Look outward to see inward

This isn't the first time I've thought about doing something new and different in my career. In fact, I think it is the fourth time. My first ambition was to be a faculty member but consulting wages drew me away from the life of poverty and study when I was a PhD student. I consulted for a few years with the sole focus of making money. A few years later I got an interesting opportunity to start an IT Services company and I did that for a while. I didn't quite know enough at that point in my career to be effective which meant that I worked really hard and lost money. I transitioned back to consulting again but missed the sense of belonging. That’s when I decided to try being an employee. After working for a couple of companies I couldn’t get far enough away from my technology background so I went back to school to get an MBA to try another startup.

During the volatile times in my career, I've found it very useful to look inward, to try to identify my core interests. You see, when I get excited about something new, I can get very passionate about it. But, as my wife once said very eloquently, love isn't in the falling, it's in the staying. Maintaining a passion for something beyond the initial idea is much harder, especially if it doesn't really align with your core. As I look inward though, I find it is equally important to also look outward; to get input from others about what they see as my strengths and weaknesses. I find this helps keep my ego in check.

Let me give you an example. When I worked at PTC I started as a consultant and, after a year, decided to take a full time position. I had set some personal goals and objectives and was aggressively marching toward them. I moved my way into a quasi innovation/strategy role, trying to get support for a new product. I was contributing in unique ways to the company and that was making it hard to really classify my role. When I started, I was reporting to a director but soon I was soon reporting to the CTO. All of his direct reports were Senior VP's and I wasn't even a VP yet and my ego started to get the better of me. I tried to pressure him into promoting me, and though I got the sense he was trying, I got frustrated by the pace and ended up quitting in a huff. After I left I talked with a coworker who commented that the CTO had been trying to get my promotion through but that there was a lot of politics involved with staff that had been there a lot longer than me, like 10+ years longer. He thought the CTO was laying the ground work so that I didn't end up in an untenable position after the promotion. In my egotistical view of the world, I missed this and realized late that leaving was a sign of immaturity. If I had taken the time to talk to others I would have realized that I had support for my ambitions and a title, or a lack of one, didn't affect my ability to achieve these goals. In retrospect this was a blown opportunity and I vowed I wouldn't make that mistake again.

So I believe that soul searching requires input from others to truly get a complete picture. My first stop in exploring others’ input was to talk to a friend who runs a startup. We've been friends since grad school and I have a lot of respect for his opinions. He commented that if I was running the company, I had to own the failure. Being closer to the situation, I thought differently but he pointed out it wasn’t my opinion that mattered. He thought I either needed to take a step back and return to being a technologist/strategist or start my own company. A great suggestion was to look for a company that is known for doing spinoffs - shooting for the best of both worlds. This seemed like great advice and in the end, I left the meeting feeling really fired up.

This left me with 2 very different paths to explore: find a role in a company that would think about spin-offs, or do my own startup in either a products or services space. Though the goals of these are similar, i.e. to get back to running a company, the approach to getting there is very different. One way starts with a paycheck and ends with a little equity, and the other starts without a paycheck, but ends with a lot of equity. It's time to evaluate my finances, talk to my wife and continue the soul searching.