A few years ago, I was going through cycle instructor training in Dallas. 

I entered into the process as a certified yoga sculpt instructor already, convinced that learning how to teach this other modality would last a few easy weeks at most before I’d find myself saving a horse and riding a stationary bike, with my mic, Soundcloud remixes, and glory in tow.

Six months and hundreds of hours of training later, I realized: I was embarrassingly, hilariously wrong.

It’s because my instructor coach (now one of my closest friends and dubbed one of Dallas’s top instructors by D Magazine) was so hell-bent on wringing the perfectionism out of me. 

For most of my life, I wore perfectionism like a badge. It was my go-to job interview “weakness” answer, a humblebrag disguised as a problem. “I’m just such a perfectionist,” I’d say, thumbing through my color-coded planners and polishing my 4.0 GPA. “I demand flawlessness of myself.” 

I didn’t learn until later that the second half of the sentence was, “...because I don’t believe I’m inherently deserving of anything good on my own.”

Somehow, I thought my perfectionism made me better—like I wasn’t willing to accept anything less than 110% (I’m intentionally choosing a mathematically impossible quantity here, mind you).

That didn’t fly with my coach. She once infamously brought me to tears during one early-morning training session wherein I sobbed under an unforgiving spotlight (yes, a literal spotlight) as Ariana Grande’s “break up with your girlfriend, i’m bored” echoed through the room, because she had instructed me to let loose and “pop off more.” She could see through my tight, restrained, “perfect” approach—avoiding mistakes and coloring inside the lines weren’t working for her. She was frustrated. I was frustrated.

“Why doesn’t it look like you’re having fun? You look miserable. Take your ponytail out or something,” she instructed, having mostly given up on the morning’s session.

Me, through wails: “I (sob) just (sob) don’t (sob) know (sob) what you want me to do.” (Code: Give me instructions! Give me a handbook! I’m lost with my own lack of intuition and confidence up here! I don’t trust myself to behave on instinct!)

Perfectionism, it turned out, isn’t some gold star handed out to the best and brightest. It’s usually a defense mechanism for those terrified of fucking up—so afraid of making a mistake that they’d rather not do anything at all than do the “wrong” thing. It stems (unsurprisingly) from deep, crippling insecurity. There’s nothing cute or humblebraggy about it, despite how I framed it. 

Admitting you’re a perfectionist is akin to admitting that you don’t trust yourself.

Perfectionism, procrastination, and paralysis 

“Katie, isn’t this a personal finance blog? Why are you talking about crying atop a spin podium?” Yeah, yeah, Bridget—we’re getting to it. Enjoy the ride, baby, because we’re taking the scenic route today.

While I was never fully comfortable “popping off” in a sports bra in front of 50 people, I did feel pretty at home inside my budgeting software and spreadsheets. I marveled at how quickly my interest in dipping from full-time work before age 65 transmuted into an obsession with wealth-building. When it came to money, I had no trouble popping off.

And when friends would express feelings of paralysis and procrastination around money, I’d stand there, watching them cry on their metaphoric podium, asking, “Why aren’t you having any fun? Just let your hair down and set up the automatic transfer, baby!”

Most of the financial advice I encountered was steeped in an evangelical, patriarchal obsession with discipline and self-sacrifice. It was like Dave Ramsey and his acolytes were screaming at my peers: “What’s wrong with you? Why can’t you just buckle down and do this? It’s just math, idiot! Maybe if you hadn’t fried your brain from all those pumpkin spice cold brews, you’d be able to figure it out.” 

(Typing such a disparaging sentence about pumpkin spice cold brew pains me.)

But one woman’s stationary bike is another woman’s Roth IRA. The haunting perfectionism that left me paralyzed (and procrastinating on my eventual ascent to the teaching schedule for six months) is often the same defense mechanism that keeps droves of people from taking the 15 minutes to create an account, make some elections, and add some cash. 

It’s the fear of messing up. The fear of not doing it “right.” The fear of taking the “wrong” step, even if it’s a step forward, and resisting the small knowing that something deeper is going on. 

There’s a reason the “extreme sacrifice and discipline” approach doesn’t work for a lot of people (and women in particular)

If you’ve ever felt intimidated, beaten down, and discouraged by personal finance advice that hyper-focuses on self-discipline, self-denial, and a sprinkle of self-loathing, there's a good reason for that. 

Consider this: In her book Quit Like a Woman: The Radical Choice to Not Drink in a Culture Obsessed with Alcohol, Holly Whitaker unpacks the way most addiction therapy (in particular, the 1930s-born Alcoholics Anonymous) was designed by and for upper- and middle-class white men. 

She points out that historically marginalized groups who suffer from addiction don’t identify with some parts of the ubiquitous 12-step program, particularly the ones that emphasize acknowledging you aren’t God and can’t control the universe. She emphasizes further that these groups don’t drink in excess thanks to an overdeveloped sense of ego or a pathological lack of humility; instead, they often drink for the opposite reason, and—at the risk of overgeneralizing her argument—to numb their experience of relative powerlessness.

(I promise I’m about to relate this back to money; hold my alcohol-free beer.)

If I have a spending problem because I believe on some level that I’m a worthless piece of shit, telling me that I’m a worthless piece of shit and shouldn’t be spending money doesn’t help me—it just reinforces the feelings that make me want to spend in the first place. 

The blunt force trauma of advice that emphasizes scarcity and sacrifice does more harm than good for those who already feel beaten down and paralyzed by fear. It’s well-intentioned for certain groups; if you fancy yourself the metaphoric Big Man on Campus® driving around in a financed, lifted F-250 because you believe you’re better than everyone else, being “cut down to size” by Ramsey & Co. may be exactly what you need to rein in your spending and build a plan.  

