12/13/2024

An honest exploration of the psychological whiplash that comes with building a company, and why we keep coming back for more

Written by: Jonathan Haas

The Dance of Euphoria and Despair

9:00 AM: You just closed a major client. You’re unstoppable. The world is your oyster. This is definitely going to be a billion-dollar company.

9:15 AM: Your lead engineer quits.

Welcome to founding a company, where emotional whiplash isn’t a bug—it’s a feature.

The Daily Oscillation

Let me paint you a picture of a typical founder’s day:

Morning: Your inbox has three potential investor intros. You’re practically practicing your TechCrunch interview responses in the shower.

Afternoon: A key customer’s implementation is delayed. Again. You’re updating your LinkedIn and wondering if Starbucks is still hiring.

Evening: A product breakthrough. You’re back to changing the world.

Night: Lying awake wondering if you’re delusional.

Repeat. Forever.

Why We’re All Slightly Insane

Here’s the thing about founding a company: it’s not just that you experience highs and lows. It’s that you experience them simultaneously. You’re Schrödinger’s entrepreneur—both crushing it and failing miserably until someone forces you to pick a reality by asking “How’s business?”

The truth? It’s both. It’s always both.

The Things Nobody Tells You

1. Success Feels Like Failure Most of the Time

That’s not impostor syndrome talking. That’s the reality of building something from nothing. The goalposts aren’t just moving—they’re sprinting away from you.

2. The Highs Get Higher, The Lows Get Lower

As your company grows, so does the amplitude of the emotional swing. That first $1,000 deal felt huge. Now you’re landing $100,000 deals and somehow feeling even more pressure.

3. It Never “Gets Better”

You just get better at riding the waves. The rollercoaster doesn’t slow down—you just learn to eat lunch while upside down.

The Weird Psychology of It All

The real mind-bender? You start to crave it. The stability of a “normal” job becomes the scary option. Because once you’ve lived in this state of perpetual possibility—where any day could be the day everything changes—normal feels like settling.

Why We Do It Anyway

It’s not despite the chaos—it’s because of it. Where else can you:

• Experience a year’s worth of emotions before lunch
• Feel the pure euphoria of solving an “impossible” problem
• Build something that exists because you refused to accept it couldn’t

The Secret No One Talks About

You know what’s really messed up? We love it. Not in a “this is fun” way. In a “this is who I am now” way.

The constant oscillation between triumph and disaster becomes your normal. The days without emotional extremes start to feel weird. Suspicious, even. Like the universe is plotting something.

The Real Trophy

The real win isn’t in the exit, the funding round, or the big client landing. It’s in developing the ability to:

• Feel like a complete failure
• Keep working anyway
• Repeat until something magical happens

A Love Letter to the Chaos

To every founder out there riding this insane rollercoaster:

• You’re not alone in feeling both invincible and incompetent
• The uncertainty never goes away
• That’s exactly why what you’re doing matters

The Truth About Founding

Starting a company isn’t just about building a business. It’s about becoming comfortable with being uncomfortable. It’s about learning to dance between disaster and triumph, sometimes in the same meeting.

And here’s the beautiful, terrible truth: Once you’ve lived like this, everything else feels a little too… predictable.

So here’s to the founders. The crazy ones who choose this life of perpetual uncertainty. Who wake up every morning ready to feel like both a genius and an idiot, sometimes before coffee.

Because maybe the real success isn’t in avoiding the rollercoaster.

It’s in learning to love the ride.

Even on days when you’re desperately searching for the emergency brake.

Especially then.

Sometimes the best therapy is knowing we’re all in this beautifully chaotic boat together.

See you on the rollercoaster.