Sailor, Nomad, Manager, Recruiter, Explorer, La Ventana, Mexico

I met Ms. Jessie Stehle in La Ventana, a small kite surfing town on a Mexico’s Baja California Peninsula. We discussed Jessie’s passion for sailing, what it takes to survive an ocean crossing, and compared our unorthodox lifestyles. But it wasn’t until we took on an arduous singletrack bike trail the following day, when I witnessed Jessie’s grit and determination firsthand. Flying through the cacti, Jessie completed the course without one complaint, midday sun and all.

Ms. Stehle’s self-label says it all: artist, explorer, sailor, manager, nomad, recruiter. I’d add tough-minded trailblazer. Jessie’s story reminds us of what it really takes to chase our goals, have the courage to turn our backs on those who doubt, aim to minimize our evolution, discredit our ambition and discourage our strive for adventure.

1. Name

Jessie Stehle.

2. Where is your hometown?

Aliquippa, Pennsylvania.

3. What is your profession/career/title/self-label/designation?

Manager, Recruiter, Artist, Explorer, Sailor, Athlete, Nomad.

4. What was the journey like to get where you are (in life and career-wise)?

Super hard! I was one of those kids who had to figure it out on my own. Breaking out of the poor working class of society in America was and still is the hardest thing I have ever done in my life.

I was determined to go to college even though past generations in my family did not even graduate high school, my only remaining grandparent still to this day can not read or write.

But I was lucky in that I found something that I was great at early on. Through hours and hours of swim practice and race after race, I received a scholarship to college for swimming. This covered the huge college expense that I was unable to afford. That, by no means, was the end of the challenge.

Once I graduated I found myself in a down economy, it was 2003 and Pittsburgh Pennsylvania as a city was on a steady decline. So with the $2,000 in my bank account from my bartending job, I got in my car and drove to California. Keep in mind at this time most of my family have never left the boundaries of Pennsylvania. So to them I had not only lost my mind but lost their support. I left that morning on my journey to California without a single goodbye or a hug and set off for the only place in America where I knew opportunity still existed: Silicon Valley.

Once I arrived, I could only afford to live in Oakland. The $2,000 was immediately consumed for my first months rent and deposit. I landed three part time jobs to help pay for my share of the rent in a house located on MacArthur Blvd near Lake Merritt. Within six months I had been able to stabilize my bank account and began my search for a career.

My background was in computer arts, and I wanted nothing more than to be a designer for an advertising company. I applied to thousand jobs with no response. At the time I didn’t know how the system was rigged, I had no clue about all the Ivy League school networks of parents and alumni etc… It took a while to figure it all out. In order to go from one class in America to another it's not about the skills you’ve developed or learned, it's about who you know.

I therefore tried something new, even though it was not who I was. I went to a meetup with other designers and I acted as if I belonged. I acted as though I came from money. I acted as though I was the new hot shit that just arrived to San Francisco and they were the lucky ones to have met me. It worked! I got an opportunity through a referral of a person I met at that event to work at Organic, a really cool digital advertising and marketing agency in San Francisco.

In America, In order to go from one (social and economic) class to another it's not about the skills you’ve developed or learned, it's about who you know.

One year later, after being a production designer in what I thought was my dream job I quit and went back to school for my Masters. I had learned enough to know that my passion and a love of art was not something I would ever make money with again. Instead I wanted to learn more about the business, I wanted to work closely with people. So when I graduated from my business school two years later with a focus in HR Management, it seemed to align well with what I had dreamed of.

This time entering the workforce was a whole new game. I knew how the system worked and I quickly landed a job at an Executive search firm. My initial job was a researcher (now called sourcer) and I loved it. Looking back I got to speak to some really interesting leaders early on such as Steve Jobs who I interviewed in between his employment at Apple. But it wasn’t until the company was given a search called Executive Creative Director did all the puzzle pieces fit together.

