"Someday" Is Not a Day of the Week
The most dangerous delays in life rarely feel dramatic while they are happening
“A bucket list is not really a list of things you want to do. It is a list of things you postponed.”
There are things I thought I would have time for. Not vague ideas or passing interests, but real things I was capable of doing and, at one point, close enough to see clearly. These were not fantasies. They were opportunities that required effort, timing, and a willingness to act.
I wanted to record an album. I was not guessing about that. I was an accomplished musician, and I had reached a level where it was realistic. Other people saw it as well. But life has a way of slowly renegotiating your priorities, and if you are not paying attention, you begin renegotiating with yourself. What once felt urgent becomes optional. What felt necessary becomes something you can get to later. By the time you look up, later has come and gone, and what once seemed inevitable becomes something you explain instead of pursue.
I wanted to coach football at a high level. Not recreationally, but at the college or professional level. I have coached for sixteen or seventeen seasons, and I understand the game in a way that most people do not. I think in terms of structure, tendencies, and adjustments. I see patterns early. But understanding something and acting on it are not the same. I never made the move. I never forced the issue, and like many things, it remained in the category of something I would eventually get around to doing.
I wanted to produce a movie. I have lived enough life to tell a story that would matter, whether it was my own or someone else’s. That idea never disappeared, but it never moved forward either. It stayed in a holding pattern, waiting for the right time, the right circumstances, the right moment that never quite arrived.
At one point, I also wanted to do something that reached beyond my own life. I was serious about joining the Peace Corps. Whether that would have been the right decision is not the issue. The impulse behind it was real. It reflected a desire to do something meaningful with the time I had. Over time, that impulse did not disappear, but it was redirected, delayed, and eventually buried under more immediate concerns.
That is how most things do not happen. Not because they are impossible, but because they are postponed.
How “Someday” Takes Over
For a long time, I worked what I would now describe as a corporate job in the worst sense of the word. I stayed there for more than six years under a boss who seemed to dislike me from the beginning and never made much effort to hide it. It was the kind of place where everything was monitored. Screens were tracked, activity was recorded, emails were reviewed, and even the office temperature could be controlled remotely from his home. It was less a workplace than a system built on control and distrust.
On weekends, he would go through employee emails and obsess over grammar, tone, and wording. This was not occasional. It was routine. At one point, he told me, completely seriously, that he believed I was trying to take over the company. That gives you some idea of the mentality involved.
The irony was that when he hired me, he said he did not want a “yes man”. I took him at his word. I offered ideas in meetings, respectfully and thoughtfully, because I assumed that was what he meant. But what he actually wanted was not honesty or initiative. He wanted compliance, and the moment you understand that, a great deal of workplace behavior begins to make sense.
The effect of working in an environment like that is not always dramatic, but it is cumulative. Over time, you begin to second-guess yourself. You hold back. You conserve energy rather than invest it. The most damaging thing such an environment takes from you is not simply time, but momentum. When you spend your days being watched, corrected, and quietly diminished, the last thing you have left at night is the drive to go build something meaningful of your own.
That is where the idea of “someday” begins to take hold. You tell yourself you will get to your real ambitions later, when things calm down, when the pressure lifts, when you are in a better position to move. At the time, that feels reasonable. Looking back, it is easier to see the cost. A life can be redirected not only by failure, but by delay.
The Quiet Accumulation of Regret
Looking back, there are other areas where the same pattern shows up. I became a father at forty, which changes how you think about time. You become aware of how much of it you have already used. I have had good years as a father, and I have had years I would handle differently if I had the chance. The phrase “If I knew then what I know now” is repeated so often that people stop hearing it, but it remains true. Experience teaches, but it does not give refunds.
The same is true of marriage. I have come through a great deal, and I have made mistakes along the way. Some came from inexperience, some from stubbornness, and some from simply not paying attention when it mattered most. None of that is unusual, but that does not make it insignificant.
Health follows a similar pattern. It is easy to assume there will always be time to correct course. Weight can be managed later. Habits can be adjusted later. Effort can be applied later. That assumption holds, right up until it does not.
There were also choices that slowed me down in ways I did not fully appreciate at the time. They were not destructive choices in the obvious sense. They simply made everything take a little longer. That distinction matters more than people think. You do not have to fall apart to fall behind. You only have to move slightly more slowly than you could have, and over time that difference compounds.
That is what regret usually looks like. It is not one major mistake. It is a series of small delays that accumulate into something larger.
What Is Still Possible and What Is Not
Which brings me to the idea of a bucket list. A bucket list is not really a list of things you want to do. It is a list of things you postponed. Some of those things are still possible, and some of them are not. The difficulty is that most people do not separate the two.
I am trying to work through mine. You will probably see me playing music somewhere at some point, and you might even hear me recording it. That is one of the things that does not have to remain in the "I will get to later" category.
But there are other things on that list that belong to a different category entirely. I never met Ronald Reagan. I never met Thomas Sowell. I never met Jim Rohn. Those are not things I postponed in the same way. Those are opportunities that passed with time, and when people like that are gone, the chance to engage with them directly is gone as well.
That distinction matters because it forces a more honest way of thinking. Some doors are closed, and no amount of reflection will reopen them. Others are still open, but they require action. Not intention, not discussion, not interest. Action.
A Placeholder Is Not a Plan
The difference between people who eventually do things and people who do not is rarely talent or intelligence. It is timing, and more specifically, whether they decide to act while the opportunity still exists.
There is no shortage of people who can explain why something did not happen. That is easy. What is far less common is a clear answer to when something will.
That is where the word “someday” reveals what it really is. It is not a plan. It is a placeholder, and over time, placeholders tend to become permanent.
The only way that changes is when something is taken out of that category and given a specific place in time. That does not guarantee success, and it does not remove risk. It simply makes the effort real, and that is the point most people avoid.
Because once something is real, it can succeed or fail. It can move forward or fall apart. It can justify the effort or expose the lack of it. “Someday” protects you from that, but it also prevents anything from happening.
At some point, those trade-offs become harder to ignore. That is where I find myself now, not at the beginning and not at the end, but somewhere in the middle where the difference between what is still possible and what is not becomes clearer.
Everybody reaches that point eventually. The question is what they do when they get there.
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