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Right after we graduated from college, my best friend wanted to buy a real bed. He'd slept on gifted beds, Craigslist-ed beds, found beds, futons, couches, and I even think there was tatami mat in there, but he decided graduating college made him an adult and needed a real, adult bed.

He saved a good amount of money and did research at multiple mattress stores testing for firmness, pocketed coils versus continuous coils, pillow top or memory foam — he tried them all. He finally settled on one that was as adult as a mattress can get. It was a Bonnell coil system king-size mattress with a memory foam pillow top. It had a temperature regulating system to assure neither overheating nor shivering, and he was convinced that this mattress would be the end to his minor-yet-chronic backaches. He waited for a somewhat decent sale, purchased it (with free delivery), and his mattress arrived.

After buying a bed frame that took up most of his Brooklyn apartment, he was ready to live the good life.

The first night, he couldn't sleep. Second night, same story. He couldn't tell if it was too firm or not firm enough, if it contoured to the curves of his back perfectly or not all. The seemingly simple act of falling asleep was just confusing. He had a rather sleepless week and then called to exchange it. But since he bought it on sale, they wouldn't do their normal bed exchange. He kept trying to sleep on it while trying to sell it for a decent price, and when that didn't happen, he ended up settling for a nearly $2,000 loss. He bought a used IKEA mattress off Craigslist and has slept perfectly since.

Guilt settles in

My friend talked a lot about the financial guilt he felt after saving for so long and then losing so much money. He made the bed a priority and his priority backfired on him. We could break down his researching of the bed, that he should have read the return policy fine print more carefully, or how he could have been more assured of his purchase, but for now, the deed was done and he had nothing but the consequences. I remember hearing him on the phone with his mother who pretty much said get over it. Move on.

Normally, I consider this sound advice. And maybe so does Shakespeare:

“Things without all remedy should be without regard; what's done is done.”

Taken out of context, Shakespeare is siding with all the live for today, forget regret rhetoric that we often encounter. That said, this quote is by Lady Macbeth, chastising her husband for being such a wimp for feeling bad about murdering people. The inability to experience regret is a diagnostic characteristic of sociopaths. Guilt is a utterly human emotion and should be allowed to be experienced. Quit feeling guilty about the guilt, that's the first step.

Mistakes happen. Instead of trying to live without any regrets, what if we learned to live with it in a way that serves us?

Overcoming the guilt

I think it's interesting to see what we regret and feel guilty about. According to a study from the Kellogg School of Management, only 2.5% of the guilt we feel is because of financial reasons.

Decisions (or non-decisions) about education, career, romance, parenting, and self all beat out our decisions about finance in terms of our longterm levels of regret (finance even loses to how we spend our leisure time). And though a 23-year-old may regret the $20,000 she owes after graduating college, it's more likely that the 35-year-old will regret never having gone. Granted, this isn't even close to a sure-fire statement, but it demonstrates that we regret decisions about education more than decisions about money, to the tune of almost 30%.

We all know what it's like to make a large purchase and having that pit-of-the-stomach, sick feeling. Whether it be a necessity or a decadence, that feeling is unavoidable, and it's not likely that you'll ever eliminate it completely. I think my stomach will always drop when I make a big withdrawal from my checking account, even if it's something exciting and purchased responsibly. Tickets to Paris? My bags are packed! Seeing the cascading numbers on my online savings account screen? I could do without that.

What we can change now

American journalist Sydney J. Harris said, “Regret for the things we did can be tempered by time; it is the regret for the things we did not do that is inconsolable.”

Learn from what you regret. Write down your financial regrets, past and present, not only the times that you did spend, but also those that you didn't. Many of our more profound regrets come not from the things we did, but from the things we were to busy or bullheaded to get around to doing. You still have time to make that next step, whether it be a future investment, that long sought after degree, or just a new skill — regretting what we haven't done is often easily remedied.

Listen to that pit-in-the-stomach feeling. If you spent months saving for those airline tickets and you're meeting your other financial goals, the anxiety is probably nothing to worry about. But if you feel guilt every time you buy the pricey olive oil or the new must-have app, that's worth thinking about. Don't “move on” or “forget” until you've asked yourself why you feel badly. Are you buying out of boredom? Are you charging it to your credit card? Are you spending more than you earn?

We can't live life without guilt and regret. Every day, we do things. Most of those things will be in the positive column, and as for the rest, chalk them up to experience. What's done is done, and we should let residual emotions run their course, but we also can learn from the negative experiences, and hopefully not repeat the same mistakes.

What have been some of your larger financial hiccups? How quickly did you recover, and what did you learn from it?

