point I’d work for myself. Yet, at no point did I write down “Be my own boss” or “Work for myself” as a goal to work towards. It seems as inevitable as aging and “trim earhair” is not a Goal To Write Down. Yet, before I turned 30, I was president of a corporate entity, invoicing clients, depositing checks into a corporate account, and paying myself a regular salary, all from the spare room. Unfortunately, I didn’t really believe it. It all seemed just so flimsy and abstract. Of course, any day now someone will offer me a position at an actual, concrete entity. Any. Day. Now. Well, the mortgage is still due, so I’ll keep on keeping on.

When my third child was born and I looked into the clear skies of his newborn eyes and I was met with a:

“Are you serious? About working for yourself, I mean. Are you actually serious about making that – work?”


He was right to ask. One kid didn’t significantly impact my lack of work life balance. And while it was significantly more challenging – two kids didn’t provide cause to rethink things either. Three however. And to be perfectly honest – I wasn’t serious. I hadn’t been serious. I was walking backward. He didn’t blink though. He wanted an answer. I needed to decide, either be serious or get a damn job.

Fine, fine. Ok, I’m serious.

Off I went meeting with more clients, closing more business, booking more projects, promptly overwhelming my calendar and myself. So, despite the many strong recommendations against the idea, I hired employees. I needed to ensure they were doing that magic combination of; work they were good at, work the client asked for, and work I wanted to sell. All this added far more than 3 straws to my camel’s back. At its apex (or nadir), I was hunched over a laptop struggling with some tiny client project on a beautiful summer day while the rest of the family was laughing and swimming in the river. Yes, I had my best year ever. Yes, I regret not being in that river.

Since then, I’ve let all the employees go and continually revisited the question Augustus asked me when we first met. It took me a few years, but I think I finally understand his question. It wasn’t really about working for myself – it was about knowing why I was. Beyond “nobody’s hired me yet” I had never answered why I wanted to work for myself. Answering ‘why’ took less than 3 minutes:

  • to spend time with him, his siblings, and my wife throughout the banality of the day
  • to be in control of my work environment
  • to have low overhead so I can be selective and excited about the clients I engage
  • to provide my clients a value-rich, intimate, and unique engagement
  • to focus on long term leverage, not short term fixes
  • to continually provide opportunities for my own personal and professional development

Many times in the past decade I’ve failed to be serious in these 6 areas. I’ve failed to take advantage of these 6 benefits of working solo. I’ve too often been a horrible boss — to myself. No more. After spending the past 5 weeks focused on my family, getting my office just about where I want it — I’m enthusiastic about my current projects.

And I have a goal for the next decade — written down. A bunch of them in fact. One of them is work from the park more. StrengthFinder 2.0 says I do better with written down goals.