My Story

It’s June 2013. I’m 24-years-old, and have found myself reading my kindle on the edge of an infinity pool overlooking the jungles of Costa Rica on a vacation with my cousins. The house was up on a crazy mountain cliff that looked like it was straight out of Jurassic Park. I remember looking up from the digital page, experiencing a cloud-clearing moment of: ‘this could be my life.’ I could travel to incredible places all the time. I could be free. I filled up with so much excitement - buzzing with, “what if”? This book, The 4-Hour Workweek, helped me realize what I had already known deep down inside: there was a different way to live. 

For me, it wasn’t about working 4-hour-weeks.

It was about the idea that I could get the lifestyle AND the career I wanted. I could have BOTH.

That blew my mind.

I still didn’t know what my dream job was.

But, for the first time, I could finally see the design on the puzzle box.

And it included a pretty epic view. Toes in the sand. Fingers typing away.

Back in 2013, when not on my one annual vacation, I was working all the time in a prestigious, but entry-level job. I’d gone through life and checked the boxes. Boyfriend. Check. Good job. Check. Cool apartment. Check. And yet, I was miserable.

The truth was, I was trying to unsuccessfully piece together a “good life” based on what I saw other people doing. Traveling for two weeks a year. Working for a mission-driven company.  Living with someone who loved me.

But it wasn’t working.

I couldn’t figure out how to make it work.

I didn’t love my job and didn’t love the life I was living. I was far from having a dream job or living my dream life. I felt lonely, crazy and deeply unhappy.

I had succumbed to numbing myself with wine & Netflix.

I was overwhelmed weekly by the Sunday Scaries.

And I had no clue what to do.

Though I could finally, sort of, see the design on the puzzle box, I didn’t know what I’d actually be doing on the other side of that computer.

I didn’t grow up with big dreams - I grew up with working hard. I grew up with straight As & tons of extra-curricular activities & working since I was 13.

I remember when people asked me the question as a kid, “What do you want to be when you grow up?”

I used to copy my friends’ answers when I was in elementary school and said I wanted to be a vet. I can’t stand the sight of blood, nor am I the biggest animal person you’ve ever met.

No one around me was living their dream life. No one talked about dream jobs. People talked about working hard and getting into the best college you could.

How did I end up here?

When it was time to decide what career path to take, I had just returned from a year living in Buenos Aires. This was my fourth major trip abroad since I was 15. As soon as I returned, all I wanted was to be abroad again. I loved it more than anything.

Travel was the thing that made me feel whole.

I didn’t have to be anyone other than myself when I traveled. There was no one’s approval I needed. There were no expectations. Perfectionism didn’t exist on the road. It’s hard to people please when you don’t speak the language. I could just BE. Though I had no idea about what I wanted my career to look like, living abroad seemed like the best place to start. 

Early Senior year, I applied for a Fulbright Scholarship to teach English in Spain. I knew that I needed something that was “prestigious” if I was going to go abroad again...that is, if I was going to earn my family’s approval and enough money to pay for my life.

After nearly 9 months of applying, interviewing and making it to the final round, I didn’t get it.

I was heartbroken.

I couldn’t bring myself at the time to teach English in some other program because I was afraid of the judgement I’d receive for not getting a “real job”.

I dropped the idea and looked for more traditional jobs. Eventually, I had offers from Boeing & Teach for America (both v. prestigious, one well-paying & one well-meaning).

The two paths for my future so ironically laid out in front of me: make money OR make an impact.

But not both. Definitely not both. 

Like so many 21-year-olds, I really didn’t know what I wanted to do for my career. All I really wanted was to be abroad, but that dream had been shattered.

Instead, I chose what I thought would at least look good on my resume and allow me to do some good in the world.

That’s how I found myself, four years out of school, & three jobs later in an entry-level position doing fundraising for TFA. Living with my boyfriend at the time, who I knew I wasn’t going to marry. Checking all the boxes that I thought I was supposed to, yet, feeling completely trapped in a life I didn’t want. Hustling because that was all I knew.

