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 She blogs at 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.”

Hello Captain Awkward,

I have a long question about how to get a family member to pay back the money they owe you. First bit of background: I recently got married and moved to another country VERY far away. It’s been almost a year now and really wonderful (except where my sister is concerned).

My “close knit” family (ie- intrusive at best and emotionally abusive at worst) has not taken it well. My sister and I grew up incredibly close and she was an ally to me with our parents/extended family (usually). She’s one year older than me but we always hung around together and went to the same college ect. Long story short, she’s always been a high achiever but also immature and VERY emotional/needy. There’s some deets behind that but I won’t get into it.

Well cue a few months after the move she informs me she just booked her tickets and is coming for 10 WEEKS and can’t wait to STAY WITH US! We live in a studio apartment, are still getting settled, money is tight, and we are literally newlyweds. I tell her hey this may not be the best idea but she insists she has so much travel she’ll be doing she’ll hardly be there plus it’s booked and she’d have to pay a massive fee to change. Okkkk i guess? She comes and is an absolute bitch. Every day she wants to go out (spend heaps), never pays for anything like groceries or household items, even makes my husband do her laundry (long story), and complains shes bored. Has more than one crying session about me making her feel like she’s “not a guest”. Everything is about her even when she literally lit the kitchen on fire – really tho, big fire (really long story). Apparently it’s so hard for her to be home all day with nothing to do but refuses to do anything by herself (except lighting the kitchen on fire – that was all her). She’s a passive aggressive bitch and I’m stressed to the max.

Turns out that travelling she wanted to do… She thought I’d be going with her (but not the new hubs) Ugh. I refuse to take more than 2 weeks vacation. Those 2 weeks were all about her and quite frankly stressful/not fun at all. She takes up all my additional time and is so HORRIBLE even my new burgeoning friends notice how mean she is to me. But hey it’s family and I’ll deal. In hindsight it was like she took every script out of our mother/family’s emotionally abusive playbook and threw it at me and I should have kicked her out.

Anyways, here’s the real issue. She kept asking my husband and I to pay for things on our card because “hey we’re booking together it’s easier to just do it at once” and she’d pay us back. Also at one point her wallet was stolen/lost and she had to get new cards sent ect which took a while. Recipe for disaster I know (now) but I also know how much she makes (ALOT more than me – we’re talking mid 6 figures) and that she would definitely be able to pay back. We had a long talk about her paying us back right away – she agreed. We’ll long story short, trip ends we present the spreadsheet with everything she owes us and she says she’ll pay asap, when she’s home no problem.

Now that she’s left she won’t pay us back, is dramatically bad mouthing me to all our family – who in turn are sending me harassing emails, says I’m bullying her ect. And she will not respond to any of my emails (they are actually quite nice). I’ve said basically is everything OK? I’m concerned about you. If you can’t pay back now lets determine a timeline/payment plan. NO RESPONSE at all. We didn’t even ask her to pay the apartment deposit that we obviously lost because of the fire she started (possibly/likely on purpose). Which was a lot of additional money!

It’s been 6 months since she left and we really need the money. I’m at a loss about what to do and honestly devastated that one of my closest relationships has been ruined but also that she’s ruining a lot of my other family relationships which used to be really important to me. With me being so far away I can’t defend myself and I’m feeling really isolated (I’m sure that’s her intent).

No one in my family is helpful and basically have all sided with her in a very “I don’t want to get involved but…” way. So no allies there. Some of our mutual friends have stopped speaking with me as well and it’s hard to enough maintain contact with the distance even without this drama. I think I have some details on the BS she’s telling people but it’s so long I can’t really fit it all in here.

Please help me with scripts to use with her – at this point just to get that money back, but also with other family members and my parents. I just have no idea how to handle this anymore.

PS- she’s gone on multiple vacations since she gone back to the US (long weekend skiing in Vale, now she’s just gone to some exotic island for a week long “girls trip”, 2 different weekends in Vegas) all of which are clearly on the luxury end. My parents love to tell me how great she’s doing, how much money she’s making and how great it is she can afford to travel so much, and she didn’t need to even move out of the US. Which is very upsetting.

B*+ch better have my money

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Dear Captain Awkward,

I have a great, strong, smart female friend who has fallen head over heels for her boyfriend. They’ve been dating for under a year but already live together.

This friend has been attending a weekly trivia night with us now for over a year. When the new guy came on the scene he said how much he loved trivia and asked to join. We are a very inclusive team with friends from all over so of course we let him.

While he isn’t the favourite at trivia (he is very competitive and we are very bad at trivia but we have fun) things had been mostly fine, until he lost his job. He has been unemployed now for about 4 months, which I get is tough. However, he went from having a few beers at a casual Monday trivia to having 6+ over the course of 2 hours.

