Side Hustle Success: Transitioning from Teaching to Full-Time Personal Finance Writing

A few months ago, I published an update I wrote last summer. Here’s the promised follow-up.

I haven’t written anything on this blog in three years. It’s hard to explain why I stopped writing completely after five or so years of consistent posts, even to myself, but a lot of it had to do with my full-time teaching job, my freelance writing gig (more on that in a second) and not having any creative margin in my life that allowed me to sit down and write for fun. Oh, and Covid.

When I started this blog in 2016, my life looked very different than it does now, as lives do. I had two young children, aged six and nine, a part-time job as an ESOL teacher and my family lived in New Hampshire. This blog became a very real way to organize several nebulous ideas and dreams into a concrete, actionable plan that ultimately changed the course of my life. The premise of the blog was to document my family’s progress toward location independence by 2019.

Ultimately, we achieved our goal a year early, in 2018, which completely shocked me at the time. Our location independence looked more like a permanent move to a home we purchased in North Carolina, but that was ultimately what suited my family best.

I took a year off after our move to help us get settled, then found a full-time job teaching Spanish at a local private school. I blogged through that school year and into the next, but by summer 2021, when I switched jobs again and moved to a local charter school, I had no more time for blogging.

Instead, one of my main creative outlets became freelance writing for Women Who Money, an awesome website run by Vicki and Amy, two lovely ladies I met at FinCon back in 2018. I was writing about personal finance and earning some side income at a very manageable pace.

My new job, though I didn’t realize it at the time, was not at all manageable. It had a punishing pace. I was thrown into a new school with little training or support. I had about 150 students, many of whom had very real emotional struggles that I felt unequipped, time and energy-wise, to help them with.

The pay gap from New Hampshire continued to upset me. I felt massively underpaid and that, coupled with the huge workload, created a resentment I couldn’t shake.

I read a statistic last night that in the U.S., nearly half of American teachers come from the bottom third of their classes (that statistic comes from Jared Diamond, in the book Upheaval). That’s because of the pay. American teachers have the lowest relative salaries, relative to average national salaries from all jobs, among major democracies. Contrast that with South Korea, where teachers must score in the top 5% of their version of the SATs and 12 teachers apply for every high school teaching position in the country. Our country has chosen to spend more on our industrial prison system than our educational system.

So I retired from teaching in May of 2023 and began looking for another job.

I assumed I would find a job in the education field, since that’s where I had worked over the last eight years. I applied for consulting, marketing and tech jobs with educational companies. I didn’t hear back from anyone for months, which I hear is pretty typical in this post-Covid, work-from-anywhere, AI-resume-reading job market.

In an effort to help my job search, I bought the premium LinkedIn subscription and used their AI bot to rewrite my profile. The bot highlighted all of the freelance personal finance writing I’d done over the years which I had not included.

A recruiter reached out the next day to set up an interview for a – get this – personal finance writing position. I told her I honestly hadn’t considered writing as a career because I thought AI would make writing jobs obsolete pretty fast.

Despite this somewhat premature statement, she invited me to submit a sample article, and after I’d done so and had four more interviews, I was offered a job by the company.

Frankly, you could have knocked me over with a feather. This was a dream position, to be able to write personal finance articles full time.

After I negotiated the heck out of the salary and was ultimately offered a Senior Writer position, I took the job. That happened last November.

Since then, I’ve been adjusting to a new type of schedule. Writing full time is intense, but a different kind of intense than teaching. There’s so much more flexibility and I don’t have to work as many hours. I do have to be extremely focused when I am working.

Nice to be able to work from my patio on a lovely day.

That flexibility, coupled with a much higher salary means I am much happier in this role. Yes, I miss some parts of teaching, mainly my students’ energy and enthusiasm. But it’s really nice to be able to manage my time and continue my slow morning routine I enjoyed so much while job-hunting. Start work at 6:50am or 9am? Hmm, let me think…

As we plan for Mr. ThreeYear’s retirement in the mid-term, it’s also helpful to know that my job can continue to provide healthcare, income and benefits while the kids are in college, while allowing us to travel or live long stretches in Chile or wherever else we’d like to explore.

Will AI take over my job? Maybe. We already use it a fair amount at work, to write briefs, help us find different research paths to explore, and combine large amounts of data (like customer reviews) into manageable and meaningful chunks. But I also feel like I’ve proved myself enough at work that I could fairly easily move into an editorial position if needed. And the quality of writing AI produces is still so low I don’t see that happening anytime soon.

I guess the moral of the story is, don’t be afraid to make a career jump if you can. I fully admit I was able to because I wasn’t the main income earner and Mr. ThreeYear was chill enough to agree for me to jump off the job cliff, so to speak.

Also, I think it’s pretty cool that my side hustle turned into my main hustle. Another reason why it’s worthwhile to pursue side hustles.

Will I keep blogging? I honestly don’t know. Life is busy right now. Junior ThreeYear is now a senior in high school (waaaa) and life feels busier than ever, even though my job is easier. Although I never wanted to believe it, teenagers really do need a lot of emotional support and time.

But blogging is such a creative outlet and a great place to pin my brain ideas and turn them into more concrete thoughts and plans. So we’ll see. And now that I’m rounding on a year at my job, things are feeling a bit more manageable so we’ll see. And I definitely need to update you on my successes with budgeting, because that’s been a fifteen-year journey.

As always, thanks for reading. Enjoy your Labor Day holiday!

How Other People Can Help You Reach Your Goals

We all need a little help in life. When it comes to staying on track with our goals, friends and partners can make a huge difference in your success rate.

Sometimes you need a bit of outside help to keep you on track for those big financial goals. Here's a list of the people who can help! @lauriethreeyear #financialgoals #frugalfriends #pfadvice

Running Partners

For example, I’m currently training for a half marathon. A college friend reached out to me to see if I wanted to sign up with her. We live about 40 minutes apart, so we can’t train together, but we text each other our stats.

On Saturday, I needed to run 8 miles. I’d arranged with another neighborhood friend to run early Saturday morning. The night before, Friday night, a friend had a get-together. If I had to run those eight miles by myself, with no one to support me or keep me on track, I’m sure I would have stayed way too late at the get-together and would have found a reason not to get up the next morning. 

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How to Help Your Economy

Over the last several years, household debt across the world has been slowly increasing. That debt includes mortgages, car loans, and credit card debt. China’s household debt now stands at 49.1% of GDP, relatively low compared to many developed nations, but worrisome because of its 30 percentage point increase in the last decade. Shockingly, Switzerland leads the world with household debt at 127.5% of Gross Domestic Product. That means, for every $100,000 of GDP a household produces, they hold $127,500 in debt!

The average citizen in Switzerland, which has traditionally been an extremely wealthy country, has substantial assets (net worth) underpinning this debt, or at least four times more assets than the average American.

Even so, Switzerland, as well as nine other economies including Canada, Finland, and Australia, have debt levels that are high and rising quickly, at a pace that mirrors that of the US right before the housing bubble

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