How can I make sense of having invested so much and chosen to stay, then losing the dream anyway, so that I can move forward?

I once worked with a colleague who had spent about ten years as an engineer and project manager at a large technology company. He believed he had found a kind of electronic glass with features that would become very popular, so he left his job and started a company with several colleagues. He put a great deal of his own money into making a special product. For two years, they solved one problem only to meet another. Eventually he had spent all his money. He had even sold his home, so he no longer had a place to live. In the end, the project failed, the team separated, and everyone had to look for work again. He came to our company and became my colleague. When he talks about that time now, I think he would choose differently if he could go back. He might have stayed at his old company instead of trying to build one of his own. His experience changed how I think about risk. The challenge may be exciting, but sometimes we need to think even more seriously about the difficulties waiting inside it.

I grew up hearing that when something fails, I should look for the reason in myself: What did I do wrong? What can I improve? That can be useful, but it can also become misleading. It can make every outcome feel like evidence about who you are. I remembered this because of a difficult period at a previous company. A new manager seemed determined to diminish me. At the time, I kept asking myself what I had done wrong. I assumed that if I worked hard, treated everyone well, and was capable, people would like me. But the situation was more complicated. I was one of the strongest engineers in the organization, and senior leaders already knew and trusted me. The new manager was also trying to establish authority and prove their technical leadership. Looking back, I can see that the conflict was not simply a performance problem or a failure on my part. I was young then, and eventually I decided to leave. Now I think the important thing is not to treat yourself as the dominating factor in everything that happens. The world is made of many people and many conditions, and you are only one of them. That applies to success as well as failure. When you succeed or lose, it is not just you. Remembering that makes life easier—and most of the time, better—because you do not torture yourself trying to fix what was never yours alone to control.

In 2018, I had some money and thought, I should invest this. I found a small plaza in another city and bought it for about a million dollars. The math seemed simple: if I rented it out for ten years, I would get the money back. I didn’t think too much beyond that. Then the fundamental problems appeared—the foundation, the roof, things that needed money straight out of my pocket. The pandemic made everything worse. One of the two restaurants kept paying, though with reduced rent. The other closed. I had a well-paying job at the time, so I used my own money to keep paying the loan. I tried to sell in 2022 or 2023. When I counted everything—the repairs, the money I put in, the income, and the sale—I was down somewhere around twenty to thirty thousand dollars. That was the direct loss. There was also the indirect loss: I had sold a lot of company stock to keep the property going, and that stock rose afterward. That part still stings. People can call it a win because I didn’t lose more. I can call it that too. But it was still torturing. My takeaway is that I don’t want to touch property again. It isn’t liquid, and you can’t always turn it into cash when you need to. When this week’s topic came up, I immediately remembered that plaza—and the feeling of having given so much just to get out.