A Story About Paying Off Debt and the Obstacles Along the Way

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My Career Break One Month In: Ask Me Anything!

Four weeks ago, I pulled the plug on the worst job I've ever had (a job that capped off a series of other not-so-great employment situations) and embarked on an indefinite career break.
In the 28 days since then, I've been doing a lot of what I thought I'd do with my time off: blogging, cooking, running, working out, learning Italian, catching up on Netflix series, spending time with my son, napping, daydreaming, and basically letting myself meander. I've also done a few things I wasn't planning on, like applying to a couple of dream jobs, starting a petsitting business, and meeting some of my favorite personal finance bloggers.

I don't always have something specific to do, but I'm rarely bored. As trite as it sounds, it's been everything I hoped it would be and more.

To celebrate my first month of freedom, I took to Twitter and invited (begged?) people to ask me anything about the experience so far. Props to those of you who indulged me. Here's what some of you wanted to know:

How did people you know IRL react to your decision?

There's an Olin Miller quote that says, "You probably wouldn’t worry about what people think of you if you could know how seldom they do!" It's so true. Almost everyone I told has been supportive, at least to my face, but I suspect many of them are thinking nothing more than, Cool, that's nice. Friends and family who are happy in their work have congratulated me for doing what's best for my well-being; those who are dissatisfied with their work lives have generally expressed a desire to walk away from their jobs, too.

My break has spurred some really thought-provoking conversations with a few of my friends about workplace culture and expectations. Almost everyone has a handful of nightmare stories about previous or current employers. Clearly, we have to advocate for ourselves - which may include walking away if we're being treated unfairly or subjected to unsustainable circumstances.

I did encounter one particularly awkward situation right after I quit. I was with a group of people, some of whom I knew, some of whom I didn't, and everyone had to take turns saying what they did for a living, which in my opinion is a strange way to introduce yourself. My response was met with polite silence. I was feeling raw and self-conscious, so that was hard for me. I've also encountered people who want to give me unsolicited career advice. I know they're trying to help, but I wish they'd ask first.

Do you wish you'd done it sooner/pulled the plug this way from your prior position?

Hindsight being 20/20, I wish I'd never taken the last job at all. Had I known what it would actually be like or that my employer wouldn't pay me my final paycheck (that's right, they've ghosted me, and I may never see that money), I would have never pursued the position. I suppose I wish I'd stuck with my former job for a few more months, saved as much money as possible, and then quit to take some time off, which was actually something I started considering early last year. But I jumped into the most recent job because I saw it as an opportunity to learn some new skills and grow my career in a different direction.

In reality, my work hasn't been working for me for years (I'm sure it's partly me, but friends have also told me that I've had a string of really bad luck with jobs), and a career break was probably inevitable at some point. It was just a matter of when.

What is the thing you're missing about your job? 

This question stopped me in my tracks because it made me realize that the only thing I miss about my most recent job and the two before that is the paycheck. That's it. I do not miss the stress, the micromanagement, the unclear expectations, the many pointless tasks, the lack of room for creativity, or the feeling of being a cog in a big machine designed to make substantial money for a handful of people.

Note to self: the next job cannot be anything like the previous three jobs.

What’s been the scariest thing you’ve experienced in this career break?

For me, the scariest thing is not knowing what's next. I wish I could say that I have some sort of plan, but... I really don't. By nature, I'm a planner; I like to have a sense of what my next move is. In this case, though, I have no idea. Few things sound good to me at the moment, in part because I feel so burned (and hurt, if I'm being honest) by my last job. I'm terrified of getting into another bad situation.

For now, my strategy is to sit tight (thinking back to that "what to do when you get lost" analogy in my quitting post) and go with what feels good to me. Applying for full-time jobs willy nilly, scrambling to land freelance work, and networking for the sake of finding an "in" don't feel right at the moment. Spending time with friends and family, exercising, chilling out, and working on my own creative projects (like this blog) do. The same goes for petsitting. I have no idea whether that'll be an occasional fun gig or whether it will turn into something that brings in some reliable income, but it's something that energizes me, so I'm pursuing it.

What anxieties have changed, disappeared, or have been replaced by something new? 

Although my anxiety has not disappeared since quitting, it is now manageable. Some of my mental health issues are innate: I'll always be prone to anxiety and depression. For example, I felt pretty panicky yesterday, but with some focused breathing and exercise, I was able to work through it by lunchtime. Other aspects of my mental health are clearly exacerbated by certain situations (like impossible 60-hour work weeks!) Take away the negative situation, and boom, I'm calmer, more relaxed, and more in control. I think that last one is really important for me: I hate feeling like someone else is in charge of what I do hour to hour, minute to minute, all day and on a daily basis. It makes me feel trapped.

My hunch is that many modern workplaces, with their unrelenting focus on productivity, personality, metrics, and feedback, are breeding grounds for mental health issues. Once I distanced myself from that toxic brew, I felt better immediately.

Are you finding it easier or harder to stay on your new budget?

Easier! It's been a thousand times easier to adhere to our budget now that I'm on a career break, and I think there are two reasons for that. One, we know we have to conserve our money, and we have an enormous incentive to do so. Every penny we don't spend is a penny we can use to buy more time. Time feels more important than anything right now, and if sticking to the budget means I can afford a longer break, well, I'll stick to the budget.

Two, because I feel less stressed out (see above), I don't feel the need to look for diversions or stress relief. For example, going out to eat used to be a way for me/us to let off some steam after a long week of work. Our evenings are so much more relaxed now. Eating dinner at home provides the same benefits as going out used to do.

It helps that we have a little miscellaneous spending ($100/month) built into the budget. For the most part, we're using that money to purchase things for our son, like replacements for his ripped pants (I don't know how, but he destroys them) and admission to the summer soccer league. Although we want him to understand why we're on a tight budget, we don't want him to miss out on all the things he needs and cares about.

In reality, I don't feel like we're missing out on much. If anything, we feel richer in time.

Would this career break have been possible if you were a single parent or had a spouse that also wasn’t working full time?

I think it would have, but it would have taken far more planning and saving. My partner's salary covers about 3/4 of our monthly expenses; our savings cover the rest. Therefore, I have quite a bit of runway for this break even though we don't have tens of thousands of dollars in our bank account. If I were a single parent or had a spouse that wasn't working full time, I would have wanted to have at least a year's salary in savings (maybe more) before calling it quits. It would have taken a long time to accumulate that money.

What would you tell someone considering similar?

First, I would tell everyone - EVERYONE, even people who are happy at work and have no current desire to leave - to start saving now. You need an emergency/FU fund because you never know what will happen at work. Gone are the days of employer loyalty and workplace stability. All it takes is one reorganization, one bad boss, or one poorly conceived office policy to throw your entire work life into disarray.

