25 Years After My First Job, How I Would Start My Career In Costa Rica

This year was both my 25-year college reunion and my oldest daughter’s own college graduation. She’s starting her career, as I celebrate 25 years into mine.

When I landed my first job 25 years ago, Costa Rica wasn’t even on my radar. Now, as Scott and I have Costa Rica top of mind for our second acts, I wonder if I could have skipped my first career altogether and established myself in Costa Rica from the get go.

I loved the first act of my career – traditional corporate jobs for 15 years and then building a six-figure lifestyle coaching business for the past 10, all the while raising our kids in New York City, close to my family.

Starting out in expensive New York City was challenging to be sure, but also perfectly suited to me. I wanted to work in and around the financial markets and what better place to do that than New York, the financial capital of the world! Scott and I also had kids young and what better support network than a large extended family.

As my own daughter starts her career, could she skip the expensive, competitive bustle of NYC for the pura vida lifestyle of Costa Rica?

Re-envisioning my career path

What would it have looked like if I tried to replicate the values and priorities of my first career and early life in Costa Rica, instead of New York City?

Marrying shortly after college would likely not have happened

Sure, Scott is totally on board with my globe-trotting plans now, after 20+ years of living the corporate grind. But I can’t imagine I would have convinced him to drop everything and move abroad. I myself wasn’t that interested in traveling back then. We were too single-minded on the traditional corporate career path.

An alternative lifestyle like the digital nomads you see today wouldn’t have enticed either of us. If I had wanted to spend extended time abroad, it probably would have been solo.

Raising kids amidst large extended family might still be a possibility

Let’s say I somehow convinced Scott to move with me and so kids are in the picture a few years into our careers. Neither of us have family in Costa Rica, so we wouldn’t have the same support network every day. However, since Costa Rica is a desirable tropical destination, I may have convinced enough family to visit.

Given the much lower cost of living, I would likely have been able to land much larger living quarters in Costa Rica and host visitors for longer.

If we lived in something like our spacious Casa Salita, complete with a guest casita, I could have had family move in.

Working in the financial markets would require a different career path

My initial career choices would have to be very different. Tamarindo is a beach town so there is no industry there, much less a financial industry. My early job choices in investment banking and management consulting are not available. However, there are other finance jobs – retail banking, investment management, insurance, accounting.

My day-to-day would have looked very different, but if I really wanted to work in and around the markets, I could have found a way. (Yes, market regulations and work eligibility would be a hurdle, but I am assuming there’s a workaround there too if you really want it that badly.)

My portfolio of projects would include different elements

After a few years in finance, I moved into recruiting, which was my foray into the career I have today. Today I have a lifestyle business that is a portfolio of different projects about all things career. I coach, recruit, teach, speak, and write, and a typical week has me working with half a dozen very different clients.

As there’s no big business or dominant employer in Tamarindo, developing a career there would likely have been a portfolio career from the start.

If I started in Costa Rica, my career might end up the same but built up backwards

If I had to build my career in Costa Rica today, I would likely end up with similar elements but in a different order.

I wouldn’t have started in big business – – there isn’t any. My career would be flipped – starting with teaching, writing, and other diverse projects I could do as a freelancer. I would have gotten to real estate sooner since the price points and therefore the barrier to entry are lower. If I got into the markets, it would be later in my career, when I had enough money to invest.

Of course, I have no idea what Tamarindo was like 25 years ago – I can have a virtual freelance career now because the Internet connects you to the world. Back then I would have been serving a local market and probably would have been better off in and around the capital city of San Jose.

Advising my daughter where to start her career

If I would advise my daughter on starting her career today, I could make a case for either New York or Costa Rica. You really can build a career from anywhere in the world now.

The case for New York City

In New York City, my daughter is pursuing the traditional employment path.

She has a first job relating to her college major and previous internship experience, and has already begun building a network of peers and a personal support structure.

She loves what she does, and I could see her building a fulfilling career from this.

The case for Costa Rica

At the same time, she has lots of elements that lend itself to a career in Costa Rica. She speaks excellent Spanish. She has several marketable skills she could build a business with, including a certificate in hypnosis, which I could see fitting right into the healthy living community in Tamarindo.

Our two-bedroom Condo Boom would be a perfect live/work solution because she would always have a room free for hypnosis clients!

Maybe we can both begin in Costa Rica

There was a seven-unit complex for sale in Tamarindo a few blocks from the beach. It needed a lot of clean-up but was actually already rented both with long-term and short-term tenants in its rustic condition.

If we weren’t tied to New York City still (our youngest still has to finish high school) and my oldest was game to live abroad, I would have loved to turn that unit into an eco-lodge as a family project. The complex was taken off the market as the owners decided to keep it because it was renting so well, and my daughter wants to stay state-side to start. But it’s still fun to imagine possibilities.

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I still look at real estate listings – right now there is a food truck business for sale…