Looking around realizing that I didn’t want anyone else’s jobs around me.

I didn’t even want anyone’s life I saw.

Then, during a 1:1 in the midst of another bland, unremarkable day at work, my boss turned to me and asked a question that would completely alter the course of my career—and life.

He asked, “Emily, what’s your cause?”

Once my knee-jerk reaction to be completely offended by this question subsided, I realized I didn’t know what my cause or my purpose was.

But, I knew I wasn’t pursuing it, whatever it was.

Looking back, it’s not that I didn’t care about education—I deeply cared about the fight for educational equity—but what he was calling out was that there was a disconnect.

I didn’t know what my purpose really was.

That conversation triggered me so deeply because in my heart, I knew I was meant for something bigger, something more. And I knew that those old dreams of travel held some clues - some information that would lead me to my purpose.

But, I just didn’t know how to get there.

Though I didn’t have any answers, I began asking myself some really. hard. questions.

I knew I wasn’t happy, so what would make me happy? What did I really want? What mattered to me?

I spent the next two years ping-ponging between ideas, asking myself hard questions, and conducting career experiments. I went on a seemingly endless scavenger hunt for answers.

I still didn’t have a clear dream job, but I was starting to get some answers to what a dream life might look like.

Inspired by the 4-Hour Workweek, I asked my boss if I could take my entry-level fundraising job remote and work from Thailand.

He said, “Ummmm, no.”

I started travel blog called letsroamwild.com, attended a travel conference and eventually began making $75/blog post for Viator.

That wasn’t going to get me very far.

I applied to business school. Harvard, Stanford and Northwestern, to be exact. They’ve got study abroad programs, right?

Maybe not the best reason to invest hundreds of thousands of dollars and countless hours into graduate school?

I quit my job to travel Asia, fell in love with scuba diving on a little Thai island and realized, if I could live my dream life on $50/day, I didn’t need business school.

One step forward.

After six months in Asia, I got hired to work remotely for Teach for America as an executive assistant.

Definitely not the dream job, but another step forward.

In June, 2015, I was emailed a landing page to a new business a friend from high school had started.

His new business took remote professionals on trips around the world. In an effort to show him support, I emailed him some ideas for coffee shops his professional clients could work at on my favorite Thai Island.

He emailed me back immediately and told me he was hiring.

My dream job had just smacked me in the face.

After two years of asking myself hard questions, messy career experiments, and taking big risks, I landed my dream job traveling the world and working remotely for Remote Year.

I landed a dream job without actually ever knowing what my dream job was, without going to grad school (though I did apply to business school). and without cold applying to a million jobs.

I did it without sending in a single resume.

I share this story to say this:

You have a dream job, regardless of if you know what it is. There is a way for your career to bring you the fulfillment & joy & freedom you crave.

And it is so much easier to find than it might seem, if you know how to do it.

Almost seven years from when I first started asking myself those hard questions about the life I wanted to live, I have now created TWO dream jobs for myself.

My first was that job at Remote Year. I got to travel the world for four years, leading a team of nearly 30 sales people while working remotely from over 40 countries.

My second dream job is what I do now: I’m an Intuitive Career Strategist and I lead a 90-Day Career Accelerator called Path to Purpose.

I’ve taken everything I’ve learned from:

• teaching 5th graders how to turn their dreams into reality

• years leading a team of sales people who helped remote professionals follow their dreams of traveling the world

• creating TWO dream careers myself

and created a neuroscience-backed proven methodology that I now use with clients to create their own dream careers (and lives).

My story isn’t that unique.

We’re all capable of landing creating our dream jobs.

We just have to know how.

You might choose to do it the hard way, like I did.

It’s an option - throwing spaghetti at the wall to see what sticks.

Or, you can do it so much faster and easier. You can do it with a community of people who just get it. And you can do it with a mentor, a teacher who can guide you and show you the way.