I failed. I feel like I wasted my last 11 years with an obsession. What to do now?
I’m 29 years old, and for the last 11 years, the only thing I’ve cared about is founding my own company. I come from a middle-income family, and I’ve put every ounce of my energy into this dream, but right now, it feels like I’m just running in place while the world moves on without me.
Before Covid, I started my first startup, a hardware device for water conservation. I had no technical skills and no experience, but I managed to build a working prototype. During this time, I moved to Germany to do my Master’s at the Technical University of Munich (TUM), thinking the network there would be my big break. I tried everything to find an investment: UnternehmerTUM, the START Munich community, every networking event possible. Nothing worked. My teammates left, I ran out of savings, and I eventually had to give up.
What made it harder was watching everyone around me succeed. One friend sold a game he developed after three months. Two others raised $40M for a gaming studio. Another sold a fintech startup to a major player. Comparing myself to them killed me. I felt like I was just picking the wrong idea, so I jumped into the next thing.
In 2021, I started developing a travel planning app with a friend. Back then, there were only a few players in the market unlike today. We got good traction of 1,000 users with zero marketing worldwide but also zero revenue because we didn't even have a paywall for the first year. (Amateur entrepreneurs) I was at my absolute financial rock bottom. I couldn’t even afford the $50 to open an AppStore account, so my cofounder paid my half but I was happy because I finally had something people actually used.
While visiting my cousin, one of his wealthy friends asked about my vision. He trusted my work ethic and decided to invest. I combined his investment with a crowdfunding round and managed to raise a small seed amount to finally found the company. We spent the first year hiring a small team and trying to figure out how a real business works. But because the budget was tight, my co-founder and I decided to learn the technical side ourselves to save money. We both have a management background but I became the iOS developer and he became the backend developer. We were obsessed with making the product perfect and fully ignoring the monetization. We spent half the investment on development and saved the rest for marketing, but then AI hit the scene. We realized we’d be obsolete if we didn’t pivot, so we poured everything into implementing AI features.
Fast forward to today, we have over 250,000 users. Because the subscription revenue wasn't enough, I went out and hunted for B2B advertisers. I successfully brought in over 50+ paying companies to advertise on our platform. This gave us the fuel to survive, but it still wasn't enough to quit our day jobs. We are sitting at $3k MRR, but it all goes back into the business expenses like advertising on Facebook, Google, taxes, and servers, but we as founders take nothing. We also had to let go all the employees. We now try pivoting to B2B AI tools for hotels and tour operators but after 40+ meetings, we haven’t closed a single client. It feels like a toxic relationship. I know it's not working, but I’ve put four years of my life into this and I can’t let go. I still have a small chance of a VC to invest but this can be just another illusion.
To keep my residency permit in Germany and pay the bills, I had to take a full-time corporate job after I graduated in 2023. My life is now a cycle of waking up at 08:00, working a job that is way below my capacity, coming home at 17:30, and grinding on the startup until 02:00 AM. I have no social life. My girlfriend is unhappy because I’m never truly "there." I even lie to my employer. When they ask what I did over the weekend, I tell them I played video games, when really I worked 20 hours for a project that pays me nothing.
My family, girlfriend and friends are telling me to quit. They say I’m chasing an empty project and they’re right. I have no answer for them. I see successful founders on social media and I’m filled with a level of jealousy that I’m not proud of. I want to be the one giving the presentations, the one people are inspired by, but I feel miles away from that.
I’m 29 and I feel like I can’t even think about starting a family because I can't provide. Getting married or having a kid feels like a joke when I’m struggling this much. People tell me to take six months off to relax, but I feel like time is slipping through my fingers. I feel like I have to be successful now.
I’m stuck. I hate the corporate world, but my startup is draining me dry. How do you know when to finally kill your "baby" and move on? And more importantly, where to move on? I know I cannot silence the fire in me if I found a well paid corporate job.
How do you deal with the feeling that you’ve wasted your 20s chasing something that might never happen? I need some perspective from people who have been in this "middle-ground hell."
Thank you for reading and all the advise. Please be real. No need to be kind. I have to hear the truth.
Jobadvisor
I will be direct, because that is what you asked for.
You did not fail in the way you think you failed. But you are failing right now in how you are managing risk, time, identity, and self-deception. Those are fixable problems. Continuing on the current path is not.