The search firm decided since my background was in design this would be a good opportunity for my first solo search as a recruiter. I nailed it, and the next one, and so forth. I got so good at this, so quickly that I opened my own business. Within 2-3 months I was a 26-year-old nobody making 200K salary. My parents were proud and life was much much easier now. I then decided to apply for a United States Passport!

What are some accomplishments you’re most proud of, and what was the turning point to set you on a current path in life?

Accomplishments would include my ability to continue to pick myself up after every fall or a mistake. And to never stop dreaming.

5. What did you study in school?

BA in Design, MBA in HR Management.

6. How is your life different from what you pictured at 20?

Honestly not that different. I have more money than I thought I would, but everything else is right on-point. I never wanted children, I always wanted to be married someday to a really kind and adventurous guy. I wanted to travel a lot and I wanted to work closely with design or art in way that helped people.

7. Was there a time when life knocked you down or out and how did you get back up on your feet?

In 2009, the housing crisis hit and the recruiting industry was hit hard! I was forced to shut down my business but took up the opportunity to speak with a company I had only known at the time as the MySpace’s competitor. I went on to build Facebook’s design teams across the United States and the world.

8. Advice for other women?

Stop trying to please everyone by be “ladylike”. Go ahead fuck up, break shit, make some mistakes. Once you’ve learned where those boundaries are only then will you be unstoppable.

9. Knowing what we know now in current political climate, can women be "all that we can be" in today's world?

Absolutely not! We are progressing, and fast. Especially in the western world.

What is the way forward, as you see it, for "feminist values"?

Through balance.

Men seems to battle over the stupidest shit. As a matter of fact if women started all the wars throughout history, men would have put a stop to us a long time ago. However, as women, we seem to be okay with this situation reversed. Women in my opinion are exactly what this world needs in order to continue.

10. Where in the world do you feel “tallest” (i.e. where is your happy place)?

Out in the open ocean with the wind at my back.

11. What extracurricular activities/hobbies are you most proud of? Why?

One of my favorites was doing the AIDS Lifecycle ride from San Francisco to Los Angeles on a bicycle. I love to ride my road bike, love the community around this race, and I love supporting research through my fundraising.

12. What do you want to be when you grow up? Future goals/challenges?

Not sure yet, but ideally something nomadic in nature.

13. What fears are you still hoping to overcome?

I still hate flying, but even though I have a small freak-out on every flight I never let it stop me from doing what I love to do.

14. Anything you'd do differently, if you had another go at life?

I wouldn’t date until I was 30. It’s a total waste of time until you are able to know yourself and be independent. Which for me was around the age of 30.

15. What inspires you?

A lot of things inspire me: nature, art, science, but right now the grassroots initiatives being lead by people like Alexandria Ocasio-Cortez.

16. What are you hopeful about?

Permanently living on my boat and never having a place to call home other than the boat itself.

17. What are some ingredients to a good life?

Family, friends, love, curiosity, empathy, passion, and laughter.

18. What is a quality you most love about yourself and why?

Even though I have been told at every step along the way, “You aren’t good enough!”, “Girls don’t do that!”, “You aren’t smart enough”, “You aren’t feminine enough” etc., I NEVER listened.

19. What advice would you give your 14-year-old self?

Yep, you are right. You don’t fit in and that is great!

20. What are you reading now? (what books do you gift most and what are your favourite reads?)

For work and career: Radical Candor. For fun: The Historian.

21. Who is a WOW Woman in your world who inspires you and why?

Definitely my mom, because she has always been my champion. And even though she never had the opportunities that I did around education, she is the most intelligent, strong, and hard working individual I have ever met.

Can you nominate three (or more) women you know who perfectly fit WOW WOMAN description?

Georgina Miranda. Marta Anyse Napoleone. Mia Blume.

What would you tell them if you had an opportunity, of why you admire them? Each one is so inspiring. I often catch myself reading their stories or updates on social media and feel motivated by what they are doing and accomplishing.

22. Where can others find you/your work (links to websites, blogs, etc.)?

Just LinkedIn, I’m not much a social media person these days mostly due to my time working at those companies :)