We Did It

This weekend marks five years since I left my growing and rewarding Wall Street career at Evercore. February 2021. A one week old baby. I left to pursue something radical and risky.

What I wanted, what my wife and I both wanted, was to be free.

What does that mean exactly? The idea that we did not have to live anywhere in particular. Did not have to go anywhere we did not want to go. Did not have to do what someone else told us to do. Did not have to follow a particular path. That we could get up and go anywhere we wanted. Work from anywhere. Pursue whatever ventures we wanted. Invest in anything we wanted. Raise our kids anywhere. Travel anywhere. The so called global lifestyle, but real, not performative, and without having to become an influencer, which is its own all consuming and time intensive job.

It is the unarticulated idea that lives in us as children and slowly fades as real life pushes those instincts out. Practicality arrives. You have to get a job. You need money. You need the house. The car. Save for this. Save for that. Stay in one place. Follow the path. All very traditional. All very post war. Pax Americana. Pax Puritanica. Predictable. Stable. Domesticated.

Yet almost every childhood story is some version of the hero’s journey. Overcoming a monster. A system. A villain. Finding oneself. Leaving home. Going on an epic adventure. Why do you think these stories resonate so deeply? Because it is what we are made for. Anything short of that kind of lived experience can quietly become a life surrendered in the name of practicality or “that is just not how real life works.” Keep telling yourself that. Then ask yourself if you still believe it in 30, 50, or 70 years. When there is not much runway left. Ask whether you would give the same advice to your 20 year old self. Your 40 year old self. Your 60 year old self.

For me, this started as a challenge to myself. I had real skills. Real perspective. Real expertise. Why was I giving all of it to an employer, even a good one, even a prestigious one? Not because employers are nefarious. Because the structure itself is inherently constraining. Why not try to build something from scratch? Monetize these skills. Start with one brick and see what happens.

People often ask what kind of safety net we had. Maybe two, possibly three years of living expenses saved tops. That felt acceptable because we figured we could both work if needed. We are both healthy. And in the worst case, I could always go back and get another job with a clearer perspective and stronger experience than before.

Somehow, the plan worked. Year one was slow. Year two accelerated. Year three we moved abroad. Year four was transition and instability. Year five is now at all time highs with real momentum.

Is this path easy? Not at all. It requires a lot. More discipline than people expect. More uncertainty than people are comfortable with. And yes, it can be stressful at times.

Along the way, we have traveled to over a dozen countries with our kids. They are bilingual now, which is incredible. At the end of the day, we do this for them. My dream is for them to be more adaptable, more independent, more worldly, and better prepared for this chaotic world than we ever were.

And is everybody happy all the time? No. You can never be perfectly happy, anywhere, under any circumstances. This life is not a permanent vacation. There are tradeoffs just like there are in any life. Not everybody around us is perfectly happy either. We have friends and family back in the US who we miss deeply, and who miss us. We also have family here, which helps, but it is still a tension that never fully goes away.

There are also practical realities that people do not see on Instagram. Global taxation. Immigration rules. Visas. Paperwork. Bureaucracy. Uncertainty. It all adds up. There are days where it feels like you are constantly solving logistical puzzles just to maintain the life you have chosen.

And the truth is, we still do not know where we will live long term. The US. Europe. Somewhere else. It is not a straight line. It is a moving equation. A puzzle that is never fully solved.

There is no denying there is an ego element. A quiet sense of “look, I did it.” But the deeper motivation is “you can too.” That message matters more.

That is why my X account has grown to over 21,000 readers, many of them high achieving professionals with real ambition. What connects them is not dissatisfaction with success. It is a deep, persistent sense of wonder and yearning for autonomy that exists in almost everyone, whether they admit it or not.

That feeling does not disappear. You can suppress it. You can rationalize it. You can outgrow many things. You do not outgrow that.

But these decisions are ours and ours alone. Nobody will make them for us. Nobody else carries the responsibility. Nobody else owns the consequences.

And that’s exactly the freedom we wanted.

We did it.