If you're even slightly unhappy in your job right now, this is the time to save aggressively. Sure, it's possible that your situation will improve or that you will develop effective coping skills, but it's also possible that your situation will continue to erode or that all the coping skills in the world won't be enough to shield you from the BS being thrown your way. Depending on your salary and your budget, it could take you months (or longer) to build a sufficient FU fund. So don't wait. Begin contributing to that FU fund ASAP, and save enough that you could sustain yourself for an extended period of time without a salary. (I know that sounds much easier than it actually is.)

Second, I would also say that if your job is seriously impacting your health, you need to get out. Personally, my sleeping habits are my canary in the coal mine. If my job is making me feel so stressed out and anxious that I can't sleep at night, it's time to leave. On the same note, if your job is making you feel suicidal and your coping strategies aren't working, you need to leave as soon as possible - even if your safety net is flimsier than you'd like it to be. I know others would disagree, but as someone who's been in that situation, staying can be incredibly dangerous. (I feel obligated to say that if you are suicidal, you need to prioritize yourself and reach out for support. In the U.S., contact the National Suicide Prevention Lifeline at 1-800-273-8255 or, if you're like me and hate the phone, send a free and confidential text to the Crisis Text Line.)

Third, if you do have a financial cushion and you want to leave, just go for it. Let's face it: unless you've achieved financial independence, there will probably never be a great time to quit your job and take a break. So yes, it is a bit risky, but with a little planning, you'll figure it out.

At least, that's what I'm telling myself. I'll let you know how that goes.

Lastly, if you do take a career break, realize that it's like any big life change in that it involves an adjustment period. You're going from doing a lot all the time to doing perhaps not that much. Slowing down can be a challenge, and it's easy to feel guilty for not being productive. For me, that sense of "I'm so lazy" lasted about a week. Then I started to lean hard into those afternoon naps.

Did your outlook on life change?

I think I've always been kind of resistant to traditional work, which is probably one reason why I've struggled so much in my previous jobs. I've been happiest in low-stakes part-time jobs, in jobs with lots of time spent outdoors, or when I've had the freedom to approach tasks and problems without being micromanaged. This career break is reminding me that I'm at my best when I'm not trying to stuff myself into a situation that I'm clearly not designed for, and I hope I won't try to do that anymore. It's also reminding me that contrary to the unremitting message that our capitalist society sends to us, there are many ways to approach life and work, especially if one is willing to live frugally. Although there is nothing wrong with 9 to 5 work - in many ways, it's ideal - there are other options, too.

Career breaks are becoming more common and more popular. I'm choosing to believe that decent companies won't hold it against you when you're ready to jump back into the employment pool. In fact, some people - like this guy (who, granted, is probably rich) - take career breaks on a regular basis because they see them as a way to stay fresh in their fields:

What’s surprised you the most during your career intermission?

I've been most surprised by how this intermission seems to be impacting my family in positive ways. There's a part of me that feels guilty for not bringing in an income, for expecting my family to adhere to a tight budget, and for putting the aggressive repayment of my partner's student loan on hold - not that Fortysomething has ever indicated that he's resentful of any of these things. In reality, everyone seems happier now that I'm more relaxed. My kid gets as much time as he needs with me when he comes home from school; we go over homework, study for tests, and talk about his day without me having to worry about getting back to work. My partner just seems relieved that I'm not crying and ranting on a daily basis. It's clear to me that my job stress was putting a strain on our relationship. That strain is gone now.

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Stretching Our Budget While Living On One Income

As I begin writing this, I'm 19 days into my career break. Almost three weeks ago, I fired my employer and walked away. I didn't know what I was walking to, and I still don't. My main goal was simply to distance myself from the flaming bag of dog poop that was my last job.

I'm happy to say that since then, my anxiety has plummeted, I'm less irritable, and I've been able to think more clearly. I'm no longer running on fumes. I'm not making decisions based on fear. People I see on a regular basis have told me that I look different, as if a weight has been lifted.

Nevertheless, I occasionally wake up in the middle of the night to a herd of questions thundering through my brain. What do I want to do next? How many months will our money really last? Will our side hustles pan out this summer? Why aren't there more part-time gigs listed on the job boards? What if I never get hired for another job ever again? 

Just Breathe

I calm myself down by reminding myself of a few things:

First, we've budgeted for this break as carefully as possible given the circumstances. At best, I can afford to be unemployed until the end of the year; at worst - if unexpected expenses come up or Fortysomething's bonus is less than we've predicted - we still have several months of runway.

Second, we've spent the last two years saving and budgeting, and we've developed wallet-friendly habits and strategies that are pretty much second nature by now. For example, we have only one car; Fortysomething and the Kiddo walk to work and school, and we usually spend less than $30 a month on gas. We don't go on expensive vacations. We don't impulse buy. We don't spend unnecessarily on things like home decor or new clothes. We've cut way down on going out to eat, and when we do, we often use a gift card. By slowly changing our habits over a long period of time, we've acclimated to a relatively frugal lifestyle. That's paying off for us now.

Lastly, we've recently implemented several additional, effective measures to conserve our savings and staunch the flow of cash from our bank account. Some of these measures involve us bringing more money in, while other measures involve spending less. Either way, they're helping us stretch our savings as far as possible, which is important because we can't afford to live on one income indefinitely. This career break comes with an expiration date.

Five Ways We're Stretching Our Budget

1. Fortysomething adjusted his W-4. 

As soon as I quit my job, Fortysomething met with his payroll administrator and updated his W-4. Previously, he'd been claiming zero allowances; now he's claiming two, which means less of his paycheck gets funneled to taxes. The upshot is that his paycheck has increased by approximately $180/month.

Sidenote: Definitely check with someone who's actually a money expert, but if you're currently claiming zero allowances on your W-4 and you're paying off debt or dealing with a tight budget, making a similar adjustment may be worthwhile for you. Your tax refund won't be as large, but the "extra" money you bring in throughout the year can catalyze your debt payoff and/or give you more financial breathing room. The W-4 form includes a series of questions that can help you determine how many allowances to claim.

2. We've cut our grocery bill.

Admittedly, our grocery bill has always been a bit high. Okay, really high. Food is expensive here, we like to eat, we're big on fresh produce, excuses excuses, and so on and so forth. In the past, we've spent as much as $900/month on groceries!

Our grocery bill presents a prime opportunity for us to save some money. We're taking three specific steps to cut our costs in this area:

We're couponing. I can't take credit for that; it's all Fortysomething's doing, and he's getting good at it. Last weekend, his efforts saved us about $25.

We're planning out our dinners, always our most expensive meals, in advance. We don't go so far as to schedule specific meals for specific days, but we assemble a list of options to choose from. This week, we've got tacos, pizza, salad, mac n' cheese, veggie burgers, and huevos rancheros on the docket. These meals are all easy to make and relatively cheap.

Homemade pizza to please both meat eaters and vegetarians

We're shopping just once a week. We've learned that we spend less money on groceries if we shop for everything all at once. If we hit up the store multiple times in a given week, we tend to spend more in total.

Our current goal is to spend no more than $150/week on food and see if we can slowly reduce that total over time.

