The room where I felt small.
And why that’s exactly what I needed.
Dear readers,
Last week I went to a get-together in Cape Town. Standard networking thing.
I grabbed a drink, introduced myself, made small talk.
Then it hit me - this wasn’t a normal gathering.
Read here why...
Best, Xaver
If you’d like to put your product, service, or announcement in front of 5,000 newsletter subscribers and 30,000 LinkedIn followers, you can sponsor a future edition of The Honest Founder.
Last week I went to a get-together in Cape Town.
Every conversation I had went like this:
“What do you do?”
“I exited my company a few years ago. Now I’m advising a few startups.”
“Oh nice, what was the exit?”
“€200M to [Big Tech Company].”
Next person:
“I ran [Company You’ve Definitely Heard Of] for 8 years. Stepped down last year.”
Next person:
“Built three companies. Two exits. One IPO.”
I looked around the room.
Ex-founders. Successful CEOs. People who’d done extraordinarily well in their careers.
And me.
Who sold my company for €60M.
Which suddenly felt... small.
For about 20 minutes, I felt like I didn’t belong there.
Everyone else had bigger exits. Longer track records. More impressive stories.
I was the youngest person in the room by at least 10 years.
My inner voice started:
“What are you doing here?”
“These people are in a different league.”
“You got lucky with one exit. They built empires.”
Then I caught myself.
And I remembered something important.
This feeling this slight discomfort is exactly what I need.
Let me explain.
For the past years since my exit, I had been struggling.
Not financially.
But emotionally. Mentally. Directionally.
I’ve talked about this before the post-exit depression, the identity crisis, the “now what?” phase.
And honestly? Most of my friends can’t relate.
They’re still building their first companies or working in a corporate.
They’re where I was almost 10 years ago.
Which means they can’t help me with where I am now.
But the people in that room?
They’ve been exactly where I am.
Ten years ago, they were in their 30s, fresh off an exit, wondering what’s next.
They’ve navigated the identity crisis.
They’ve figured out what to do with the money, the time, the freedom.
They’ve built second and third companies. Or stepped back. Or found entirely new paths.
They have the knowledge and experience I need right now.
This reminded me of something I’ve learned over and over:
If you want to become a better version of yourself, you have to surround yourself with people who are ahead of you.
Not slightly ahead.
Uncomfortably ahead.
When I started my first company, I was the least experienced person in every room.
At founder meet-ups, everyone else had raised more money, built bigger teams, hit higher revenue.
It was uncomfortable.
But that discomfort pushed me.
I learned faster. Asked better questions. Raised my standards.
When I started fundraising, I forced myself into rooms with VCs who’d backed unicorns.
I felt like I didn’t belong there either.
But being in those rooms taught me how to think bigger, pitch better, and build relationships with people who were 10 steps ahead.
And now, post-exit, I need to do it again.
I need to be in rooms where I’m the least accomplished and experienced person.
Where my €60M exit is the smallest in the room.
Where everyone else has already figured out the thing I’m struggling with.
Because that’s where growth happens.
Why Comfort Is the Enemy
Here’s the trap:
After some success, it’s tempting to surround yourself with people who make you feel good.
People who are impressed by your story.
People who ask for your advice.
People who look up to you.
And that feels great…
But it doesn’t push you.
If you’re the smartest person in the room, you’re in the wrong room.
If you’re the most successful person in your circle, you’re in the wrong circle.
If everyone around you makes you feel like you’ve “made it,” you’ve stopped growing.
The advice I wish I’d heard earlier
If you’re building something right now:
Find people who are years ahead of you.
Not your peers (comfortable, but not challenging).
Years ahead = close enough to relate, far enough to push you.
If you’ve recently had success (exit, promotion, big milestone):
Find people who’ve been where you are now.
The post-success phase is lonely.
Most people can’t relate.
But the people who’ve been there? They get it.
And they have the map you need.
Growth requires discomfort.
Not suffering. Not comparison that makes you feel terrible.
But discomfort.
The discomfort of being around people who make you raise your standards.
The discomfort of realizing you have so much more to learn.
The discomfort of being the least accomplished person in the room.
That night in Cape Town, I felt small.
But by the end of the night, I’d had three conversations that changed how I’m thinking about the next 10 years.
I’d been introduced to two people who might become mentors.
And I’d been reminded of something critical:
The rooms where you feel small are the rooms where you grow the most.
So here’s my question for you:
Are you surrounding yourself with people who make you comfortable, or people who make you better?
If you’re the smartest person in your circle, it’s time to find an additional new circle to grow.
If everyone around you is impressed by what you’ve done, you’re not challenging yourself enough.
If you feel comfortable in every room you walk into, you’re not growing.
Feeling small is a signal you’re finally in the right room. Comfort is just ego maintenance 😅