How to Go On a Sabbatical That Will Change Your Life

I achieved my dream of being a digital nomad when I was 23.

I've traveled to places like South Africa, Mexico, and Vietnam. All while working from my laptop.

After dropping out of college with no plan to live my “dream life,” I felt on top of the world.

So why in the hell did I quit everything, move back home, and study chess full-time!?

Tam’s Chess Sabbatical

The “call” first came when I was in Chiang Mai, Thailand.

Asia is the opposite time zone of the US. So after I finished my client work, I had so much time to kill during the day.

After the temples and waterfalls and the massages and meeting other travelers and eating all the street food, something funny happened.

You get bored.

In today’s day and age, it’s hard to be bored.

There’s always something to watch, people to meet, or places to go.

But it’s different when you’re alone in a foreign country.

When you're removed from all the outside BS, you start to gravitate toward what lights you up.

That might be reading fiction, studying history, making pottery, surfing, or whatever you’re into.

For me, it was chess.

I wanted to play chess again.

There wasn’t any big revelation.

I was bored. I used to love playing chess. I have time now.

Why don’t I play a game that brought me so much joy?

I played at the club level in high school. But I quit because I reached the level where you needed to study seriously to advance to the higher levels.

I chose to spend my senior year goofing off with friends instead.

I’d always wondered, “What if I actually dedicated myself to the craft? How far could I go?”

Here in Thailand, I had the opportunity to fully explore these questions. It was in Chiang Mai where I rediscovered my love for chess.

I sat in cafes for hours and got lost in the game.

• I played blitz and rapid games online.
• I challenged myself with hard tactic puzzles.
• I watched 4+ hours of chess lectures every day.
• I read e-books on chess openings and strategies.
• I drilled classic endgame positions against the computer.

I was even that obnoxious tourist who brought in their computer for a foot massage because I couldn’t wait to hear Grandmaster Varuzhan Akobian analyze his games playing the Queen’s Gambit Declined.

I listened intently behind my MacBook to learn how to win Rook endgames from Grandmaster Ben Finegold.

My friend back home asked me, “You traveled to Thailand to watch videos about chess!?”

Lol yes.

To the outsider, I sound like a lunatic. But with no distractions around me, my gut told me this was a side quest worth exploring.

“How good can I get at chess?”

I’ve always loved the idea of challenging myself to the fullest potential.

I also thought,

“I’m young - when else in my life will I ever have the opportunity to take a year off and do this?”

There was little downside (I could always get another job again) and infinite upside (an experience of a lifetime).

All these thoughts made this an easy decision.

When I came back to the US, I sunsetted all my clients and devoted the next nine months to mastering chess.

I studied every day, hired a coach, and competed in tournaments every weekend.

I pushed myself to my fullest potential, like an athlete training for the Olympics.

After intense focus and overcoming dozens of losses, my rating went from ~1400 ELO (average player) to 2000 ELO (chess expert).

That puts me in the top 4% of ranked chess players in the US. Or the top 1% of all users on Chess.com.

This sabbatical unexpectedly turned into one of the best experiences of my life.

Some of you might expect me to turn pro or start a chess business as I did with Bachata (more about that soon), to consider this a “life-changing sabbatical.”

But let me stop you right there.

The experience, on its own, was the life-changing experience.

I didn’t do it as a means to another thing.

A stop along the way to some promised land.

I did it for the experience itself, with no expectations of what would come out of it. And that’s what all sabbaticals should be.

The reward is the sabbatical itself.

Tam’s Bachata Sabbatical

After working for a couple of years, I went on a Bachata sabbatical completely by accident.

My life was a mess back in 2022.

• I couldn’t get PR (permanent residency) in Canada, so I had to leave the country
• Without PR, I couldn’t work for the Canadian company that I’d been employed by
• At the same time, I became sick with long COVID which would last for an unknown amount of time

This all sucked...

So I escaped to Mexico purely for vacation. I wanted a place to rest while I recovered from long COVID.

As I got better, I had more energy to do normal things. And one of those things was going to a Bachata class.

I loved dancing Bachata, but I had been extremely frustrated that I wasn’t getting the proper education I needed to properly level up.

(Toronto’s Sensual Bachata scene is pretty good now but back in 2019, it was trash)

I took a Bachata class in Mexico City and I had so much fun. I took a few more classes and before I knew it, I was just as passionate about Bachata as I was about chess.

Should I do another sabbatical?

The original plan was to rest for a bit in Mexico and then find a new job.

But I asked myself,

“When I’m 80 years old, will I regret embarking on this sabbatical instead of working another year?”

We have such a strong work culture in the US. Most people don’t take gap years, sabbaticals, or even use up their full 2 weeks of vacation time every year.

It's quite toxic.

I’ve already been working for 8 years at this point. I have some money saved up.

Why not take another sabbatical exploring something I love?

Isn’t that the whole point of life? To go on adventures and enjoy your short time here on earth?

Because what’s the downside? A job will always be there for me. I won’t go completely broke.

And in the worst-case scenario, I could just live at home again or crash with a friend until I get my shit together.

Plus I desperately WANTED to do it. I loved my chess sabbatical - this one may be just as enriching.

So here I go again.

I leaned into this experience without any expectations and followed my intuition.

• I went to Bachata classes and socials every day.
• I took privates with different teachers every week.
• I studied Bachata by analyzing dance videos on YouTube and Instagram.
• I created my own Notion system to track, organize, and remember everything I’ve learned.
• I traveled to Spain to train with some of the best teachers in the world and attend my first Bachata congress.

