How to deal with uncertainty as a founder (Can’t sleep!)

August 9, 2023

I want to embrace the uncertainty of being a founder

Yet at night when my eyes roll back and I fall asleep…

All I can think about is the feeling of not being good enough, the product, the value.

I feel like building a startup is like giving birth to many children.

Every time one comes out, I can’t help but think about the possibilities.

With each one, I’m left thinking… Will this one work? Will it survive?

And then 99% of them die, and I grieve it every single time. 😣

But as always, I’ll poop out another one. 💩💩💩

I went through 10 different ideas this summer. One got the most traction by far, but it still might die.

I think I need to just embrace the cycle of life and death. Embrace this as a natural part of being a founder.

How do you embrace uncertainty?

How can I be okay with the fact I will never know the truth? If my product is good enough, if I will succeed, if I can get customers…

Here is the practice I use that may help you sleep better at night.

1. Don’t react to your uncertainty

The key to eliminating these thoughts is to de-ritualize them. If these thoughts continue to surface and you’ve been attempting strategies to eliminate them, you’re reinforcing the thoughts by obsessing over them. Your fighting against them makes them stronger. By actively resisting these thoughts and suppressing them, you’re fueling them.

Here’s what not to do:

  1. Justify thinking about it:

  2. Me: “I’m worried, what if this doesn’t work?”

  3. Me: “I really need to figure this out, important”
  4. Me: “What if I fail? What would that mean? What would I do?”
  5. Me: “How long should I keep at this?”
  6. Me: “When should I start looking for another job?”
  7. Me: “This is important, I need to figure it out”

  8. Trying to reassure yourself:

  9. Me: “I’m worried, what if this doesn’t work?”

  10. Me: “I got this! I’ve been successful in the past”
  11. Me: “Wait, but smart people can still fail.”
  12. Me: “But even if I fail, I’ll keep going at it. I’m resilient!”
  13. Me: “What if you run out of money?”

2. Accept it as “harmless”

Instead, the best thing to do is to accept it (not respond). The easiest way to accept it is to remember that, hey this is just a thought, it’s harmless. Founders will always have these sorts of thoughts. It’s part of my brain. This will make your brain give up on “fighting” the thought of uncertainty.

These thoughts are:

  • “not important”
  • “harmless”
  • “Untreatable”

3. Embrace it

When you look at a brick, you can accept it’s there and feel nothing about it. But the best thing you can do is to embrace it as part of your life. Hey, this brick is part of my home. And I love it.

  • “This is the life of a founder I chose”
  • “Startups are dying left and right. It’s the name of the game and it’s what I signed up for”
  • “I signed up for a lifetime of uncertainty and here it is. Yay!”

When we embrace uncertainty, we connect it to our values. What makes being a founder and experiencing uncertainty amazing? Well, it means…

  • “I am a risktaker, I chose this life. Woot!”
  • “I value freedom. Yay for the rocky road”
  • “I’m unconventional. I don’t like stability. Yay for uncertainty!”


  • Don’t react (“What if?? OMG I can’t sleep!”)
  • Accept it (“Hey this is a harmless thought!”)
  • Embrace it (“I am a risktaker, I chose this life!”)

I use strategies to ultimately help me live with uncertainty and sleep better at night. I hope it helps you too!

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Maddie Wang founders of founders cafe solo founder
Maddie Wang
Gay / Solo-Founder / Stanford Dropout

I'm building Founders Cafe because as a solo founder, it can be very isolating. Last year, I lost 4 co-founders and a best friend on a previous startup.

Previously built a Minecraft Server ($61k), Amazon Store ($120k), and Queer Chart, where I met my girlfriend & close friends.

If you're interested in joining the Founders Cafe, let's talk and if it's a good fit, down to invite you!

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