3.  We're using Swagbucks to earn gift cards for essentials. 

If you're not familiar with it, Swagbucks is a site where you can earn points by completing tasks (like taking surveys and printing grocery coupons) and cash in those points for a variety of gift cards. Fortysomething and I each spend less than ten minutes on the site per day, and we easily rack up at least 2000 points per month. We then use our points to buy Amazon or Visa gift cards when they go on sale; in turn, we use the gift cards purchase essentials like toilet paper and shampoo. Even in a lean Swagbucks month, we'll earn at least $20-$25 in gift cards.

I would rather use my points to buy chocolate and wine, but okay

4. We found affordable, relatively comprehensive short-term health insurance for the Kiddo and me. 

In a previous post, I walked through our various career break health insurance options. These included an expensive, high-deductible ACA plan (we do not qualify for a subsidy); Fortysomething's expensive, employer-sponsored family insurance; and a short-term insurance plan. We decided to pursue the third option. The application process was quick and easy, and we were approved within 24 hours. 

Short-term insurance doesn't cover preexisting conditions and comes with some strange stipulations (for example, you can't check into a hospital for non-emergency care on a Friday or Saturday night). However, the plan we chose features a relatively low deductible, a low out-of-pocket maximum, 20/80 coinsurance, TeleDoc support, and dental coverage for $295/month. The coverage will last for six months; at that point, we can extend it for another six months. 

Is this an ideal solution? Not really, given the limitations of the plan and the fact that these short-term options will make Obamacare more expensive, but none of our options seemed particularly good. At least we have affordable coverage in the event of an emergency.

5. We've curbed our energy consumption. 

Thank goodness for spring: we no longer have to turn on the heat, and it's cool enough that we don't need to use the air conditioner yet. We spoke to our energy company and learned that costs spike between 3 PM and 8 PM Monday through Friday, so especially during that window, we won't be doing laundry, running the dishwasher, or taking long showers. We anticipate that by being more conservative in our energy use, we'll save about $100/month. Bonus: using less energy is good for the environment!

We've acclimated to this temperature, but it took months

Next Goal: Obtain Supplemental Income (But Only If It's Something I Want To Do)

Of course, the best thing we can do to support this career break is to bring in some extra income. My goal is to eventually find a part-time job or a steady freelancing gig. In the meantime, I want to experiment with side hustles.

The caveats: it has to be a job I actually want to do, and it can't cause needless stress. While I have the opportunity, I'd like to give myself some practice in selecting and doing work that I actually feel good about. For now, the only side hustle I can think of that doesn't induce mild panic is pet sitting, so I signed up for Rover, which is sort of the Uber of the pet care world. I like animals. I have some experience (I used to work at an animal shelter), and hanging out with dogs and cats is fun for me. So I'm offering dog walking and in-home pet sitting... and guess what? Someone actually booked me to look after their pet this weekend. I'm not getting paid much, but I'm hoping a positive review will help me attract more business. (Shameless advertising: If you're interested in using Rover for the first time or becoming a Rover sitter, here's my referral code. For new Rover users, you'll get $20 off your first booking.)

Other than that, I have no idea what I'd like my other side hustles to be or what I might pursue as a job. I'm just letting it be and going after the things that excite and energize me.

What are some creative ways you've stretched your income during times when the budget was tight? If you found yourself a side hustle to help bridge the gap, what was it, and was it worth it?
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Finances After 40 #3: Demolishing Debt, Building Security (Lisa's Story)

Photo credit: Rafael J.M. Souza

The third installment of Finances After 40 features Lisa, a 55-year-old writer whose blog, The Traumatized Budget, chronicles her journey to eliminate debt and secure a more stable future. In addition to her beautiful and engaging prose, one thing I love about Lisa is her transparency. Although her writing sparkles with humor and optimism, she never shies away from sharing the difficult aspects of her financial overhaul. She's relatable, compassionate, and real. I'm excited to share her story here. 

Take it away, Lisa!

A Passionate Life

I’ve been a pretty passionate literary writer – fiction and literary essay – for many years, but I’ve channeled it increasingly into blogging and humor. I’ve also been passionate about walking, just plain walking. It’s an ordinary miracle I never get enough of.

I’ve got a fine arts background, first in theatre and then later as a creative writer. I have a novel out from 2002, and essays and such in some reviews. In recent years, I’ve had more and more trouble getting traction on the time or frame of mind to do meaningful writing of this kind. I think I lost my fire for it. Blogging has been a great outlet, and my interest in money blogging made me realize I can be funny—something that’s not as apparent in my literary work, which frankly tends to be obsessed with grief and death.

"We’re struggling to make ends meet in a middle-class way: the wolf is not at the front door, but is lurking around in the back."

I worked, stubbornly, for myself for about 20 years and finally realized I can’t sustain it, so I returned to a full-time job in 2017. There’s virtually no way for a self-employed person to create the safety net for themself that an employed person has, if the employment is decent (much of it in America is not, which makes me angry). I now work in the nonprofit world in communications around how communities are developed and how we can make them more satisfying, beautiful, and equitable places to live and work.

Lisa's Current Financial Situation

My situation isn’t dire, but I’ve fallen short of real long-term security. We’re struggling to make ends meet in a middle-class way: the wolf is not at the front door, but is lurking around in the back.

I made some supremely bad choices in the years after my first husband died (I was 36 with a new baby), and some pretty good ones mixed in over the years. Most of my good choices were for quality of life instead of money. Not that you can’t have both, but, uh, looks like you can’t have both: choose money or time, I think. I was part-time and under-employed for years so I could write useless beautiful prose and hang out with my son, who’s pretty great. My third marriage is to a fantastic man who…is sorta like me in this respect. A humanist in a capitalist world. SO. My husband is a full-time grad student, not yet on the job market but earning some as a teaching fellow.

"My two big mistakes were failing to maintain a consistent budget and failing to save for the short term. We’re remedying that now."

We had so-so retirement savings, enormous credit card debt, and virtually no emergency cushion in September 2018 when I realized it couldn’t continue. My two big mistakes were failing to maintain a consistent budget and failing to save for the short term. We’re remedying that now, and we refinanced into a HELOC to help with deferred home repairs and to pay down our debt faster. It’s still really touch and go.

Our biggest challenge right now is getting enough money to keep my son in college, and making home repairs, all while trying to save and stave off debt. As we are emerging from the first phase of panic and tight budgeting, I always worry that I will become comfortable again, and start to slip and overspend.

The future is a scary place to me. I have, honestly, a fairly dark vision of it. I mainly want to make sure my son is not burdened by a financial mess and that I leave him enough to help him make choices and have some financial agency and freedom in his life. I hope I don’t die in debt.

An Artist Looks Back

I found a way to parlay my skills as a writer into really deep, satisfying work that has sustained me pretty well. I don’t regret working for myself for many years, or working part time, or pursuing the thankless profession of teaching for ten years—it was an amazing way to live—I just wish I’d seen the writing on the wall sooner and gotten a full-time office job at, say, age 45.

"I wish that young women in particular and artists in general had access to financial literacy and learned early that to be a great, independent thinker and doer and revolutionary, you must be able to participate in your own financial future."

