#159 - The Best Career Advice I Ever Got Came From Brazil

I saw this pic and couldn’t stop thinking about it:

I just love the reframe (from writer-entrepreneur Sari Azout). And believe deeply in the need to embrace and internalize it.

Knowledge work as we know it is going away. Not just because of algorithms, but because of decentralization, and waning institutional trust. Soon, what we'll be left with is human, creative work.

Not just in the content of our work -- but in the way we shape and mold our careers. After all, our work -- and our careers -- aren't just about output. They're a creative manifestation of who we are.

So tempting as it might be -- especially in this moment of deep, prolonged uncertainty -- to apply tidy, logical thinking to our journeys, that approach is off. The old playbook of planning it out, paying dues, and following the steps doesn’t hold up anymore.

In fact, we need to go the other way. Counterintuitive or not, when the world goes hard machine -- we need to go hard human.

Because in an automated age, human actions become our levers for navigating uncertain, unpredictable careers. They have always been our leverage, and they're now more potent, not less.

Careers are human challenges -- that demand human skill, effort, and thinking

Let's extend the logic in Sari's photo:

That’s the real lesson: our careers are creative acts, so the best way to build one is the way we build anything meaningful -- by being human.

We were never built for step-by-step instructions. Machines were, and guess what -- they're pretty good at it! We, on the other hand, were built to connect and collaborate; empathize and explore; imagine and create.

Those who embrace the non-linear, unpredictable nature of a modern career -- and lean into human, creative strategies for navigating it -- will thrive.

Stories of career wander and exploration

Today, I’m going to share two personal stories about career divergence. About stepping off a clear path, without a plan, and allowing curiosity and intuition to guide me. They're about new contexts, places, and experiences. But more important, they're about the human leverage that exploration creates:

• Stories that resonate
• Self-awareness that sharpens signal
• Skills that don't expire
• Confidence that fuels more healthy risk

I didn’t know it at the time, but as I wandered through these stories -- I was also picking up career capital. And next week, I'll share how I put that capital to work. How the divergent, human moves I took as I explored literally converged into a career defining moment at Google.

But first, let's push off to Brazil and Guatemala; to a backpacker from Zurich named (of course) Hanspeter, and a French non-profit. 🙌🏻

Best story wins

By the end of 2003, I was four years into one of the best jobs I've ever held.

But the dot-com bust, the stock market implosion, and 9/11 had also crippled the global economy. Layoffs were everywhere, and I decided I was going to leave San Francisco, where I lived, to travel and ponder a more meaningful next step.

After months of hoping for a layoff that would not come, I finally quit. Tearful goodbyes in an exposed conference room ensued (see above: "one of the best jobs I've ever had"). Then I put my stuff in storage, sold my car -- and started to travel.

This wasn't open-ended backpacking though. More like basing myself out of my parents' home in New York to save on rent, and jumping on cheap flights to great places whenever I found them.

During those months, one of the brilliant countries I got to see was Brazil. I pounced on a last-minute fare to Rio de Janeiro, sorted out a visa, booked a cheap hostel, and off I went. ✈️

Now: the food, the beach, the hang gliding -- the soccer?! -- in Rio? All amazing.

But my favorite memory of that trip had nothing to do with Brazil. But with befriending two Swiss travelers in my hostel named Hanspeter and Tina. The couple was 10 years older than me, and they were proper backpackers. Lucky for me, one night we went to see a Fluminense soccer match. ⚽️

During the game, Hanspeter shared that he had sold software at IBM for the past five years, but like me, had chosen to get out of dodge when the economy tanked. Only this wasn't the first time Hanspeter had done this. In fact -- it had become a full-blown strategy for the guy.

The idea, he explained, was two-fold:

One, if the market is crap -- why bang your head against a wall trying to produce? It's actually a better time to explore, see new places, and try your hand at new things. (This take would go on to inform ​my belief that our time becomes "cheap", and incentivizes exploration, in a downturn​.)

