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

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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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Finances After 40 #1: Life Settles Down After Divorce (Abigail's Story)

Welcome to the Finances After 40 series! 

This is the first of what I hope will be many posts featuring the stories of women 40 years and older. The financial (and related) issues that women in this age bracket face are somewhat unique, but I think they often get overlooked. The goal of this series is to contribute to a conversation about finances after 40 - and based on the responses I received when I first mentioned this series on Twitter, it seems like other people want to have this conversation, too. 

The first Finances After 40 story comes from Abigail Perry, a 40-year-old author, trivia whiz, and veteran personal finance blogger who lives in the southwestern US. I was lucky to meet Abigail via the Twitter personal finance community. She's encouraged us throughout our debt journey and has reached out with comfort and support during difficult times. I'm thrilled that she's volunteered to share her experience and advice. 

Be sure to check out Abby's blog, I Pick Up Pennies. You can also find her on Twitter, Pinterest, and Facebook. Furthermore, she's an author! You can pick up a copy of Frugality For Depressives here.

Take it away, Abigail!

I live in Phoenix with my cat, Josie, who still acts like an insane kitten. She keeps life interesting and loves to lie on me, particularly if I’m trying to type at the time. (She’s across my arms as I type this.) I have a trivia team (yes, I’m a nerd) that I go out with once a week, and we get together on the weekends about every other week. I’m newly divorced, so life is still settling down overall. 

Abigail's Current Financial Situation 

As a new divorcee, I’m still seeing how my financial situation shakes down. I already know that it’s significantly cheaper – my husband was a bit of a spender and had expensive chronic conditions – and easier to manage.

I make a fair amount of money for customer service, so I’m comfortable financially. But I’m getting a late start saving for retirement thanks to the fact that my now ex-husband was something of a spender. I’ve increased my retirement contributions, though they’re still not as high as I’d like, but there’s no getting back those years of compound interest. Sigh.

"I’m working on increasing my retirement contributions. I hope one day to max them out, but I’m not sure that’s feasible because I’m also trying to pay off my mortgage quickly."

I didn’t worry about retirement enough in my 30s. I knew I should make it a priority, but we had my husband’s bills to deal with (including $26,000 for dental implants) and big fixes to the house ($10,000 for new windows). So I let those take precedence, and it just didn’t feel like we had enough money to save. I’m kicking myself now. I’m working on increasing my retirement contributions. I hope one day to max them out, but I’m not sure that’s feasible because I’m also trying to pay off my mortgage quickly.

I have health issues that keep me from working a job outside the house, and competition in my company’s industry has really heated up over the past few years. It’s almost certain that my job is secure – even if things got pretty bad, I’d probably just have to take a pay cut – but anxiety is a thing. So I would like to have the place paid off as one financial worry in “What if?” scenarios.

Reflecting On Past Financial Decisions

Obviously, I should have been saving more for retirement in my 30s. (My 20s were spent unsuccessfully trying to work outside the house, then going on disability. So saving during that decade wasn’t an option.) Once our financial situation stabilized, I wish I’d have started making it a priority to max out the Roth and to finally open up a SEP-IRA through my S-corp.

To that end, we could have waited longer to get my husband’s dental implants if it meant saving more money toward retirement. Even once those and the windows were done, I didn’t max out my Roth IRA, which was just silly. I also made the mistake of being a little conservative in my portfolio. I was worried about losing what little money we were putting aside. As a result, my investments barely grew over what I was putting in. I’m being aggressive now, but again… That’s a lost decade.

But I’m glad I got my ex-husband’s teeth done even if we didn’t end up together forever. He wouldn’t have been able to afford the implants on his own, and they did need to get done or he’d have ended up with bone spurs (ick ick ick) and dentures that didn’t fit. So while I’d love to have that $26,000, it saves me a lot of guilt.

Financial Wins and Future Goals

I finally did start maxing out my Roth IRA and opened a SEP-IRA through my business. I can now make larger contributions to try to make up for some of the time I lost in my 30s. I’ve also started taking my guest house rent and putting that toward the mortgage, along with a couple hundred more each month. This means I should be able to pay off my house within the next 6 years (assuming my guest house stays rented).

I envision a paid-off house and retirement around 65 or 70. Pretty dull, but due to my slacking in my 30s, early retirement isn’t an option. And honestly, I don’t know what I’d do with myself in early retirement anyway. I’m easily bored and, thanks to my health issues, can’t go out and do a ton of activities. So having a day job, while less than fun at times, keeps the hours from dragging on quite so much.

"I think retirement becomes a bigger issue for a lot of women once they hit 40. I worry that we don’t take it as seriously in our 30s as our male counterparts."

Tackling Finances After 40: Abigail's Perspective

I think retirement becomes a bigger issue for a lot of women once they hit 40. I worry that we don’t take it as seriously in our 30s as our male counterparts. Also, once you hit 40, I think retirement age suddenly becomes a little more real/imminent than it did even at 39. So it sort of shakes things up. Unfortunately, by that point they’ve lost an important decade.

There’s also the fun balancing act of trying to save for retirement, build up savings and get serious about paying down the mortgage so that you don’t go into your golden years owing the bank. This is made all the more difficult as any kids start to creep toward college age and you have to consider how much you can/want to help them with costs.

"Make sure you’re getting a house for you, not just because you think it’s what you’re supposed to do."

Save for retirement and be aggressive in your portfolio. Do this in your 20s and 30s and you’ll be a lot less stressed in your 40s! I think [women] also need to really consider whether they want a house because they think that’s what they should do or if they really want to own. It’s a huge financial commitment, and paying down a mortgage can be a huge financial drain while you’re trying to also focus on retirement. So make sure you’re getting a house for you, not just because you think it’s what you’re supposed to do.

How To Reach Abigail

Her blog: I Pick Up Pennies
Twitter: @ipickuppennies
Pinterest: @ipickuppennies
Facebook: I Pick Up Pennies PF
Pick up her book here: Frugality For Depressives
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