An Interesting Year

In the fall of 2010 I decided to leave my solid career of 5 years and take my chances in the realm of start ups. People leave their jobs for several excellent reasons: more money, better location/commute, opportunity, frustration with their existing job, or just because. Personally, I dabbled in a few of these.

I wanted to work in San Francisco, my home, to shave 2 hours of driving out of my daily routine. I wanted to be a designer; after years as a producer doing design work, assisting design, and doing design work on the side at home, I wanted this to be my title and primary task. I wanted to work on mobile games. I love PC games, but I saw (and still see) mobile as one of the bright futures of gaming. It's a barely explored frontier with huge potential for growth and innovation. People scoff at the simplicity of mobile games, but I fully embrace the potential of a miniature computer in the pockets of millions of people with a minute to spare. I also wanted to be a part of something new. I loved the idea that on the off chance that we succeeded, I could point back in years and say "yeah, that was me!"

I took the jump and joined a friend/colleague at a new company with heaps of potential. The company was founded by industry vets with ridiculous resumes, was well-funded, had already released a few solid titles, and employed a few dozen brilliant developers. Unfortunately, things didn't work out for a wide variety of reasons. After 6 months I gave notice and left.

At this point I was in an interesting position. I explored a handful of options and unfortunately not all of them panned out. In one instance my contact was pulled into some last minute, multi-week long meetings and disappeared. I thought he had lost interest when in reality, he just wasn't on email. In other cases it was a matter of timing. Another problem is that I do NOT handle uncertainty well. I have plenty of savings and I didn't actually need a job as quickly as I accepted an offer, but the anxiety of unemployment was killing me and I was too quick to take one. I had two or three other solid avenues I should have investigated and I didn't do so. Finding a job is a big deal and it is not something you should do with haste if you can afford a slower pace. This was a mistake. Friends of mine suggested I join them at their company. I had an uneasy feeling but, hey, it couldn't be that bad, right?

After a few days I knew I didn't want to work there and I set my current plans in motion. After a few months I gave notice and left yet another job. Needless to say, it was an interesting year. I see no value in naming names or being a jerk, but I do see value in listing some things I learned. If for nothing else, it's good to get these things off my mind so I can move on with my career and life.

1. Past team leadership and experience doesn't always transfer well to corporate leadership. Running a team of developers is one thing. Steering a company is a different beast. When looking for a company, do your homework and make sure the people up top are setting up the company for success.
2. Politics will exist at every company. I've now worked at companies of thousands, dozens, and hundreds, and all of them featured politics. Learn quickly how to communicate so that you can navigate these treacherous waters. In some cases you cannot fix the problem, so learn to deal with it so you can remain happy (if possible) and productive.
3. Dig deep and ask about process in your interview. Ask tough questions. Too much and too little process can absolutely kill a company. Furthermore, process defines the parameters by which you will be doing your job each and every day.
4. Dig deep and ask who makes decisions and how the decisions are made. Companies with too many decision makers, the wrong decision makers, or arbitrary stakeholders should send a red flag straight to the top of your metaphorical flag pole.
5. Examine the back catalog. You need to be inspired and interested in what they have done as a company. If this requirement isn't met, move on. It all depends on your amount of faith. For me, I'm more interested in what a company has done than what they claim they will do. If the company is really new and doesn't have a record yet, you need to really like what their road map contains.
6. If you get a bad feeling in the interview, ask the questions you need to ask to set your mind at ease. And if you can't ask that question or get the answer, move on.
7. If you want more money, counter-offer. Negotiate. I did this once with mixed success. The worst they can say is no. Fortunately, I've always been fairly comfortable with my salary and I don't really like pushing too hard here. But, that's the thing. If you want more money and getting it will make you happier and more effective, then ask.
8. The most important thing is enjoying the people you will work with every day. You need to leave your interview knowing that a.) you will enjoy getting lunch and coffee with the team and b.) you can rely on them to do their part.

Interestingly enough, at the end of this long odyssey I'm back where I started...somewhat. I have a new role on a new team that has a creative and business focus that thrills me. I'm surrounded by people with whom I work incredibly well. I understand the strengths and weaknesses of my peers and the company. Best of all, everything I've learned this year, both good and bad, can now be put to use. 

I have plenty of regrets, but I do not regret the decision to leave. People always simplify the entire leave vs. stay decision as "is the grass greener?" and I think that's understating the issue. I think in some cases the grass is greener, but by and large I think it's more that the grass is different. Every organization has its strengths and weaknesses and it's important for you to find one that maximizes that which is most important to you. Having had this experience now, I know better understand what's important to me. I'm better at my job, happier, and I can slowly impact the changes I wish to see on my team. 

As miserable as they can be at times, interesting times are what make us interesting and valuable employees and, someday, fantastic leaders.