As my firm prepared to file its final tax returns of the 2016 fall tax season, I asked my boss if I could take some time off during a particularly slow time for the firm. He was thrilled to save on payroll for a few months, while I was thrilled to get a few months to travel full-time and dedicate more time to my side gig writing for The Points Guy. A win-win.

I figured I’d be back in January to work the spring tax season. However, September 30, 2016 would end up being my last day working full-time in tax accounting.

Here’s what led up to me leaving my successful tax career eight years ago today.

The Plan Before Tax Accounting

Going into college, I had a pretty good idea of what I would do after school. I was one of the first employees of Indigo Coffee, a start-up drive-through coffee company quickly expanding in my hometown of Tampa, FL. If you’re familiar with Dutch Bros Coffee, that was what we were doing at Indigo Coffee 20 years ago.

The plan was for me to go to college at Georgia Tech to study business management, finance, and accounting. Then, I’d come back and become the “money guy” for the start-up company.

During college, I joined the Georgia Tech Co-Op program. This let me alternate semesters between working at Indigo Coffee — where I’d become store manager for one of the new locations — and school.

However, during the spring of 2006, infighting between the co-founders led the financing partner to pull all funding out of the company. Once the company couldn’t pay its bills, the implosion of the once-growing company was quick and dramatic.

Getting Started in Tax

It was February 2006, and I suddenly found my default career plan dashed. However, I pretty quickly stumbled into what would become my career for a decade.

Katie and I had just started dating in August 2005. Katie’s mom ran (and still runs) an accounting firm north of Atlanta, and she could use some help for the 2006 spring tax season. I’d just taken a tax accounting class the previous fall and loved it, so I figured I’d give tax a shot. It’d let me test a new field and be in the same town as Katie.

In retrospect, it probably wasn’t the smartest idea to work for my girlfriend’s mom during a stressful time in a field I didn’t know much about. The situation could have gone wrong in a lot of ways.

However, I took to tax like a fish to water. Accounting let me flex my math, analytical, and problem-solving skills. Katie’s mom insisted that I was a natural.

The First Real Tax Internship

By fall 2006, I was just one semester away from finishing college, so I started a job search.

As the stock market reached a fever pitch, investment banking recruiters swarmed the Georgia Tech College of Management. I was wooed by the incredible amount of money that seemed possible in investment banking.

However, Katie and I had already gotten very close, and I didn’t want to move away for a job. Thankfully, that young love helped me dodge the bullet coming to that field over the next few years.

Instead, I decided to accept an internship with a “large local” (~75 employees in one office) tax firm in Atlanta called Smith & Howard. The firm promised the real deal: I’d be paid and treated like a full-time tax accountant. Sure, that would mean a lot of hours, but I could see for myself if this was a field I was cut out to be in.

From January 15 to April 15, 2007, I really did get to experience the real thing: 80- to 100-hour seven-day workweeks, catered dinners Monday through Thursday at the firm, and not getting home until after midnight many weeknights.

Smith & Howard hired five interns that spring, and the firm bosses weren’t shy about telling us there was only one full-time job opening for the group. Not all of my fellow interns could handle the Hunger Games-style contest, but I fed off of the competition. I scored the full-time job offer.

A Stint in International Tax

While I liked the complexities of tax, I wasn’t convinced that working at a public tax firm was the life I wanted — what with working past midnight many nights. So, I applied for an international tax internship at Georgia-Pacific for the summer of 2007.

Over just a few months, I’d end up working alongside brilliant tax lawyers crafting international tax strategies — including repatriating funds from South Africa, implementing new offshore entities, and addressing complex transfer tax situations for intangibles.

Just a couple of weeks into this internship, Georgia-Pacific’s head of international tax put me in charge of the behemoth company’s Canadian tax compliance. That involved reviewing (and frequently fixing) U.S. tax forms prepared by a team of KPMG staff. I even traveled to Toronto to visit the Georgia-Pacific manufacturing plant there and meet with the Canadian tax accountant.

I’m still stunned by the incredible responsibility and sheer amount of work that I did in just a few months.

