Probably my biggest mistake


Soundtrack for this article:

I fucked up big time when I left my job as COO of Startup Weekend. Probably the worse decision of my life. Worse than any of my other regrets combined.

I guess hindsight is 20/20.

I think it was mostly greed that led me to quit Startup Weekend and join a startup. When people asked me why I joined Kohort, I told them I “needed to go work at a startup” or “I’m jealous helping people launch startups and I want to experience it myself” or “I love the Kohort team and I believe in their mission.” That was all true enough, but I never told anyone the real reason: I thought the company was gonna be successful, I would make a lot of money and I would get a lot of attention and respect for it.

Those things mattered to me. I pretended like they didn’t, but they totally did.

It’s been a couple years since then. My savings account has grown. But I don’t feel any different. I have enough to pay my bills, provide for my family and have a little bit set aside for emergencies. I’m not sure what I would do differently if my savings was double, triple, 10x. I don’t think I’d be any more or less happy. I have what I need.

I wish I could go back and punch my greedy self in the face.

I read that humans spend more of their waking lives at work than not at work. I know now that when it comes to making decisions about your job, these are the things that matter, in this order:

  1. Does it make you happy?
  2. Does it positively impact others?
  3. How awesome are the people you’ll work with?
  4. [lots of other things]
  5. How much it pays

Looking back now, I didn’t realize how good I had it at Startup Weekend. It was a perfect fit for me. To this day, I love the effect Startup Weekend can have on a person. I still facilitate Startup Weekends because I love that feeling I get when I see that my actions actually helped someone. When it was my full time job, I had that feeling every day and it was stronger.

Somewhere a teacher is asking her students how to describe a dream job and their little innocent mind thinks of something remarkably similar to what I just said above.

I also facilitate because Startup Weekend organizers are some of the best people in the world. They are fun and they genuinely care about others. Of my top 20 most important relationships, 11 of them are with Startup Weekend organizers, facilitators or employees.

I like to fantasize about how my life would be different if I had stayed with Startup Weekend. I can see it now: I move to Seattle in 2011. I work out of the Startup Weekend office every day instead of working remotely out of my apartment for Kohort. I build strong relationships with the Startup Weekend team. Marc, CEO of Startup Weekend, becomes my best dude friend like I thought (hoped) he would. Adam Stelle – the guy that took over my job when I left – continues to look up to me instead of feeling let down. When I break the news that I’m moving to Omaha, they are sad. They throw a going-away party for me. I cry when I drive away. A few days later I arrive in Omaha and hop on a Google Hangout with the team, because I still work there.

What’s worse is that I know I had so much more to give to Startup Weekend. I had my own goals for the organization. I feel like I didn’t finish what I started. What a buzz kill. Startup Weekend has done some amazing things since I left, but I like to think it would be at least a little bit more awesome in some way if I had stayed.

Now that I’m typing this, I realize that my feelings of regret have more to do with letting people down.

Marc – if you’re reading this, I wish you had brought the whole team over to my apartment to have an intervention like you threatened to do that one time but somehow let me talk you out of it.

Still, I don’t entirely regret it. If I hadn’t worked at Kohort, I wouldn’t have met Greg Isenberg or Alison Lindland, two people I love. I also learned a lot about myself while working at Kohort. And I learned a lot of what *ahem* not to do – which has paid dividends in my current gig at Dwolla. So it wasn’t a complete bust.

A lot of people told me not to quit Startup Weekend. I wonder if they will be less willing to give me advice in the future. I wish one of them had looked me in the eye and told me I was being greedy. Maybe I would have listened.

I think the long and short of it is that I left a situation that made me extremely happy because I wanted to see if the grass was greener on the other side. I wasn’t mature enough to see my situation and appreciate how lucky I was.

And that sucks.

But the real tragedy would be if I didn’t learn from my mistake and use it to make better decisions.

I keep a deck of Oblique Strategies cards on my desk. I pulled one out to help me decide if I should write this post. It said “What mistakes did you make last time?” I swear to God this was the card I pulled. The hair on my arm stood up. Coincidence?

I put that card near my desk where I can see it:

What mistakes did you make last time?

I think the lessons here are:

  1. Being greedy leads only to regret.
  2. Money should drive as few of your decisions as possible.
  3. When everyone you know is telling you not to do something, don’t do it. They are thinking more clearly than you are.
  4. Friendship above all.
  5. If you fuck something up, try not to wallow for too long. Feel the pain. Accept what happened. Learn from your mistakes. And then go do whatever is next. Telling a few close friends about it helps me. Writing about it helps too. I started journaling recently. A few entries make it to this blog. Like this one.


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