For 7 years I pushed through a career that looked great on paper but made me miserable. I finally walked away this year. No dramatic blow up, no big revelation, just the quiet realization that I could not keep pretending I enjoyed it.
Since then, I bought half of a 40-year-old family business and started building a Miami-focused real estate platform. (Both sites were basically vibe coded by me with basic programming experience. Hiring them out would have been over $100k – irrelevant detail).
What has been insane is the lifestyle freefall.
I was always scared to become an entrepreneur because of this exact thing. Now I am living it.
One business is profitable but still early stage. The other is a startup that needs heavy lifting.
Both require marketing, ads, experiments, money going out before money comes in.
I underestimated how competitive it is just to get attention. Meta ads, Google ads, creative testing, all of it. I really thought I could just show up and grow something. Absolutely delusional.
The hardest part?
Ignoring the headhunters calling with mid six figure jobs.
I know I can go back. I know I can make money tomorrow. But that is the life I spent years trying to escape.
And then there is the identity shift.
Telling girls I am building companies instead of being the finance guy at a big fund.
Not casually dropping $200 on sushi like it is nothing.
Not skiing every winter.
Not having that easy, comfortable narrative of I am doing well.
It is humbling. Honestly, some days it is embarrassing. I did not expect it to hit this hard.
But I also have so much respect now for entrepreneurs who stuck through this phase and made it work. You do not realize how much grit it takes until you are the one staring at the ceiling at 3AM wondering if you are insane.
Rant over.
Would love to hear if anyone else went through this identity and lifestyle whiplash when switching from a high paying job to entrepreneurship.
I quit my $300k finance job at 30 because I finally admitted I hated it – and the lifestyle downgrade has been absolutely brutal.
byu/robbinh00d inEntrepreneur
Posted by robbinh00d
27 Comments
Sorry, did you not save any money before switching careers?
The identity shift hits way harder than the financial drop honestly – went through something similar when I left a comfortable tech role to start building Twine and the whole “what do you do” conversation at parties becomes this awkward dance where you’re trying to explain your vision while knowing it sounds less impressive than your old title.
Dude, “not dropping $200 on sushi” like it isn’t a huge mistake. Fix your spending habits, priorities, and then you’ll find the value in the money you make and spend.
AI
I did not go through a path like yours but I just wanted to say that your honesty and self awareness are rare. Most people stay in a life they hate just because it is comfortable or socially validated. I wish you the best
Consider deeply reflecting on whether you are making the right decision with the start up. I am a software engineer and tried to build many start ups from scratch and it’s an incredibly tough, tough road. Nowadays I buy already profitable businesses and I wish I would’ve started doing this much sooner.
If you already bought a profitable business, I would strongly encourage you to consider going all in on that and not letting yourself be distracted by the start up. Try reading the book buy then build. Good much brother
This is why I left America for Asia. I can maintain the lifestyle I want, while building the business and freedom I want.
If you need to physically be in Miami, this might not be an option for you. But perhaps if your work is 99% online, it’s an option. Or go closer, South and Latin America are just a quick flight away.
the drop from $300k must hit different but honestly props for actually following through on what you really wanted to do.
I’m still going through it and it’s been a decade.
can you share what kind of financial cushion you have before pulling the trigger on your Corp job? (eg savings, passive income, etc). thanks for sharing your experience and being so human about it.
I get it. I left a 12 year career in global media to take over a tiny struggling retail store in the suburbs. I used to fly on corporate planes and get invited to parties attended by Oscar-winning actors. Last month as I was loading up my car after a Pop Up shop – sweating and out of breath in the fall heat – I said aloud to myself, “I did not go to college for this.”
Yes, I make half of my old salary and watch on social media as my former colleagues travel the world on the company dime. But now, in my mid 40s, there is no way I’d go back to 24 hour emails and demanding bosses. Not for all the designer clothing and fancy restaurants in the world.
My advice is to find little ways to bring luxury back into your life. I love to cook elaborate meals eaten on fancy dinnerware. I adopted an inexpensive Steve Jobs-type uniform so I could splurge on fancy skincare and hair products. I gave up international travel so I could buy a nicer car.
I finally am at peace with my lifestyle. And more importantly, I’m getting to spend quality time with my parents in the last years of their lives. Something I could not have done working 12 hours a day.
Hang in there, OP.
Yes I went through this exact scenario 11 years ago when I started my company. Went from vacationing several times a year and buying whatever I wanted to living on SNAP benefits and Medicaid. I doubted my decision every day. I can’t even tell you how many sleepless nights I had.