But I don’t think I really worried about saving for retirement in my twenties, and my thirties were spent in a lot of distraction because of grief and child-rearing. I was just trying to get by. I think I wore my “artist badge” with such pride that serious thought about money felt “beneath me” until I was well into my forties. Even then, I remained more concerned about taking care of people's needs in the moment than saving seriously. I wish that young women in particular and artists in general had access to financial literacy and learned early that to be a great, independent thinker and doer and revolutionary, you must be able to participate in your own financial future. Like it or not.

I was so focused on the Sisyphean cycle of paying down debt for all those years (or is Tantalus a better comparison?) that I did not focus on how powerful short-term emergency savings are. I wish I’d given that more attention.

Finances After 40: Lisa's Perspective

For those who have raised children, the enormous financial sacrifice for most of us cannot ever be repaid in money. It’s just gone. It's not only the outlay for childcare -- which costs anywhere from $9,600 per year for one child to upwards of $20,000 in some states, by varying estimates, and has risen about 8 percent in the last several years -- but also the time lost to working at your full potential, or at all. Although I'm a slightly special case because I was widowed (or am I? One in four families are headed by single parents), I worked part time or below my abilities for nearly two decades so I could be at least a partly present parent.

"Have very, very, VERY hard conversations with anyone you consider as a partner... Don’t be an enabler or caregiver to someone with money problems."

Also, I can feel the noose tightening in the marketplace as I approach age 60. Part of my work is in earned and social media. I try to imagine myself projecting the same energy and passion into those hectic media at age 60, 65…I try to imagine an employer wanting that from me, or trusting me to know all the right sassy turns of phrase and edgy approaches to multimedia. I’m not sure I will have it, or if I do, whether it will be appreciated. I think job discrimination due to age must plague the vast majority of women over 50—thankfully not as much over 40, I hope, but there too, I bet.

Lisa's Advice For Savings And Relationships

Save consistently into two buckets: a short-term and a long-term. Have a retirement fund but also have the most you can in more liquid funds for emergencies. Play with your money, sure, but do it judiciously. If you brunch or have drinks with friends a lot, pick one or two weekends a month and set aside the money you would have spent into savings. Same with eating out on a whim—invest some time in planning and cooking. Pack your lunch. I must have pissed away so much money on these frivolous things—don’t deprive yourself, but don’t waste it away like I did.

"Save consistently into two buckets: a short-term and a long-term. Have a retirement fund but also have the most you can in more liquid funds for emergencies."

Have very, very, VERY hard conversations with anyone you consider as a partner. Find out exactly what, if anything, they owe, to whom, whether they have a history of delinquencies or other issues with money. This can be hard to discern. Don’t be an enabler or caregiver to someone with money problems.

Recommended Resources

1. I check Credit Karma all the time, although it is not a full replacement for checking with each of the three credit unions regularly and getting your free credit report each year. Credit freezes are now absolutely free under the law, so to protect yourself from fraud, join up. Just Google the credit union in question – say, "Transunion Credit Freeze" – and you should get the instructions.

2. We recently joined a credit union—they are hands-down the best source to go to for virtually any kind of financing, though different ones offer different products, so check first. Their car loans are typically many points lower than from other sources, and their home and home equity loans are, too.

3. I have also had great experiences with personal loan funds like Upstart and Lending Club; there are others now, too, like Prosper. That can be a wise first step out of bad debt if your credit rating has not yet been shredded.

4. I’ve loved shopping through Upromise for years, and have paid about $800 toward my college loans over the years just doing ordinary online shopping with them. They make it hard to find out how to pay down an existing student loan, and may have stopped offering that option now, but you can also get cash-back from them as well.

5. Last but not least, I swear by my Safeway grocery store app. The company that owns them owns a lot of national chains; other groceries have reward apps also. We save about 30% on our groceries that way.

Where To Connect With Lisa

Her blog: The Traumatized Budget
Her newsletter: https://tinyletter.com/The_Traumatized_Budget
Twitter: @cheapbohemian
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My Career Break: How Much Time Can I Afford To Buy?

A few days after I quit, I walked my son to school as I usually do. Normally, the five minutes before we need to scuttle out the door feel rushed, with me barking out orders to Put on your shoes! and Find your jacket! so that I can get him to where he needs to be before hurrying back home to start work.

On that morning, though, I didn't feel compelled to prod him along. He took his sweet time donning his footwear and backpack, and then we ambled towards campus, enjoying the warmth of the sun after months of cold, soggy winter.

"Mom," he said as we approached the crosswalk, "I'm glad you're taking time off. You're so much more relaxed."

And with that single statement, the necessity of my career break was validated. My break is not just benefiting me, I realized. It's benefiting my family, too. They deserve a mom and partner who isn't living in a perpetual state of stress and operating in basketcase mode.

I'm trading money for time, and from a standpoint of personal and family well being, it's already worth it.

Career Break Finances: Can We Afford It?

But speaking of trading money for time, I want to be transparent about the money aspect of this career break. My ability to take time off hinges on our ability to live on one salary for a few months, and that's going to take careful planning and consistent frugality.

When I quit, I wasn't thinking about just my mental health. I was taking our finances into serious consideration, too. Money-wise, I'm not an ideal candidate for a career break. Those of you who have been following our story know that although we've made some major progress over the past few years by paying off our credit cards and one of our student loans, we're still digging our way out from under $37K of student loan debt. Moreover, because we live in a high-cost-of-living area, our baseline expenses are stratospheric even when we're being exceptionally conscientious about how we deploy our money.

And a career break is expensive in more ways than one. While I'm away from work, I'm not just losing out on a salary. I'm losing out on health insurance benefits and retirement contributions, too.

The bottom line is that we can make this work, but we've got a fairly short runway, and we'll need to depend heavily on a combination of our emergency fund, bonuses, and side hustle earnings. We're not in a position to live off a single income indefinitely.

Income Vs. Expenses

Because I'm all about transparency, I want to share our financial approach to my career break.

Income-wise, here's a breakdown of what we're working with:

1. Baseline income: While I'm not working, we'll be bringing in a baseline $3000 a month via Fortysomething's regular income. There's no way this career break would be a possibility without his salary. It's the main reason I can afford to sit out for a few months.

2. Additional income: Fortysomething is expecting a summertime bonus somewhere in the range of $3000-$4000, although it's hard to predict the actual total because it depends on factors mostly out of his control. He also has a regular contract job that he works when school isn't in session. He's likely to do the same this summer, but we're waiting for those plans to crystallize. If it works out, his contract gig will bring in another ~$1000-$2000.

3. Savings: It may seem as though I quit my job abruptly, and in a way, I did. But I've been unhappy with my work long enough that I actually started considering the possibility of a career break almost a year ago. Knowing this, we've been hoarding cash. We now have approximately $8400 in our savings account.