Georgia Pacific didn’t even wait until the end of the internship to extend an offer, and I was tempted. The work was everything I liked about tax but on steroids. But then I took a critical look around the GP international tax office and realized that I had a ceiling right over my head. I didn’t have much chance of advancing in the department without pursuing a tax law degree.

Going Full-Time in Tax, And Starting to Travel

With two full-time job offers on the table, I accepted the position at Smith & Howard. After graduating in December 2007, I started full-time just a few weeks later. The previous year’s internship successfully prepared me for what it’d be like, and I settled into the long and grueling tax season.

One perk of being a full-time staff member — at least for me — was getting to head out of town for training. Smith & Howard is a member of the BDO Alliance, so we’d head to wherever BDO was hosting training that year. For my first year, we headed to Houston. While I missed Katie during the trip, I loved the chance to travel. Yeah, it wasn’t glamorous travel, but these training trips still gave me a chance to fly and stay at hotels. Best of all, work was paying for it!

Unlike future accounting firms I’d work for, Smith & Howard’s work culture was great. The cubicles were mostly filled with recent graduates, and the managers and partners liked to have fun as much as we did.

The firm paid for offsite happy hours, organized softball teams, and even held an annual roast every April 15 where one of the founding partners would (lightly) roast each member of staff. We continued the tradition of the tax department playing a prank on a certain audit partner (who had previously joked that tax staff only work a few months a year).

During all of this, I took evening classes, studied for, and took the CPA exam. I passed all four sections of the CPA exam on the first try, with an average score of over 90 (passing score is 75). Several tax partners ribbed me for clearly having wasted so much time studying.

A Big Decision

Smith & Howard was an incredible learning experience. But I needed to choose which I wanted a long-term relationship with: Katie or Smith & Howard.

That’s because Katie was determined to get a PhD in Computer Science. Academia frowns on academics staying at the same college as undergrad, so we knew she’d have to move somewhere. Although we had been dating for a few years, our relationship quickly became serious and we’d already moved in together.

Each January, Smith & Howard encouraged its staff take one last long weekend. And I had a plan to make the most of mine in January 2009. Katie and I headed to Callaway Gardens — a pay-for-admission gardens resort a couple hours south of Atlanta. We’d been several times before for their incredible holiday light show and were charmed by the resort’s butterfly gardens and its lovely chapel.

As Katie had already figured out, I had big plans for that weekend. She recollects being confused when I didn’t propose in front of the chapel, wondering if she’d read things wrong. But her hunch was right. On a hike Sunday afternoon, I proposed to Katie at a spring — saying something sappy about how my love was bubbling up and evergreen like spring.

Katie happily accepted. A older couple walking the trail with their cat on a leash happily snapped photos right afterward.

Determining Our Next Move

As Katie planned to graduate in May 2009, we weighed her options for her PhD. She’d been encouraged to take the shotgun approach, applying to around 15 different programs in the hopes that she’d get a few offers.

Between Katie’s impressive undergrad research and excellent grades, Katie ended up getting offers from seven PhD programs — including Brown University, the University of Michigan, Duke University, and the University of Texas.

Each had its pros and cons. Michigan may have arguably the best program… but what about the winters? Duke would let Katie dive deep into the theoretical aspects of computing she’d been drawn to, but would it be the best choice to set her up for her dream job as a professor?

In the end, the decision became clear: University of Texas at Austin. Not only was UT a top-5 PhD program in artificial intelligence with award-winning professors, but Katie could work on the lab’s robotic soccer project — which we’d been introduced to when we volunteered at RoboCup 2007 in Atlanta. Plus, Austin seemed like a pretty cool place to live.

With the decision made to move to Austin for fall 2009, we turned our focus to planning our wedding. We figured what better place to get married than the beautiful chapel at Callaway Gardens.

Reviewing available wedding dates, one stuck out: August 15, 2009. We’d originally made our relationship “Facebook official” on August 11, 2005. So, getting married then would let us continue to mark our anniversary around the same time.

