We had the good fortune of connecting with Haille Trimboli, Ph.D. and we’ve shared our conversation below.

Hi Haille, what role has risk played in your life or career?
As a Leo sun sign with a Sagittarius rising, I thrive on risk. In all seriousness, I view risk as a catalyst for some of the most fulfilling moments in my life and career. When I find myself too comfortable, whether personally or professionally, it’s often a sign that I’m not progressing or contributing to society as much as I could be. Our society is constantly evolving, especially with rapid technological advancements, and to add value, we must embrace the unknown and take risks.

However, risk-taking shouldn’t be done frivolously. That’s why we see Global 2000 companies dedicating entire positions and departments to managing risk, because it must be approached thoughtfully. For me, it comes down to recognizing when it’s time to change, taking a step back to remember my goals, and then approaching risk as an exciting opportunity rather than a daunting challenge. There must be a guiding force, a ‘why,’ driving the risk.

For example, I was a K-12 teacher for five years. During COVID, I began to feel stagnant and realized it was time to reassess my path and purpose. I decided to go back to school while working full-time to earn my Ph.D. My goal was to ‘change the educational system,’ and this decision led to unexpected growth. I now possess critical skills that allow me to contribute in various ways in a professional workplace, far beyond my initial aspirations.

Let’s talk shop? Tell us more about your career, what can you share with our community?
My career has taken many twists and turns, and it is only just getting started. I began working officially at age fifteen as a lifeguard and swim instructor at my local community pool. From there, I worked for the YMCA, a local city Park and Recreation Department, the Sacramento Conservation Center, camp and conference centers, yoga studios, teaching, consulting, and now in Customer Success and entrepreneurship.

What sets my career apart is the variety of skills and knowledge I’ve developed. Through my diverse job experiences, I’ve learned to work with different people in various settings, which I believe is one of the most important skills in the workplace—empathy.

I am proud of many things in my career, but one aspect that stands out is my tenacity and perseverance. I’ve always believed in myself and my ability to start again. One of my favorite quotes from a yoga instructor is: “You’re never too old, never too bad, never too late, and never too sick to start from scratch once again.” This mindset has always guided me.

One of the more challenging transitions in my career was moving from being a K-12 teacher to entering the business world. I was getting burned out from classroom teaching, and when COVID hit, like many others, I had a chance to reflect on my future. I realized one of my values was financial independence, so I decided to pivot from public education to the business realm. I leveraged the skills I had developed as an educator and ended up consulting for two organizations to help them create educational content. This opportunity was the lift I needed to secure my current role, where I consult with Global 2000 organizations on digital leadership solutions to help them move the world forward.

This transition was not easy. When my consulting gigs ended, I wanted more experience in the industry and sought it through an organization. I probably applied for over 150 jobs and had more than 20 interviews, hearing “no” repeatedly. Many people doubted my experience as a teacher would prepare me for a business role, but I eventually ended up in the best-case scenario, which is where I am today.

It was always straightforward when I worked in a clear and traditional career. As a teacher, I could tell people I taught fourth grade, and they understood and praised my work. The beauty of entrepreneurship and combining it with professional experience is that we have the agency and authority to design the life we want to live, regardless of others’ opinions.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
For the best time in Los Angeles, I would start by hiking to Sandstone Peak in the Santa Monica Mountains to show my friend the stunning nature surrounding the city.

The next day, we would drive through the canyon, pass by the iconic Pepperdine University, and land in Malibu. We’d grab breakfast at Lily’s Cafe and Pastries, then head to Zuma Beach for easy parking and a long stretch of sand to walk on. I would ensure we had surfboards in case we wanted to surf at County Line, Leo Carillo, or Broad Beach.

On another day, we would drive into the city and hike around Griffith Park, capturing must-have pictures of the Hollywood Sign. Afterward, we could explore Los Feliz and grab a bite at Alcove Cafe and Bakery.

We’d spend another day in West Hollywood, starting with breakfast at The Griddle Cafe, known for its oversized pancakes. Then, we’d head to the renowned museums around LA such as The Broad, the Hammer Museum, and LACMA.

A visit to Universal Studios would be a must for a fun-filled day, where we could explore the attractions and the surrounding Universal CityWalk for entertainment and dining options.

Lastly, we would take a chill drive through Topanga, grab food at Inn of the Seventh Ray for a unique, earthy dining experience, and then end the day with a beautiful hike through Solstice Canyon followed by a sunset on the beach.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
I’ve had more mentors along my journey than I can possibly list here, particularly women. One of my favorite books is Women Who Run with the Wolves by Clarissa Pinkola Estés. I read this book during a career transition and was captivated by her visual storytelling, which connected me to something far greater than myself. Through myths, she articulates how women can reclaim their innate strength and voice in a world that can often be challenging or intentionally suppressive.

In the same vein, I’ve been surrounded by supportive women who have lifted me up throughout my journey. My mother and sister, both unafraid to voice their opinions, have done amazing work in their communities to help others. Academic mentors have recognized my potential and placed me in positions to shine. Yoga studio owners have provided the space for me to turn inward and continue growing.

Instagram: https://www.instagram.com/hailletrimboli/

Linkedin: https://www.linkedin.com/in/haille-trimboli/

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