First: a reality check (no sugarcoating)
By any objective entrepreneurial standard, this is not a nothing outcome:
You founded two companies
You built real products
One reached 250,000 users
You closed 50+ paying B2B advertisers
You generate $3k MRR
You taught yourself iOS development
You ran hiring, fundraising, partnerships, and sales
You survived Germany’s startup ecosystem as a foreign founder
Most people who call themselves “entrepreneurs” have done none of this.
However—and this is critical—you are now past the point where effort alone justifies continuation.
What you are experiencing is not perseverance. It is sunk-cost attachment mixed with identity collapse.
The hard truth about your current startup
Let’s strip the emotion out and look at facts.
What the data says
4 years in
250k users
$3k MRR
No founder salary
No B2B traction after 40+ meetings
VC interest is hypothetical, not term-sheet-real
Employees already laid off
Founders exhausted
Relationship damage
Health damage
Career damage
This is not a “one more push” situation.
This is a lifestyle-destroying zombie company.
The most dangerous startups are not the ones that die early.
They are the ones that survive just enough to consume your best years.
When do you kill your “baby”?
Here is the rule most founders learn too late:
You kill a startup when it stops increasing your future options.
Your startup once gave you:
Learning
Narrative
Skill accumulation
Optionality
Now it gives you:
Financial stagnation
Emotional depletion
Relationship loss
Career stagnation
Immigration stress
Chronic guilt and lying
Sleep deprivation
You are no longer building leverage.
You are paying tuition forever for a degree you already earned.
That is when you stop.
Why you feel like your 20s were “wasted”
This is not about money or success.
It is about expectation debt.
You expected:
To be “the one who made it”
To be admired
To escape mediocrity early
To justify the sacrifice with a visible win
Instead, you got:
Invisible progress
Delayed validation
A non-glamorous outcome
That mismatch creates shame, not failure.
Here is the uncomfortable truth:
Your mistake was not chasing startups.
Your mistake was tying your entire identity and self-worth to a single outcome.
That is why stopping feels like death.
The middle-ground hell you’re in has a name
It’s called identity foreclosure.
You decided early:
“I am a founder. That is who I am.”
So now:
Corporate work feels like betrayal
Rest feels like weakness
Quitting feels like erasing yourself
Time off feels like falling behind
This is not ambition.
This is fear disguised as ambition.
What moving on actually looks like (not quitting life)
Moving on does not mean:
Becoming a corporate drone
Giving up on entrepreneurship
“Settling”
Admitting defeat
It means decoupling survival from obsession.
Step 1: Put the startup on ice, not in the grave (90 days)
Not “I’ll grind less.”
Not “I’ll try one more pivot.”
Do this:
Stop new feature development
Stop unpaid founder work beyond 5 hours/week
Keep the product running
Maintain advertisers if they are profitable
No fundraising
No pivots
If the business cannot survive this, it was already dead.
This is a diagnostic, not surrender.
Step 2: Rebuild your leverage, not your dreams
You are under-employed, not under-qualified.
With your background, you should be targeting:
Product Manager
Growth Manager
Technical PM
Startup Operations
Early-stage employee roles (Series A/B)
You need:
Income
Energy
Sleep
Credibility
Immigration stability
These are not betrayals. They are founder infrastructure.
Real founders know when to regroup.
Step 3: Redefine success for your 30s
Your 20s were for learning and taking asymmetric risk.
Your 30s are for:
Converting experience into leverage
Being selective, not desperate
Starting with unfair advantages
Building from strength, not depletion
The founders you envy?
Most of them:
Had failed startups before
Had family money
Had timing luck
Had invisible support systems
You are comparing your behind-the-scenes to their highlight reel.
That comparison is poisoning you.
The fire you feel will not go away—and that’s fine
But here is the truth no one tells driven people:
The fire is supposed to be contained, not allowed to burn your house down.
You don’t kill the fire.
You build a furnace.
Right now, you are standing inside it.
Final, honest answer to your question
How do you know when to move on?
When continuing costs you your health, relationships, integrity, and future optionality.
Where do you move on to?
To stability, leverage, and competence—so your next shot is taken from strength, not desperation.
Did you waste your 20s?
No. You spent them learning what most people never dare to learn.
But if you keep doing this for another 2–3 years?
Then you will have something to regret.