Dear Captain Awkward,

I am so scared. I keep messing things up financially. I just don’t know how to do it. How to DO MONEY. But it’s a paradox, because I am earning a decent amount.

It’s a paradox about which I feel rather ashamed, because I am aware of my privilege. I come from a middle-class family of financial flailers–always earning a comfortably middle-class salary, yet always lurching, always in debt, always bouncing checks, always living paycheck to paycheck, always STRESSED AS FUCK about money, yet never really changing (or seeming to know how to change) spending habits, or debt, or livingsituation, or whatever the fuck it is you do to live with lower financial stress. I am just like my parents in this regard.

I am so scared. I am always living paycheck to paycheck, and even that isn’t enough. To illustrate what I mean, I often have to stop eating for 3 days before paychecks, I tend to bounce checks once every month or two, and I’ve had to postpone my student loan payments 3 times in 4 months. It is not so easy to just move, either–my rent is pretty decent for the location, especially considering that now I don’t have a car (a crash last summer, another financial fuckeroo), it is important to live near my workplace.

I just don’t know where to start. Whenever I google stuff about getting financial advice online for free, it’s always some advice that comes in the form of happy go lucky blank slates. Like, these super-duper positive people writing how-to’s as though they are teaching the teenage children of rich and stable folks how to save their allowance. Fuck that shit! I don’t want advice that is starting from some elusive, unrealistic (at least for me, but probably for most) baseline of financial stability and emotional okayness.

I want some advice that respects my baseline of terrible credit, shitty habits, major upcoming expenses, MAJOR student loan debt, major shame and self-loathing, and total overwhelm and fear.

I feel so fucked. I am scared.

I know that here, Captain, you tend to respond to stories. However, I also know that you love advice blogs in general, that you’re an aficionado of the genre. Therefore my question is a request for help in finding some other advice blogs: do you know of any places on the internet I can go to find the kind of help, the kind of realistic, open, detailed, respectful advice I’m looking for?

And frankly if you have thoughts on my situation, I will definitely take your advice, too.

Thanks a lot,

Financially Flailing

Dear Flailing,

I hear you that you feel scared—and that you feel especially ashamed because you recognize your relative good fortune to date. Would it help to know that you are not alone, that you are now among the majority in the US? Living paycheck to paycheck—or well behind one—is common, including in folks who’ve had sound opportunity. So kudos to you for actively seeking to set straight what so far feels to you like an impossible situation.

As you’ve found, the advice common in financial guides does not apply to everyone, or at least not to everyone’s starting point. Many such resources assume a near-magical combination of higher-income, plus a naturally frugal bent, plus a supportive family, plus a state of emotional zen, plus a cognitive capacity to navigate institutions ranging from banks to universities, plus plus plus. Not everyone has all of these. Folks with barriers such as stress, grief, cognitive limitations, a difficult family history, an experience of abuse, or a disability are often left to their own devices and, like you, feel embarrassment and shame that they aren’t “succeeding.”

Many mainstream resources don’t help. In fact, they exacerbate the issue by making it difficult for folks to come out of their financial closets. I know it didn’t help me one iota when all the advice seemed to scream, “Be an entirely different person! Become an extrovert! Don’t have Asperger’s or depression! Have more physical stamina!”  Ack. Our financial path must—at its most basic level—honor who we are at our heart, not to mention at our physical capacity.

You’re smart, articulate, and educated but, as you’ve discovered, these qualities alone do not lead to financial success. But other ones do.

As a volunteer, I serve some of my region’s lowest-income people. Interestingly, some had extremely high income (think executive directors and an NHL player) before needing help to secure and then live on $510 per month. As is usually the case, their financial flailing was not about a lack of drive, commitment, hard work, or intelligence. These folks’ careers relied on these characteristics. So what else is at play?

You seem to be painfully aware that you have sufficient income and status, and that there is some self-sabotage going on. This means that while you feel like a failure you’re actually already two steps ahead of the game!

I propose five strategies to help you fulfill your dream of financial well-being:

1. Prepare. Interestingly, preparing for financial recovery involves no file folders, specialized software, or fee-based advisers. Getting ready will involve just the simple step of writing down five free things you can do when you start to feel overwhelmed. What soothes you? A bubble bath? A run? Knitting? Texting with a dear friend? Meditation? A pitch black room? The Pogues on maximum volume? Post your list to at least five key places: your bathroom mirror, your car dashboard, the top of your shoe, your wrist, wherever you will see this prompt to self-soothe rather than spend. When the judgement or panic begins to arise, implement one of your personal self-soothing options. (And if you spend instead? No big deal, because you’re going to put in place the next steps too.)