But now I’m here, 11 years later, making upper 6 figures. Just built a very nice house. Not married, did it on my own. Risk + effort + sacrifice = reward.
Why start 2 startups rather than focus on one?
I quit a $300k job to retire at 36. Money really doesn’t equal happiness. I wouldn’t trade the last two years of freedom for anything.
Can you not fuse both? Build a company with what makes you worth $300k in the corporate world.
That’s what I did, and many others do. Leave your company and build a better one with you running it.
Genuine question, what made you feel misareble? Looks like you had time for dating, vacations etc. What was wrong?
I had similar experience, I work as a contractor for US startups and was making +200k while being in Europe, I had to drop some clients and I am only working 10-15h a week now because I was really miserable lol
My plan is to grow a team and serve as a company rather than being individual, it will take effort regardless.
I am sitting on 300k finance job and man I wish I have the balls and ingenuity to start something on my own like you did
Short term gains. These corporate jobs pay you just enough to kill your dreams.
Wasting a shit ton of money on ads is what usually bankrupts companies.
I felt terrible just dropping a couple hundred once. I imagine it would have taken 1000x that minimum to really get any traction plus so much ad experimentation and such. Rough stuff man, I feel your pain.
It’s very humbling and sucks the confidence out of you. I went through it.
One thing I would tell my former self is…believe that you’ll figure it out, somehow, even though the path isn’t clear. Don’t stress (that causes both health and family problems) because stressing doesn’t impact the outcome.
There’s a good chance you’ll find pivot point opportunities as you work both companies. The challenge is keeping them profitable while trolling for opportunity.
Gaining market traction is insanely difficult. Every customer counts.
This is one of the hardest things you’ll ever do. If you can make one or both work, your confidence will go through the roof and you’ll never work for anyone again, ever.
Finance is such a fugazi. Unless you’re Medallion or something your essentially stealing old people’s money. Just put your money in spy, or 60/40 spy qqq if your young. Are we done now? Why the hell do you need to pay several hundred bands to people that cant out preform goxx the hamster. Its like selling gold coins, its a farce and it makes people go crazy. I’m a serial entreprenuer. It is the way. Nothing in the world feels better than breaking the will of the market to your plan. The money will come man, be patient, wait for your set to roll in. And do everything yourself to build a skill set. Don’t buy expensive consultant crap.
I am with you ❣️,let me know if you need any help regarding softwares
You’re living life and making “drama maxxing” choices.
Here’s what’s gonna happen. You’re gonna go back.
You’re gonna take a job making $150k and you’re gonna hate it more than your $300k a year job, and you’re gonna milk THAT for drama, too. And then you’re gonna spend every waking minute regretting walking away from that $300k a year job.
You need to break the drama maxxing cycle. Until you stop making choices based off of feelings, you’ll continue with the drama based decisions dude.
I suspect you’re not done drama maxxing though. Idk…
Damn. Feel like this could have been a post from me. I left the tech industry after a very long time. Same base salary plus equity. Started my own company. Sucked the first year ended up beating my salary from tech in 2 years and 5 years in AI destroyed my business. Now I started another. It’s doing well but I’m missing that check. Just made it back to $200 sushi myself as an entrepreneur but nope! Time to start all over. Honestly, I have no chance of ever going back and drinking the kool aid anywhere. That time has past. Sort of like once you see the light sort of thing. I would make the worst employee now so it’s not really an option when recruiters reach out. And because of AI salaries aren’t what they used to be. AI will fuck your industry up soon enough and you won’t have that temptation any longer. Keep on keepin on man. Just go to the gym and get jacked while building your business. Getting jacked goes hand in hand with business and no amount of wealth anyone has can buy a ripped body. It is the greatest flex ever and will help you get women outside your paycheck. It’s pretty revolutionary in general from someone who used my paycheck to cover my skinny fat ass for so many years
I only left 90K, couldn’t imagine. Phew. Im back to my college meals and minimal everything.
The identity shift is really hard, but life is all about ups and downs. I’ve personally experienced the journey from career → entrepreneurship → failed startup with debt → back to career, so I totally get where you’re coming from!
I’m in a similar boat. I was a software eng from big tech, and I loathed how bureaucratic and over engineered everything was. It drove me crazy. So I left and now I’m trying to build open source software that generates documentation from tests. It falls back on simple best practices (not AI) to make good maintainable software, test driven development.
So far, extremely unsuccessful. It’s like AI has poisoned the well on building software correctly. I’m just so highly skeptical from the experiments I’ve ran that AI will turn out good software.