
Six years ago, I made a deal with the Debt Devil.
The deal was this:
I would suffer however I needed to to pay off $40k in debt in return for assured success. To honor myself, I vowed that when the debt was paid, I would save up enough money to take a ‘mini-retirement’ (multi-month, likely unpaid vacation). With that freedom and time, I would write, travel and generally slow the eff down for a change.
Being a Type A East Coaster, this was no small feat, as we tend to operate with urgency in literally everything we do, and we tend to do A LOT of things.
All the time.
…and then brag about it.
We try to one-up each other with the amount of shit we’re all juggling ‘cause we’re New Englanders and we value hard work and self-sacrifice above all else.
But really, it’s because our cultural identity has roots in Puritan ideology which discouraged pleasure and leisure and that preference for righteous masochism has never really gone away, especially in the state of Massachusetts.
I wanted to break that habit and practice doing something I really enjoyed for a change.
My goal for a mini-retirement was to be intentional about practicing the craft of writing, which I had been putting off for years to focus on building and paying off debt. I intended to strengthen my creative routine so that I would never allow it to be relegated to the ‘nice to have’ pile behind work again.
The Devil is in the Details
Here’s what the deal looked like:
I realized I needed cheap rent in order to use the Debt Snowball Method. I lived with grandma and then my younger brother for the first two years for under $500, I then found my own one-bedroom apartment back in my hometown 50 miles from Boston, where the good-paying jobs were, for approximately $800 a month (utilities included). I lived in that apartment saving money for the next four years.
The Catch-22
In Massachusetts and other high cost of living states, you can’t have your cake and eat it too.
It is very difficult to live where you work or work where you live and have anything extra to put towards your savings and investments.
The median price of a home in the Boston/Cambridge area is app. $749,000 while the median rent price is $2,797/month, not including utilities.
The median home price for where I live in Worcester Country, Massachusetts is $249,600 while the median rent ranges from $1,000- 1,500.
The best paying health, finance and tech jobs paying over $70,000/year are in the Boston area.
The problem with this arrangement is that if you work a typical 9-5 schedule, this requires commuting roughly 100 miles a day which takes approximately 4 hours a day just to work your 8-hour shift. Not kidding! Traffic congestion in Massachusetts is officially the worst traffic in all of America according to a 2019 report.
(….and number 8 in the whole goddamn world butttttt there I go bragging about my misery like a New Englander again, sorry!)
Did I mention I drive stick?
Yeeeep! So that was fun.
Thanks Debt Devil!
The Financial Cost
Working an 8-hour shift plus commuting to work usually occupied 12 hours of every day.
I worked about 47 weeks a year and managed this arrangement for 6 years in total, give or take.
I slept an average of 6 hours a night.
If I’d been paid an hourly rate of $55 for those 5,640 hours that I sat in traffic kicking the clutch between gears 1 and 2 most of the way home, I’d have $310, 200 already compounding for my early retirement fund.
Instead, I lost that time on Route 2 and that money never existed.
Pour yourself a strong one and join me as we let that one sink in.

The Personal Cost
I had 6 hours a day, 30 hours a week to squeeze in:
- food shopping
- cooking
- eating
- cleaning and laundry
- socializing
- running errands
- working out
- rest and recharging
- going dancing
- playing music
- writing
While it looks like a lot of time on paper, it didn’t feel like it by the 3rd year of this schedule. By the 6th year I was checked out. All day every day I felt depleted, rushed, interrupted and unfinished in everything that I did. I simply did not have the emotional bandwidth to work on creative projects and it started to affect my mental health.
I suffer with feelings of deep regret and anger directed at myself for not figuring out a better work/write balance during those 30 “free” hours.
I criticize myself for spending too much time on other hobbies or with loved ones, imagining that if I could only be more introverted, or had better boundaries with people, I’d have something to show for all that struggle that I could point to a be proud of.
I tell myself that I chose wrong and self-sabotaged my creative life, and honestly that voice in my head really hurts because there is a degree of truth in it.
…but I also have to look at the math and the cold facts.
Those hours were consumed so quickly by basic life maintenance or by relationships and other hobbies I loved and when I sat down to review the past year’s New Year’s Resolutions with a red pen to see what I’d accomplished, my goal to write more intentionally every year was always circled indicating “Needs Attention in Following Year.” It was a failure that weighed heavily on my self-esteem.
I came across a quote from Jillian at Montana Money Adventures which I’ll paraphrase here that really captured the reality of my situation these past 6 years:
“A lot of people don’t have the emotional energy to pursue something on top of their job. Between their job and relationships and family and house, even if they have the time technically, like an hour or two a day, they have nothing left to give during those two hours! That time must be used for recharging. They still feel so consumed by it all. Our attention and energy are finite. You give so much attention and energy to these other things that you have to just step back and unplug from that for awhile before you have attention to give to a new idea.”
Taking a few months to a year to step back for awhile to let your mind and body truly rest is what a taking a mini-retirement is all about.
That quote made me feel less alone knowing others struggled with all they juggled too.