But his advice went beyond "Don't try to squeeze water from a stone". Because, Hanspeter came to realize, whenever he ducked out to avoid a bad economy -- something uncanny happened once he came back and reinserted into the work world again:

"I always got the best jobs. Because I always had the best stories". 💡

While the rest of his peers slogged out downturns in jobs they didn't enjoy, or went to graduate school to study something they didn't enjoy, Hanspeter accumulated stories. He came back with tales of adventure. But also, growth, learning and awareness. His stories were interesting, differentiated -- and resonant with employers. 🙌🏻

"Is there a doctor in the house?!"

Before embarking on all this travel -- before leaving San Francisco even -- I had gone to an information session for an international aid organization, Doctors Without Borders, at Stanford Medical School.

Knowing I wanted to leave tech for something more meaningful, I wrote the organizer to ask if I could attend as a non-doctor or nurse. After getting her reluctant "I guess so" reply, I took a half day off work, and hopped a train to Stanford's palm tree-lined campus. 🌴

It was a recruiting event, folks, and it worked. By the end of the slides, I was hooked. I had long admired Doctors Without Borders, but now I was inspired. Inspired, and determined to find a way to be part of its work.

During the Q&A I learned that the organization hired two non-medical roles to run its relief projects. One was a "logistician" -- a supply chain expert with mechanic-like skills. That was out. The other role was an "administrator" -- someone who set an annual budget, bought medications, closed monthly accounting, and kept the lights running in the project clinics by paying salaries and rent.

To be honest, that should have been "out", too. But naivete, stubbornness and my resolve to work with this organization crowded out my logic.

On the train home, I started to scheme: "How can I dupe this medical non-profit into letting an unqualified 26 year-old with a recruiting background in tech run its accounting, payroll and HR in a far-flung part of the world?"

After the event, I filled out an application, and emailed it to the team I'd met at Stanford (in other words, I didn't apply online). Weeks later -- by then in New York, crashing at my parents' place -- I muddled my way through live interviews at Doctors Without Borders' Manhattan office.

Then, it was time to wait. And wait. And wait.

The good news was I'd been put into a volunteer "pool" to eventually be staffed on a medical project, somewhere in the world in need of support. But when this would happen, how long it would take, and where I might be sent -- no clue.

So while I hoped and waited for the org to place me, I continued to travel when I found the right deal, or had friends I could crash with: Rio and back; the Dominican Republic and back; Shanghai and back; Paris, Amsterdam, Barcelona, and back.

Four months later, the HR rep finally called:

"Good news! We have a project for you!"

"Amazing! Where?!"

"Guatemala. Because you speak Spanish."

I was so thrilled, I neglected to mention I hadn't used or studied Spanish since high school, 10 years prior. 😬

No matter: a two-day training in New York, followed by onboarding in Paris (the organization's headquarters), followed by a week-long Spanish immersion course in Guatemala's colonial-era capital, Antigua -- and by Christmas day, 2003, I was in Guatemala City, handing over from the previous "Administrador" in the role.

The year I spent in Guatemala would prove hard. The country had just ended a brutal, 36-year civil war​. Guatemala City, where I lived and worked, had the highest murder rate in the Western hemisphere. My boss was a hard-charging Frenchman who chain smoked, spoke no English, and wore his nickname -- "the bulldozer" -- with pride. From day one, all the work was in Spanish.

But it was also a brilliant year. I got to try and do some good in the world. Free housing and a food stipend allowed me to save my volunteer pay. I learned a beautiful, useful language. I was exposed to a new and different context, and picked up new skills. I gained the confidence that comes from pulling off something which, to my mind, was hard to pull off.

But just as important, I gained a tremendous story. A story I would take with me, and later use.

Next week, I’ll share how all of it -- the story, the skills, the awareness, the confidence -- came together. How these "random", divergent experiences suddenly converged and helped land a transformational job at Google.

Thanks for reading and exploring with me -- and have a great end of the week! 🙏

Aki