2. Connect. The primary difference I see in people who transition from struggling to stable is emotional back-up. Many of us rely on spending to alleviate intolerable levels of loneliness, isolation, fear, anger, guilt, and more. Ironically, when we then spiral into shame about our spending, we often spend even more to cope! For this reason, I recommend your second step be putting support in place. For a sociable introvert or a person with a wild schedule, an online forum such as that offered by the Simple Living Network might be the best bet. For a person who thrives in live groups, the twelve-step program Debtors Anonymous can be a boon. If you have access to affordable one-on-one therapy, I encourage you to take that opportunity, too.

Even when these resources use financial floundering as a focus or anchor topic, much more will happen. This is because for most of us, money is attached to loss, hope, grief, attachment, and shame. When we focus on our finances, our money issues begin to resolve but so do layers of psychological struggle. When we act on one, we are inherently acting on both. So in healing financially, it is critical to have support not just to spend more judiciously, but to live through the emotional layers that arise when we shift the very way we’re interacting with our world. Your support person or group provides practical support while simultaneously (and more importantly) caring for your heart—walking you through your shame and out the other side while you implement change.

3. Envision. Take up to an hour to consider your personal goals. What are your dreams? When you see yourself in twenty years, what is your life full of? What does that look like, smell like, sound like, taste like? Pull related photos out of magazines, jot down key words, or chat about it into your phone or video camera. The sky’s the limit. Record everything you truly desire materially or environmentally. Silence? A turntable? An English country garden? The opportunity to raise a child?

4. Assess. Does your current lifestyle match this vision? If your heart tells you that in the future you want a peaceful cottage to write in, does spending $4 on ice cream today align with that? Don’t judge or kick yourself. Just notice. Watch yourself as though you are a scientist—a neutral third party curious about the patterns.

5. Record. On any given day, write down every penny that comes in to your life and every penny that goes out. This includes the dollar to the busker and the auto-debit for the internet bill. This activity can seem intimidating, because we anticipate seeing evidence of unmitigated disaster: pen hitting paper minute by minute, volumes of scrawled notes. It needn’t be overwhelming, though, and in fact can be strangely soothing. When we record in a notebook every penny as it goes out or in, we begin to see the power we have—the choice we get to make from moment to moment. We give ourselves a glimpse of our healthy decision-making capacity. Record nothing from before this moment, and nothing from beyond now. Just this moment’s transaction. As you record, accept your feelings. (Rely on your list for self-soothing.) Don’t try to modify your spending; no one else need see the information. Just record. Do this in as many moments, on as many days, as you feel up to it. Your consciousness will take it from there.

Once we have these five elements or practices in place, we naturally take steps to increase our income—asking for a raise, babysitting for a neighbour, snagging that grant—and decreasing our expenses—applying for a halt in student loan interest, canceling the gym membership we never use, inviting friends to a potluck in place of our usual Friday night restaurant outing. We do these one at a time, as our support team helps us to.

When we’ve connected more deeply with ourselves—and recognized our right to honor our truest self—we begin spending on that which aligns with our own deepest values, and declining to spend on that which others told us we should want: marriage, a magazine subscription, the university degree. Of course, the actual details of what we spend or save on are unique to each person, which is why our financial journey is often one of achieving physical, psychological, and relational freedom as well.

When we align our finances with who we really are at heart—ditching other people’s priorities in favor of honoring our own values and dreams—the perplexing paradoxes resolve. In the end, it seems that near-magic is involved after all, but it’s you who creates it.

Joon Madriga was marginalized by a severe yet undiagnosed brain-based disability, which left her on the streets. She subsequently found her way to help herself, then thousands of others. Her recently released book, Rising: Strategies for the Broke, the At-Risk, and Those Who Love Them, is available on Amazon.com. She blogs at financialtipsforthebroke.com and welcomes your questions and struggles there.

Moderator Note: Readers, feel free to recommend other resources & techniques in the comments. I’d prefer to see recommendations in the form of “X site/forum/tool worked really well for me, here’s how and why” over “You should try X.”