Falling In Love With Travel

With a move to Austin and a wedding planned, an extended-family Alaska cruise scheduled for mid-July, and a bit of savings in the bank, I turned in my notice to leave Smith & Howard as of June 30, 2009.

Katie and I planned to take full advantage of the work gap, piecing together a month-long trip up and down the West Coast. After Katie attended the International Joint Conference on Artificial Intelligence in Pasadena, we rented a car and meandered up the California coast to the Bay Area, visiting wineries, sights, and hiking trails along the way.

After hopping a plane to Anchorage, Katie overcame her fear of biking as we explored the city on two wheels one day and then climbed Flattop Mountain to see the city from above the next day. We took a train down to Seward early to hike a glacier. After a spectacular cruise, we explored Vancouver and drove across the US-Canada border with my parents to explore Seattle.

After dropping my parents at the airport with the plan to see them in a couple of weeks for our wedding, we continued exploring the area around Seattle, visiting the many aspects of Olympia National Park and even sleeping in our rental car when we didn’t realize how the Twilight movie craze would mean no vacancy anywhere around Forks, Washington.

This spectacular one-month pre-honeymoon trip gave us a crazy idea: What if we took a gap year to travel after Katie finished her PhD? After all, Katie would surely need to move universities again to continue advancing in her career in academia. Perhaps we could stretch that transition period into a full year. So, that became our goal.

Moving to Austin

Just two days after our wedding, Katie and I packed our cat Grace and remaining belongings into our two cars and began driving toward our new lives in Austin.

After taking a semester to finish most of my remaining educational requirements for my CPA license, I landed a job in tax at a local accounting firm, Atchley & Associates, starting in January 2010.

Despite my landing a well-paying tax job and Katie now earning a PhD stipend, we lived more like broke college students than young professionals. We clipped coupons, took advantage of sales when we needed to buy something, shopped at Goodwill, and I continued driving my 1999 Subaru Outback well beyond when it should’ve been replaced. We wanted to do whatever we could to build up our savings so we could take a gap year.

Trials and Tribulations

That savings would come in handy sooner than I thought. With tax season underway in January 2012, Atchley & Associates HR casually dropped non-compete agreements at each desk, asking everyone to sign and return it.

I wasn’t the only person to notice the extreme terms of the non-compete. The agreement required signing away our ability to work in “accounting” across the entire Central Texas region for two years — regardless of the reason for separation from the firm. When there was pushback, HR made it clear that staff must sign the non-compete or their employment would be terminated.

With most staff living paycheck-to-paycheck, most couldn’t risk losing this job — especially with other firms already staffed up for tax season. Under advice from an employment attorney and thanks a healthy emergency fund, I refused to sign the non-compete and was terminated.

Onward and Upward

While pretending to drag out my decision on whether or not to sign the non-disclosure agreement, I reached out to every large tax firm in Austin. One couldn’t believe their luck. Durbin Bennett was looking for an experienced senior tax accountant to fill a vacancy. Atchley & Associates’ gamble led me to get a better-paying position at another firm.

For the next four years, I’d work practically nonstop at Durbin Bennett — moving up the ranks from being an experienced tax preparer to supervising a team of staff. I found the work fascinating, from working with a massive real estate investment group and helping lead the preparation of over one hundred trust returns tied to a single family to working on extremely complicated tax returns for actual billionaires.

But the work was exhausting. The lead partner prized himself on coming into the office every single day of the year — with maybe only Christmas Day being an exception. And that office “face time” became an unwritten expectation.

The firm did an excellent job of filling any slow period with work, meaning there was never a slow period to take vacation. I’d end up only being able to take a couple of weeks each year to attend RoboCup and explore the host country afterwards. It was like pulling teeth to just string together a few days of vacation to take a trip.

During my review at the end of 2015, my managers praised me once again for my hard work. In return, I had a request: Rather than getting another raise, can I just get a fourth week of vacation each year?

The answer was a resounding no, and I was rebuked for not being satisfied with three weeks of vacation a year. Not content to spend 49 weeks a year in an office (where remote work was possible but not allowed), I began looking for other opportunities.

