Top of My Class & Rejected from Every Job: A Cautionary Tale & Terrifying Alternative

mi familia espanola

Top of My Class & Rejected from Every Job: A Cautionary Tale & Terrifying Alternative

Have you ever made a seemingly small decision that ended up redirecting everything?

That’s what I’d like to share with you today: the story of that one decision and the ripple it’s had on my world, in the hopes it will help you through whatever decisions of your own – big or small – you’re considering right now.

To start, I think it’s time you meet my Spanish family. Pictured above from left to right, they are: Juan Antonio, Juan, Maria and Rafa* (and Chelsea).

Twelve years ago I spent five months living with these amazing, hilarious and generous souls. They taught me Spanish, gave me my obsession with tapas and olive oil, and showed me that there was a totally different way to live and prioritize life than I was taught (or knew existed) in the U.S. – choosing to put family, community, passion and experience over status and money. Their way of life was the epitome of what it means to work to live, instead of live to work.

I didn’t see it then, when I made that initial decision to go, but those five months forever changed my direction, perspective and every major decision I’ve made since…

I left Sevilla with eyes wide open, addicted to their way of life and determined to come back.

A year later I finished college, and proceeded to be rejected from every job I applied for (despite graduating in the top 5% of my class!). While I was crushed at the time, it also meant I had nothing to come home to after a 6-week graduation trip around Europe. So instead, I moved back to Sevilla and spent a year building my first business with a good friend (teaching English to students and professionals), attempting my first door-to-door sales calls (in Spanish = terrifying!), being a tour guide on the weekends and taking in another hefty dose of passionate Spanish perspective.

I left Sevilla Part Two with plans to live a lot differently, and to do much more exploring…

Which is likely why I didn’t last a day over seven months at the fancy, yet slightly mind-numbing, corporate job I got in San Francisco upon my return. I fired myself, determined to find something I could actually screw up (i.e., have an impact).

That sent me on what’s turned into a 10-year quest to help others (and myself) spend our time doing things that make us come alive – a quest that eventually became Live Your Legend.

This year that quest turned into a trip around the world, hosting events for our local communities, visiting and connecting with many of you, hearing your stories, and pursuing a dream that my wife and I have had since that first taste of Spain more than a decade ago.

And that has led me right back here, to Sevilla, our latest stop on the World Tour – to reconnect with the culture, family and experience that taught me there was indeed another way. The place where a lot of things unknowingly began for me. The place that forever sent me down a less-traveled path.

The picture above was taken last Sunday, at my Spanish family’s house, where Chelsea and I reunited with them for the first time in a decade, for a divine 8.5-hour(!) paella lunch and one of the best days I’ve had in a long time. I felt like I’d come back home. I owe those people a lot.

And to think, 12 years ago, I almost never went.

I was terrified of all the usual stuff: a new foreign place, not knowing anyone, and the scariest of all – everything I was sure I’d miss out on at home.

The week before I was set to leave, I was SO close to canceling that study abroad trip. At one point I was certain I would (I had gotten a serious cold and it felt like the perfect excuse). Thankfully, my parents saw the bigger picture. So I left by convincing myself I could always go home the next week if it was unbearable. But we all know how much less likely turning back becomes once we start.

Now that I think about it, I had a very similar experience (and emotions) near the end of last year as we packed our life into a couple of carry-on backpacks.

Choosing Adventure

It’s obviously impossible to know where one decision may or may not lead. And, with a good head about you, most can lead to worthwhile places.

But my choice 12 years ago was simple. And it’s the same one we faced before setting off this year. One that all of us face in some way each day…

Stay home around what’s easy, comfortable and familiar, or choose adventure?

Since then, choosing adventure has become a habit. Almost a reflex of sorts – one that’s also helped avoid a lot of regret and created even more serendipity.

It wasn’t until last Sunday at lunch, as I offered up my best Spanish toast in an attempt to communicate the above, that I could really feel what Steve Jobs meant when he said you can only connect the dots looking back. They rarely make sense looking forward.

And choosing adventure tends to make those connections a lot more interesting, and the looking back more satisfying.

Or as Robert Frost put it in the last stanza of one of my favorite poems…

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.

That poem was one of the first things I published on my first website, which eventually became Live Your Legend (read the full poem at bottom of my bio page). A framed version, from my parents, hung on my wall for years – and will again as soon as we find a home upon our return!

So what’s the lesson?


The only terrifying thing about any of this would have been convincing myself not to do it in the first place – and if one of those companies after college wouldn’t have rejected me!

When in doubt, choose a little adventure.

That seems to make all the difference.

– Scott

P.S. Got a story about rejection, choosing adventure and how the dots connected? Please tell us about it in the comments!

P.P.S. Oh, and one more lesson: If you (or your children or those close to you) are considering studying abroad, do it. It was by far the most practical and applicable part of my college education, and set off one hell of a chain reaction. 🙂

Right before leaving on this trip, I gave a talk to my high school on “The 4 Things I Wish I Would Have Known at 17,” where I cover this and a lot more. I plan to publish it for all of you soon. 

*Sending a lot of love and remembrance to Tito, the only family member not in the above picture. He’s the 85-year-old uncle who fought in the Spanish Civil War and taught me, during our three daily meals together, more about history and life than I’ve learned from any book. Sadly, he passed away a few years after I left, but his lessons live on in a very big way.