The Three Stages of Founder Loneliness (And Why Stage Two Almost Broke Me)

Published September 5, 2025 • Based on Founder Reality Episode 13

Nobody talks about how lonely this path really is.

When I started my entrepreneurial journey five or six years ago, I thought the hardest part would be finding product-market fit or acquiring customers. Those are hard, sure. But the real challenge? The psychological journey of choosing a completely different path than everyone around you.

Today I want to walk you through the three stages every solo founder goes through - because if you're in the early stages, I want you to know it gets much, much better.

Stage 1: The Excitement Stage (The Honeymoon Period)

I was 22, maybe 23, working on SimpleDirect. I felt like Neo in The Matrix - I could see everything that everyone else couldn't see. While my classmates worried about assignments and internships, I was thinking about product validation and talking to customers.

I was making some revenue early on. Working late nights felt productive and fulfilling. I genuinely believed I was ahead of the game, choosing freedom while everyone else chose security.

This stage feels amazing because everything has potential. Every idea could be the next big thing. Every late night feels productive. Those were good days - exciting, learning-focused, self-fulfilled days.

But honeymoon stages don't last forever. Mine lasted maybe six to eight months before reality hit.

Stage 2: The Brutal Stage (Where Most People Quit)

This is the longest stage, and it's where most people quit. For me, it lasted three to four years - way longer than I expected.

By fourth year, all my friends had graduated and gotten real jobs with real salaries. $60K, $70K, $100K+. They had steady paychecks, benefits, clear career progression. They were working at banks, tech companies, consulting firms.

Meanwhile, I was sitting in my apartment trying to figure out why my startup wasn't working. We were making money, but probably what my friends made in one or two months of working. While they enjoyed weekends and social gatherings, I was the outlier still figuring out if this would work at all.

The worst part wasn't financial uncertainty - though that sucked. The worst part was the self-doubt and social isolation.

The Social Isolation Problem

When people at parties asked what I did for work, I'd freeze for a few seconds before explaining a business idea that wasn't making money yet. People would say "Oh, that's really cool!" and then move on. I knew they didn't actually think it was cool at all.

Dating was weird too. How do you explain that you're 22 or 24 with no steady income because you're "building something"? It sounds like you're unemployed with delusions.

The Lowest Point

Three years ago - so not long ago - several of my co-founders found well-paying jobs. I started doubting myself seriously. I even reached out to a successful founder friend who'd raised hundreds of millions, asking if he might have a job for me.

That was probably the lowest point of my entire career. My parents were encouraging me to get a job too. I was approaching what I thought was the end of my entrepreneurial journey.

Fortunately, he didn't offer me a job. I'm grateful to this day because he understood the self-doubt phase. He was kind but firm: "We're founders and we're entrepreneurs. Employees are just employees. I don't think you'll be a good employee, and I don't think myself would be a good employee either."

That loneliness wasn't just about being alone - it was about self-doubt that maybe I'd made the wrong choice while watching everyone else make the right choice.

What Shifted Me Out of Stage 2

It wasn't success that got me out. It was starting to take care of myself.

I started tracking sleep, workouts, food. I became more intentional about my time. Most importantly, I stopped comparing myself to friends and co-founders and started listening to myself.

I realized I was trying to be everything while being nothing. I needed to be true to myself - I have strong opinions, strong beliefs, and I understand my personality better than anyone.

I know I'm not going to be a good employee because I'm not, and I tried. My dad's an entrepreneur too - I can't imagine him working for someone else, even though his ventures didn't technically work out.

Stage 3: Self-Acceptance (Where Everything Changes)

There wasn't a magical date where I became Stage 3. It's about being in full agreement with your path.

I understand that I'm working on my own destiny and controlling my own fate. If I screw up, that's my fault. If I succeed, that's also because of me.

When my friends complain about their jobs now, I don't feel envious. I feel grateful that I chose differently. Even if I hit rock bottom again, I wouldn't be envious - I'd focus on building and feel grateful for the freedom to do what I want, where I want, when I want.

The Confidence Shift

When people ask what I do now, I can explain clearly and confidently. I'm not seeking validation anymore. I know what I'm building, have a history of building, and know why.

The loneliness is gone because I'm not lonely - I'm independent. There's a huge difference.

My social circle has evolved too. I have relationships with other founders and builders who understand this path. We talk about what we've learned and missed - truly valuable conversations.

People see the change when you're confident in your choices and building something real. They respect it. Many even envy it.

Key Insights for Each Stage

If you're in Stage 1: Enjoy it, but be prepared for Stage 2. It's coming, and it will be hard.

If you're in Stage 2 (where most solo founders listening probably are): This is temporary. The isolation isn't permanent, but you have to do the work:

• Take care of your health
• Manage your time well
• Focus on building something real, not just impressive-sounding
• Find your people - online communities, local meetups, other builders

Stage 3: You're in full agreement with yourself. You control your destiny, and that freedom is something others will respect and envy.

The Compounding Effect

Here's what's crucial: your finances and money have nothing to do with these three stages. It took me four to five years to reach Stage 3, but knowing where you are might help you get there faster.

The path of building something unconventional is lonely by design. But that loneliness teaches you things about yourself you cannot learn any other way. All the pain, loneliness, and effort you're putting in - it's not going to waste. It's compounding, even when you can't see it.

Trust the process. One day it will break through the surface, and you'll understand why you chose this path.

Final Thoughts

The thing you're working on now might not be what you work on in the future. I've iterated through several ideas. Don't hold all your eggs in one basket - be ready for change and adaptation.

Most importantly: do something that compounds. Choose consistency over perfection. The beginning is always slow, but compounding becomes powerful once you hit that inflection point.

If you feel lonely, you're not alone. There's a community of builders out there. Find them online, find them locally. We're all choosing this unconventional path together.

The loneliness you feel today is building the independence you'll treasure tomorrow.