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 FIRE Feels

Boardwalk at beach
How FIRE feels

(This was written last summer in 2023 and I just decided to publish it).

It’s been a few years since I’ve written anything on this blog. There’s a reason for that. Full-time teaching became all-consuming, and I had no time or mental capacity to type out blog posts.

Now, though, I find myself pulled toward the computer screen, desperate to type out how I’m feeling, and that’s no accident. This past May, I sent my school a resignation letter and I retired from teaching. I am currently looking for work in other fields, but I have been able to take several months off to rest and recover.

I realize I am incredibly fortunate to be able to take a break from working, and it’s due to a lot of reasons. One, and most importantly, my husband still works full-time and earns a good salary. Two, I didn’t earn a lot of money as a teacher working in North Carolina, so we didn’t rely on my salary overmuch. Three, we are debt-free (except for our mortgage) so we can cut some savings goals while I’m not working and be okay.

My husband had a taste of financial freedom himself back in 2022. After a series of painful and unfortunate events, he left his job. It took him a few months to find another role, but he had some time to rest, visit his family in Chile, and reflect on what he wanted to do next. Because he received severance pay, we were not concerned about our monthly bills, and I had health insurance, so he was able to enjoy his time off, as much as anyone enjoys time off while still looking for their next job.

We reflected on our situation last year and compared it to how we felt when he was laid off twice in 2008. That was really the beginning of our journey out of debt, and when he was laid off more than a decade before, we were in crisis mode. Because we were newly married, we hadn’t developed the assets to carry us through a crisis. We had a 95% mortgage on our home, car loans, credit card debt, and a one-income household. We had an eighteen-month-old toddler. We’d never faced such a stressful situation before.

In 2022, however, we were in a completely different financial situation, and it was thanks to that crisis from 2008. We had substantial assets in the bank, both in taxable and non-taxable accounts that we could tap into if absolutely necessary. We had healthcare and money coming in thanks to my job. We had no car loans, no credit card debt, and the ability to decrease our spending should we need to. Additionally, as a preventative measure, and in an extreme stroke of good luck, we refinanced our ten-year mortgage to a thirty-year mortgage, at 2.5%.

Mr. ThreeYear, in typical form, found an excellent job by March, so he spent a total of not-quite-three-months unemployed (he is a paragon of what to do when searching for a new job, whereas I am much slower with my own search these days).

Taking a few months off has given me glimpses into retirement. And it’s definitely given me nudges about how FIRE feels. While we’re not completely financially independent, and not retired, we are hopefully about five years away from both, and since I have time off and Mr. ThreeYear works from home, we have some moments that feel close to FIRE. Here is how I imagine FIRE feels based on my glimpses of it with my slower schedule.

A Slow Start

One of the things I hated the most about my job was my early start time. I had to be at school at 6:50am and start teaching at 7:25am.

Imagine facing a room of high school freshmen at 7:25am, and channelling the energy to get them excited about learning Spanish. They’re nodding off or slowly sipping at their watery Starbucks drinks (I taught in a super bougie school) and I am using everything in my arsenal to wake them up and get them to answer my questions, in a foreign language they don’t speak all that well.

If you know me IRL, you know that mornings are not my best time of day. I require several cups of coffee before I will answer questions or talk to you, and I like to get moving at a lot slower rate than I had to with my teaching job.

Now, though, mornings are lovely. They feel like this: I get up at 6am (which is still excruciating). I caffeinate myself and sit on the sofa budgeting on YNAB until it’s time to get up and pack the boys’ lunches. They come down, we tell them goodbye, walk them out to the car, and then my oldest son drives them away to school.

Mr. ThreeYear and I put Lucy on her leash, then head out for our 2.5 mile walk around our neighborhood. We get sunshine, exercise, and a chance to connect, all before 8am. When we get home from the walk, I eat breakfast, do my chores (making beds, cleaning the kitchen, doing laundry) and then head upstairs to start looking for jobs once I’ve taken care of the house.

Being in charge of my own time in the morning is life changing. I don’t ever want my mornings to feel different, because this routine feels so good.

Margin

Leaving my job gave me margin, which I lacked before.

I have space,

time,

room in my schedule and in my life to think, to write, to plan.

I have time to prioritize my health, by fixing myself healthy fruit smoothie breakfasts and giant salads with air-fried sweet potatoes on top.

I have energy to check in with the boys when they get home from school, and help NotSoLittleThreeYear with his homework whenever he’s ready to do it.