As for our expenses, here's a breakdown of our current monthly budget:

Health Insurance
Student Loan
Campground Membership
Car & Renter’s Insurance
Car (Gas)

Estimated difference between baseline income and monthly expenses:

The Wild Card: Health Insurance

As you can see from the budget, health insurance is potentially our largest expense outside of our rent.

I spent an inordinate amount of time last week researching health insurance options. My first stop was healthcare.gov, where I wasted two hours filling out an application with the expectation that we'd qualify for a subsidy. Only after my application had been approved did I find out that, due to the nature of Fortysomething's health insurance, we are not eligible for ACA assistance (I won't get into it here, but it's known as the ACA family glitch). A bronze plan with a sky-high deductible would cost us $850/month.

Option #2 is to buy into Fortysomething's insurance, through which he already has coverage. He pays almost nothing, but adding me and the Kiddo would cost $750/month. With a $10,000 family deductible and a $12,500 out-of-pocket max, it's not exactly a Cadillac plan. On the other hand, preventative services (including dental) are free, so... there's that?

Option #3 is to purchase one of the new, controversial short-term plans, which could cover us for up to a year in our state. The plans are inexpensive, but they also come with a host of weird rules and stipulations, and they generally do not cover pre-existing conditions. I'm skeptical, but I managed to find a plan with a $1000 deductible, a $2500 out-of-pocket max, dental coverage, and Teledoc access for $250/month. Except for mental health issues - many of which are exacerbated by working shit jobs - I'm healthy, and so is my kid. Plus, I'm familiar with insurance lingo and know how to interpret the plan brochures. So I'm not ruling out this possibility.

I'm not sure which route to take. I don't feel comfortable going without insurance, but I also don't want to spend hundreds of extra dollars a month for a half-assed plan that we might not use much. I may apply for short-term insurance to see whether we even qualify; if we don't, that makes our decision more straightforward.

Where We'll Be Cutting Costs

Some of our budget line items are set in stone, including our rent, campground membership, health insurance, and Internet and phone bills. Other items, like gas, already require little in the way of money (a benefit of having only one car and living within a mile of pretty much everything we need). But we'll be cutting costs in several other areas:

1. Groceries: I know our grocery budget may seem high to many of you, and I have several reasons/excuses for that. One, food where we live is expensive in general. It's a small town with very little in the way of local agriculture, and most food is shipped in. Second, we don't have an Aldi or Trader Joe's here, which is unfortunate because it seems like those stores offer massive savings. Third, my family eats a lot, especially now that we've got a 12-year-old who seems to burn calories as fast as he takes them in. Lastly, we do buy plenty of fruits and vegetables, and we eat them all. Fresh, healthy food is important to us, and we're willing to invest in it. 

Nevertheless, there's plenty of room here to dial it back. To reduce our expenses, we're meal planning, couponing, and making detailed grocery lists. We'll be eating more rice and beans, pasta, and inexpensive produce like sweet potatoes and carrots. We're also earning Swagbucks gift certificates that we can use to order some grocery items for free.

2. Utilities: We've become more aware of our energy use over the past year or so, but we can and will be more vigilant, especially in the coming months. For example, we'll limit the number of loads of laundry we do in a given week and avoid running our appliances during peak times (between 3 PM and 8 PM, according to our energy provider). I've stopped taking hot baths at random, something I was doing when I was super stressed out about work. And we'll hold off on using the air conditioner as long as we possibly can.

3. Miscellaneous: After two years of tracking our expenses, budgeting, and saving, we're pretty frugal. We don't go on shopping sprees or make many impulse purchases. But we do go out to eat a couple times a month, and we often take road trips during the summer. While I'm on my career break, we won't be going out to eat unless we have a gift certificate, and we won't be traveling without the aid of credit card points.

That said, I'm reluctant to slash our Miscellaneous fund altogether because there are a few things I do want to cover over the summer. For example, the Kiddo is desperate to play in the local soccer league, and there's no way I'm going to discourage that. He also needs some new (or gently used) clothes.

4.  Student loan: Fortysomething's loan is a federal student loan. Technically, we could ask for a deferment or apply for forbearance, but we'd like to continue making steady (albeit slow) progress with our current payment plan unless finances get really tight.

So How Much Time Can I Buy?

Let's say that between bonuses and contract work, we make an additional $5000 this summer and immediately dump it into our emergency fund for a total savings of approximately $13000. Depending on the insurance route we take, I have a career break runway of about 6-10 months. If I can line up a part-time job, contract work, or some freelance projects, I can further extend my timeline.

I won't sugarcoat it: I'm nervous about the financial aspects of taking time off, especially because I don't have a crystal-clear sense of what I want to do next. Our bank account certainly isn't bursting at the seams, and our emergency fund is less robust than I'd like it to be. I know there are people who might see this as a financial risk not worth taking. 

I keep asking myself whether job stress is really enough of an emergency to justify dipping into our oh-so-carefully hoarded savings, and I keep coming to the conclusion that it is indeed worth it. I couldn't have continued doing what I was doing, and my health was suffering (if you're losing sleep over a job you dislike, that counts as a health problem in my book). The job was breaking me down both mentally and physically.

From that standpoint, the money we're spending on this career break isn't a loss. Rather, it's an investment. It's an investment in my family, my health, and my future. It's an investment in my search for a sustainable job, whether that's a traditional job or a job of my own creation. In order to make this investment worthwhile, I really have to go all-out on this break. I need to make sure I'm healthy by the time I go back to work. I need to make sure I don't put myself into the same untenable position I've been in for the last four years.

A Career Dyno

Although I'm not a climber myself, I have a weird affinity for climbing documentaries (probably because they always feature iconoclasts who shirk societal norms). I've seen Meru, Free Solo, and Valley Uprising multiple times. But my favorite one as of late is The Dawn Wall, about Tommy Caldwell and Kevin Jorgeson's attempt to scale what basically amounts to a nearly perfectly smooth, seemingly unclimbable slab of granite on El Capitan in Yosemite National Park.

At first, the star of the show is Tommy, one of the most gifted and interesting climbers in the world. But about halfway through the movie, the attention shifts to Kevin as he attempts to traverse Pitch 15. Pitch 15 consists of an ~8-foot-wide section of rock that has no handholds, footholds, or fingerholds whatsoever. To make it across, the climber has to literally spring off the rock face, leap across the wall, and attempt to snag a hold on the other side. The move is called a dyno, and it looks utterly insane.

Tommy manages to conquer Pitch 15 fairly quickly, but Kevin gets stuck. He gets stuck for days. He tries and tries and tries the dyno to the point that his fingers are bleeding. Eventually, it becomes apparent that he may not make it. Tommy considers proceeding without him, but at the very last minute, Kevin manages to succeed. He puts his uncertainty aside, throws himself across with everything he's got, and finally finds purchase. He and Tommy then finish the climb together.

In my own way, I relate so hard to Kevin.

My career break is not only about taking some time off from work. It's my attempt to find a way from where I'm at now (somewhere I can't stay) to somewhere new, without much in the way of security or assistance or a clear path. It's hard and it's scary, but it's something I want to figure out, and badly.

