For most of my adult life, one song has followed me around. Frank Sinatra’s version of My Way is not something I put on to feel inspired. It surfaces on its own, usually at an inconvenient moment, and it is always the same line: the one where he says his regrets were few, and too few to mention. The English lyrics were written by Paul Anka, adapted from the French song Comme d’habitude.

I am not an artistic or sentimental person. Most music slides past me. But a small number of songs, pieces of writing and ideas have lodged themselves somewhere and stayed for decades, and this is one of them.

I have a specific ambition tied to it. I want My Way played at my funeral, and I want the people in the room to hear it and believe it was true of me. Not because I was exceptionally successful, wealthy or accomplished. I want it because I want to have lived deliberately, made my own decisions and gone after what mattered to me.

The uncomfortable part is that I have regrets. More than a few, actually. And when I think about them, I realize that many aren’t mistakes I’ve made. They’re things I never did: opportunities I noticed and let pass, roads I looked down and didn’t take, decisions I never made because not deciding was easier.

I come back to this idea often, and I want to be careful with it, because I don’t think it is a universal truth. Some actions have terrible consequences. Responsibilities are real. There are decisions where the cautious choice is plainly the right one. But in my experience, a failure is something you can examine. You can understand what went wrong, absorb the cost and put it behind you. The question of what would have happened if I had tried has no such ending. It can sit there indefinitely, and it does not shrink with time.

None of this means I’m unhappy with the life I’ve built. Quite the opposite. But being satisfied with where you are doesn’t mean you stop wondering about the roads you didn’t take, or the ones that might still be open.

Jeff Bezos has a way of framing this that I find useful. When he was working at a Wall Street firm and weighing whether to leave and start an online bookstore, he imagined himself at 80 and asked which choice he would regret more. As he tells it in an interview with the Academy of Achievement, he concluded that he would regret not trying more than he would regret trying and failing. He called it a regret minimization framework.

What interests me is not what happened to Bezos afterward. The value of the exercise is that it changes the time horizon. Most decisions feel enormous when viewed from this month, with this budget and this list of reasonable objections. Viewed from 80, a lot of those objections look different.

I came across Matt Bertulli’s original Live 50 Lives piece, and it had a bigger effect on me than I expected. I later wrote my own take on the idea for this site. The essential idea is that we do not have to follow the same trajectory for 40 or 50 years. Someone can build a corporate career, start a business later, live in another country, rearrange their priorities or begin an entirely different chapter.

Equally, someone who genuinely loves their career, their family, their community and their existing life may have no reason to change anything. The objective is not perpetual change. It is having the freedom to choose. I don’t think an unconventional life is better than a conventional one. A person who chooses the conventional life while knowing the alternatives has lived as deliberately as anyone.

This is the connection to the work I do here. Financial independence, investing, foreign real estate, business ownership and geographic flexibility are not goals in themselves. They are ways of creating options, which is how I think about personal sovereignty: having the choice, whether or not you use it.

There is a contradiction in that, and I see it in myself. It is possible to spend decades accumulating the resources to live freely while continually postponing the living. There is always another financial milestone, another promotion, another sensible reason to wait a year. Each reason is rational on its own. Together they can add up to a life spent preparing. I am not writing this from a position of having figured it out. If anything, I am writing it because I haven’t.

I have a wife and children, and my decisions affect them. I don’t romanticize abandoning responsibilities to chase personal ambitions, and I have little patience for that story when I hear it told. Family is part of the life I chose, not something preventing me from living it. At the same time, responsibilities should not automatically mean giving up every other ambition or possibility. The balance changes throughout life. What is realistic in one stage of family life is not realistic in another, and I try to be honest about which stage I am in.

So the line stays in my head. I still want My Way played at my funeral, and I want the people listening to believe it. I won’t get there without regrets, and I already know it. What I want is to reach the end knowing I made a real effort at the things that mattered to me, so that the song has been earned and not just played. I am not there yet, and I notice that I am still putting some of it off.