Lean into Failure
Because betting on yourself is terrifying sometimes
Last week, I wrote about how easy it is to get stuck in the idea phase, that cozy space where everything still feels like it could be your ticket to freedom. You’re sketching logos, mapping funnels, imagining quitting your job in a blaze of glory. You’re “working on it”, but quietly dodging any real risk.
So this week, let’s talk about what’s usually lurking just beneath that cozy idea purgatory:
the fear of failure.
This is a fear that hits entrepreneurs differently.
It’s not just a fear of losing money, it’s a fear of what that failure means about you.
You had a big dream, talked about it, maybe even built an audience around it…and now you’re terrified that if it doesn’t work, you’ll be exposed. That you’ll have to go back to your day job with your tail between your legs while people whisper, “Guess it didn’t work out, huh?”
I’ll go first.
I’ve definitely been there. I’ve been the guy who didn’t launch, the guy paralyze by fear, more times than I’d like to admit.
It’s not that I lack ideas. Far from it.
I’m usually three steps ahead of myself before I’ve taken step one. Before I have my first customer, I am planning my exit strategy.
The vision is there, how it scales, how it frees up my time, and how I’ll grow the team. But when it comes time to actually hit “publish” or ask for the sale, I start thinking:
“What if this doesn’t work? What if no one buys? What if I tell everyone I’m doing this, and it flops?”
That’s the real fear: not just that it’ll fail, but that it’ll fail publicly.
Because in 2025, your business isn’t just between you and your bank account.
Your family knows. Your friends know. Social media knows.
And if you’ve been posting about “building something,” you feel like you’ve got an invisible audience waiting to see if you make it or fizzle out. Often times, it seems like they are rooting against you.
And then there’s the emotional weight of not being able to fully step into the business.
For me, the dream has always been to pivot fully, to take one of these businesses I’m working on and make it my only thing. So failure wouldn’t just mean a project didn’t work. It would mean being stuck in the in-between: still needing a job to support the thing I wish could support me.
It’s frustrating. Paralyzing, even.
And it’s easy to mistake this paralysis for “being strategic” or “waiting for the right time.”
But if I’m honest? It’s fear, plain and simple.
What I see in others
When I talk to other entrepreneurs, or people who want to be, the fear is often the same.
They’re afraid of the financial risk. They worry about debt, about sunk costs, about disappointing their family or having to explain to their spouse why their life savings just bought them 200 custom t-shirts and a Shopify store with no traffic.
A lot of people put everything on the line, and if it doesn’t work, they feel like they’ve lost their identity. Like they failed not just at business, but at life.
And the worst part? Most of them keep going, not because they still believe in the business, but because they feel like they have to.
They’re stuck.
It’s the sunk cost trap.
They’ve borrowed money, made public declarations, sacrificed sleep, and now the thought of pulling the plug feels like admitting defeat, so they keep pouring in more time, more energy, more cash.
It’s painful. But it happens more often than you think.
So what do you do?
Here’s the perspective I’m trying to adopt, and maybe it’ll help you too:
You don’t have to win to grow.
You just have to try.
If you give something your all, your best work, your full attention, your strategic brain, and it still doesn’t work? That’s not failure. That’s real-world experience. That’s the kind of MBA you won’t get in the classroom.
You’ll learn things that will take years to learn at a 9-5.
You’ll develop instincts, resilience, resourcefulness.
You’ll understand your limits and your potential better than ever before.
And all of that will serve you, in the next business, the next pitch, the next version of yourself.
No one wants to fail. But I truly believe that controlled failure, the kind where you’ve done the prep, taken calculated risks, and protected your downside, is not only survivable… it’s essential.
I’m not saying bet your house on your startup.
I’m saying: build the plan, run the numbers, talk to people who’ve done it, and take the shot.
Make sure your risk doesn’t ruin you and take it.
Because playing it too safe?
That’s a quiet kind of failure that takes longer to notice, and hits harder when it finally shows up.
Let’s Talk
Are you building something and feeling the fear?
Have you already built something that didn’t work out?
If you’ve tried and failed, I want to hear from you.
I’m writing a book about lessons from failed businesses, and I’m looking to talk with people who have stories to share, the messy, painful, insightful kind that can help others do better.
I genuinely believe the greatest lessons come from failure, and sharing those lessons is far more valuable than the typical “here’s how I succeeded” story.
If that’s you (or someone you know), reply to this email or shoot me a DM.
You can stay anonymous, or you can comment below…your call!