Most of my life I thought it was a lesson in hard work. Get up early, start before everyone else, stay disciplined, and success will follow eventually. Lately, though, I’ve started to wonder if I’m misunderstanding it completely. Maybe it wasn’t for getting up early at all. Maybe it was about being willing to do something before you knew exactly how things would turn out.
That thought crossed my mind recently when I was talking to a young colleague about investing, when Bitcoin came up. Like millions of people, I have a Bitcoin story. Around 2013, I had just started my first business and was still learning what it means to be an entrepreneur, which mostly involved finding new ways to worry about money. Every invoice mattered, every client mattered, every dollar mattered. One of my clients mentioned Bitcoin almost casually, convinced that it represented an amazing opportunity. If memory serves, it was trading somewhere around the $300 mark at the time. I listened politely and then I could do nothing at all.
Looking back, it’s tempting to tell that story as if I just missed a once-in-a-generation opportunity. Hindsight makes that narrative almost irresistible. But the truth is more interesting than that. I wasn’t sure, I was scared. Not for Bitcoin, and not even for losing money; I was afraid to make a mistake, and that difference is important.
Over the years I have accumulated an amazing amount of such stories. When Facebook was in its early years as a public company, I would have invested then, too. Ironically, I was building a digital marketing agency at the time, spending thousands of hours helping businesses benefit from Facebook advertising. I deeply believed in the future of the speaker, and my life increasingly depended on it. I didn’t believe enough in my thinking to invest in it. It strikes me now as a strange contradiction. I was willing to bet my job on Facebook; I just wasn’t willing to bet my money on it.
Fear causes financial inactivity
The more I thought about those times, the more I realized that all the opportunities I turned down had one thing in common. The overwhelming emotion was not selfishness or fear of loss, but fear of making the wrong decision. I suspect that fear has cost me more over the course of my life than any financial mistakes I’ve made—and believe me, I’ve made my fair share.
At that time, my mistakes were very painful. Today, they feel like a learning curve, painful but among the most valuable lessons I’ve ever learned. Opportunities I’ve never pursued feel different. There’s something uniquely haunting about wondering what might have happened if you were just willing to try.
My partner laughed, then told me his version of the same story. He constantly watches the markets, reads the news, follows trends, researches companies and listens to podcasts, and keeps telling himself that he is going to start investing. He just didn’t. Every time he gets close, the market feels very rich, so he waits for the next pullback, or maybe the one after that. Different generation, different investments, but same feelings.
I thought about that conversation for days, because it made me wonder if we were both talking about investing at all, or something much bigger. How many financial decisions do we put off because we fear getting them wrong? We are waiting to buy a house because the prices may come down eventually. We endlessly compare credit cards, put off writing our wills, and stay with the same bank because switching feels like an unnecessary risk. Every delay feels reasonable—responsible. Sometimes it is, but usually, it’s just procrastination wearing a more convincing disguise.
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Too much information, not enough certainty
That rings especially true today. Previous generations were often skeptical because information was hard to come by. Now, the opposite is true. Between YouTube, TikTok, podcasts, Reddit, and AI, you could ask 10 experts if now is a good time to invest and get 11 different answers. We dive into information while somehow standing for certainty.
A few weeks ago, I admitted something to a group of financial experts that would never make it into an investment book. Every year, for 30 to 60 days, I quietly leave the market. Not because I can predict anything, but because sometimes the world feels like it’s falling apart and I appreciate a few good nights of sleep. Then a retired financial planner I respect explained the best way to do the same thing. His advice was considerate and perhaps superior. It sailed over my head again, because soon it was another choice, another chance to get something wrong. A perfectly reasonable option did not make me more likely to act. It made me lose weight.
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Somewhere, personal finance seems less about making good decisions and more about making perfect ones. Most of the time, there is no single right answer waiting to be found. There are quite a few that make sense, and the differences between them are more important than picking one and moving forward.
Why our brain resists taking action
There is a reason this is so difficult. One of the most well-known theories in behavioral economics comes from psychologists Daniel Kahneman and Amos Tversky, whose work on prospect theory suggests that losses are greater than gains: the pain of losing $100 feels twice as strong as the joy of gaining it. Our brains are simply wired to prefer avoiding mistakes over pursuing opportunities, which helps explain why doing nothing often feels like the safe choice, even though it isn’t. Choosing not to invest is still an investment decision, and you can see it in the numbers.
TD’s 2025 survey found that nearly four in 10 Canadians who held money inside a TFSA were not investing it. The money was just sitting there. The hard part wasn’t opening the account, but deciding what to do next.
Confidence comes after action
And that leads to confidence. We tend to think of it as something necessary to do something, when I suspect we have it backwards. No one learns to ride a bike by learning about bikes. Experience comes first, and confidence follows. You gain confidence in making decisions that are imperfect enough to realize that very few of them forever define your future. The mistakes I made rarely bother me, because they taught me something. The opportunities I missed are still happening, not because I want to be rich, but because I wonder who I would be if I had confidence sooner.
None of this is an argument for negligence. Some decisions require months of consideration, and many have consequences you cannot undo. But most don’t, and far more of them are reversible than we believe.
This brings me back to the bird. For years, I thought the lesson was that success belongs to whoever comes first, but I’m not sure anymore. The bird does not leave the nest because it knows exactly where the worms are. It goes anyway. Sometimes, the biggest financial mistake isn’t the wrong decision, but the one you waited too long to make.