I had to do something about my lifestyle – fast.
I needed time to unwind, recharge, show down and practice holding space for the things I really wanted to do with my life.
Like writing.
The Dare
After I finished paying Sallie Mae back, in 2016, I went to work trying to save back that money because I had plans for that money.
I was convinced that if I had no debt and enough money saved to pay my bills for a year (with a little extra for traveling and educational courses), I’d be able to quell the constant anxiety and fear about not having enough money to avoid sinking back into the poverty I came of age in.
I told myself that if I could buy myself some confidence long enough to unwind and learn some new skills, I could redesign my life so that I never spent 60 hours a week on a commute and job again.
I told myself that once I had a little more than one year’s living expenses saved, which totaled $50,000, I’d either quit my job or not look for another one for a few months next time there was a corporate buyout and my team happened to find ourselves on the chopping block.
My wish came true at the start of summer: I was working as an Instructional Design contractor for the past year and while I was already on vacation working remotely, I got word that the project was ending and my contract would not be renewed. I had known that was coming soon so I had socked away extra money and packed a few extra pairs of underwear, just in case. I met with my supervisor at the local office in Atlanta where I was vacationing and turned in my badge and my computer.
Walking away I was stunned to realize I had started to skip, and I was grinning ear to ear. I hadn’t quit, I hadn’t been fired, it was just over, and I was officially jobless, unemployed, bolstered by savings and a plan and finally free to actually do this and get down to the business of practicing my craft.
I had given myself the choice to embrace the free time or freak out and look for another job.
I chose to embrace the free time.
I bought a one-way ticket to Seattle where I used to live to visit old friends, meet my writing coach and convene with the mountains and the glorious Puget Sound. Then I took a road trip to Hood River, Oregon. I bought a round-trip ticket to Maui to stay on an off-grid farm in a yurt with a college buddy living the dream there. Then I flew to Sonoma County to float the Russian River with family I only see once a year. Then I flew to San Diego to see more cousins and an old friend who came up from Mexico to spend the day at Pacific Beach with me, scooting around on electric scooters. Suddenly, a 10-day vacation turned into a 7-week $2,000 romp around the country and I couldn’t have been happier.
I returned home in August for three weeks to plan a cross-country trip I’d take with my boyfriend to Southwestern Utah for the Fall, and that’s when I started to freak out about having no income and spending so much to travel.
Having Second Thoughts
Those few weeks at home triggered my work routine muscle memory and anxiety. I had to admit to myself that I’m more uncomfortable living without an income than I thought I would be.
That’s frustrating because I practiced living well beneath my means for six years so that managing my money responsibly would just be second nature. I’d lived off of savings in my 20s when I’d saved far less, but it was harder 10 years later.
Despite having $50,000 saved up to ride out the year, I didn’t feel safe. The anxiety gave me second thoughts about my choice to not work and it sounded like this:
“I’m not going to make it”
“I’ll never get hired again for taking this much time off”
“Something catastrophic will happen with no way to recoup that money quickly”
“I’ll lose my relevancy in my career”
“I’ll lose my apartment and freeze to death in New England”
“There’s no one to bail me out if I fuck this up”
“I can’t afford to pursue my dreams”
That record is stuck on repeat in the back of my head.
It goes off while I’m enjoying beautiful sunsets, taking in a breathtaking mountaintop view or being still listening to the sounds of nature.
I miss things happening around me because I’m silently screaming at That Voice telling it to shut the hell up and enjoy the goddamn view!
Why does it keep saying this shit to me?
It’s afraid that if I enjoy myself too much, I’ll damage my work ethic, and since only hard work is rewarded, I’ll never be able to earn an income again.
This is guilt. I feel guilty for taking my time. For enjoying my life. I feel guilty for sensing my burnout and planning for self-care to deal with it.
Maybe it’s a result of a deeper influence than just where I grew up.
American society is influenced by a mix of Christian views of morality and a profit-driven capitalist work ethic. This leads us to believe that we have a moral obligation to work.
Oddly enough most of us must work for private corporate owners. They’re the ones with the money for good salaries and crucial life-enhancing “benefits” like health and dental insurance that we can’t otherwise get without a job or reserve moneys because of the way our country is set up.
Our culture sees the generation of profit by our labor for company shareholders as ‘goodliness’ and ‘success.’ We interpret it as lazy and selfish not to work, “freeloaders” we call people who don’t have jobs or aren’t actively looking for one, like me.
There is a hidden underpinning in our culture regarding this. Wage labor is seen as virtuous, in that it is the antithesis to idleness. As the old Proverb goes, “Idle hands are the Devil’s tools.”
What I never understood was that if we’re always working for someone else, putting in the kind of hours I did for my job and lifestyle, when do we have time/energy to produce our own work?
When can we toil to provide for our own needs and wants?
When are we ‘allowed’ to welcome the inspiration that inevitably pops out of ‘idleness’?