My Last Tax Job

Once again, another firm was thrilled to have the opportunity to pick me up. The partners at Cary, Trlica & Wood were looking to develop its next generation of leaders to take over the firm.

But with Katie close to finishing her PhD, I couldn’t in good conscience lead them to believe I would be there for the long haul. I explained I was happy to help them for a year or two through this transition, but I’d likely be setting off on my gap year soon. The honesty was appreciated, and we had ourselves an agreement.

Once again, a move led to both a raise and a promotion. But this time, it came with even better terms: Every hour of overtime that I worked during the busy season would be an hour I could take as vacation during slower times.

I’d never been more excited to put in 80-hour weeks. I was thrilled to have the opportunity to bank an entire week of paid time off each week I worked. But those weeks were even more grueling than the overtime I was putting in at the tax firm. That’s because I was quickly becoming a critical part of another team. But before I get to that, I need to take a step back.

JT’s Flight Deals

Between my love for travel and desire to save money, I’d always been drawn to flight deals. While there were websites and some social media pages that would post flight deals, I didn’t feel like any of them were doing a good job of targeting deals at the right audience.

So, I started the JT’s Flight Deals Facebook page in 2013. Rather than simply posting deals for everyone to see, I used a feature Facebook had just introduced to geo-restrict posts. For example, for a deal from Houston to Europe, I’d limit visibility to followers in Texas and maybe Louisiana.

Katie and I used our combined tech and spreadsheet knowledge to develop a Google Sheet to scrape thousands of flight prices from dozens of websites and analyze them to flag the best ones. Katie even tested scraping flights from Google Flights, an action that would lead to our home IP address being blocked from Google for a three-day timeout.

My following was growing, and I received plenty of positive feedback from followers. However, I wasn’t getting much revenue from all of this work. I’d include an affiliate link in each post, but nothing stopped followers from seeing a post and using that information to search for a flight on their flight search website of choice.

Starting With Miles Collecting

Since my first credit card, I’d always focused on earning rewards from my spending. And I always listed my airline rewards number each time I flew. But it wasn’t until the fall of 2014 that I entered the travel hacking world.

All of my cheap flight skills weren’t helping me find a decently priced flight to China for RoboCup 2015 being held in Hefei, China. Despite being a provincial capital with millions of residents, international flight prices were over $2,000 round-trip from the U.S. — an amount I couldn’t stomach paying.

So, I began looking for a better way. Through the FlyerTalk messaging board, I’d heard of a website called The Points Guy and started following them. Shortly later, the website boasted of a best-ever offer on the Ink Plus card: 70,000 Ultimate Rewards points.

I read on to learn that those points could be transferred to United MileagePlus. I checked United’s award chart (at the time) to find that I could fly between the U.S. and China for 35,000 miles each way. I couldn’t believe my luck. I could sign up for just one credit card and earn enough miles to fly round-trip to China — saving me over $2,000!

Ever the maximizer, I pieced together an epic around-the-world round-trip award. My outbound from Austin to Hefei via San Francisco and Beijing would include a flight on the recently introduced 747-8i while my return from Beijing to Austin would connect through Frankfurt, Vienna, and Toronto with an overnight layover in Vienna to explore another country!

Even better, I’d earn a grand writing about this trip.

Starting With TPG

In March 2015, TPG hosted a South by Southwest (SXSW) party in Autin. Readers interested in attending were encouraged to message the TPG social media team with a short story about how technology improved travel. I wrote about the game-changing experience of having a smartphone with a local SIM for Katie and my trip to South Africa earlier that year.

At the party, I mentioned to Brian Kelly (“The Points Guy himself”) that I had a flight deal site. Just my luck, TPG wanted to write more flight deals and was looking for a way to originate the deals themselves. TPG’s Chief Operating Officer pledged to be in touch.

One of the earlier deals I shared was a deal to Beijing on Air China. I’d been monitoring flights to China for RoboCup and was blown away by how cheap some fares were getting.

