Why I Decided to Take the Wheel

For a long time, I drove on a road paved by others.

It was straight, well-marked, and seemingly safe.

I began my career at JPMorgan, moved into tech and sales at IBM,

then pivoted to marketing at Microsoft —

after earning an MBA from one of the world’s top programs.

My work expanded beyond the Korean market, covering the entire Asia-Pacific region.

Projects succeeded, results were quantifiable, and titles stacked up.

From the outside, it looked like a perfect career.

But deep down, a question lingered.

"Is this really my path?"

Most of the strategies and plans I was delivering weren’t truly mine.

They followed frameworks handed down from headquarters;

my role was to localize and implement.

Within the company’s system, there were countless rules and limited space for true ownership.

I often wondered:

"If you strip away the company’s name and title, what’s left of me?"

All the Right Moves, Still Not Mine

Uncertainty had always been my shadow.

I wanted to see a bigger world.

After a few years of building my career, I decided to hit pause.

I left Korea to pursue an MBA in London —

a conscious step to reframe my thinking and grow beyond the familiar.

Living abroad, immersed in a different culture and surrounded by new standards,

my sense of "average" began to shatter.

Every day, I met people who were smarter, faster, and more accomplished.

I began to question:

"Who am I in this game?"

After graduating and stepping back into the industry, the pattern continued.

Each time I pushed myself to level up, the bar only rose higher.

I was chasing new goals, hitting new milestones —

but somewhere along the way,

I realized I was no longer enjoying the work I was doing.

When Success Felt Empty

Despite the doubts, I kept moving forward.

At Microsoft, I led major projects —

facing setbacks, receiving tough feedback, and battling through moments of self-doubt.

But I kept pushing, determined to get better.

Eventually, after years on a bumpy road, a promotion came.

It felt like a dream come true, and I thought the happiness would last.

Then one day, an email arrived:

The CEO announced a 10% global workforce reduction.

Three months after my promotion, my team was gone.

Neither my achievements nor my title could protect me.

And for the first time, I faced a different question:

"What have I been running toward all this time?"

For the first time, there was no role I wanted,

no company I was eager to join.

Lost and Found in Chiang Mai

I hit pause again.

This time, I decided to take a one-year sabbatical —

no plan, no roadmap — and moved to Chiang Mai, Thailand.

There, I met digital nomads from around the world:

A hotelier-turned-developer who taught himself to code,

solo entrepreneurs building businesses from scratch,

self-made founders charting their own paths without outside funding.

For the first time, I truly understood:

"There are far more ways to live and work than I ever knew."

I studied blockchain, experimented with coding.

But none of it filled the void.

New skills weren’t the problem.

A deeper question kept surfacing:

"If you remove the company name and title from my résumé, what value remains?"

It became painfully clear:

The skills I had mastered lived only inside someone else’s system.

I wanted to build my own system.

But I didn’t yet know how.

The Moment I Reached for the Wheel

In Chiang Mai, people started asking for my advice —

startup founders, entrepreneurs seeking to expand overseas.

Go-to-market strategies, marketing roadmaps, customer journeys.

That’s when I realized:

What I once took for granted —

corporate systems, scalable strategies, operational frameworks —

were distant dreams for many startups.

They had read about them, but few had lived them.

For the first time in a while,

I felt it again:

I still had something to offer.

Of course, there were challenges —

resource constraints, steep learning curves,

the wide gap between aspirations and execution.

But perhaps,

this was the beginning of finding my own way.

To start from zero.

To design my own path.

To take responsibility for it.

Maybe that’s what I had been searching for all along.

From Passenger to Driver

I returned to Korea and joined a B2B tech startup —

a company ambitious about expanding globally,

eager to build a true go-to-market engine.

As is typical in startups, I wore many hats:

Head of marketing, customer journey architect,

and lead for PR, IR, AWS strategic partnerships, and Gartner research collaborations.

It wasn’t easy.

Corporate strategies couldn’t be copied and pasted here.

Everything had to be rebuilt from the ground up.

And yet —

every experience, every success, every failure —

became fuel for this new journey.

I realized:

In the past, I had been a passenger —

moving along paths drawn by others,

at speeds set by others,

according to maps I didn’t design.

But now, the wheel was in my hands.

It’s not an easy road.

Convincing others, drawing from my experiences,

building something real from a blank canvas —

it’s messy, it’s unpredictable.

But for the first time,

I’m enjoying the ride.

Hop in. Let’s drive — together.

Today, under the name JJ Can Drive

I’m documenting this journey.

It’s not just a career story.

It’s a story of building my own road,

rebuilding myself along the way.

If you find yourself sitting in the passenger seat,

I want to tell you:

The road isn’t predetermined.
The speed doesn’t matter.
What matters is —
you must hold the wheel yourself.

Hop in.

Let’s drive — together.