my two cents

‘Why Am I So Bad With Money?’

Photo-Illustration: The Cut; Photo: Getty Images

I have a real problem with ignoring anything related to finances. I’m not a disorganized person in general, but my brain shuts down when it comes to money. This has led to big issues with bills being paid on time and other important financial decisions like opening a 401(k). I’ve paid late fees on my credit-card bill countless times, even though I almost always pay it in full when I force myself to look at it.

My finances aren’t that complicated. I’m 28 and single and have a salaried job that offers retirement benefits. I rent my apartment, so I don’t have a mortgage or anything. My student loans are still on pause, so there’s only so much trouble I can get into with those right now. As far as I know, I’m up to date on what I owe, but that’s mostly because I keep things as financially simple as possible since I’m scared of what will happen if I don’t. 

I know I need to grow up and figure this stuff out. For example, I should start putting money into my 401(k). I think I might even have money somewhere in a 401(k) from my old job, but I don’t even know where to begin with that. The prospect of trying to find out sounds so torturous that I would prefer to just lose the money, which is ridiculous. My question is, How can I get past this mental block? What’s wrong with me, and what can I do to fix it? 

The crux of your problem is not that you’re bad with money. It’s that you’ve decided you’re bad with money. Then every time you encounter something finance related, a trapdoor opens in your brain and you fall into a black hole of how bad you are, embarrassingly bad, the worst.

This is the classic setup for avoidance. Once you develop negative associations with money (how bad you are with it, truly terrible, you suck), then of course you won’t touch it with a ten-foot pole. Unfortunately, ignoring your finances just causes more problems. When you finally take a peek at the damage, you’re so horrified that you slam the door shut and berate yourself again. And the cycle continues.

I know all about this because I used to do it too. For most of my 20s, I regularly overdrew my checking account, left bills unopened for months, and got sweaty palms whenever I approached the ATM. Like you, I was pretty orderly in the rest of my life, which made me all the more ashamed of the skeletons in my finances. At one point, I even thought I might have dyscalculia, a learning disorder that affects the brain’s ability to deal with numbers. (I don’t, which was disappointing because I desperately wanted an excuse for my behavior.)

The causes of money avoidance are myriad, but you sound like a pretty textbook case, according to Dr. Brad Klontz, a psychologist who studies how people relate to their finances. “A lot of money-avoidant people are well-educated, highly functioning, and high earning,” he says. “The issue is that they tend to have a negative association with money. They often believe that there’s virtue in having less money or that money is somehow ‘dirty’ or beneath them.”

Regardless of the root of your avoidance, the solution is the same: You need to break out of the cycle and find a way to engage with your finances on a healthy, regular basis. Here’s how to do it.

1. Begin with itty-bitty steps.

Whenever you feel overwhelmed by your finances, stop looking at the big daunting picture. Instead, identify one step you can take, even (or especially) one that’s laughably tiny. “The magic question is, What’s the next action? Make that action as small as possible,” says Dr. Tim Pychyl, a psychologist who studies procrastination at Carleton University in Canada.

For example, if opening a 401(k) makes your brain shrivel up like a moldy raisin, resolve to read one thing about the process. Instead of trying (and failing) to pay your stack of bills, just deal with one bill today. My personal favorite strategy for tackling things I hate is to set a timer for ten minutes and promise I will stop when it goes off (sometimes I do, but other times I realize it’s not so bad and keep going).

After you complete one of these steps, identify the next one, and then the next after that. Remember: You only have to do one at a time.

By focusing on your actions (“I just need to open this one bill”), rather than your emotions (“I’m afraid I’ll never understand this. I’m stupid”), you’re getting started — and suddenly you’re doing the thing you thought you couldn’t do.

2. Create positive associations with money.

Right now, you hate dealing with your money because you’ve lumped it together with feelings of failure and inadequacy. Naturally, you do not enjoy this! But if you improve the emotional and physical environment in which you do the thing you’re dreading, a funny thing happens: You hate it less.

So do your best to suspend your self-judgment. Make yourself a cup of hot chocolate. Light a candle. Invite someone over to talk you through the process or even just sit with you. Put on comfy pants. Financial therapist Bari Tessler calls these “money dates,” and they can be solo or with a friend or partner. Similar to watching a show or listening to music when you work out, the point is to gussy up an unappealing but important task so it feels less like a slog and more like a nice thing you’re doing for yourself, which it is.

Then do it again. Put it on your calendar every week as you would a regular standing date, and stick to the ritual. With practice, you’ll override your negative associations with money and start feeling closer to neutral, at the very least.

3. Acknowledge your progress.

Another reason to avoid finances is that the goals are often too abstract. Long-term outcomes like saving for retirement or paying off student loans aren’t very motivating compared with your immediate plans and deadlines for this week. No one calls to congratulate you for paying your electricity bill on time or reducing your debt by 11 percent this year, which is why you have to celebrate your own progress yourself.

I know it sounds trite and cheesy, but researchers have found that acknowledging your “small wins” makes you more likely to stick with bigger, more amorphous challenges. So set manageable benchmarks for yourself, even daily, to keep yourself engaged. For me, that’s as simple as automating a text every morning that tells me my bank balance so I can’t ignore it, or writing down all my spending for a week. If it gives you a sense of accomplishment, do it.

4. Be patient with your “maintenance phase.”

Change is tough, and sticking to change is even harder. I may be reasonably good at dealing with my finances now, but I still don’t enjoy it. Which is why I’ve automated as much of it as I can. I set my bills to auto-pay, and I use savings apps to take money out of my account when I won’t notice. I basically treat myself like a teenager who will blow her allowance every month. In other words, I avoid mistakes by giving myself fewer opportunities to make them. Plus, after the initial jolt of “getting your finances in order!” wears off, automation trumps willpower any day.

The “maintenance phase” of dealing with financial avoidance is often overlooked. People assume that once you’ve ripped the Band-Aid off your money phobia, you’ll be forever changed. But chances are you’ll be grappling with these tendencies for the rest of your life. (This can become especially difficult in relationships, so be prepared!) The key is to acknowledge it and have some self-compassion when regressions inevitably happen.

The Cut’s financial-advice columnist, Charlotte Cowles, answers readers’ personal questions about personal finance. Email your money conundrums to

‘Why Am I So Bad With Money?’