It’s awkward when he gets drunk for sure, but again I could have put up with this. I get it being sad about not having a job is hard. However, in the last month there has been a pattern of him not paying for said drinks. The bar we go to refuses to do separate tabs, so what often happens is people put their cash down and go. Consistently it seems he doesn’t put enough in or any at all, and by the time we realize those of us who are left are stuck with the bill. It’s one thing to forget once or twice, but it seems to be a pattern.

I’m not really sure what to do. I don’t want to embarrass him, and I don’t feel we are good enough friends for me to confront him about it. But I also know my best friend wants to spend the rest of her life with this man, and I’m worried that if I bring it up she’ll get angry with me. Money is such an awkward subject, what do I do?

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Can I say how much I love this LW’s original email subject line: “A Soap Opera Problem–families torn apart over money, demanding parents, undutiful daughters who are me, sons trying to bear the whole burden.” Yeah!!!!

Dear Captain Awkward,

I’d really appreciate your advice on a family problem. Dad grew up
privileged, then was mostly-disinherited and lost his job when I was a
kid. Instead of retrenching, he incurred debt. Mom demands luxuries,
cheats, and is an alcoholic prone to rages. Now Dad asks me and my
brother A for money constantly, always at crisis moments.

Dad always believes that his financial issues will be over soon.
Unfortunately there’s a company he has a part in being sold, meaning
he might get some money one day—there’s some basis in reality but not
enough. He refuses to sell his house, because he wouldn’t get enough
money, and claims to be always economising because he doesn’t go on
holidays though Mom does and he belongs to an elite gentlemen’s club.

A and I have precarious jobs in which we are paid in irregular lump
sums, so we have the money to give him. We both consider ourselves
lucky. The emotional toll of these emergency requests is huge. We also
cannot afford them. Over 5 years, between us we’ve given Dad over

I wrote to Dad saying his behaviour is disordered and deeply hurting
us. He refused to go to his bank with us, blamed A for not giving him
enough, and hardly seemed to have read my message. He’s past hearing.
Saying he’s a good father otherwise is asking Mrs Lincoln how she
enjoyed the play otherwise.

I tried cutting him off altogether years ago: it ended when my
siblings exerted pressure on me to do a family Christmas. I’m proud of
my siblings (A, B & C, all younger) for getting through our childhood,
but I’m the one who rocks the boat. A gives money to Dad without me
knowing, so as not to risk alienating me. A has a more optimistic view
of the situation. My sister B agrees with me mostly, but B and C are
more sheltered (by me and A). C is college age, still living with my
parents. He’s begun suffering from panic attacks. He plans to get out
of the house next year: I’ll help him.

I’m considering not going home this Christmas, but I know it’ll upset
my siblings and I want to see C as neither of us is great at
long-distance. If I do go I’d like a script for talking to A, and my
other siblings, about this, and to make a plan for us going forward,
in how we’re going to react to my parents and stick together. I’ve
asked A to promise me not to give money to my father without telling
me: so far he hasn’t promised. It would make me happy if I could get A
to agree on no more money given directly to my father.

Thank you so much.

–Saving Only Siblings

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Ahoy Captain,

Several years ago my fiance and I started hanging out with a guy named Devon*. At the time we started hanging out with Devon he was having a lot of personal problems. He was living in a hotel that he could barely pay for, slept all day and stayed up all night, and seems to have had a minor drug problem. Fiance and I, seeing that he was in a difficult situation, invited him to come live with us for a few months.

It’s been two years.

I like Devon, a lot, and I enjoy hanging out with him. He’s a sweet guy and being around him is simple and fun. I don’t necessarily want him to move out, which I guess is good for me because it doesn’t look like he’s going to any time soon.

Devon is now has a job, doesn’t do drugs, and kinda sorta pays rent *sometimes*.

My real problem, though, is housework.

I think it’s only fair that Devon take some responsibility for the house work. I’ve tried to talk to him about this so many times I’ve lost count. He always brushes me off, says he’ll do it ‘later’, he’s tired from work, or that the dishes in the sink aren’t ‘his’.

These excuses are childish the point of hilarity. I don’t argue about whose shit stain is whose on the toilet when I clean it, why does it matter whose dishes they are??. I brought it up again last night and he said “well I keep my room clean”. Well yeah, that’s all fine and dandy, I don’t expect him to clean my bedroom. I DO expect him to help with the kitchen and bathroom, which everyone uses every bloody day.

I’ve tried multiple tactics:

I’ve tried telling him what is expected of his as a member of our household

I’ve tried gentle encouragement

I’ve tried reasoning with him

I’ve tried yelling at him

I’ve tried explaining that it’s not fair for all the housework to fall on my shoulders since I’m not a damn maid

I have even tried boycotting all chores in the hopes that the revolting state of the house would encourage Devon to pitch it. The only outcome of that is, after a few weeks, the house (especially the bathroom) became so disgusting I couldn’t stand it anymore and I cleaned it myself.