Essentially, now is the time to launch myself into a kind of career dyno - an all-out, putting-full-trust-in-myself, funded-on-a-shoestring leap towards something that I can actually see myself doing for another couple of decades.

Regardless of what's in our bank account, I have to find a way to make that happen. I have to make that jump. 
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I Quit. I'm Taking A Career Break.

A little over a month ago, I wrote about my overwhelming situation at work and the crippling anxiety I was experiencing as a result. I was just six weeks into my new editing job, and it was already a disaster. I was a disaster. At night, I was plagued with insomnia; during the day, I was battling panic attacks and fighting to focus on the words on the page - problematic, since the job required rapid, quality editing of multiple manuscripts on a daily basis. I was cranky and irritable. My family tiptoed around me like I was a human minefield.

Although I’ve grappled with anxiety for most of my life (and particularly with work anxiety over the past five years - you can read alllll about that here, here, and here), this time it felt different. It felt damaging and dangerous and wrong. A lot of you got that impression, too, and in your comments on my post, you suggested I walk away.

But I forced myself to hang in there a little while longer, first because I wanted to save as much FU money as possible (update: you can read about the financial side of my career break here), and second because I needed to make sure that the problem wasn't simply my lack of confidence. 

So for a few weeks, I gave it my all. I talked to my manager and received an extended training schedule. I flipped open my laptop early every morning and resolutely made my way through each manuscript. I worked as long as it took to get the job done. I met my quotas. Outside of my job, I started seeing a therapist. Talking about my anxiety helped me get my sleep schedule back on track.

But every week, the quota increased, and every week, I raced to work fast enough to keep up. One week the training team told me my edits shouldn't take more than 26 hours; it took me at least 45, and I accomplished that feat only by tearing through my assignments with the precision and delicacy of a tank. Working on the weekends became a necessity (I wasn't alone - many of my colleagues did the same).

I felt like I was hanging on by my fingernails.

I cried daily.

Last Monday, I opened up a manuscript in Word, read the first line, and found that I was staring into a jumble of letters. I read it again. I read it three more times. It still made no sense, so I moved on - only to find that the following words, sentences, and paragraphs were also gibberish. The next few papers produced similar results.

It dawned on me that my brain was done.

I Did Everything I Could To Make It Work

The truth is, I liked several aspects of the job. I liked working from home, I liked reading papers about research in my field of study, and I liked editing. I liked seeing how a light application of minor tweaks could make a paper sparkle with clarity. I liked honing my editing skills. I thought I had potential - and so did my manager.

"You've got the best edits on the team right now," she said at one point. "You're a natural."

I was slow, but since it appeared that I was doing well, I thought the job might be worth fighting for. I looked for solutions.

Borrowing inspiration from The Fioneers and Tread Lightly, Retire Early, I mustered up my courage and asked if I could transition to a part-time schedule so that I wouldn't feel so rushed and stressed. It was something that the employee handbook listed as an option. I'd crunched the numbers; the budget would be tight, but we could make it work.

I figured it was a win-win: I'd be able to proceed at a slower pace, continue to bring in a paycheck, and improve my editing skills, and they'd get a return on their training investment. Plus, they wouldn't have to cover my health insurance.

Instead of entertaining the possibility of a compromise, my boss came back with an unexpected ultimatum: get with the program and meet the quota requirements for a full-time editor, or leave. "Maybe this isn’t the right fit for you," she said (days after telling me how well I was doing). "Not everyone can edit at the pace we require. If you want to leave, we will support that. But part-time work isn't an option because your efficiency isn't there."

And with that, I was done. I'm not a word-crunching robot, and I never will be. I want a reasonable job that utilizes my skills and experience and generally makes me feel good about what I'm contributing to my organization. I want a job that energizes me rather than depletes me. I want a job with an employer who is willing to work with me and help me be the best I can be. I want a job that doesn't make me feel like I'm as disposable as a piece of trash.*

I sent in my letter of resignation the next day. I let them know I was quitting immediately.

Have I done my best? Yes. Have I given it time? Yes. Is it super disappointing? Yes. Am I scared? God, yes. Even though quitting was the best option of the options available, it's accurate to say that I was terrified to make this call and make this leap.

But I'm also concerned about my own health. Even though most people in my everyday life can't tell, I know that I've reached a breaking point. You can't hear the sirens going off in my brain, but I can. So it's time to press pause.

I Have Nothing Lined Up. At All.

Several people have asked if I have something else lined up. I do not.

Contract work?



Not yet.


No. Nothing.

Instead, I'm taking a career break for the next several months.

Going into this job, I was already burnt out. Ever so diligently, I'd been following that well-worn advice to never leave one gig without something new in the hopper. When I quit my part-time retail job, I had an advising job lined up. When I quit advising, I had a teaching job lined up. And when I quit teaching, I had the editing job lined up.

Perhaps I was being responsible, but the problem was, this approach didn’t give me any time to reflect on my experiences or recover my energy. So when the workload piled on at this latest endeavor, I didn’t have the wherewithal to cope. I buckled, and quickly.

Jumping Off The Hamster Wheel

I have to remind myself that this isn’t the first time that I’ve jumped off the 9-to-5 hamster wheel. I've done it before, and it's worked out.

When I was 25, just after I'd finished my Master's degree with a sociopathic advisor, I decided to walk away from it all - quite literally. I went to Europe and spent two months hiking in the Alps and crewing on a sailboat. When I came home, I got a job at Starbucks and devoted the next six months to slamming out peppermint mochas and caramel macchiatos (while listening to clueless customers tell me to go back to school, get a degree, and find a real job). In my free time, I wrote. I smelled like sour milk, but I was pretty happy.

Hiking in Italy
A few years ago, I gave notice at my dysfunctional academic job, and we bought an RV. We sold most of our stuff and slowly made our way out west. At the time, Fortysomething was a contractor, and I was picking up some online classes every now and then. Mostly, I ran, parented, cooked food in our tiny RV kitchen, and explored. We didn’t have much money, but I wasn’t particularly worried. I felt free and optimistic, and daily life was simple. When we finally landed in our small town, I got a job at REI. Once again, I was completely and totally fine with the situation.

Living the big-sky RV life
We're in a much better financial position than we were back then. I'm really glad we've gotten our spending and budget under control, and I don't want to slide back into debt. We've worked too hard to let that happen.

But money isn't everything. I also want to get back to feeling more like myself. 

The fact is, I'm not sure that full-time employment is for me. I'm not sure it was ever for me. Between my mental health constraints, my desire to do what I want to do, my hatred for unnecessary meetings, my disdain for pointless tasks, and my resentment of micromanagement, perhaps I'm not a good fit for corporate culture. I did it because I thought it was something I had to do. I did it because I was told that I was above making coffee and selling Goretex... and I believed that, because our culture has brainwashed us into thinking that some jobs are more dignified than others.

But I don't have to do it that way. I won't do it that way. There has to be room for those of us whose brains aren't built to deal with the seemingly ubiquitous dysfunction, who can't think properly in a cubicle, and who won't drink the corporate Koolaid.

