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?

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.

In 2018, I put all my money into a business property—a small plaza with several office and restaurant units. I was passionate about the investment and believed in it. Then the pandemic arrived. Most of the businesses shut down, I could not find new tenants, and I had to use my salary and stock investments to keep paying the loan. After I got married, my wife and I looked at the balance sheet and realized we were constantly losing money. We had already spent a lot on renovations, and things were beginning to improve, but we still worried about what would break next and what the future would bring. Maybe part of me wanted to prove that I had been right—that I could eventually recover the money. But I kept asking myself why I was staying in an investment that continued to lose money. We sold the property in 2022. The selling price was roughly what I had paid, after agency fees, but when we counted everything we had put into it, we had lost around $40,000 or $50,000. We had also lost the chance to use that cash elsewhere. Still, I felt very relieved. After we sold it, everything became much better: I still had a good job, some cash, and the freedom to invest differently. Sometimes you lose money, but when you cut something off and leave it behind, things can finally get better. I did not have to stay trapped trying to prove I was right.

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.

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.

The thing I keep coming back to isn't a big moment. It's that my kit is still in my trunk. In the art department, you have a bag with your own stuff in it—tape, blades, a staple gun, whatever. I drove two days to get here in August and unpacked literally everything else, including my kitchen stuff, but I didn't bring that bag inside. It's been in there ever since. My mom asked if I wanted to put it in the garage, and I said no. She didn't push it, but I could see her clock that. Because if it's in the trunk, it's like I'm between jobs. If it's in the garage, it's storage. That's the whole difference, and I know that's insane. It's a bag. The dumber one is that I'm still paying for my software: twenty-nine dollars a month for something I haven't opened since June, on a computer that barely runs it. I see the charge and think about canceling, and then I don't. I make about sixteen dollars an hour right now. People here assume something went wrong, that I got screwed over or couldn't hack it. But nothing went wrong. I was working. I had credits. I was in it. My rent went up two-fifty, and I sat down with a spreadsheet and there was no version of the numbers that worked. That's it. I did the math, and then I drove home.

My husband and I have been married for twelve years, and our relationship was still good. Two years ago, trying to break through the boredom of marriage, we agreed to enter an ethically non-monogamous relationship. We made detailed rules: no bringing anyone home, no talking about feelings, only sex. Six months ago, one of his regular partners unexpectedly became pregnant. She decided to have the child independently, according to her own beliefs and life choices. The child will carry my husband's genes, and I have to face the fact that our marriage has been permanently entered by an outside life. We did not betray the contract we made with each other. That is part of what makes this so difficult. Nothing technically happened outside our rules, but my whole world still collapsed. The roof we share no longer feels like shelter from what exists beyond our marriage; it feels like I am living beside a future I never agreed to, but cannot make disappear.