How can I stop hating everything about money?

Welcome to Ask Amanda, Sherwood’s Financial Advice column. Have a thorny money matter you need help with? Get Amanda's insight by writing her at advice@sherwood.news

Dear Amanda,

I am at a loss with money and for a long time ignored it because it felt overwhelming or boring or frustrating, but I'm trying to get over myself and take better care for the future. I worry that I'm starting too late, though. I'm 50, am divorced, have a teenager and only a handful of investment accounts I don't really do anything with (I don't contribute, etc. — when I was married and filing jointly, I was told to not contribute and wait till the end of the year to see what the numbers were, and I never remedied that set-up). I also don't have a college fund — my kid's dad opened it in his name, so it's his now. My parents have an account for my child as well.

What do I need to focus on to get my affairs in order? I also have a little credit-card debt that despite making large payments and moving a large portion to a no-interest-for-18-months card, I can't seem to make a good dent in. There are always things coming up with high costs that take any extra money I have (weddings, car trouble, kid stuff).

I'd like to buy a house in about six to eight years, not in a major city.

How can I change my relationship to money and investing that will help me be more thoughtful and proactive when it comes to saving and planning for the rest of my life?

Thanks,

-I hate money and want to ignore it

Dear IHMAWTII,

Let’s begin by meeting you exactly where you are: hating all of this and wanting to ignore it. 

Why there as opposed to, say, recommending a program of abundance mantras and deep-breathing exercises to help you white-knuckle your way to a 10-year plan? Because those feelings you describe are the truth, and suppressing that truth takes so much energy that there’s very little left over for the constructive actions you’ve identified. 

Money is overwhelming, boring, and frustrating. It’s also exciting, enraging, threatening, and titillating. Money pushes all kinds of buttons, so before we can come up with any strategy to manage money we need a strategy to manage feelings. If we don’t address these feelings, we can expect to see patterns of avoidance punctuated by impulsive attempts to fix problems, all of it narrated by what I imagine is a pretty negative self-talk soundtrack that starts blaring in your head every time you open your banking app. 

So let’s hate money. 

Why? Because I want to show you that hating it is not the problem. “Hate” is simply the label we use to describe a conditioned fight-or-flight response attached to deeper feelings of pain and vulnerability. 

As the negative association gets repeated over time, aversion to money tasks becomes strengthened, and avoidance becomes the predictable response. The result of this cycle is that “I hate money” becomes not just a description but a destiny, one that becomes part of our identity, if we let it. 

And that’s not you, or more accurately, that’s not all of you. A part of you has learned to manage emotional regulation by limiting the attention you pay to money. But if we create a process to approach money safely, we can decondition the intensity of the aversive response and give your brain and body the opportunity to repattern around feelings of competence, purpose, and self-trust.

As an example, let’s start with what seems to be the most straightforward item on your list of financial concerns: having multiple unattended investment accounts. A simple goal might be to make an updated list of your accounts and their current balances while staying present with your emotions throughout. 

Here’s a template for this task:

• set a timer for 20 minutes 

• sit down; take 2-3 minutes to transition 

• ride through the peak of your emotional discomfort 

• make your list 

• transition out 

• give yourself a reward 

That probably sounds like a lot of steps for a simple list! But remember, the hard part of this work isn’t the accounting; it’s the avoidance. Let’s break down the components of how this works. 

The time boundary

Think about the last time you sat down to “do money.” What was that experience like? For those of us who operate in an ongoing state of looming financial to-dos, delving into money can be like opening Pandora’s box, an unknown territory where reading a credit-card statement might turn into a three-hour rabbit hole of stress and frustration. We’re not taking that risk today — we’re “doing money” for exactly 20 minutes. 

Establishing a time boundary reduces avoidance by telling our brain and body that the unpleasant task that we’re going to undertake is not going to last forever. When working on ingrained avoidant patterns, I recommend starting with regular, brief exposure sessions where there is a focused and concrete task. The goal is to practice opening the money box, doing the task, closing it, and putting it away. 

Transitions

What do early-childhood experts know that adults tend to forget? That humans don’t change focus in the blink of an eye. Classroom best practices include time to move between arrival to morning work to lunch to quiet time. This need isn’t something we outgrow. 

The transition is where we coax the “I hate it” part of you to sit down at the table, and we do that by listening to what it has to say without judgment or self-censoring. My favorite transition tool is music because songs can help us express thoughts and feelings we struggle to articulate on our own. They also provide an opportunity to incorporate the body by singing or dancing to move through our physiological arousal state more efficiently, and, importantly, the average pop song lasts about two to three minutes. Perfect!