Now comes the task of decompressing and figuring out what's next.

For the next couple of months, I won't be looking for work. Instead, I'll tinker with the blog, get back into running shape, visit family, spend time with Fortysomething and the Kiddo, read, hang out with friends, and maybe volunteer. I'd like to set up a regular writing schedule for myself. I'd like to re-learn calculus.

In mid-summer, I'll start job hunting. I can tell you this right now, though: I won't be seeking full-time employment unless an absolutely perfect position hits me in the face. I'll be seeking freelance, contract, and part-time positions so that I can have more balance in my life. And I'm going to be very, very picky.

Just Stop

On that trip to Europe when I was 25, my hiking guide offered the following advice:

If you don't know where you are, stop walking. You will want to move because when you move, you feel like you're taking action. You feel like you're making progress. In reality, you're probably getting more lost. Fight the urge to keep going, and sit down. Wait. Look at your map, orient yourself, rest, and trust. You will either figure out where you are, or someone will find you. 

I never got lost in the wilderness, but feel like I've gotten lost in my everyday life. Each career move has been an effort to find my way back to the right path. Instead, I've become increasingly disoriented - not just with my career, but with who I am. So now I'm going to stop right here. It’s impossible to know if I will figure it out myself or if the right situation will find me, but regardless, I have to trust that it will work out.

As for how this will work financially, stay tuned. I'll be sharing our budget along the way. One thing's for sure: from a financial standpoint, this decision is a bit risky. But is it worth it? Absolutely, because mental health is priceless.

*If I sound bitter and angry, it's because... I am. I'll get past it, but a little anger is a perfectly healthy thing.
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Finances After 40 #2: Building Her Business, Finding Her Purpose (Kassandra's Story)

I'm thrilled that the second installment of Finances After 40 features 42-year-old Kassandra Dasent,  personal finance consultant and owner of Minding Your Money, LLCKassandra's goal is to help people "go from broke to woke". She offers personal coaching and hosts monthly Facebook Live video events in which she discusses financial topics and challenges, particularly those that pertain to Gen X. This August, she's slated to speak at the Fearless Women's Summit in Ottawa and the Lola Retreat in Seattle. 

Kassandra is one of the most thoughtful, generous, and genuine people I've met in the personal finance community, and as you'll see, her story is inspiring. Over to you, Kassandra!

"At the core, everything I do is for the betterment of my family and others; my work has a fundamental purpose."

I live in Orange Park, FL with my sound engineer husband and our adorable dog Riley. I and am a long-distance stepmother to our 11-year-old son who lives in Trinidad. I am also a long-distance caregiver to my elderly mother who resides in Montreal, QC, Canada.

I not long ago quit my well-paid corporate job as a software project manager in Engineering in order to preserve my mental health and start my own business, Minding Your Money, LLC. I am a personal finance consultant, educator and speaker who primarily serves Gen X women and the disadvantaged. In addition, I am a singer-songwriter and perform live as often as I can. I love to travel, and I am fluent in French.

Kassandra's Current Financial Situation

We are not yet financially independent, but we are in a healthy financial position. I paid off $55K of consumer debt in 2012 and have maintained a debt-free status for 6+ years. We only have our mortgage left and hope to pay it off within the next five years. We have self-directed retirement accounts and a brokerage account. We have enough saved in our Kiss Off Fund to have afforded me to quit my corporate role and fund my business venture.

"I can afford the time to teach and share with women what they can do to create their own definition of wealth regardless of their starting point."

Due to our late start investing for retirement (late 30s), we usually max out our contributions every year, in order to give us the best possible shot of a decent retirement. Since I started the business this year, I am not certain what we can contribute to our accounts, which irritates me and makes me slightly anxious. For 2019, instead of immediately investing our cash, we will keep it in a high yield savings account and make our investing decisions near year end. I do regret that I did not save a lot more for my retirement when I was in my twenties and early thirties. Those lost years to a debt lifestyle have a lasting financial effect, but what is done, is done.

Work With A Fundamental Purpose

I'm proud of being able to afford the time to build my business. Having saved up enough money to be able to take a step back and identify what I truly want to do is something I am very proud of us accomplishing. We were able to buy a measure of freedom. Having the means to pay some of the costs for my mother’s private residence and care and helping out other family members is also a source of pride for me. At the core, everything I do is for the betterment of my family and others; my work has a fundamental purpose.

I firmly believe that we will attain a level of financial wealth that will allow me to truly make a lasting impact on the lives of others. Not solely from a charitable standpoint, but I can also afford the time to teach and share with women what they can do to create their own definition of wealth regardless of their starting point. I especially want to encourage people of color to build generational wealth. I have already started to do this through my business, but I want to magnify my efforts.

Tackling Finances After 40: Kassandra's Perspective

There is a sense that many women 40+ are struggling with where they are in life. They are asking themselves, “Is this all there is to life?” Feeling unfulfilled or devalued in the workplace or at home, dealing with the pressures of life, raising children, caring for other family members, rising costs for just about everything we consume, not having enough or anything saved for retirement. It feels overwhelming and there is a financial impact and cost that compounds the anxiety of not being able to do enough for themselves and/or their families.

"There is a sense that many women 40+ are struggling with where they are in life. They are asking themselves, 'Is this all there is to life?'"

Without a doubt, present and future healthcare costs is the biggest concern. My husband and I are both self-employed and pay a high cost in monthly premiums. I was born in Trinidad and lived the majority of my life in Canada, before immigrating to the USA in late 2013. As a Canadian, I often took it for granted how accessible and affordable basic health care was to me, until I moved to the States and learned how the healthcare system operates and its complexity.

Advice For Other Women

If I could turn back time and impart wisdom on my younger self, I would tell her to never marry her self worth to her net worth and to not numb her pain through mindless spending. I also married my ex-husband when I was 24 and divorced him at the age of 30. Although living through the divorce was a very painful process, I know that it was absolutely the best decision for both him and myself. My ex-husband and I are both thriving in life and that is a desirable end result.

"Focus on building your self-esteem and financially advocate for yourself, whether in the workplace or as a business owner."

I encourage women to savour their youth and take advantage of it as well. It may not feel fun to save and invest, but if they do, they will surely thank themselves down the road. They have time to weather the fluctuations of the market, so it’s important to educate themselves about investing and make financial decisions from a place of confidence. Also, they should focus on building their self-esteem and financially advocate for themselves, whether in the workplace or as a business owner.

How To Reach Kassandra

Her website and blog: www.kassandradasent.com
Email: kassandra@kassandradasent.com
Facebook: Minding Your Money
Twitter: @kassandradasent
Instagram: @kassandradasent
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Our Financial Journey Two Years In

From a budget-friendly hike we took back in April 2017
Amidst all of the current craziness/life anxiety, I suddenly remembered that we started our financial overhaul two years ago. It feels like it's been eons. It feels like yesterday. It feels like I should acknowledge our progress in some way, so here I am.

