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Once a week, I take one idea and put it under the microscope. Sometimes it’s about business, sometimes it’s about how people think, and sometimes it’s simply an observation about the world around us. If it challenges the way you see the topic, then it has done exactly what it was meant to do.

I had to make an unplanned trip to Canada last week.

Crossing the Atlantic and then crossing it again in less than seven days, moving through seven time zones in each direction. The kind of trip that requires you to simply decide you are going and then go.

I would not call it enjoyable. I would call it a business class seat and a lot of time to think, which turns out to be something I do not find easily at home.

There is a version of this I have read about somewhere — an author facing a deadline, unable to finish a book, who bought a round-trip ticket from San Francisco to Tokyo specifically because a plane is one of the few environments that cannot reach you.

No notifications. No errands. No one who needs something from you. Just the hum of the engines and however many hours of uninterrupted thought.

He finished the book by the time he landed back in San Francisco. I believe it. The plane does something to you. It removes the ordinary friction of being reachable and replaces it with a kind of enforced stillness that is surprisingly productive once you stop resisting it.

So I spent the crossing thinking about the things I regret not doing sooner.

There are things I got right early. I found writing early and built a life where I get financially rewarded for doing it well. I encountered the ideas of marketing, influence, and communication at an age when they could genuinely shape how I operate.

I met my wife before either of us had money or status, which I now understand was an enormous stroke of luck. From everything I have observed about people who try to sort out their romantic lives after achieving some kind of career or wealth, it is a different and much harder problem. Trust becomes complicated. You can never fully separate what someone sees in you from what you represent.

In those things, I was fortunate. I have no complaints.

The regrets are elsewhere.

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Now, as I was saying…

One of my regrets is how long it took me to leave a bad situation. I grew up in Israel, and at some point, I started thinking about moving to North America.

From the first time I genuinely entertained the idea to the moment I actually pulled the trigger was roughly five years. From first thought to landing in Toronto, about seven.

Seven years.

I tell that number to myself with a kind of discomfort, because I know what was in those years. I know the opportunities I missed, the connections I was not in the room to make, the compounding that does not happen when you are in the wrong geography for your ambitions.

And I know, because I have watched it happen to other people, exactly what leaving sooner would have meant.

A friend of mine started his immigration process about two years after I did. He did everything correctly. His paperwork was complete. His case was solid.

The Canadian government shut a talent visa program while his application was sitting in a pile, days before it would have been reviewed. He found another route and completed all the requirements for that one too. The program closed again. He missed it by weeks.

He is now likely going back to a country where he is not particularly welcome and faces real friction. The window was there. The window closed. He was not far behind me — he was just far enough behind.

The second regret is investing. I started in my mid-thirties, which means I left somewhere between ten and fifteen years of compounding untouched.

I read about investing. I understood the concepts well enough to explain them to other people. I just never got in the game, because getting in the game requires doing the thing rather than studying the thing, and I had apparently decided that enough study would eventually produce the confidence to act on its own.

It does not work that way. The confidence comes from being in the game rather than from preparing to enter it. If I had started investing in my early twenties and lost a hundred thousand dollars in the process, I would still be significantly ahead of where I am now, because the market keeps moving upward and losses are survivable in a way that complete absence from the market simply is not.

That is a lesson with nothing to do with strategy. Almost any coherent approach would have left me better off than no approach at all. The issue was that I kept reading and studying and listening, and then declining to act.

On the plane home, I kept coming back to the same idea. Moving fast and breaking something in the process is still better than moving slowly or not at all.

There are exceptions. There are decisions that genuinely benefit from patience and careful thought. (How many of them there actually are is a question worth sitting with — fewer than I used to believe, I think.) There are almost certainly fewer high-stakes situations where delay is the right call than the anxious part of us wants to argue.

For most things that matter, the cost of delay is invisible in the moment and obvious in hindsight. How many decisions are sitting in your life right now that you already know the answer to?

I am working on noticing it sooner. The unplanned trip to Canada was a good reminder. Sometimes the decision gets made for you, and all you have to do is move.

P.S. If you enjoy these ideas, you’ll love the deeper conversations we have on the List Building Lifestyle podcast.