The mental struggle in-between startups

I’m in a place right now that I’m guessing a lot of other entrepreneurs find themselves in at some point — the in-between stage. This is the stage where your last company has failed/sold/gotten away … whatever, and you’re floating around aimlessly trying to find a higher purpose. You’ve got a half dozen ideas running through your head, but nothing concrete enough to get you excited. You’re still a bit connected to the last thing you were doing and can’t quite shake the last turd from the hole.

This is where I’m at right now and I’m not sure what to do. 

Smart money says get a job or a freelance gig until the next thing feels right, which is fine, but not the answer. That’s just an extension of the in-between stage. 

I’ve been here before, but this time it’s different. It’s more then the next paycheck, or the next idea. It almost feels as if it’s time to figure out what I want to be when I grow up. Only, I am grown up. 

Lately I keep coming back to the question of what I’m in search of — fame, money, legacy, etc., but can’t seem to figure out a way to find the answer. It seems to me that until I can find the answer, whatever I do next is meaningless. 

First world problem, but this seems like the place where those kind of problems are accepted. 

Anyone else go through this? 

  • I went through the fame/money/legacy search in my 30’s… for a few years. I’m now in my 40’s and I don’t know if I know the answer… but I don’t think about it anymore.

  • Yeah, I’m totally there. I’m 30, my last company failed, and I’m not sure what to do. While I figure it out, I have decided to get a job, so I’m working at another startup, where the money isn’t that good but at least I keep myself busy and around people.

    Now I don’t know if I should give it another shot with a new startup (I have a few ideas and some connections that could help me make it happen), to seek a job at a big corporation that pays better where I can make a career (it’s quite late being 30, but I think I still have like a last shot at that given my age), go back to journalism (a job I did in my early 20s that I loved, but paid very badly), or go back to the university and get a new degree, just for the sake of it. So as you can see I’m a big walking doubt. I hope I figure out what to do soon, because right now, all I feel is that I’m wasting my time.

  • Get a contract to solve money issues short term. Don’t worry, it probably won’t distract you that much.

    Then, start listening. Avoid following random ideas that occur in your head. Figure out how to get paid to do something that people want. Make sure it scales. Cut out anything that doesn’t fit your thesis.

    Rinse, repeat. There’s no rush.

  • I feel for you. I’m facing the same problem. Failed my startup. Now jobless with perhaps two or three more months left to survive on my savings. I feel that I’ve become a great generalist unsuitable for a corporate career but at the same time I find it hard to work on somebody else’s vision right now. :-/

  • I know that feeling. I call it the dip. It happened a few times over my career where you feel lost. I just got over one recently. Was in the dip for about 4 months.

    This is what I did… I got a spreadsheet put in what made me happy as a kid, passions, sports etc. Then I listed every job I had in my career and worked out which made me happy and which I was good at. Then I jumbled them around a bit, mixing and matching to see if I can come up with ideas. After that I started to research things on the web and looked at the different markets and industry.

    After testing and trying a few things I started letting people know I am looking to do JVs and get my teeth into a few projects. This created momentum and I started to get the buzz again. Then due to the buzz I got from it; even more ideas. Basically, your brain is like weight training. If you keep bench pressing your brain it gets better at coming up with ideas.

    There is no time limit nor can anyone tell you exactly what to do to get there and when.

    Have you ever noticed when you are happy you find most things come easy and when you are sad everything is drawn out?

    You need to find the touch point to get out the rut and get momentum.

    The key thing to remember is nothing is perminent. But when you are in the rut you think the mojo has gone forever; it hasn’t.

    Good luck! Feel free to ask more questions I am happy to shoot back some feedback.

  • Im 35 and just shut down my business after 5 yrs. I was releived to be honest ..but yes find myself in a dilema. Im told I cant get a good salary because ive been out of the workforce.and frankly I abhor the thought of working for someone. But ive decided what I want my next thing to be.. and to raise capital for that im going to take up a job first. I struggled a lot with the “is this my life purpose” especially since a month before I shut down shop ,my dad (my last surviving parent ) died. So believe me when I say im so mindf*****. But be kind to yourself. Try differnt things. Fuck what everyone says.. it may take you a month.. or maybe 2 yrs. But pat yourself on the back for asking this question and trying to live a life true to yourself.. good luck !

  • Yep, I’m in it now, too. It’s not fun, especially for someone who has always had too many opportunities to even look at. But everyone thinks I’m still in the one that just failed and I’m not sure if I’m ready to give it up, so I’m in the Dip (or perhaps the Desert?), and therefore no one is approaching me about anything new. Which is fine.

    The weird part of the Desert is how after 3 years of brutal hard work and then failure, I just don’t give a s$%# about doing anything new. It all feels like bland cardboard in the mouth. All I see in the startups is the hundreds of mistakes that they’re going to make, and in the corporates how they’re not doing anything interesting.

    What’s even weirder is that I’ve had a successful career: former VC, Inc. 500 winner, entrepreneur of the year etc. Many failures and various successes in the past. And yet with one failure in something I really, really cared about personally, now I feel like a real d$%^. More than just self-esteem hit, which I can weather because these deals often don’t work, it’s more of a hit to my belief in the entire game. Like, “look at all the monkeys run around chasing bananas.” And realizing I’m one of the monkeys.

    Stepping back, it’s really pretty funny. Monty Python might parody what the startup world looks like in 2014, with all our BS, fear, greed, and egos. And even when we make a difference–which in past deals I have–it’s not really that big of a difference. So the Dip is about reflecting on the core existential ennui of a life we have to commit to give it any meaning, and yet seeing as we get older that it’s all just a drama in which the dramatis personae become less interesting to play.

    Anyway, sort of a meandering reflection. But I will say that I am using the ennui, this moment of deep exhalation, to sell the nice house and stuff we own and engage with my wife in a really deep pivot of what we want the next 40 years of our lives to look like. Because the only real failure is when you quit, and one of the biggest successes in my life might be the day I quit being one of the monkeys.

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