The situation back in April of 2017 looked like this:

We’d moved to our town six months prior and were still in our new-place honeymoon phase, basking in the cool mountain air and taking every opportunity to wander through the pine forests. Our tiny apartment was dingy and hadn’t been updated since 1985, but the view out the front window was priceless. We were earning a solid combined income - Fortysomething was working as a contractor, I'd just started an academic advising job - and we were generally feeling pleased with the trajectory of our lives.

But our finances were another story.

We’d never had a budget and generally had no idea how much money was in our bank account (on average, not much). We'd splurge on last-second getaways and goodies from Target, and thus, we lived paycheck to paycheck. We went into overdraft more often than I’d like to admit. We had no savings, no emergency fund and very little in retirement. We had over $50K in student loan debt and at least $26K in credit card debt.

Although it seems batshit insane to me now, we were not at all concerned at the time. We lived in blissful ignorance. It helped that we’d managed to dodge the kinds of expenses that can wipe out a paltry bank account in a matter of minutes.

And then one day, after purchasing an overpriced, brand-new piece of furniture, it suddenly dawned on me that we were in code red territory. We couldn't afford it. We'd be paying it off for months. We had no money but we were buying expensive things.

Then I became concerned.

At first, I didn’t know what to do, so I watched every episode of ‘Til Debt Do Us Part and Money Moron than I could find on YouTube. Then we took everything we’d learned from our DIY Gail Vaz Oxlade crash course and created a budget and a tentative 5-year debt repayment plan.

We jumped in with enthusiasm, knowing that it was going to be a long road and that we’d need to conjure up major motivation to make it happen over the next few years. But we got started, and we followed the plan.

For the past two years, we've followed it with fervor. Sure, we've had some missteps along the way. Sure, it's gotten really fucking old at times. Sure, I'd like to splurge on a nice vacation at some point. Overall, though, we've been consistent. We've resisted backsliding.

We stuck to our budget, cut our expenses, and found some frugal hacks we could live with (like checking out books from the library rather than buying them at the bookstore, purchasing clothes at thrift stores, ditching most of our subscriptions, walking instead if driving, etc.) We took advantage of the local outdoor scene and did all the free outdoorsy things. We paid off our smallest debts first and celebrated every win, which helped us stay motivated. We built up some savings.

Taking advantage of our parks pass

Two Years Of Imperfect Consistency

After nearly 730 days, I’m here to say that two years of imperfect consistency can make a giant difference. Here’s the rundown:


Debt then: >$76,000
Debt now: ~$37,000

When we started our financial overhaul, we had about $50,000 in student loan debt (two student loans - one for me, one for Fortysomething) and $26,000 in credit card debt (three credit cards in total). We also had a small balance of $1,500 remaining on our car loan.

Now, all of our credit cards are paid off. The car loan and my student loan are gone. We're just chipping away, penny by penny, at Fortysomething's student loan.

Over these two years, my attitude about debt repayment has changed. I still think it's important, and I still think people need to get rid of their high-interest debt as fast as they possibly can. But I'm no longer of the opinion that every other financial maneuver should get sidelined while you pay off your loans. If you don't have savings, you run the risk of having nothing to work with in the event of an emergency. If you're not contributing to a retirement fund, you lose out on compounding interest (the good kind) and tax breaks.

My perspective is a lot more nuanced than it was back in 2017, but I'm glad we went all-out on the first half of our debt. Not having a monthly credit card bill or car payment is huge. It frees up a lot of space in the budget for other things (like saving).

I'll admit that we're far more focused on savings and retirement than on the student loan right now, but we hope to go back to making large debt payments later this year.

I didn't start tracking our debt repayment until June 2017 - so actually, we probably had well over $76K of debt in April of that year.


Savings then: $0
Savings now: $8500 and counting

I kind of can't believe it (what were we thinking?), but we didn't even have a savings account when we started our financial journey. Once we finally opened one, we built up our cash reserves slowly, mostly because debt repayment was the real priority for us. We started with the Dave Ramsey-mandated $1000, then moved into the realm of $4-$5K once we'd paid off our credit cards in summer 2018.

Now we're sprinting to build this baby up to $10K or more. That's mostly because I don't know what to do about my job, and I want to be able to cover several months of expenses in the event that I decide to quit. I kind of wish I'd started this process sooner, but then again, at what point does one really feel secure enough to walk out on a regular paycheck without something else lined up?


Retirement funds then: $1,000 (somewhere around there - I wasn't paying attention)
Retirement funds now: $17,000

Okay, so YES, we are very behind. But that's not the point of this post. What I want to emphasize is that in just two years, while most of our disposable income was going towards debt, we were able to put $16,000 into retirement. And that's with pretty small contributions. Only recently have we ramped up our contributions to ~10%.

Honestly, it's this aspect of our finances that makes it so difficult to ditch this shitty job. In just two months, thanks to the employer match, I've socked $2,000 into my 401K. My health is important, but it's hard to say no to free money when I kind of need it.

I haven't shared our specific retirement fund numbers until now because I don't want anyone to swoop in with criticism regarding our lack of planning. On the other hand, I know there are other people in similar situations. We're late to the party, but hey, we're here now. Let's cheer each other on!

Net Worth

Net Worth in November 2017: -$65K (somewhere around there)
Net worth now: -$13,600

We still have a negative net worth, but look at that rate of increase! We anticipate hitting the $0 mark sometime this year.

The point is, you can make a lot of progress in a relatively short amount of time if you keep at it. That doesn't mean you have to earn hundreds of thousands of dollars a year. It doesn't mean you can't have any fun. It doesn't mean you have to be a perfect steward of your finances. It just means... you have to keep going, one step at a time. That is literally the only way to make it happen if you're a person with an average income and a lot of debt.

It's Not All About Money

Currently, the thing I'm most struggling with is this idea that money isn't everything. Historically, that hasn't been a tough concept for me. Until 2017, I just... didn't care about money. We didn't have a lot of financial security, but I didn't let money stop me from taking risks and having adventures, none of which I regret. I look at our debt and I see the bad. I also see the good it brought. (Unpopular opinion alert!)

In contrast, the past two years have been an unprecedented season of financial responsibility and restraint in my life. We've made our finances a top priority. But now I'm worried that maybe I should be prioritizing other things, like my health. Toying with the idea of taking a career break brings up a lot of emotions for me. It feels scary to pull back when we've finally built up momentum. It's like trying to run a marathon on a broken leg and not wanting to quit because you've come so far.

It's hard for me to walk away from financial security now that I've gotten a taste of it.

At the same time, I appreciate that our hard work has brought us to a point where we have more options. That's really the most important aspect of money, isn't it? Not that it allows us to buy more stuff, but that it gives us an opportunity to consider more possibilities. It gives us some breathing room, some freedom.

Anyway, guys, that's what I've got right now. Please ignore any and all awkward wording, misspellings, and grammar issues. I'm just glad I found the time to stop and reflect.

Thanks for reading. Thanks for your encouragement.
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