Robert SheddBlogging about the business, technology, and life of startups

I was recently having a conversation with an aspiring entrepreneur and the topic of why I left IBM came up. It’s been just over a year since I left the consulting world and joined Three Screen Games full-time to lead the product team – I left May 1, 2009 – so I have a bit of perspective on the decision now.

…

Why did I leave IBM?

First, let me say why I didn’t leave: I didn’t leave because I hated the company, the work, or the people. Almost without exception, I loved the people that I worked with. If you want to get to know your co-workers really well, go into a high-travel consulting job where you spend each and every week with your co-workers in a strange city. Where you eat more meals with them than you eat with your family. Where you sleep in a hotel room down the hall from them. You get to know them better than pretty much anyone else. I really enjoyed the people that I was working alongside – hugely talented, driven to do the right thing. I have a great respect for IBM in its ability to amass a formidable talent pool. As for the work and the lifestyle, I loved the consulting life – seeing different companies, each with its own culture and unique challenges.

So, why did I leave? In short, I’ve known for a long time that I wanted to be involved with a startup. After doing independent consulting during high school and college, I knew that I had the entrepreneurial bug. I initially went to IBM to see how the “big guys” solved all of the consulting issues that I ran into when I was working with clients independently. Finding that many of the issues were the same, just multiplied by millions of dollars, gave me a lot of confidence in my abilities.

While the people were great and I enjoyed the lifestyle, I was frightened of becoming complacent. I was afraid of getting to the point where I became used to the salary and the lifestyle. Flying around in first class, working on high profile projects, earning a nice salary, stock options, etc. – it’s all really easy to get used to. I knew that once I became used to it all, I would reach the point where I wasn’t able to take the 100% paycut to join an early stage startup. And so, I was afraid of somehow missing the ability to pursue one of my goals – helping to create a company from the ground up.

James Kwak does a really great job of describing what I was afraid of in his recent post Why Do Harvard Kids Head to Wall Street?: “…[O]nce you’re in the door, the seduction begins….Your expenses grow to match your income. As the decades pass and you realize that no, you’re not going to save the world, the money becomes a more and more important part of the justification. And when you have kids, you’re stuck; it’s much easier to deprive yourself of money (and what it buys) than to deprive your children of money.”

I think often we know what we should do, but it’s hard to actually go and do it. It certainly doesn’t get any easier with time, and in many cases, things just get harder. It wasn’t exactly an easy decision to make, to decide to leave my position last spring, with the economy still uncertain, and still getting a lot of experience and having a lot of mileage left in my career at IBM. But I knew that it was one of the few opportunities I’d ever have to take the leap, and I’m very happy that I did.

Part of this is the self-awareness that I believe is needed to be effective as an entrepreneur and wrote about earlier. In this context, do you know what you need to feel confident enough to make that kind of a jump? Is it a strong team, some validation of your concept, an early customer? Figuring that out will help you recognize when you’ve made enough progress to make the move. For me, some of that was having a business partner and a team that I was confident could hold up their end of the bargain, and having a top notch group of advisers through DreamIt Ventures. (Having people in my life that supported the decision and encouraged me was a big part of it, as well.)

Who knows where things will take me next, but I consider myself fortunate to have had the courage to take advantage of an opportunity and accomplish one of my goals for myself.

….

Back to the anecdote that inspired this post – the aspiring entrepreneur that I was talking with was unhappy with the ‘big company’ internship that he had for the summer. It wasn’t going to give him the experience that he was hoping for and would be essentially worthless busy work day after day. He had pretty much already made up his mind before talking to me, but perhaps some of these thoughts helped him feel less crazy for walking away from a “perfectly good job”. In my mind, as I discussed with him, if you’re not getting the experience you want, especially when you’re young, there are few reasons why you should stick it out and so many reasons why you should take the leap to follow your dreams. After all, you may not get another chance.

I have a quote from Steve Jobs on my personal home page that I think speaks really well to this point:

“We don’t get a chance to do that many things, and every one should be really excellent. Because this is our life. Life is brief, and then you die, you know? So this is what we’ve chosen to do with our life. We could be sitting in a monastery somewhere in Japan. We could be out sailing. Some of the [executive team] could be playing golf. They could be running other companies. And we’ve all chosen to do this with our lives. So it better be damn good. It better be worth it. And we think it is.”

This is your life. Make sure you’re getting what you want out of it.