Lessons From A Failed Founder #4: When Being A Founder Simply Sucks

Many entrepreneurs agree startups are like a roller coaster, but few admit to feeling lost, lonely and defeated. Let’s talk about it.

Failed Founder
failedfounder
5 min readMay 8, 2019

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Photo by Stefan Spassov on Unsplash

Wednesday night, around ten o’clock. Time to finally head home after what has been another pretty useless day. Let me quickly check my inbox one more time, turn on the dishwasher, close all windows and doors. The servers are humming quietly, its LED lights casting an eerie glow on the cheap IKEA furniture surrounding the rack.

I didn’t accomplish anything today.

Sure, I dutifully went through last month’s financial statements, I discussed open tickets with the Support team, and my co-founder and I debated the endless list of things that needed to be done. While many initiatives depended on future funding, the perpetual state of many startups, the bigger problem was that I simply didn’t feel like executing them.

I’m not sure what triggered me to mentally check out; but I knew my heart wasn’t in it anymore.

While I wasn’t sure what triggered me to mentally check out, that Wednesday night I realised my heart was no longer in it. I felt beaten down, disillusioned and downright burnt out. The days were long, the pay was low. Nothing seemed to happen. No progress, no hope. As I locked the door, I faced the truth: I just wasn’t feeling it anymore.

Photo by yang miao on Unsplash

I am not writing this article to cheer you up, dear entrepreneur, or to give you tips on how to overcome your professional depression. I just want you to know that I understand your situation all too well. Oh, that bitter moment when your entrepreneurial adventure doesn’t feel like a calling but rather like any other office job. What a drag!

Believing you could earn way more by doing way less at any big corporation doesn’t make things better, does it? It’s downright depressing if you ask me. And to make things worse, it seems like every other startup selling mattresses or aggregating cars and houses is raking in millions in funding. Why can’t things go that well in your company?

Your startup is going down, but not before you go down first.

For some reason, admitting you feel lost and scared makes you a weakling. Unfit to be a founder, not cut out to be an entrepreneur! After all, aren’t founders supposed to be superhumans? Healthy, intelligent, driven People With A Purpose? You know, changing the world one pizza delivery at a time. What’s not to love about it?!

Your startup is going down, but not before you go down first. And while you feel yourself sinking into the quicksand of your own making, you bounce off your doubts and anguish on fellow founders. You are hoping to hear candid stories about their own frustrations, the loneliness that comes with entrepreneurship, the sleepless nights. Don’t count on it.

Photo by Good Free Photos on Unsplash

But don’t be hard on yourself: You’ve got plenty of pressure from everybody around you. Investors expect a big ROI, many employees take everything for granted while putting in the minimum hours. And nobody will every thank you for organising that barbecue. Not a single person will tell you, you did a good job. It’s simply expected.

You’re alright, dear founder. It’s normal to feel this way. While everybody is keeping up appearances, you are simply being honest. You are not sure if things are going to work out. In fact, you aren’t always sure if you want to be a founder. Maybe you just want a simple life with a nice check and a healthy work-life balance. And that’s okay.

Not a single person will tell you, you did a good job. It’s simply expected.

You’ll be hard-pressed to find fellow entrepreneurs speaking openly about their despair. But with the notion that you’re the only depressed founder on Earth out of the way, I can tell you what worked for me: Regrouping. I decided to put a clear distance between my professional time and my personal life. Here’s what I did:

  1. Going home means going home
    Whether I close my laptop at six or eleven; when I’m done, I’m done. No more emails, no more spreadsheets: I confine my job to the office.
  2. Mellow Monday, Easy Friday
    Committing to two nights a week where you’ll be home early does miracles for your work-life balance. Go to bed early, watch a movie. Live a little!
  3. Bring back the weekend
    Relax, take a road trip, try a new restaurant. Pick up a hobby. Do nothing. Let your mind wander but save your work thoughts for Monday.
  4. No email or Slack on your phone
    Deinstall your communication apps entirely and deactivate your work email account when you leave the office. It can all wait.
  5. Hang out with non-founders
    Stimulate your brain by talking about other things than term sheets and MVPs. What was the last good book you read?

And if you feel like talking to a complete stranger who knows exactly what you’re going through, you’ll find my email address in the footer of this post. To sign off, I say —

Be your own best friend: There’s more to life than being a founder!

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Failed Founder
failedfounder

Lessons From A Failed Founder is a series of blog posts by a thirty-something entrepreneur who made all the mistakes in the big startup playbook, and then some.