If at first you don’t succeed

How I Money
How I Money
Published in
2 min readMar 5, 2021

Aaliyah (rest in power) knew what she was talking about: “If at first you don’t succeed, dust yourself off and try again.” That advice is great for a lot of things in your life, but I’m specifically going to talk about it in the world of my finances and yours.

I feel like I know a decent bit about saving, investing, living frugally and setting financial goals. Overall, I’m doing okay. But that by no means I’ve made every right decision. Oh my lord, not even close. I wrote about quite a huge blunder I made just last year, for example.

And I’ve made plenty of other mistakes! For one thing, I chose a relatively low-paying career out of an abundance of youthful idealism (“Money doesn’t matter!” Yes, little one, it does. It can’t buy happiness but it sure is nice to keep a roof over your head.) I didn’t really know anything about saving money in my early 20s, and in fact cashed out a small retirement account when I left my first job (big mistake! Keep the money invested!). I have managed, not once but *twice*, to buy property right at the market high, just before a real estate crash. And just recently, in fact, I bought an incredibly ugly pair non-returnable jeans that I instantly regretted, just because I was bored and wanted some kind of excitement in this pandemic world we’re living in. (These are some really ugly jeans. Instant buyer’s remorse. Ugh!)

But here’s the thing: Yes, I sold out of the market at the wrong time… but then I pulled on my big girl pants and I got back in. That relatively low-paying career? I’ve done my best to negotiate salaries and raises to earn a wage that lets me live a pretty decent life while also socking away money. Cashing out that retirement account when I was 22? Well, I learned from that mistake; I’ve had plenty more retirement accounts since then, of both the IRA and 401K variety, and I’ve kept those invested. The ugly jeans… well, I’ll figure something out. But they were only $4.97, and if I made a five-dollar mistake, well, next time I’ll know not to waste the $5 just because I want 20 seconds of excitement in my life.

The point I’m making is that, just like the song goes, I didn’t succeed at first, but I picked myself up, I dusted myself off and got right back into things. Sure, I might have taken a few moments to throw myself the world’s tiniest pity party, table for one… but I didn’t let that stop me from trying again… and again… and again.

Don’t beat yourself up over your mistakes; use them as opportunities to learn so that you don’t make that mistake again in the future. Is my entire sense of self-worth worth $5? Nope! So why would I beat myself up over wasting $5 so badly that I get paralyzed and don’t do anything else? I know I’m worth more than that — and I know you are, too.

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How I Money
How I Money

45-year-old New Yorker working on her finances. Trying to have my cake and eat it, too.