I’m imagining you sitting down at your desk, and before you dig out your investment account log-ins, you blast “I Wanna Be Sedated” by The Ramones. If ’70s punk is not your vibe, here's a helpful playlist of angry songs to speak to your rebellious heart. Alternatives to a musical transition include aerobic activities like jumping jacks or giving your limbs a vigorous shake, grabbing a pen and doing a brain dump, or writing down scary thoughts like “this money problem is too big to handle,” and then tearing the paper apart with your hands. 

Peak and flow

Ideally, the transition helps us ride through the peak intensity of that initial avoidance. We know we’ve passed the peak when we’re able to hold the nuance of both, “This is so friggin’ hard,” AND “Look at me doing something hard!” That is the sweet spot of effort, and with repetition it’s how we soften the intensity of the avoidance cycle. 

Task specificity

You’ll notice that in the instructions for this activity, we selected the most straightforward financial task from your list. That’s because it’s important to set ourselves up for success, especially in our early efforts. 

Structure each brief money session as an opportunity to award yourself one gold star for accomplishing one specific task. (These can be metaphorical gold stars, where you take a moment to bask in the warm feeling of a job well done, or it can be an actual sticker chart because, no shade, those things work.) Resist the old Pandora’s box goal creep where you keep working until your exhausted collapse. No, I want you to think of each task as a separate opportunity to gobble a gold star like Pac-Man devours pellets. 

Transition out

Before you say “But Amanda, clearly you don’t understand that my financial life needs a complete overhaul and there’s no way that can be achieved in 20 minutes!” please let me assure you that I understand the pressure you feel. In fact, we should assume that you will end many of these engagements, especially in the beginning, feeling acutely aware of all the things you are not yet getting to. 

The Transition Out part of the activity is where we park the “Can’t relax, have to keep going!” fear. Write down your next steps and use that to map out your plan for the time, place, and focus of your next session. 

And what if it just went really well and you want to keep going? No matter how compelling it might feel to ride that productivity streak while you’ve got it, it’s still important to end here. In fact, stopping while you still feel like you’ve got energy left in the tank helps your body code this experience as safe to engage in the next time. 

Reward

Your very next step is to seal this conditioning experience with the best part of the process, the planned reward. What people find rewarding can vary by person. Some of my clients have followed their efforts with a glass of wine or an episode of trashy television. I’d be lying if I didn’t admit to a fair amount of sugar, sloth, and sin rewards in my own various self-improvement journeys, and this may be one of those areas where you want to extend yourself some grace. However, make sure to keep the planned part front and center so you don’t inadvertently slide from “reward” (an episode of TV, a glass of wine) into self-soothing (binging an entire season of content or using substances to numb out).

Repeat

When do we get to the part where this changes your life? We get there one 20-minute session at a time. With each exposure, we incrementally improve our situation by accomplishing a concrete task, and we weaken the intensity of our emotional aversion by learning to move through the feeling instead of reinforcing it with avoidance. 

How often should you schedule these sessions? My frequency recommendation depends on the urgency of the circumstance balanced with the level of resistance you experience when overwhelmed. 

You mention a mix of concerns, from managing cash flow and debt repayment in the immediate term, to longer-arc goals like financial preparedness for your child’s college and your own retirement. Using that as the framework but being mindful about overdoing it, you might set an initial goal of four weekly sessions, two to review and plan your cash flow, and two for tasks related to planning and investment. Whatever your exact plan, make sure to put it in your calendar! After that first month, assess how it went, and the next month, see where you can keep going or need to adjust. Step out of the pass-fail mentality. Experiment, plan, and play, but above all keep bringing yourself back to the arena. 

Because you’re worth it

When we’re used to suppressing and invalidating our emotions, it can seem self-indulgent to prioritize our felt experience. I hear this when you say you need to “get over yourself” and do better here. You even worry that it’s already too late. 

These are cognitive distortions that shut us off from possibility by telling us that the change we seek is too hard, not worth it, or requires an impossible trade-off (like the sacrifice of our emotional truth). 

But here’s a different way to think about it: your money is providing you with an incentivized path to grow and heal. It sounds like there were some painful relational dynamics in your marriage that played out in the planning and investing space. To remedy those, we don’t need to get over it; we need to get into it.

We can assume money is going to continue to kick up feelings — both good and bad — as you navigate the challenges and chapters of your life. But by learning to move through these states instead of getting stuck, you retrain your body and brain to react differently. This is the foundation of a healthier relationship with money, and that definitely deserves all the gold stars if you ask me. 

Previously on Ask Amanda: How can I stop spending all my extra money on junk?

Amanda Clayman is a financial therapist whose work has been featured in The Atlantic, The New York Times, and The Wall Street Journal, and her podcast, Emotional Investment, is available on Audible.