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How I Went From a High School Teacher to a C-Suite Executive Through the Power of ‘Yes’

I built my dream career by saying 'yes' and showing up.

When I was in law school, I heard about the power of positive affirmation and decided it was worth a try.

I bought a bunch of index cards, scribbled the word “yes” across them, and pasted them all over my house — in the bathroom, by the toaster, on the front door. When things got tough (as they often did), I’d look up and read those little signs. When I felt crazy, discouraged, or worried, that three-letter word reminded me of my strength and kept me going.

That wasn’t the first or last time I experienced the power of “yes” — not by a long shot. My career path has involved multiple twists and turns. I’ve gone from teaching high school in downtown Los Angeles to becoming the chief operating officer of an international luxury brand. In between is a life I’ve built block by block. Some moves didn’t make sense to people — some didn’t even make sense to me at the time — but by saying “yes” and showing up, I’ve arrived in a place even I couldn’t have imagined.

Learning to Say ‘Yes’

After graduating college, I started teaching. I loved my students, but was itching for some adventure.

I visited New York City and fell in love with its wonderful energy. Everyone was hungry to do something great.

Three months later, I packed up my car and moved across the country. I didn’t have a job or an apartment; I just showed up and said “yes.”

I took whatever jobs I could get my hands on. Each one gave me a skill I could build upon. I moved from healthcare education to project management at a nonprofit before deciding, as a 32-year-old mom, to go to law school. I hardly slept for three years. I went to school all day, picked up my kid, read him bedtime stories, studied until 2 a.m., and did it all again the next day. I was determined to make my risk pay off. So I threw myself into that sleepless life, and after graduation, I said “yes” to a job at a top law firm.

I started right in the middle of the economic downturn. With regular rounds of layoffs, I had to keep saying “yes” to new challenges and opportunities. Yes to golf and aircraft finance, yes to whatever it took. But I survived the downturn, and eventually, I became a senior vice president at Christie’s International Real Estate and later the chief operating officer at Sotheby’s International Realty, something I would have never thought possible only a decade earlier.

Here are just a few of the lessons I’ve learned along the way:

1. Feel the fear — but don’t let it stop you.

People sometimes look at my résumé and assume I’m fearless. And while I’ve taken risks, I’m not immune to fear. I feel it; I just face it and move through it.

When I decided to go to law school, friends and family told me I was crazy. And during my first year, I’d lie in bed exhausted, wondering whether they were right. But while I let myself feel that fear, I didn’t let it paralyze me. During my moments of doubt, I’d visualize the toast I would give on graduation day, picturing my pride at having achieved this goal. So I carried on, and three years later, I gave that exact speech as I toasted with friends and family.

Whether you’re looking to go back to school, pursue that seemingly out-of-reach promotion, or change careers altogether, it’s about evaluating the opportunity, weighing the risks with the rewards. Face the fear, then imagine the outcome you want and how good it will feel, and take the next step.

2. Construct your foundation one building block at a time.

Just out of college, thinking about the whole career ahead of me was daunting. Where to start? Where did I want to wind up? How would I know when I got there?

Rather than ruminate on these questions, think of your life as a series of building blocks; each opportunity is a chance to learn something new. I couldn’t have gone from a high school teacher to an executive in one leap. It took many individual moves, each one adding a new skill to the set I’d already developed.

Adopting a mindset like this can also help you make the most of the job you’re currently in. When I was studying for the LSAT, I worked as a temp for Merrill Lynch. I needed the job, but I didn’t just show up and do my time. I saw the opportunity to learn about what was happening on the trading floor, and because people saw that I was interested, they wanted to teach me. I ended up getting way more than my job’s worth. Later, the knowledge I’d gleaned from my colleagues helped me become a better transactional attorney.

3. Stretch yourself just a little bit more.

My career progression has always been about taking that next risk by using the skills I already possessed, then stretching them just a little bit beyond what people expected of me.

When I was transitioning from secondary education to healthcare education, I remember prepping for the interview, which would be conducted in Spanish. I spoke the language and considered myself pretty fluent, but I’d never used it in my job. There was a stretch element to the position, and I had to bite something off before I was 100 percent sure I could actually chew it.

Push yourself, prepare yourself, and don’t let the fact that you don’t have the exact qualifications or experience stop you from taking the leap.

My career may not look like a straight line, but it has been a satisfying journey and has brought me to a great place. Each unexpected step pushed me into new territory that strengthened and prepared me for the next challenge. By saying “yes” and showing up, you, too, can surprise yourself by exceeding your own expectations.

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