The ‘idleness’ has afforded me more time to write, that’s for sure. It’s still hard to finish pieces because I’m still learning the craft, but certainly being well-rested and having clearer thoughts for much of the day has helped me to produce work for myself simply because I want to and I have the time to do so.
As the months pass though, I feel like time is slipping through my fingers.
I feel that if I don’t rush urgently towards employment, it will pass me by like a river and I’ll be left to live my life forever a bum on its banks.
That’s fear talking. It gets louder when I’m running through money faster than I used to trying to take extra classes or buying another flight, but I have to keep telling myself that this was an intentional, well-planned out choice and I am in control. I can go back to work whenever I feel like it, but I don’t feel like it at this time.
Yet, when I’m back in Massachusetts a switch gets flipped. In my apartment between trips sitting in the sunshine slowly waking up with my tea for once, I listen to the Monday morning traffic below my window schlepp off to another work week. That used to be me, I think. Battling depression around 5 o’clock on Sundays just dreading the 2-hour Monday morning commute to come in 12 hours.
Commuting like that sucked until I got to the office, then it felt good to be making money. Making money meant that I was a successful and respectable citizen who fit in and had her place in society. I wasn’t a freeloader. I could buy whatever I wanted and eat out whenever I didn’t feel like cooking. It felt good to have my American Dream Membership Card.
Back at home listening to the traffic pass instead of sitting in it, a thought crosses my mind: Maybe taking a small contract gig won’t hurt… it’s better than not earning any money at all. I’ll surely have enough time to work on my writing…….
The needle drops again on the warped and broken record and sings something like this:
“Am I wasting my best income-generating years by taking time-off to learn to write better?”
“Am I hemorrhaging my life’s savings just to fail at being a writer?”
“Am I damaging my career by taking this much time off already?”
“Am I too old to do this?”
“Am I too young to retire, even if its mini?”
Feeling that familiar, visceral fear of not having a safety net to catch me or enough money in times of crisis, I schedule 5 job interviews and field calls from recruiters as I freak out about living off my savings.
My heart is screaming ‘’No! I don’t want to go back to work yet! I haven’t even earned my writing sea-legs yet!” while I’m trying to calculate how much money I’ll make after taxes during each interview.
I’m reconsidering plans made 7 years ago with my boyfriend to drive across the country in 2 weeks in case a job is offered. I’m on the brink of aborting my plans to enjoy my mini-retirement in an attempt to get money so I can feel safe from financial strain and poverty creeping back into my life.
It occurs to me that this irrational response is exactly why most people don’t intentionally take time off from work to self-fund the trip of a lifetime or practice a hobby. The fear and uncertainty is just too great.
There is tremendous risk in leaving something one does well to master something new.
The Battle
There is a bitter conflict of interest duking it out in my body right now.
My ego is having a hard time letting go of its control over my engrained ideas about money and professional ambitions.
My heart is treading water trying to stay afloat long enough to grab any time it can get to explore. It needs someone to fight for its right to be idle for a spell so it can gain strength to stick around next time I get busy with a job and life.
The hardest part about being intentionally unemployed is that you must come to terms with the ways you procrastinate and avoid doing the hard things that are attached to your self-worth.
Work and daily life can so thoroughly exhaust you that it’s easy to chalk up your creative negligence to being fatigued or too busy with extra work at the office.
With your job, you don’t have control over what you work on that day. During an intentional mini-retirement like mine, you do have that control. You have to look at what you did in a day and own the fact that you chose not to practice your craft because you spent the day anxiously scouring job boards for remote jobs you might be able to do on the road.
Managing your anxious bad habits and negative self-talk is a job in and of itself.
It’s also something I believe I can overcome or I wouldn’t be doing this.
Forward-Thinking
My brother texted something to me recently that made me pause: “For someone who is taking the year off, you sure are busy. Perhaps more so than when you worked full time.”
That’s just it: this time off is limited and I feel the need to thoroughly embrace every free moment I have. This time away from earning money is about strengthening what is important to me so that it’s such a priority in my life that it can’t take a backseat to any job again. This is why managing the negative self-talk is part of being successful in this endeavor.
In the words of Billie Jean King, “It’s all about what you want to look back and say.”
I want to look back decades from now and say that one year in my 30s, I decided that my personal goal was important enough to take seriously until it actually was a very serious occupation.
I want my job to work around my life, not the other way around. I’ve been living the alternative my whole life, and I don’t want to spend another year longer allowing what’s important to me to take the backseat to what I do to make money and survive.
I want to look back and say that taking a mini-retirement in my 30s wasn’t a deterrent to my career, but an effective pivot.
It gave me the chance to live a little and take a step back to look at how I was choosing to live my life to decide if it was how I wanted to continue or not.
I want to look back and say that I took the time I needed to make significant changes to my value system and now I have a successful career writing about topics that are important to me
…even if I still have a day-job.
This is such a real feeling – I had a job for a while that was only 10 months out of the year, and I thought I’d be able to relax into a good writing routine for the 2 remaining months… not as easy as it looks! Thanks for being so open about the challenges of it.
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