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!

Effort, Achievement, and FI

This article, written over a year ago now, is timely. I’ve been looking for jobs for next year. Looking for jobs isn’t fun. It’s an exercise in humility, effort, and rejection required to be undertaken daily. One of the reasons I blog is to remind myself of lessons I’ve learned that I can easily forget as time goes on. I wish that I could learn a lesson once and internalize it forever. Alas, these life lessons are to be learned over and over again. 


As educators, wrote an article I recently read, we must teach our students the relationship between effort and achievement. That is to say, there is a direct correlation between the effort we expend on a particular endeavor and the likelihood that we’ll have success in said endeavor.

Effort, Achievement, and FI--www.thethreeyearexperiment.com

This may sound like a basic concept, but, like so many basic concepts, once you take a minute to unpack it, it has profound implications.

The more effort I put into something, the more likely I am to have good results. 

Many times, I water that advice down in my head. I pretend there’s not a direct correlation between my level of effort and my achievements: “I’ll just run three times this week instead of four. I’ll skip the mid-range run.” Every time I skip a mid-range 6-mile run, my longer 10-12 mile run is super painful and I’m slower. Over an entire training period, that means I’ll run (even) slower on race day.

“I’m tired, so I’ll wake up at 6am instead of 5am. I can still write a blog post.” That’s when I publish 2 posts per week, not three. Over time, I notice my page views slipping and readership going down.

“I’ll just wing it in class, instead of preparing a lesson plan for the week. I can prep before class each day.” My classes are not as good, I’m scrambling for activities to fill the time, and over time, my students don’t make as much progress learning English.

The truth is, consistent, daily effort pays off. It pays off in life, and it pays off (literally) when you’re working towards financial independence.

Making More Money

In the past two and a half years, I have expended a great deal of effort towards my new career–ESOL Teacher. When I started teaching in September of 2015, I knew very little about teaching English. I worked very hard to network with other teachers, observe their lessons, ask questions, and take copious notes. I started a Master’s Degree in Teaching English to Speakers of Other Languages, and many nights and weekends were spent reading, on our online classroom, or in class, an hour and a half away. Continue reading “Effort, Achievement, and FI”

The Six Streams of Income We’ll Rely on in Early Retirement

Now that our family has moved to North Carolina, our next big financial goal, ten years’ hence, is retirement. We’ve decided to wait until Little ThreeYear graduates before we retire (although we could always change our minds).  Since we’ll be retiring somewhat early, before the “official” age of 65, we’ll need to structure our retirement so that we have access to different pools of money, or streams of income, to tap into.

Though Mr. ThreeYear and I primarily invest in index funds (we have a “slow and simple-don’t get greedy” philosophy), we currently plan to have several streams of income available to us when we retire. Some will be passive, and others active. While this wasn’t necessarily a conscious plan on our part, life has worked out this way and we’ll take these streams of income we’ve developed along the way. Continue reading “The Six Streams of Income We’ll Rely on in Early Retirement”

Can Optimism and Hope Increase Your Wealth?

This post contains affiliate links. Please see my full disclosure for more information. Thanks for supporting the blog! 

Is it possible to increase your net worth through optimism and hope? Last week, I was listening to this episode of the Australian All in the Mind podcast featuring American positive psychologist Martin Seligman, speaking on the power of positive psychology and optimism in changing our outcomes.

One of the reasons I was drawn to this podcast was because Seligman is an academician. He’s interested in quantifiable research in neuroscience that psychologists can use to improve people’s outcomes, that is, their happiness levels. Seligman is the Director of the Penn Positive Psychology Center at the University of Pennsylvania and is widely known as the founder of positive psychology (here’s a TED talk he did from 2004).

In the podcast, Seligman shares how early on in his career, he realized that his colleagues were focused on the alleviation of misery and suffering, but he was interested in how to increase happiness: “I said, look, when you lie in bed at night you are generally not thinking about how to go from -8 to -5, you’re thinking about how to go from +3 to +6 in life. Psychologists have never worked on this, we’ve never worked on happiness, well-being, the stuff that is above zero.”

It became his mission to figure out how to teach optimism. Continue reading “Can Optimism and Hope Increase Your Wealth?”

How to Be a Rockstar at Your Job Part 2

When you’re building wealth by saving and investing, one of the things that can help you save much more rapidly is earning more. In Part 1 of “How to Be a Rockstar at Your Job,” I detailed three ways Mr. ThreeYear and I have been able to increase our wages over the years: taking responsibility, working as contractors, and tooting our own horns.

Today, I’ll offer several more ways we are able to become rockstars at our jobs in order to increase our salaries as much as possible.

Find a Mentor

Jalpan from Passive Income Engineering cited finding a mentor as one of the key ways he’s been able to progress in his field in intellectual property.

A mentor is a co-worker at your job who’s ideally a couple of positions above you, or someone who has more experience in different areas. He or she can teach and guide you, answer questions, and generally help you become better at your job.