In deciding whether or not to write about this deal, TPG folks wondered: Is Air China economy any good? I pointed out that I just so happened to be flying Air China to Beijing that summer and proposed writing a flight review. That got my foot in the door.

After providing a writing sample from my blog (this blog!), I got a chance! Even better, TPG opened the door to additional flight reviews if I did well on this assignment.

So, you better believe I poured everything into that flight review. TPG published it while I was still in China, and the TPG readers lit up the comment section:

• “I love down-to-earth, realistic reviews like this. Keep it up.”
• “TPG – please note that we need more Economy class reviews on TPG.”
• “Well written, down to earth article that is applicable to me as an economy flier.”
• “Very informative and a fun read… More articles like this please!!!”

I have no idea if this actually happened, but I imagine Brian Kelly and Editor-In-Chief Zach Honig looking at each other and agreeing that neither of them wanted to do economy flight reviews, so why not let this new guy write more economy reviews for TPG?

Thanks to the positive feedback, my flight review pitches for my flights back home were approved: Lufthansa A380 from Beijing to Frankfurt and Air Canada 787 from Vienna to Toronto.

The feedback on those reviews was great as well. With that, I established myself as TPG’s economy reviewer. But I wouldn’t be just an economy reviewer for long. After writing a few supporting guides, I created another break.

TPG Nights and Weekend Writer

In early November 2015, I caught some points and miles news that hadn’t been reported yet. Since this was different than the pitches I’d done so far, the travel editor connected me with TPG Editor-In-Chief Zach Honig for this pitch. Again, I got a shot to take on a new challenge. And again, I took advantage of the opportunity.

Later that day, Zach emailed me just one susinct line: “Excellent job with this! Any interest in becoming a regular news contributor?”

Of course I was!

Since TPG staff covered the news throughout the workday, I focused on writing posts that broke late in the day or over the weekend. Loving the work I was doing for them (and the extra money), I scaled up to do as much TPG work as possible.

It was under this backdrop that I switched from Durbin Bennet to Cary, Trlica & Wood in January 2016. The spring 2016 busy season was a blur between working as many hours as possible at the tax firm and working any spare moment for TPG. Suffice to say that I didn’t sleep much or have any social life through April 15.

The Flight Deal

Late at work one night during tax season, I got an alert. Japan Airlines was selling “full-fare economy” tickets between Taipei and secondary U.S. markets for around $200 round-trip.

Katie and I hopped on the phone to discuss. If we were going to pay to position all the way to Taipei to fly a cheap flight back to the U.S., we shouldn’t book just one trip… We quickly came up with a crazy idea: What if we mileage-ran these deals enough to earn top-tier American Airlines status?

Before the deal died, we booked five round trips spanning late November through early January 2017. The first would take us to South Carolina for my family’s Thanksgiving get-together. Then we’d fly from South Carolina to Alabama to visit my sister — via Taipei. Then we’d fly from one Alabama city to another to visit my grandmother — again via Taipei.

Since these flights booked into Y-fare class, they’d earn a ton of miles. Through these trips alone, we would earn top-tier American Airlines Executive Platinum elite status for 2016 and make significant progress toward 2017 earnings.

A “Sabbatical”

On Friday, September 30, 2016, I handed off the last tax return I was responsible for and asked the founding partners if they needed help with anything else. Everything was set.

So, I broached the topic of taking some time off — especially in November through early January. After all, I had all of these flights booked. These flights were fully refundable, but — after working in an office for so many years — even the idea of cramming myself into economy for almost a dozen transpacific flights sounded like a dream.

Also, there was a conference called “Chicago Seminars” in mid-October that I really wanted to attend. Plus, TPG was really interested in having me fly the first American Airlines flight with premium economy seats…

Would it be too much to take off time in mid-October as well? It wasn’t long before we agreed that it wouldn’t be a problem if I wanted to take off the rest of the year — as long as I could come in and work if a project came up.

With a handshake agreement, we agreed I could take off the next few months to travel and write more for TPG. I’d exhaust my built-up overtime pay and then take the rest as unpaid time off.

As I stepped out the office door that day, I had no clue that would be my last day working full-time in tax.