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


Career Break, Month Two: Eight Things I've Learned About Myself

As I begin to type this post, I've been on my career break for 68 days. I'm kind of astounded at how much time has passed and how quickly it's gone by since I kicked Nightmare JobTM to the curb. (Guys, THAT GIG WAS A SHITSHOW. How did I last even two months?!)

On the other hand, I often feel as though the days themselves pass more slowly than they did when I had a traditional job. Sometimes I'll lie awake at night and think, "Wow, did I really do that today, or did it happen earlier this week?" It's possible to pack a lot of activity into a span of 16 hours.

That said, month two of my career break was challenging for me. It felt very different from the first 30 days, when I was basking in every moment of freedom and enjoying the shiny newness of owning my time. Month two was more like, OMG, what am I even doing with my life (cue panic, doubt, lack of self-confidence, etc.)

Plus, my energy seemed to tank. Right after I quit, I felt ready to conquer the world; more recently, I feel ready to take a nap. I chalk this phenomenon up to life settling down and me finding more of a routine. Abigail from I Pick Up Pennies warned me that this might happen - that I might need some serious rest and downtime to recuperate from what boils down to years of stress.

Basically, month two was a time of reflection, figuring out what's working and what isn't, settling into a new lifestyle, and grappling with the question of, Where do I go from here?

Here's what I've learned.

1. Despite my Type A proclivities, I would make a really good retiree.

As a quintessential Type A personality, I went into this career break with serious concerns about how I would respond when faced with boredom or a super slack schedule. Predictably, the lack of productivity and aimlessness that I faced a few weeks in made me nervous and uncomfortable - but only briefly. After a short adjustment period, I found myself relishing the opportunity to stay up late and sleep in (although now that I've given myself permission to do so, it happens less often than you might think), stare off into space while nursing three cups of coffee at breakfast, go for long walks or runs, dive down random Wikipedia rabbit holes, and scroll mindlessly through Twitter.

I mean, I'd like to accomplish more than that in a given day, but it turns out that the world doesn't fall apart when I don't. And... wasting time is kind of fun.

I'm impressed that I've been able to relax to this extent. Apparently, I'm not as attached to productivity as I thought I was.

2. That said, there's always something to do.

My days can be empty, but they can also be jam-packed with activities - and it's not hard to find things to do. Recently, I've filled hours with things like learning Italian, running, reading, hiking, going to my kid's soccer practice, hanging out with friends, baking, and petsitting.

In other words, you don't need a job in order to create a completely full schedule.

We're trained to think that work is necessary in order to find meaning and structure in life, but based on my super-scientific study of n=1 (me), I'm here to tell you that this is a lie.

3. I don't want to be a freelance writer.

I went into my career break with the vague sense that perhaps I should pursue freelance writing as a job. It seemed like a good idea: after all, I've watched many friends in the personal finance community find success in the wordsmithing arena. I've even received a couple of emails asking if I can write about certain topics.

When I was a kid, my mom used to say to me, "When you WANT to do something, you're really good at it. When you don't want to do something, it's impossible to make you get it done." As annoying as it is to admit that she might have known me better than I thought, it's true. Even if something sounds like a good idea, something I should pursue, my level of interest is always reflected in whether I actually do it.

Because at the end of the day, no matter what I say or promise, if I don't want to do something, I simply... won't.

That's how it's been with writing. Do I enjoy it? Yes - but only when I feel like it, and generally only when I'm talking about my own life. To be a paid, professional writer, I'd need to move beyond my little me-bubble and actually do what editors want me to do. I'd have to research stuff and, you know, take direction.

Right now, I don't want to. Maybe that will change. For the right gig, I might do it, but it's become apparent to me that professional writing is not something I'm ready to pursue at the moment.

4. Petsitting is a different story.

I started petsitting with Rover a couple of weeks into my career break to make a few extra bucks. At that point, it was the one side hustle that sounded even remotely palatable to me. One, it didn't require me to be parked in front of a computer. Two, it's something I can do even when I'm not feeling particularly sharp or energetic (more about that in a minute). Three, although I often feel overwhelmed and depleted by other people, especially in a work environment, I'm great with animals and am naturally comfortable around them.

I landed my first gig in early May, and since then, I've had only a handful of days without at least one drop-in visit. Because I set my rates low in order to quickly land clients and reviews, I haven't made a ton of money - but I've made enough that I'm now eying the possibility of turning petsitting into more of a full-time job. In fact, I'm seriously thinking about starting my own business.

5. I don't think my brain is built for traditional employment.

This is something I wasn't fully aware of until I quit. When I was doing traditional 9-5 work, I almost always felt like I was dragging my brain through sludge. On average, I felt confident and alert and on just one or maybe two days a week. I thought this was normal. I figured everyone goes through their working life alternating between exhaustion, anxiety, and cloudiness. I also figured that I was just a weenie who wasn't handling adulting as well as everyone else.

What I've discovered is that even when I'm not working, there are many days when I'm operating in sloth mode and can't pull myself out of it. I've had a full physical and a full set of blood tests, all of which came out squarely in the "normal" range, so it's not that I'm facing some sort of underlying health crisis.

I think the truth of the matter is that I am a highly sensitive person whose circuits get overloaded very, very easily. And when the circuits get overloaded, the whole system shuts down. I need time and rest to get back up to speed, and by time, I don't mean a few hours. I mean a couple of days.