I have time to focus on spending our budget more intentionally, which I had little time to do while teaching. With teaching, I used grocery delivery, eating out, and impulse purchasing to feed my family and soothe my own frustrations.

Since I’ve left teaching, I have made budgeting one of my top priorities. I’ve taken on several previously outsourced tasks, like pest control and house-cleaning. I’ve slashed our grocery budget from its inflated highs in the Spring, and worked so hard to eliminate unnecessary spending.

Intentional

I’ve never been great about being intentional. I usually end up doing things because I get talked into them (I know, I have terrible boundaries).

Since I’ve stopped teaching, though, I’ve worked hard at being more intentional.

I say “no” a LOT. Whenever people ask me to volunteer for something, no matter how small, I say no. Especially if they say “now that you have all this time.” I won’t have time if I volunteer for everything I’m asked to do.

I think about whether or not I want to do an activity before I commit. For example, I rejoined my neighborhood tennis team, and I get asked to play more than the two days per week I committed to. I think hard about whether I will have the physical energy and time I need to take care of home and look for jobs, and often I’ll say “no” to extra practice or games. This is a big deal for me.

I say yes to very few evening engagements. I am plant-based and don’t drink, so half the time they’re not super fun for me anyway. And I don’t enjoy going out in the evenings in general. I like to read in my bed, so I do.

How Fire Doesn’t Feel

Leaving my job didn’t cure all my issues. I still regularly over-schedule my day. I fight low-grade depression. I battle FOMO. I yell at my kids. I ascribe too much importance to tennis. “Wherever I go, there I am” stuff. Even though I knew that I would struggle with the same issues I had when I worked, I conveniently forgot that life wouldn’t get easier when I had less paid work.

Let me repeat: life doesn’t get easier when you have less paid work.

Mr. ThreeYear asks me how I’m doing a lot, and I say, “tired.” I still get tired, but more often I’m physically, rather than mentally or emotionally overloaded.

I battle the anxiety of an unknown working future. I have to work through some boredom. It still takes loads of restraint not to over-consume coffee. If the weather is gray, I have to turn on all the lights in my house to lift my spirits.

I thought I’d have cleaned out all of my closets and drawers by now. I have not. I am slow to tackle small home projects, as I always have been.

Wherever I go, there I am, in other words.

But I like this glimpse of FIRE. It’s really nice.

How to Stay Motivated to Save When Your Investments are Booming

Like so many of my posts, this is one I’m writing for myself. Because my spending is…

Luckily, our investments are doing well (as are pretty much everyone’s at this point). Mr. ThreeYear and I have been investing most of our adult lives, and are finally at the point where our net worth increases more each year than we make.

We’ve never been particularly frugal (I haven’t, especially), so we are cruising through life at this point, eating out, buying food (food is always our Achilles Heel), planning vacations, and generally not being especially careful with our money.

Luckily, our old standby tricks of saving are helping, somewhat, but as I look at our cash reserves throughout the year, they are decreasing, precipitously, as the months roll on.

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Semi-Minimalist Home: Updated

Years ago, I published pictures of what I called our semi-minimalist home in New Hampshire. Minimalism isn’t a contest and there is no right way to undertake it, but I hesitated to call myself a full-one minimalist because I don’t believe I have gotten to the place where I eschew material items enough to warrant the full title.

Still, we practice a reduced aesthetic in our family, and while we still consume too many material goods, we regularly reflect upon and rid ourselves of extraneous belongings in order to make our home calmer and more inviting.

I gave you a tour, four and a half years ago now (wow!), of our New Hampshire home, and I thought you might be interested in seeing how we’ve organized our North Carolina home. It has taken a lot to get our home pared down, as it is a full one thousand square feet smaller than our previous home, but luckily it has more bedrooms, so we have been able to create spaces for everyone in the family (and for Mr. ThreeYear’s office!) and to make our home work. And we’re trying valiantly not to move into a bigger home, given that we would probably have to spend double to find a larger home in this crazy market.

Our home was built in 1999, so it is a bit of an older home, but it has been a great home in a solid location for three years now.

First, here is our living room.

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Eating Plant-Based: How’s It Going?

In early November, I posted about how our family had made the decision to eat plant-based. Ok, I made the decision to eat plant-based and made my family go along with me.

So how’s it going?

It’s been approximately eight months since we transitioned to a plant-based lifestyle, meaning we mainly eat veggies, fruits, and grains (lots of grains to keep full) and rarely or ever eat meat, cheese, or other dairy products. I say rarely because I have occasionally eaten ceviche and cheese, and my boys eat meat as often as they can, which is usually when we go out to eat.

