We asked some brilliant entrepreneurs, artists and creatives to reflect on lessons they’ve learned at prior jobs. We’ve shared highlights below.

Jim Crye

Before I became a personal trainer I was a high-school teacher for 17 years. I also was a semi-pro level rock musician for several years. Being a musician was my dream since childhood, but the universe had different plans for my life. I’ve been a fitness enthusiaist for several years and finally earned my PT license in late 2024. I now work as a fitness specialist for Seniors in a retirement community. The most important lesson I have learned is about myself. I have learned that my purpose is to inspire people to achieve their goals by example. Read more>>

Maricsa Trejo

The biggest lesson I learned was that you learn more from failure than success. There is no crying over spilt milk or burnt meringues. My first job ever I ruined a whole ovens worth of meringues for dinner service, which take hours of baking to perfectly dry out. I ended up having to call in my Chef and cut his morning off short. He came in with two coffees in hand, one for him and one for me, and was completely understanding. He told me not to cry over egg whites and sugar. He lectured me on being more aware of my surroundings but ultimately, he was not mad at me. Years later I felt myself getting upset at one of my bakers and I had to remind myself of where I started. My past had humbled me more than once and I will forever be grateful to my mentor for teaching me this lesson. Read more>>

Zhenzi Shi

When I was in high school, I confided in my older sister about how I had felt insecure and lacking in self-worth since I was a child. I was constantly worried about how others perceived me—whether they looked down on me, or whether I had done something wrong. I was always trying to “read the air,” afraid of upsetting my friends. I rarely dared to go after what I wanted and never saw myself as someone who stood out in a crowd. I was clumsy and made many mistakes, and my name was rarely associated with praise or excellence. Back then, I really didn’t like myself. Read more>>

Ashley Hart

During my 9 years working at Sewell Automotive Companies, I was deeply influenced by the principles in Carl Sewell’s book Customers for Life. At Sewell, “Service” wasn’t just a department — it was a culture that extended far beyond the service drive. As a Service Advisor, and later a Service Manager, I learned that true success comes from building lasting relationships…not just completing oil changes. Every interaction was an opportunity to create loyalty by exceeding expectations, handling concerns immediately, and treating every client like a valued guest. Those early years in my career shaped how I serve my real estate clients today: with genuine care, attention to detail, and a relentless focus on delivering an exceptional experience that earns trust for life. Read more>>

Danny Kopsak

It’s important to understand that you may not love every design you create. This may sound strange, but it highlights the distinction between designing for yourself and designing for others, which is crucial for any professional designer to recognize. It’s not about having personal affection for every piece you produce; rather, it’s about appreciating the purpose behind your work: connection, functionality, and impact. Read more>>

Jemi Crookes

Working in the top levels of executive recruiting—alongside teams placing CEOs and board directors for some of the world’s biggest companies—taught me a lesson I carry with me every day as a business owner: even the most revered leaders are just people figuring things out. That insight hit me most when I helped plan CEO dinner series in cities like New York and San Francisco, gathering some of the most recognizable CEOs in the world. Despite their stature, they would show up with notebooks in hand, eager to learn from one another’s experiences. Seeing that kind of humility and openness firsthand taught me that true leadership isn’t about having all the answers; it’s about surrounding yourself with people who make you better. Read more>>

Michelle Reed

The most pivotal experience that prepared me to become a business owner was my role as a Program Director. In that position, I wasn’t just managing people—I was building systems, creating culture, and leading visions. I oversaw both full-time and part-time staff while simultaneously developing programs that addressed the needs of diverse communities. These weren’t cookie-cutter solutions—we had to build pathways that helped students succeed in school, adults thrive in the workplace and for both to carry those skills home with there loved ones. Read more>>

Aaliyah Landcekd

When I stepped into entrepreneurship, I had no blueprint. I felt unqualified, insecure, and overwhelmed by doubt. I didn’t know how to sell my services, how to show up as a graphic designer — especially when trying to reach clients outside of the Netherlands. And let’s be real: most people only know my country for cheese or the soft drug policies. That alone made me feel like I had to work twice as hard to be seen. Read more>>

Rachelle Bodle

I thought being the perfect therapist would make me happy, and everything would fall into place until it didn’t. I burnt myself out with back-to-back sessions, skipping lunches, hyper-fixated on knowing everything, and trying so hard to fit in at an agency, in an attempt that they would eventually hire me. I had this fear that someone would find out I wasn’t good enough or I was a fraud. I thought I had be “on” all the time to be seen as worthy to even take up space. I remember the day when everything fell apart. I was working at a mental health agency, doing everything right! Taking on extra projects, mentoring new therapists, keeping myself small to fit in, and never once complaining about it. I thought if I just worked hard enough and followed all the unspoken rules, I would be seen as valuable. Read more>>

Francesca Fuentes

I found that there was a lot left to learn about being an artist when I worked as a publicity intern for a literary PR firm called Wunderkind PR. Prior to this experience, I had finished college and was working as a waitress to fund my music career. I did not know what I was going to do now that graduation had passed. I thought staying in food service and simply working on my craft was going to help me get where I wanted to go, but I was wrong. That could only get me so far. Read more>>

Joe Prosit

I retired from the US Army in 2023 and immediately transitioned into a career as a full-time fiction author. At first glance, the two jobs couldn’t look any more different. In my previous career, I worked as a staff member organizing large operations with a major focus on logistics. The job was all about moving large numbers of people, equipment, and supplies to various locations on sometimes little to no notice. Read more>>

Harmony Young

Nearly a decade ago, I co-founded a home staging company—an ambitious step that marked my transition from being a stay-at-home mom for 15 years to becoming a business owner for the first time. Fueled by a deep passion to pursue something fulfilling beyond motherhood, I found the world of design and decorating to be a natural and exciting path. Staging felt like the perfect fit—and in the beginning, it was. Read more>>

Dr. Maya Faison

“I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” – Dr. Maya Angelou I have always been an overachiever, used to being at the top, I typically received very little criticism because I excelled at most things I did. Until I went to work at NC State University as their recruitment strategist. I was charged with creating a strategy to increase the number of highly qualified candidates of color for their education degree program. I used data in new ways that created a targeted approach to outreach; crafted new events and initiatives to build excitement about our degree programs; and built authentic relationships with potential new students and their families. Again, I was excelling. Read more>>

Patrick D’Arcy

Gratefulness. It changes everything. Whether it’s grounded in your faith or in your personality. In my experience it is always the better road in a given situation. I was very fortunate to get a job in animation straight out of high school in Ireland. The company that produced the original Teenage Mutant Ninja Turtles series was looking for production staff in Dublin and so I applied and took a test. I passed and worked as a cell painter for a couple of years. This was back in the days when that meant using paint pots and brushes! I loved the process of it and the people I worked with, and the money! Ireland was not a wealthy country in those days and things like money were quite scarce. Read more>>