What am I supposed to do about the cleaning short of kicking him out? I feel like I have tried everything. It’s driving me completely batty. In the past few months I don’t even bother doing more then a perfunctory clean because everything is always messed up 5 minutes later anyway. Sort of like in that episode of The Simpsons, “Bart Gets an Elephant” where the kitchen door opens on a clean kitchen, swings closed, and opens messy (sorry couldn’t find the gif) [Ed note: FOUND IT]!

Kitchen from Bart Gets An Elephant


I can hear him cooking in the kitchen now and just dread the stupid mess of discarded vegetable parts that will be everywhere in about 20 minutes.

I have been very explicit about my expectations but he just doesn’t hear it. I’ve even asked my fiance to speak to him about it in the hopes that maybe he would be more inclined to listen to an older man. Nothing. Same brush off.


Molly Maid

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Ahoy, Captain!

My partner and I have been together for about three years now. We don’t live together, but lately my partner has been saying that he would like to start cohabiting –  not necessarily immediately, just at some point. Mostly I’m the one saying “let’s not.” There’s a few reasons for that, but a major one is financial.

I work full time at a higher wage than my partner, who works part time. He’s frequently out of money by the time his next paycheque comes, while I can count on one hand the number of times I’ve been straight-up broke, even when our incomes were more comparable. When we go out, I usually pay, which is not a problem for me; I’ve also occasionally lent him money for things he really needed, like a bus pass at the beginning of the month, and when something is clearly expressed as a loan, he’s fairly good about paying me back. However, I’m not totally on board with the way he prioritizes his spending. For example, his bed frame has been falling apart for the last year and a half. He said he couldn’t afford to replace it – but in that time, he’s definitely spent more than the price of a cheap Ikea bed (let alone a Craigslist find) on books and games.

I’m not criticizing him for spending his money on things he likes. It is, after all, his money! He’s a grown-ass man and he earned it. I’m also not his mom, and neither he nor I wants me to nag him about financial responsibility. Basically, I just slap a big ol’ Not My Problem sticker on about 90% of his cash flow crap and move on with my life.

My concern is that if we do move in together, I will start shouldering not just most of our financial responsibilities, in accordance with my larger earnings, but ALL of them. I worry that if we did get together, he’d know that the rent would get paid and food would get bought no matter what, so why not go ahead and spend whatever he feels like – not inconsistent with what I know about his spending habits. He’s also got a big pile of student loan debt, and if we’re cohabiting and eventually end up being common-law, I don’t want to take on responsibility for that.

It feels cold, but basically, I’m afraid that moving in with my partner will mean taking a financial hit. It’s not necessarily one that I can’t afford, but it is one that I don’t want.

I’m not immediately on fire to move in with my partner right now – it probably wouldn’t happen anyway, for a number of reasons – but should I mention this to him as part of my reasoning? If so, how do I do that? And if we do decide to make that commitment together, how do we address this problem as a couple?

Many thanks,

Not Subsidizing Anyone

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Ahoy Captain,

I’m writing this after reading about the LW who kept getting stuck with the check.  I’m in the inverse of a similar situation, and I’m not sure of the best approach.  I’ve just started a job in an awesome place with a bunch of wonderful, appropriately friendly co-workers.  Apart from loving what I do there, this job will (slowly) get me out of a pretty grim financial situation created by student loans and intermittent work over the past two years.  For now, though, I’m on a skeleton budget and can’t afford much by way of unnecessary stuff, which is where the problem starts.  My co-workers have all worked together for a while, and they do this cool thing were they go out to lunch together a lot and take turns either paying for lunch, or collecting money from the office to run out and get food.  They invite me frequently, and once or twice have covered me for lunch on the rare occasion I forgot to pack one. I’d love to participate, but I can’t at the moment due to being behind on a lot of crucial bills.

The trouble is that it’s getting to the point were it feels really weird to be constantly opting out of these lunches, especially since we’re a small office, and the fact that I don’t volunteer to pitch in for food runs is creating some very awkward situations were I’m constantly removing myself from the rest of the group.  I know I’m coming across as either stingy or unfriendly, which concerns me because I really want to make this job a pleasant environment.  But it’s realistically going to be a few months before I can afford to do this, and I don’t want to explain my financial situation to my colleagues.  Are there any scripts or tips you and the awkward army know of to navigate this embarrassing situation?


Economic Casualty

Dear Economic Casualty:

The first ever Captain Awkward reader question was about a similar topic, with friends and money and eating out. So, hey! We’ve come a long way.

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