How has the transition gone, and have we noticed any benefits or any negatives to this lifestyle?

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Why We No Longer Strive to Be Location Independent

For much of the life of this blog (five years in October?!), I have talked about my family’s desire to be location independent. When I first began blogging, Mr. ThreeYear and I considered the possibility of moving abroad, teaching in international schools, or becoming digital nomads.

In the end, we moved to North Carolina. Although we were technically location independent when we moved, we have since made decisions that tie us firmly to one area of the world. We bought a house, I got a location-dependent job there, and I now have a second location-dependent job that I hope to stay in until at least both boys graduate high school (in May of 2028, which is crazy close for us to be empty nesters! Whaaahh!!).

We haven’t talked about, or really even thought about, moving, moving internationally, or otherwise taking advantage of location independence in three years.

Why did our goals and dreams change so much?

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Boundaries

I recently listened to an excellent podcast on Boundaries, We Can Do Hard Things (Episode 2). In it, author Glennon Doyle and her sister Amanda Doyle discuss setting boundaries in many parts of your life (one thing in particular they said really stuck out to me, “You are not responsible for people’s feelings about the boundaries you have set.” How great is that piece of advice?).

I admit, I am not someone who has strong boundaries, or even completely understands the concept of boundaries. My boundary-setting is apparently so bad, my friend’s husband recently gave me the book The Book of No: 365 Ways to Say It and Mean It.

So this blog post is my exploration of and attempt to better understand boundaries, specifically boundaries around time, organization, and finances.

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Our Kids’ School: Next Year

Hello! I am not dead, as I hope you’ll be glad to hear. I’ve been overwhelmingly busy this spring with school (which coincides with students going back full time and my mornings no longer being quite as flexible to blog).

This post is a follow up to my post Why We Put Our Kids in Private School. In it, I detailed our decision to put our kids in an expensive private school (where I worked) and outlined our thought process to get there.

If you had asked me five years ago whether or not I would put our kids in private school, I would have laughed in your face. Then again, my ability to imagine a global pandemic was limited. If this past year has taught me anything, it’s that we have to make the best decisions we can, in real time, given the unique set of circumstances we face.

We chose to put both boys in private school for this school year and they had an incredible year. Truly, it was magical.

Now, let’s talk about next year.

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How to Shop Costco

Mr. ThreeYear and I fell in love with Costco when we lived in Atlanta. It was conveniently located, the prices were great, and you could occasionally find very good deals on cool items for your yard or your house. But in New Hampshire, the closest Costco was over an hour away. So, for eight years, when we lived in New Hampshire, I occasionally shopped BJ’s Wholesale Club (we could get a discount membership through Mr. ThreeYear’s work). But it really wasn’t the same.

Fast forward to December, 2019, when my good friend and fellow deal lover took me to the newly-opened Costco near our house. I bought a membership that day, loaded up my buggie, and several hundred dollars later, decided I needed some ground rules regarding how I shopped at Costco.

Only Shop with a List

First of all, if you are browsing in Costco, prepare to check out with a much-higher grocery bill than you planned. You will be tempted by the fourteen-pack of ready-to-eat Indian Chana Masala, the chocolate-covered almonds, or whatever your weakness is. Costco is a master at products that entice you to buy them when you weren’t planning on it. I think their products have some weird electronic signal that attracts you to them.

Instead, when you go into the store, have a list of what you’re planning to buy. It’s okay if your list is vague, like “Boys’ Pants”–sometimes you don’t know exactly what they have for sale–but have an idea, and a price range, of the items you’re looking for. Otherwise, you will buy things you don’t need.

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Our Half-Bath Makeover

I decided to budget a portion of our end-of-the-year bonus to updating our downstairs half-bathroom.

It was in terrible need of a refresh, since it had holes in the walls, mismatched paint, and dated fixtures. It was not a place I wanted to welcome guests when they came over.

Still, I knew the bones of the room were good, and it had a decent pedestal sink, so I felt pretty confident we could get by with a cosmetic makeover.

I’d always wanted to try peel and stick wallpaper, and I thought it would cover the holes in the sheetrock without me having to do much, so I decided to incorporate it into my budget.

Still, I wasn’t exactly sure how much everything was going to cost. I priced out a few fixtures online, a new light (the current one was a 90s monstrosity of painted-rust vines), and some wallpaper, and ended up with a budget of $650. I figured that would probably do it, but decided I could budget more later if I needed to.

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