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

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Part-Time Lifestyle And Income Report #1 (Week Of August 5)

Income Report Context

Earlier this year, I was earning a salary of $60,000 in a job I despised, and my family was making over six figures annually. We were able to pay off some debt, invest, and save. After many months of searching, I took a lower-paying job that I hoped would be a better fit. The new gig turned out to be a total horror show, so I eventually quit and embarked on a career break.

Now I'm trying to figure out my next steps. I don't feel like I'm on a break anymore, but I'm also not working 40 hours a week. Instead, for the time being, it looks like I will be cobbling together freelance and hourly gigs to help bridge the gap between our family's expenses and income. This is an entirely new journey for me: until now, I've always worked full time.

Fortysomething's job covers many of the bills, but not all of them. I need to earn ~$1000 a month after taxes in order for us to break even. Ideally, I'll earn more than that so that we can put money into savings and investments.

I thought it might be fun and informative (if only for myself!) to post a weekly recap of what I'm referring to as my New Part-Time LifestyleTM.  Assuming I can make myself stick with it, I'll stop in every Friday or Saturday to share what I've earned throughout the week, any challenges that have come up, and how I'm feeling about my new approach to work life.

Personal Income This Week 

Rover: $94 (after Rover fees)

This week, I booked a few one-off drop-in visits as well as a steady four-day dogwalking gig. To be honest, I'm not sure it was worth it. I drove across town on Monday to discover that the owner had forgotten to leave a key. Another person booked me to walk a super-shy dog who refused to come out (which was fine, but I felt bad that I couldn't meet the owner's expectations). In a couple of other instances, I walked into my clients' homes to find that their roommates were home and were unaware that I'd been stopping by. It was awkward.

Dealing with one or two of these situations on a weekly basis is okay, but having to manage unexpected, people-related issues or challenges at every visit is exhausting.

As I mentioned on Twitter, I've kind of had it with Rover at the moment, but I'm going to keep going to see if I can get some better bookings over Labor Day. I've found that the best petsitting gigs are those that span several days; that way, you have a chance to get to know the pet, develop a routine, and figure out what to expect from the owner.

Online Teaching Job: $264

My new part-time online teaching job started on Tuesday. I'm slated to work 12 hours per week. This week, those hours were quickly allocated to administrative tasks, meetings, review of course materials, and grading. My position has been open for a while, so by the time I'd met my hourly quota, I still had piles of tasks to finish... but I stopped, because I'm not working for free.

Overall, the job is enjoyable. Online teaching was my bread and butter for years, so even with new policies and new courses, it's still relatively easy for me to dive in and get things done without feeling overly stressed out.

I've already asked my boss if I can work a few additional hours next week to help get them caught up, and she said yes. Yay for some extra income on the horizon.

Total income this week: $358

This Week's Challenges

Aside from the petsitting debacles and typical new job anxiety, my biggest challenges this week were an insurance issue and being ghosted by the organization that interviewed me for a full-time job I was pretty excited about.

The interview took place two weeks ago. I've heard nothing since then, except for a brief acknowledgment of the thank you note I sent. It's upsetting. Some people will probably argue that this is just the way it is and that I should move on. I agree, and yet I still feel angry and frustrated, probably because this situation serves as yet another instance of being treated like shit by a supposedly professional organization. I prepared for this interview. I researched the people and the mission, and I gave a lot of thought to how I could contribute. I took time out of my day to attend the interview and spent money on parking. I gave real, honest, and detailed answers to every question they asked. I did not BS my way through any of it.

Ultimately, the entire experience was a complete waste of time and energy, but there was no way for me to know that at the outset. How am I supposed to trust prospective employers when so many of them behave so badly? Why would I want to continue doing this to myself?

As for the insurance issue: the company that offers my short-term insurance is the same one that offered my insurance at my previous job. My employer-sponsored insurance ended in April, and my self-sponsored insurance started in May. I had a skin cancer screening at the beginning of July, at which time I provided my self-sponsored insurance card to the doctor's office.

For whatever reason, the insurance company decided to file the claim under my expired insurance instead of my active insurance. And WHAT DO YOU KNOW: expired insurance covers a grand total of nothing! So now I have to get on the phone with the company and try to get it sorted out, because nothing about insurance in the U.S. is ever straightforward.

How I'm Feeling Overall

Overall, I'm feeling that I do not want to drive my car off a cliff, which is a substantial improvement over how I was feeling earlier this year. So... win? I have no regrets about quitting my old job, taking time off, and starting over. No regrets whatsoever.

At the same time, I do worry about being able to make ends meet, and I feel frustrated about some of the things associated with this new part-time lifestyle:

  • Job searches are a giant pain in the ass.
  • Shitty insurance is a giant pain in the ass.
  • Dealing with people can be a giant pain in the ass.

Also, before someone hops onto their soapbox to tell me to JUST BE POSITIVE, I keep this blog mostly as a record for myself and my family. Therefore, I'm writing things down the way that I see and feel them.

So how was your week?


  1. NEVER STOP BEING NEGATIVE. I need you in the dark with me, muttering and cursing!

  2. It seems like the online teaching gig is going well. Yes, insurance sucks. My doctor's office regularly bills the wrong insurance and then blames me for switching jobs and insurance too often. Sorry for wanting a job where I treated well. There may be lots of jobs in this economy but the employers suck!

    1. Thank you! It is going well!

      The insurance thing is finally sorted out. Yay!

  3. That's really shitty about the insurance. I hate sorting these things out because the patient/member ends up being the one with all the responsibilities to sort out someone else's problem. You'd think it would be the administrative responsibility of the other parties involved, no?

    Sorry that Rover's being a pain but yay for online teaching!

    I don't suppose a move down to the bustling metropolis of Phoenix (or the academic adjacent town of Tempe) might be a possibility, eh?

    1. I couldn't deal with the heat in Phx. I don't know how you guys do it!

      The insurance did get sorted out, and crazily enough, both the doctor's office AND the insurance company were helpful. Am I living in a parallel universe?

  4. Yeah, sorry about the interview but that seems to be typical from what I have experienced. Generally, they will interview, and then select second interviews, do background checks, and get accepted offers before they get back to the first group that they didn't get it. I interviewed in March(started talking to the company in Jan) and just heard back yesterday that I didn't get the position. ugh.

    1. Ohhhh man. That is such a long time!

      I did finally contact the hiring manager. Apparently they're still finalizing a decision, which seems bonkers to me for a position that a lot of people could do well. But... yeah, maybe this is just how it is.

  5. You are hanging in there, and that right there is a positive! The teaching gig sounds promising, or at least it helps with filling in the cracks. With schools starting back up, could you perhaps do some private tutoring?

    1. The teaching gig IS going well! I'm really enjoying it, and I'm hoping that maybe I can convince them to give me more like 15 hours a week on a regular basis.

      I am quickly learning that I get burned out on any job involving face-to-face communication. I do like people (I promise!), but my brain doesn't seem wired for any lengthy amount of interaction. So I'm a bit hesitant to pursue tutoring.