10/13/2025
1- Chasing titles instead of freedom
I spent 10 years at JP Morgan chasing promotions and titles.Every new role felt like progress — but the higher I climbed, the less control I had. I was working 60+ hours a week, seeing my managing director more than my wife and kids. I thought I was winning… but really, I was trading my life for a business card title.
2- Chasing money instead of meaning
I told myself the next bonus or pay rise would finally make me happy. I hit 6-figures, then multiple 6-figures… but all it bought me was more stress and longer hours. I was chasing money, but I never stopped to ask what that money was actually buying me. The answer? Not freedom, not peace — just more stress.
3- Trusting the “safe path”
For years, I did exactly what the system told me to do: Max out my 401(k), invest in the S&P 500, save, be patient. I thought by 65 I’d finally be able to live the life I wanted. But when I ran the numbers, the math didn’t add up — my retirement savings wouldn’t even cover the lifestyle I already had.
4- Overvaluing job security
I thought loyalty to a big bank meant stability. But then I watched colleagues with 20+ years in the firm get walked out with cardboard boxes. That’s when it hit me: one paycheck, no matter how big, is the riskiest plan of all.
5- Underestimating boring businesses
I used to laugh at the wealthy clients who bought HVAC companies, laundromats, or pool services. I thought: “I’m in finance, I’m smarter than that.” But those “boring” businesses were making more cash flow than I did in a year… while their owners worked 20 hours a week. Meanwhile, I was stuck on calls until midnight.
6- Believing more work = more success
I convinced myself grinding 60–70 hours a week was the only way to win. I was always the first in, last out. But all that work didn’t buy me freedom — it just stole time from my kids, drained my health, and left me exhausted. I was making my boss rich while missing the moments that mattered.
7- Not seeking ownership sooner
My biggest failure? Waiting too long to step into ownership. I had the chance to start buying businesses years earlier but I was too scared. This cost me millions on the long run