One coping option is to make the system - i.e., my brain - work more efficiently. I've tried that. I've attempted different eating plans, sleeping plans, workout plans, not drinking alcohol, drinking more water, etc. etc. etc., and none have made a significant or lasting difference.

The other option is to accept that this is how I am and stop putting myself in situations where I'm setting myself up for failure on a daily basis. In other words, as a highly sensitive person who gets overwhelmed by interactions with other people, I should probably avoid jobs that involve frequent interactions with other people. I should probably create or find a job that gives me the time and space I need for regular recuperation.

6. I am a pretty good person.

This might seem like kind of a ridiculous statement. I think most people who've met me would say that I'm a good person - or if not good, then relatively average and mostly tolerable. Most people don't seem to think I'm a jerk.

But over the past four years, I haven't felt that way about myself. I viewed myself as:
  • angry
  • impatient
  • bitter
  • frustrated
  • disorganized
  • scatterbrained
  • inarticulate
  • generally dissatisfied in a lot of areas of my life
I felt that way because work made me feel that way.

Now that I've separated myself from my former workplaces, I see more of my innate positive traits surfacing more often (or maybe they never stopped surfacing, but I couldn't see them through all of the negative emotions). I'm more aware of my kindness, generosity, creativity, ability to listen to and empathize with other people's stories, and sincerity.

I mean, nobody's perfect, but I'm not the asshole I was starting to suspect I was.

7. There are a lot of things I really, really want.

This one surprised me. I'm typically not a materialistic person. I hate shopping, and I generally buy new things only when I absolutely need to replace something (like if there's a hole in the butt of my jeans or if my running shorts are literally falling off). 

But this whole being-on-a-super-strict-budget thing has brought out the wanter in me - big time. All of a sudden, I'm a 40-year-old with a list for Santa.

I'll tell you what I want, what I really, really want:
  • a new phone (the screen on mine is doing weird, poltergeisty things)
  • a mountain bike
  • new running shorts and tights
  • entries to three different races
  • a trip to FinCon
  • a trip to the next CentsPositive
  • a weekend getaway with Fortysomething
  • a vacation in Colorado 
  • dinner at my favorite pizza restaurant 
  • regular visits to local breweries
  • a donut
They say money can't buy happiness.

I understand the sentiment, but trust me, a lot of things would be easier and more fun if we had more money.

8. I'm less worried about our remaining debt than I thought I'd be.

After spending almost two years obsessing about our debt and paying off credit cards and student loans with almost religious devotion, I'm a bit shocked to discover that it's been easy to let go of our original debt payoff plan. Yes, we still have an obnoxious student loan to destroy, and yes, the balance is still something like $37,000. Yes, $400 a month is going towards this loan. Yes, it's money that could be used elsewhere.

But what're you going to do. We're in a pay-just-above-the-minimum mode, and that's how it needs to be for now. It'll get paid off eventually. 

Going into month three

I'm excited to see what the third month of this career break will bring. More running, more naps, and more petsitting, I hope.

I've applied for a handful of jobs so far, and I plan to ramp up my application efforts over the next few weeks. In the meantime, I'll keep taking whatever petsitting jobs I can snag and try to get a better sense of whether establishing my own business is a viable possibility. Between working for someone else and working for myself, I'd rather choose the latter - but we'll see what happens!


  1. Sorry to hear that the crash did happen, though I'm not surprised. It sounded like you'd been running yourself ragged for a while.

    I think it'd be great if you were able to make pet-sitting viable. Besides working for yourself, it would fit your criteria of fewer interactions with people. And of course dogs are just great. So there's that.

    Keep taking care of yourself. And yes, you seemed like a good person to me when I met you.

  2. I'm sorry to read about #6. Some work environments weigh heavily on our souls. I'm glad you bounced out of your previous job if it was making you feel that way.

  3. It’s amazing to see how much more relaxed you are in two months. I’m crossing my fingers for this pet sitting thing because your change in attitude without an awful job has been palpable.

  4. I was also expecting that you would experience "the crash" although that is not what I wishing for you. I am glad that pet sitting is not only something you enjoy but can see yourself building even further. Continue to allow yourself the time to heal and re-discover you.

  5. Detox crash was definitely to be expected, I hope you get a chance to let it all out during this period. I'm glad you're finding yourself again. What a terrible thing for work to destroy our sense of selves.

    1. P.S. I meant to say also - I totally want a LOT more things than I like to admit. Sometimes I have to say it out loud just to call myself out and also to stop the daydreaming.

  6. I'm so glad you have given yourself the time and space to figure out what it going to work for you, and be sustainable in the long run. If I could find a way to spend my days with doggos, I certainly would - I hope this is something you can really build upon and make work, as it sounds pretty ideal. Good luck!

  7. Oh wow I loved reading this! I've been following you on Twitter (sunburntsaver and now melissahobe) and really enjoyed your updates. My husband is in month 9 of early retirement (he also would like to go back to work eventually, he loves his career, we just moved states and he wanted to take some time off) and he's... ready to return. He's doing Rover with me, which is fun, but it's interesting to see month 9 vs. month 2. He's not as productive as you though haha :)

  8. Looks like you are finding your place. I'm sure you will find ways over time to increase your income. Good luck.