Your Start-Up Failed? Go Ahead and Have Fun

I chatted with a friend, who has decided to close down his start-up. He worked on it for a few years, underwent a major pivot, and, in the end, realized, it wasn’t going to work out. All this while having his first child, too.

He is closing down the company. He called me to ask for advice on various jobs for his next gig.

“None of them,” I told him. “At least, not right now.”

I then became even more blunt: “Leave the baby with your parents and take your spouse for a long weekend away. Re-connect with her, express gratitude, and have fun together.”

I think it’s very easy to leave a job behind, but it’s very difficult to articulate one’s next step unless you allow for some “simmer time.” It’s easier to articulate why you want to leave a job; it’s much harder to articulate to where you want to go next.

“From” vs. “to”: they are very different situations.

I told my friend that he was probably feeling guilty that his start-up failed, particularly as his spouse was earning most of the inbound cash and that they had a tight budget. That he was probably feeling internal pressure to overcome that guilt by finding a new job quickly.

I’ve written before that self-criticism is an entrepreneur’s biggest obstacle, IMO. We criticize ourselves, and, if we are not careful, sabotage ourselves.

So, the irony is that, after failure, giving yourself a break is usually the best thing to do. Give yourself permission to mourn the end of a company. But, give yourself permission to have fun, recharge, and relax before the next job.

I hope my friend and his wife will have a wonderful time.

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5 thoughts on “Your Start-Up Failed? Go Ahead and Have Fun

  1. This is doable if the founder is a trust fund kid or managed to get some cash out of “failure” – but if my company fails I need to be applying for jobs the next day.

    1. I respect that there are a variety of financial situations in which people find themselves. For example, my friend is going to take a few days alone up in Maine. It will be low-budget.

      My point is not to take a lavish trip but to give one’s self the permission to sort out some powerful emotions.

  2. I second the idea of taking a break, post-shutdown. (Actually you should do this after any long and stressful situation)

    We tend to build up emotional momentum in these situations, and don’t even notice its presence day-to-day.

    But it affects our perspective (“this is my reality”) and influences our decisions about next steps (“need to get back on the next horse that comes along”). Ultimately, it blinds us to the other possibilities that should be explored.

    Ideally, you should take a few weeks/months to decompress and burn off the old momentum before you begin the next chapter (this period is also known as ‘unemployment’ and reinforces the importance of a savings account).

    You’ll make clearer, more insightful decisions about your future.

    Regarding Self-Criticism:

    I’d suggest that most entrepreneurs need to think more critically about what they’re doing: before, during, and after, the startup adventure. It must be constructive critical thinking, not negative.

    But many would-be entrepreneurs are seduced by the ‘startup porn’ that pervades the industry, and dive into startup situations without really understanding what’s involved and why their venture has a chance at succeeding as a business.

    Without some education and critical reflection, especially with the help of clear-eyed advisers and observers, the failure will just be written-off and the root causes missed. Then the flawed assumptions and structural mistakes will be repeated in their next chapter. As Mark Twain observed: “History seldom repeats itself, but it often rhymes.”

    In other words: Don’t Fail Fast, Learn Fast

    1. Very thoughtful, Scott. Thank you for writing. I firmly believe that the brain needs to “reset” after a very stressful situation, and almost go into rebuilding mode. “Clear your head” is an underutilized tool, IMO.

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