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 real estate tech platform.
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. On top of that shit that I have never thought of or needed to implement in my life.
I underestimated how competitive it is just to get attention. Meta ads, Google ads, creative testing, all of it.
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 small 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.
It sounds like you're navigating one of the most challenging yet transformative phases of your life. Based on the most helpful WSO content, here are some insights and advice to help you through this:
1. The Lifestyle Freefall is Normal
2. The Identity Shift
3. Entrepreneurship is a Grit Game
4. Headhunters and Temptation
5. Respect the Process
6. Practical Tips for the Grind
7. You're Not Alone
Keep pushing, and remember: the grit you're building now will pay dividends in ways you can't yet imagine. You're not insane—you're just in the middle of building something extraordinary.
Sources: Life after Investment Banking, part 2, Leaving the buyside, Life after Investment Banking, Life Goes On..., To Those Who's Had A Successful Career In CRE, What Advice Do You Have For Younger Generations?
I’ve got nothing to add to this convo but appreciate your perspective. Looking to maybe make a similar step out myself soon. Trying to tee up as much in my evenings and weekends ahead of time but it’s clear this needs full time attention if it’s going to have any chance of working. My biggest fear is one you called out where I’m simply underestimating the marketing and finding customers side of it all.
I've been feeling this way as well. Hit 3 years in banking and after another 1-2 years, I need to make a major pivot. The one-sided personalities in the field, performative nature, and politics drains me
I'm stuck at a crossroads too working in finance. Curious about your decision making process. Do you feel happier that you don't have to deal with the office politics once you left? Does building something thats your own feel more fulfilling even though financially its going to be a rough couple of years?
Yes, 100%. The drain of walking into an office with people you are fundamentally misaligned with is difficult to convey. I am learning real skills and having to think critically. The business is mine and no one can take that from me. That being said, the lifestyle shift and blow to ego is significant and it is taking all of my mental strength to not go back into the corporate world. This goes against basic human instincts. It is basic survival instinct to chase safety, salary - not venture out in the deep end and potentially fail (failure being not being the big investor / corporate guy you once were)
appreciate the context here. it is tough i agree. having comfort, safety, a stable income gets inherently wired into your dna as you get older, get more risk averse and lose that vitality to chase risk. a couple of last questions,
how much did you have saved up from 7 years of your jobs in finance?
is it because you had a decent nest egg you decided to take this risk?
people in IB and PE always think they can be better business operators than their clients but in fact we are just sitting on the sidelines and theorizing what we could do to improve the business.
how was the transition from corporate jobs to running a business? any things you were surprised by and any specific aspects that were huge learning curves for you?
also, on a side note - how did you manage your social/dating life while working in finance and even now?
have you decided to just go all in on making this business work before thinking about that?
i've personally found it almost difficult to impossible to be sacrificing free time after work or weekends because i know that will basically put a full stop to achieving any means of freedom.
alot of questions here but i am also navigating this juncture of my life. thank you for your previous responses and hopefully this can help other people on the forum figure out their progression as well. i've kind of realized that as i pass time by in banking, you just have to pull the plug at some point and throw yourself into the deep end and figure it out.
Also considering leaving my MF to pursue something entrepreneurial. Couple of questions for you:
You have my respect for making that leap. Definitely a risk that most people wouldn’t take, but I bet it’s an incredible learning opportunity as a businessperson to actually fully run a business yourself
These ChatGPT posts have to stop
+1, this was so cringey to read.
Run tha score up YN…ya got to play to win…or risk losing it all…
“To dare is to lose one’s footing momentarily. Not to dare is to lose oneself.”
- Søren Kierkegaard
"One can choose happiness, or one can choose BB IB. Either/Or."
-Soren Kierkegaard
This is now my favorite quote
For whatever it’s worth, it took me and a lot of my friends about 12-18 months post leaving PE to feel like our pre finance selves again. No doubt you’re under a lot of stress and pressure now, but some of the existential dread of leaving PE and self imposed neuroticism will fade the longer you work with non PE people.
Second this. OP will experience significant growth and feel dramatically different in 18-24 months. You have to go through the various stages of grief. It's basically bereaving the death of an identity. The high finance career path is so all-consuming that it's nearly impossible to not invest a substantial part of your personality in it, if not almost all. Don't overthink the feelings or fret about what you left on the table, but also don't suppress them and allow yourself to air these feelings with friends and family to lessen the burden. Seek out others who are on similar paths for support. If you've put in 7 years at a high level and concluded that going off the path is the right thing, stay convicted on that belief knowing that you've seen it for yourself. This is the inner game that you didn't haven't had a chance to train for when the external validation of a prestigious brand did all the work for you. But remember - you were only renting the brand, and it could've been taken away at any time.
If you can get over the initial feeling of insecurity stemming from the loss of an identity, you will start to rebuild. There's going to be a lot of learning and un-learning. Know that the time you've put in "on the path" doesn't just vanish from your life experience and you didn't leave anything "behind". Rather, you're reaching "forward" for more.
You picked up skillsets and networks that are incredibly useful outside of that narrow context. The way will show itself if you apply the same level of drive and focus on the next thing. Your peer group will start to balance out more with non finance people - and you will see that working with creative, entrepreneurial, and down-to-earth individuals outside of IB/PE dronery is a reward in itself. There are incredibly smart civilians in the non-finance business world and they will respect the path you had walked on and want to benefit from your expertise. Unapologetically be of value to them.
You will know that you've fully recovered from the rat race identity crisis once your mindset shift as follows:
(1) When seeing one of your former peers who chose to grind it out on the unhappy "path" get promoted / have a big bonus year, etc.
Before Getting Over: Wow John stuck it out and he will make so much more money than me and everyone respects him. I could've had that.
After: Wow John is so talented but it's a shame that mustering up the small courage to unshackle himself doesn't occur to him. He could be so much more with that work ethic and mindset applied to something more broad-reaching and creative.
(2) When staring down potential risk and tough patches in your new venture:
Before Getting Over: Wow this is tough and risky. I'm afraid every day that goes by where I'm not getting back on the "path", that door is shutting harder. I'm going to fret and fantasize about what it would be like to just go back and stick it out another 5 years, meanwhile self-loathing and self-doubting about whether my decisions were impatient and weak.
After: Wow this is tough and risky. But there is no way I can go back into the matrix. I've already been unplugged and can't unsee the whole world that I now know is here. If this fails, that will hurt but the experience and learning will compound into the next thing. I'm not afraid to fail as long as I know I won't give up. If I was going to fail on my own, I would've failed on the path. I am in control of my own outcomes and I don't need the crutch of someone else's institution to will them into existence. I'm going to enjoy the journey today and the destination will take care of itself.
Ignore title - left my MFPE role to pursue something more entrepreneurial, albeit still within the realm of finance; joined an up and coming growth fund as hire #4.
The identity shift is real. I work in MFPE hits different than saying I work at -small no name fund- that launched recently. While I know what I am building, there no longer is that immediate stamp of approval and it's crazy how much I held onto that without even realizing.
Nothing to add, just thought I would share and validate the emotions I am sure many people who do similar moves go through.
Rooting for you bud.
Gay
Keep going - I’m ready to bet you’re living the dream of many people. I’m sure there’s a lifestyle shift but at least it feels real and at least you’re building something tangible.
What’s the worst that can happen? This industry is not going anywhere. You can come back anytime.
Be proud of what you did, I’m sure you’re building memories and experiences that will last a lifetime.
Did you really think sitting at your nice desk in a nice skyscraper while playing in your little excel model was harder than running a company?
Did you think there was anyway to start the business while you were at your job? At a similar crossroads
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