We Are Not Our Worst (Financial) Mistakes

I’ve been seeing a lot of posts on Instagram lately with personal finance content creators listing their top money mistakes. They range from the more simple, like buying an expensive piece of clothing they never wore or not investing sooner, to more substantial like buying individual stocks they wish they hadn’t, panic selling their shares, or taking on a loan to start a business or side hustle that didn’t work out. All these different posts/examples/graphics have got me thinking about the words we choose to use in these situations, particularly the words mistake and regret. How we use them, what they mean to us, and how they serve us in the world.

I listened to two of Oprah’s Super Soul podcasts recently that each gave me eerily similar reactions. In the first episode, Oprah was talking to Bryan Stevenson, author of the book Just Mercy. Stevenson is a lawyer who has devoted his life to helping the poor and the incarcerated. On his website, in big bold letters, is his quote: “Each of us is more than the worst thing we’ve ever done.”

On the podcast, he shared that through working with people on death row, he has come to believe that no one deserves to die. Whether or not you happen to agree with this is not my point. My point is this: how nice would it be if we were all able to give ourselves grace, to all be able to come to believe that we are not defined by our worst mistakes?

In the other Oprah Super Soul conversation I was listening to, she was talking to Wes Moore. Oprah was not interviewing Moore as the newly elected Governor of Maryland, but as the author of the book The Other Wes Moore. In this book, Moore describes the lives of himself and another boy of the same name, both growing up in Baltimore but going down very different paths in life. The “other Wes Moore” is a drug dealer, robber, and murderer who winds up sentenced to life in prison without parole. After learning about “the other Wes Moore”, Moore sends the other guy a letter in jail, gets a response, and the two stay in touch, even having in-person visits where the other Wes Moore is incarcerated.

On the podcast, Moore shares how very few people understood why he would have a relationship with the other Wes Moore. How could he befriend a murderer? And Moore shared a similar lesson to what Stevenson had shared: we are not our worst mistake.

These two podcasts really got me thinking. How can we all be so quick to judge, and yet we all make mistakes every day? Sure, we may not be going around murdering people, but many of us have done many things we aren’t proud of. Many things we’d take back if we could. Maybe if we were all more open to hearing each others’ stories, if we were all willing to befriend the other Wes Moore’s of the world, it would be easier to see how things may be different in someone else’s shoes. It may be easier to have compassion.

Because how often do we ourselves mistake a mistake, and feel so guilty about it? And wish more people had compassion for us?

I think it’s time we all accept that we are not our worst mistakes.

The same is true, I believe, for financial mistakes. How many times do we come into a relationship, a friendship, with tons of financial baggage that we are ashamed to share? Credit card debt, no savings, loans with ridiculously high interest rates?

Shannon McLay, host of the Martinis and Your Money podcast,* always says that all financial mistakes are fixable. I, too, believe this to be true. We have seen in our community people getting out of thousands, tens of thousands, and even in some cases hundreds of thousands of dollars of debt. What seems impossible is indeed possible when it comes to money.

I believe that the hardest part of a financial mistake is not actually fixing the mistake. I believe the hardest part is letting go of the shame of a financial mistake. Just like we should not be defined by our worst mistakes, we also should not let a financial mistake define us, who we are, or what we value. We can still be good people despite our mistakes.

When I think of my worst financial mistake, a certain experience immediately comes to mind.

Something really shitty happened to me in a previous job. I got sick to the point where I couldn’t carry out my job duties any longer without accommodations. Even though they were reasonable accommodations approved and backed by the ADA (Americans with Disabilities Act) coordinator at the institution, they wouldn’t allow me to work with said accommodations. The institution eventually forced me out (while making tons of shady decisions along the way that I knew about but couldn’t prove).

I was so angry at the time, and everyone I talked to about the situation told me I should seek out a lawyer to help me file for wrongful termination. I didn’t really want to go to a lawyer, I am very nonconfrontational by nature, but I let other people’s advice and beliefs get to me. I met with several lawyers over the course of months. I didn’t want to pursue anything unless I felt satisfied from that first consultation. Nothing was feeling right. But even then, my close friends and family kept pushing. So when I found a lawyer who really seemed passionate about my situation and about helping me, I went for it.