A good mentor will challenge you, encourage you to apply for promotions you might not feel ready for, and help you understand situations that come up with your boss or peers. Continue reading “How to Be a Rockstar at Your Job Part 2”

How to Be a Rockstar at Your Job

Last week, I wrote about building wealth, and how Mr. ThreeYear and I began saving and investing.

I would be remiss if I didn’t discuss one of the major ways we’ve been able to save: our incomes. Mr. ThreeYear has worked hard to increase his earnings over the years and now earns a very competitive salary for his field.

While I work part-time (as a teacher no less), I have increased my hourly wage with my job so that were I to work full-time, I would earn a very competitive salary (higher than the average teacher salary).

Mr. ThreeYear and I have worked hard to rock our jobs, and this is one of the key ways we’ve been able to pay off debt, invest, and increase our net worth.

ESI Money (which stands for earn, save, invest) discusses earning as one of the keys to increasing your income, and has some great posts on the subject, like how to ask for a raise.

Earning more during your working years is one of the fastest ways you can increase your savings, especially if you’ve developed the discipline of banking your raises.

Many financial bloggers talk about side hustles, building your own business, or buying real estate as a way to increase your income. These are fantastic ways to earn more money, but today I’m going to focus on increasing your wages as an employee (or a contractor–we’ll get to that).

Continue reading “How to Be a Rockstar at Your Job”

How I Met Mr. ThreeYear and Became a Financial Nerd: Guest Post on Chief Mom Officer

Hi all! Today, I’m really excited to have a guest post over on Chief Mom Officer’s awesome site on how Mr. ThreeYear and I met and how I became the financial nerd I am today. Liz, AKA Chief Mom Officer, and I have been “blog friends” for almost as long as I’ve been blogging, and we’re now IRL friends, too, since we got the chance to meet in person in Boston last fall.

How I Met Mr. ThreeYear and Became a Financial Nerd: Guest Post on Chief Mom Officer--www.thethreeyearexperiment.com

The things I love about Liz are how focused and no-nonsense she is, and how passionately she advocates for financial literacy for women and moms. She gets a LOT done in a day, a week, and a year, and part of that is because she has crystal-clear goals: Continue reading “How I Met Mr. ThreeYear and Became a Financial Nerd: Guest Post on Chief Mom Officer”

When Life Gives You a Kick in the Pants

Last week I got some news. One of my English Language Learner students, a newcomer with whom I’d spent several hours a day, was returning to her home country.

How thrilling for her! She is Puerto Rican and came to New Hampshire after Hurricane Maria. As much as she likes our school and learning English, she left most of her family there, including her dad, her dog, and her cat. And she misses the warmth! She misses going to the beach every day. Now she gets to go home. She is so happy.

As excited as I am for her, I’m bummed for myself. Because I worked with her so much each day, I’ll now have a lot less to do each day. And my income will drop significantly. I enjoyed teaching her, and all of the hours I worked with her provided a significant bump in my paycheck. This is a downside of being a contractual ESL Teacher, though. I can’t choose how many students I work with–it’s entirely dependent upon who moves into the district. Continue reading “When Life Gives You a Kick in the Pants”

Location Independent, International Jobs: Andrew

Hello! Welcome to “Location Independent, International Jobs,” the Wednesday series where I showcase stories from people who have become location independent, work internationally, and/or continuously travel.

In today’s interview, you’ll hear the story of Andrew, who lives in Dubai with his wife, Jamie, and their two young sons. 
This interview will cover:
  • how to get an international job (hint: your network is important!)
  • the benefits of an MBA
  • how to become an international entrepreneur
  • some cultural shocks from Dubai
  • the financial benefits of fasting
For the complete story of how Andrew made a life in Dubai from Atlanta, Georgia, keep reading! 
Can you tell us a little bit about your background?

I am an American from a small town in north Georgia.  My wife and I have been living in Dubai since 2008.  We have two boys named Jack (who’s six) and Zain (who’s three), or as we call them, Thing One and Thing Two.  They were born in The Emirates.

Location Independent, International Jobs: Andrew--www.thethreeyearexperiment.com
The Waskey family all dressed up for Halloween, Dubai-style.

I graduated from Furman University with a degree in Spanish.  I earned an MBA at Georgia State University in Atlanta.  I attended part time for a few years while working for DHL (the delivery company).

How did you make the decision to move internationally?

My wife and met while in graduate school for international business. Both of us wanted to live overseas – mostly for the adventure [Laurie: Andrew has traveled to over 80 countries!] . As a part of our graduate school program we had to intern overseas. I worked in China and she worked in Argentina. After we graduated we got jobs in Atlanta and then when an opportunity to work overseas just before the Great Recession. We never planned on living in the Middle East and we thought we would just stay for a year.

Continue reading “Location Independent, International Jobs: Andrew”