It was an intense year of training.

I learned more in this 1 year than I had learned in the 3 years prior.

After everything was over, I got a day job to make money again. But unlike chess, I wanted to keep going in Bachata.

This passion led me to live in Mexico indefinitely and even go back to Spain to continue my training.

People noticed my fast improvements and asked how I leveled up so fast.

I told them about my sabbatical and the Notion system that I had been using to track my progress. They were super curious about my Notion page, so I just shared it with anyone who asked.

Eventually, the demand told me there might be something here. I templatized my Notion system and sold it for $15. This became the first version of Bachata Library.

To my surprise, people actually bought it! I recorded tutorials and added more moves to improve the template, then put it on sale again. More people bought it.

I talked to more dancers about their struggles with mastering Bachata. I resonated with every single one of their pain points. I knew there was potential here to build something that would further help the dancers.

A year later, I quit my day job to go full-time on making Bachata Library the most comprehensive Bachata course on the internet.

Unlike my previous attempts at entrepreneurship, arriving at this idea felt so natural.

Never would I have imagined myself as a dancer, let alone a dance teacher. Or that I’d one day start a business in the arts.

I was just living my life. Exploring my passions and curiosities. Not knowing that everything I had been doing would culminate in where I am now.

I wouldn’t be where I am today without taking a sabbatical to fully explore Bachata. But I’m so glad I did.

The real value you get from taking a sabbatical

Steve Jobs famously said,

“You can’t connect the dots looking forward. You can only connect them looking backward.”

If you’re thinking about going on a sabbatical, you really can’t predict what will happen after.

Sometimes, nothing will happen at all. You’ll just return to your normal life like me with chess.

That’s 100% OK.

No one can take away your sabbatical experience from you. And THAT is the real reward of doing a sabbatical.

The sabbatical is worth doing for the experience alone, with no promise of a payoff in terms of productivity, profit, or enlightenment.

Other times, a sabbatical can offer you the next chapter in your life like me and Bachata.

I fell deeper in love with Bachata and found a market with a problem that I felt I was uniquely capable of solving.

Sometimes, the best thing to do to find your calling is to stop aggressively searching, and patiently for the “call.”

This was the most frustrating piece of advice for someone who wants to get after their goals by any means necessary.

It's like people who tell you you'll find love when you finally stop looking for love.

But when you stop running, you realize love, or your calling, has been trying to catch up with you all along.

Questions to help you plan your sabbatical

If you had all the time in the world, what would you want to explore?

• It could be an old hobby, a new destination, or a topic you can’t stop talking about. It could be about meeting people from different cultures. It could be a combo of everything. There are no wrong answers. This is YOUR sabbatical.
• It doesn’t matter if people think you’re a lunatic. You’re not doing this for Instagram. You're doing this so you can LIVE your one wild and precious life.
• Don’t try to make your sabbatical productive or efficient. I encourage you to “waste time” and just explore your curiosities, even if it’ll lead nowhere.
• A sabbatical isn’t always about the destination or some Eat Pray Love BS. It could just be uninterrupted time to fully explore something you normally wouldn’t have time for in your everyday life.

How long can your runway sustain you?

• You don’t want to feel financially stressed while you’re in “explore” mode. So save as much money as you can before you go on your sabbatical. My recommendation is 6 months of runway.
• During my chess sabbatical, I shamefully had to borrow money from friends to keep myself alive because I chose to live in SF lol. I paid them back immediately after I got a new job and promised myself I’d never do that again.
• For my Bachata sabbatical, I chose to live in places where the cost of living is low to extend my runway. I never paid more than $1000/mo in rent, even in Toronto or Spain. Going to a Bachata class + social in Mexico was $5 USD. Privates were $25/hr USD max.
• People assume that taking time off and traveling will cost a million dollars. When you do the math, the expenses really aren’t that bad. There are tradeoffs, like not being able to save much money. But that’s the tradeoff I’ve accepted because I can always make money later.
• During my chess sabbatical, I taught chess to kids in schools and private lessons. During my Bachata sabbatical, I did small freelance work to keep me afloat for 10 hrs/week. Working part-time didn’t detract that much from my experience and it helped me be more financially calm.

What needs to happen for you to take a sabbatical?

• There is no perfect time to quit your job or start a family or whatever. But let’s be somewhat realistic - ensure that you’re not going to go into debt or your family will starve without you.
• Do what you need to do to get your ducks in order. But most importantly, go on that sabbatical. Set a date. Plan for it. Go do it.

“What if everything goes terribly wrong?”

• The real question you should be asking yourself is, “What if everything goes unexpectedly better than you could have ever hoped for?”
• In the grand scheme of things, there’s very little risk in taking time off to explore. But there’s infinite upside - it can literally change the direction of your life.
• Ask any mega-successful person (not your local doctor or lawyer) about their sabbaticals and they’ll tell you dozens of stories of doing “random” things that didn’t make sense, but eventually led them to where they are today.
• Bryan Cranston (Breaking Bad) took off on his motorcycle for two years to get lost and he came back with an epiphany of wanting to become an actor. Sam Altman (OpenAI) took a year off to read textbooks, explore random business ideas, and meet interesting people–all of these were seeds that later helped him in his future ventures. The list goes on.

If you're in a position to be able to take a sabbatical, I highly recommend it. Your life could change dramatically. Or you could have a soul-enriching experience in this beautiful journey we call life.

Keep me updated on your adventures - DM me @mrtampham.