I went in blind. I went in naive. And before I knew it, I had a $5000 bill and a plan to get me my job back. Hold up. I in NO WAY wanted my job back, and I had been clear with the lawyer from the beginning that this was the case. That I didn’t want my job back. That I wanted to pursue wrongful termination. She told me that after going over my case, she felt that I had a better shot of getting my job back than of winning a wrongful termination case. She said she couldn’t help me with wrongful termination, and that I would need to pay for all the work she’d already done. 

I was crushed. I thought I was doing the right thing, what everyone else told me to do, and I ended up exactly where I had started. Except now I was $5000 in the hole.

Thanks to my savings and my emergency fund, I could have paid this as a lump sum, all at once (which I know is a very priviledged place to be in). At the advice of someone else (yes, I kept taking advice from others, I know, but this time it was good advice), I asked the law office what the minimum payment was, and proceeded to pay $50 a month until the bill was paid off. That at least gave me some satisfaction. I still remember how I felt on the day I sent that last payment through the mail.

But overall, it hurt. It was a dark time. I felt so much shame. I blamed myself for the situation. It was by far my worst financial mistake.

And you know what? The people in my life still wanted me to fight it. They told me I should find another lawyer. Keep going. Make the institution where I had worked pay for what they did to me.

But this time, I listened to myself. I could have continued fighting. I could have kept going until I found a lawyer that would fight for me. I could have gone around complaining about how life wasn’t fair, how I deserved justice. But I decided not to continue to spend my hard-earned money on something that was quickly becoming part of my past. I decided to choose me. I decided to choose peace. I decided to let it go.

Because what is most important to me is my time and my sanity. I took the whole experience as a lesson, and I moved on.

However, the shame did not go away as quickly. Even after I decided not to pursue the situation further, the shame stuck around. As a long-time saver, and as a smart, successful woman with a PhD, I was mortified by what had happened. The experience made me question myself. The shame took hold of my body and swallowed me up. And essentially losing $5000? That stung then, and it still stings now when I think about it. 

I wish someone had been there to tell me then how I am not my biggest financial mistake. But I had to do the work on my own. And I’m here to tell you the same thing now if you carry any shame around a financial mistake.

We are not our worst financial mistakes. Say it with me, and say it again.

I leaned on gratitude. I thought about how much worse it could have been. How much more money it could have been. How I could still find another job. How the experience didn’t ruin my reputation. How I didn’t hurt anyone else in the process.

I could still be grateful about it all. Grateful that I didn’t have to go into debt to get that $5000. Grateful that I could have paid that bill off in full if I had to. And most importantly, grateful that I still had my health and that I had left a toxic work situation where I was nowhere near being treated with respect.

And you know what? I’ve never once regretted not pursuing the situation further. I’ve never once wished I had spent more money on the situation.

Regret is a funny thing. I heard a definition of regret once that changed my whole attitude toward it. The definition I heard was that regret was wishing or longing for a different outcome, that things would have turned out differently.

I don’t feel that way at all about this particular situation. Losing out on that job was like a little kick in the pants from the universe. Losing that job led me to the job I have today. A job that I am WAY more happy with than that previous job. Had I not left that institution, I know I wouldn’t have the same life I have today. I wouldn’t have the same community that I know and love. 

If I hadn’t spent that $5000, if I hadn’t even tried to find a lawyer in the first place, I would have always wondered if I had a case. Even though I had friends and family backing me up and pushing me to pursue wrongful termination, part of me thought I had a chance too. I don’t think I would have had the closure that I have now if I hadn’t pursued it.

And sometimes I picture what life would have been like if I had had a case, if I had won that fight. I know I would have had to spend even more money to go farther down the road. It certainly wouldn’t have been a short process. And I would have stayed tied to that toxic community of people I worked with who didn’t support me. I probably would have thought about it all day, every day, until it was all over. And then what? Would I have felt happy? Would I have felt justice? I’ll never know, and I’m ok with that.

Instead, I got to put the past behind me, and start fresh. And sometimes a fresh start, a gentle (or not) kick in the pants, is just what we need to start living the life we were actually meant to live.

We are not our worst mistakes, or our worst financial mistakes. Don’t ever forget that those mistakes make us who we are. For better or for worse. So my friends, let the mistakes in, and let that shame go.

---

*A dream came true for me this week: I am the guest host on the monthly happy hour episode of Martinis and Your Money!! We talk all about FIRE and different FIRE alternatives. Check it out and let me know what you think!