But if you already feel—subconsciously or consciously—that you’re undeserving of wealth, security, and comfort, you don’t need to be cut down to size. You need to be right-sized into believing that you’re capable and worthy of financial security. The Old Testament fire-and-brimstone approach is unlikely to work for you.

Recovering from perfectionism and taking the first small step

I’m a shameless fan of optimization to the nth degree. Identifying ways to optimize your money for each incremental 1% gain is—in some ways—my job, and what I (get paid to) think about all day. 

Sure, we could quibble over whether it’s better to start paying off debt or investing first, or whether we’re better off renting or buying, or whether we should be opening a Roth IRA or a taxable brokerage account, or whether we need more Small Cap or Large Cap exposure. 

But if these endless, circular debates are creating analysis paralysis—a fear of your first step being the “wrong” one—we’ve lost the plot. It’s important to lovingly acknowledge when we’re using these debates as excuses for inaction.

Whitaker talks about the mountain of shit that was wrong with her when she began her recovery journey (her words, not mine): She was a drug user. She was drinking herself sick. She was eating too much sugar. She was getting jacked up on caffeine. She had six figures of credit card debt. She was intermittently bulimic and anorexic. She described how she felt so overwhelmed by how much was “wrong with her” that it prevented her from taking the first step for a very, very long time.

But she knew the big piece—the piece that was hurting her most actively—was the drinking. So rather than trying to quit all of it, all at once, she focused first on the alcohol. She didn’t try to quit smoking pot, or cut out sugar, or pay off her debt. She just focused on getting the drinking under control and—eventually—eliminated it entirely. 

Once the alcohol was out of the picture, the eating disorder subsided, too. Once she stopped binging and purging, she felt more capable of abandoning the drugs. She paid off her debt. She knew that her assortment of maladies was arranged in a “domino effect,” and that by taking out the big player, she’d removed the power the smaller ones held over her.

The point is, sometimes the best step is picking the thing that feels the most damaging or self-defeating in your financial picture and starting there, regardless of what the money gurus tell you is the “right” place to start. 

The reasons we abstain from action are often not because we don’t logically know what to do, but because we’re terrified of making a mistake (and its consequences), and we keep waiting to be “ready enough.” We don’t trust ourselves.

Pick the financial issue that bothers you the most, and start there

If you can’t sleep at night because of your debt and it eats up too much of your mental bandwidth to even consider learning about investing, then make your debt the “first step” focus—even if the interest rate is low, even if you get a 401(k) match, even if you also have a spending problem. 

Release the idea that a “perfect” way to build financial security even exists, and trust yourself to focus your effort and energy on the thing that’s right for you. Once the debt is gone, focus on the next-most important thing—but give yourself permission to ignore everything besides the debt while you’re chipping away at it. This process will take time and may be full of mistakes. Do it anyway.

Maybe it’s your spending. Maybe it’s the fact that you don’t have an emergency fund. Maybe it’s your $0 401(k) balance. Maybe you’re even retired and find yourself unable to spend money, because you’ve equated spending with irresponsibility and a lack of discipline for your entire life, just to be able to retire.

Whatever it is, grant yourself permission to not do it “perfectly.” Concede that your financial progress is not linear; a spending bender one weekend does not mean you’re a hopeless mess who’s once again fallen off the wagon. No—instead, you dust yourself off, get back on the metaphorical podium, and acknowledge that you’re in the process of recovering from your perfectionism paralysis and learning how to trust yourself to make good decisions for Future You. 

Even with the mistakes that’ll happen along the way. 

Forgiveness (and building something better)

Even though my cycle instructor training was almost three years ago now, it opened the door for me to see myself a little more honestly. It required me to explore how to forgive myself for not being perfect. 

(Oh, great, she’s launching into a self-love diatribe—just what the internet needs! But bear with me.)

When I talk to people who are in a lot of debt (or who have “wasted” too much time and feel they’ve missed the boat on building wealth entirely, so they’re paralyzed about how to move forward), I don’t see people with too little discipline or too many trips to Mykonos. I see people who are very, very angry with themselves. 

Feelings of resentment, guilt, and shame toward “past us” prevent “current us” from taking responsibility, learning, and moving forward. The emotions feel like a just punishment, but they’re ultimately counterproductive. (And when the personal finance advice we’re reading reinforces those feelings of shame and guilt? Whew, look out.) 

Whether it’s the perfectionism-driven fear of messing up (most often identified by the statement, “I don’t feel ready to start!”), the belief that you’re not worthy of financial security (most often represented by feelings of anger or shame around money), or the self-defeating behavior that lands you in a pit of loathing every time you open your credit card statement, we cannot establish a better way forward if we continually blame and abandon ourselves. 

Even if it feels cheesy, say—out loud!—to yourself: “I am ready to forgive you for [x].” I am ready to forgive you for getting us into debt. I am ready to forgive you for spending too much sometimes. I am ready to forgive you for waiting until now to start investing. I am ready to forgive you for avoiding the stuff that felt insurmountable at the time.

Fortunately, even if it feels ridiculous, your subconscious mind doesn’t know the difference. If you’ve tried blunt-force discipline to no avail but haven’t tried gentle forgiveness, releasing the idea that the first step must be a perfect one, and trusting yourself to focus on the “right” thing, that’s a great place to begin. 

And if it has to start with an Ariana Grande-induced public cry, so be it.