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

Tone Woolfe

Which job?? I’ve had so many jobs before choosing photography as my career. I was a server for 6 years, I was in logistics, sales, a high school coach at some point and most importantly – I was also a semi-successful rapper. Many would say, those paths don’t make any sense but the main things I learned across the board was multitasking, contracts and networking. Read more>>

Robert Cook

At 63, I hoped to have a litany of bon mots to enlighten up and comers about how the world works. I’ve given up on that. However, I do have a few random thoughts that really don’t add up to anything except I’m old. Regardless— Read more>>

Don Cimorelli

Early on in my first position at IBM, I learned the importance of asking myself the following question when preparing to move on to my next position. The simple, but powerful question is: What is different about the role I previously held than when I first assumed it? The gist of the question is that if nothing is different when you leave a role compared to when you assumed the role, then you did not do your job. Read more>>

Arnaud Gibersztajn

Mine was an unusual route to the art world. I painted for years, and I supported myself working as a waiter and maitre’d at a restaurant in New York City. This part of my story is common—the struggling artist whose day job supports his true passion. It was one of those restaurants you read about in glossy magazines, where pop singers and movie stars go, as well as gallerists and art collectors. Read more>>

Fern Esturilho

Take a chance on yourself. Read more>>

Ruksana Hussaina

I talk a lot about the importance of learning to say no and actually say no as a business owner to opportunities that come our way that don’t necessarily serve us well in the grand scheme of things. One of the lessons I learned early on was not to simply say yes to everything that came my way, which actually goes against what a lot of business owners do. An editor reached out to me on my website through a simple search for freelance writers and asked if I’d like to contribute to their quarterly magazine. Read more>>

Brad Kugler

came from a different industry entirely. I sold DVD/CDs online for years i was actualy a pioneer there getting to meet Jeff Bezos, having buyout offers from Overstock.com and other start ups. The industry was eventually disrupted by streaming media and new technology. I tried to convert the business to this model but capital requirements prevented that. Read more>>

Sofia Rochin

The previous job I worked at was an awesome store that encompassed coffee, flowers, and amazing gift goodies! I was drawn to this shop because of how they layered each element of their store into one cohesive experience. It was during covid that I moved home and began looking for jobs and was intrigued to learn more about two of my favorite things: flowers and coffee! Read more>>

Joseph Pacheco

Build your dream or another person will hire you to build their dream for them! Jobs dont offer any guarantees for employees now days! Most people are comfortable waiting for a pay check. I had to get out of that comfort zone and go get what i really wanted. Besides I seen a lot of people with great career jobs struggle once they retire living pay check to pay check. Read more>>

Ade Ramirez

After dedicating a decade to the hospitality industry, specifically in hotels, and spending nearly five years at a prestigious country club, I have gained profound insights into the nature of human preferences and behaviors. Over the years, I have come to realize that people have an inherent fondness for consistency. They appreciate knowing what to expect and find comfort in reliable experiences, whether it’s impeccable service, a consistent ambiance, or unwavering quality. Read more>>

Maya Angel

The most important lesson I learned, while working at my last 9 to 5 job was that punching in and being on the clock “felt like work.” Read more>>

Judith Goldstein

I always say that I learned from every great boss and I also learned from the bosses I watched that didn’t do things right. I think in every situation with my formers employers the difference between a great leader and a bad one, was based on how they treated their staff, what kind of example they set, and the attitude they came into work with. The bosses I had that showed gratitude for their team, made sure to make them feel appreciated and those that led their team with strength and compassion were the ones that had the most success in their business. Read more>>

Parry Ray

My journey as a singer songwriter has been a circuitous one, but I knew I wanted to do this from the age of about 7 and I really feel it was meant to be, because every time I thought about stepping away, I always got a clear opportunity or “sign” telling me to keep going. Read more>>

Rose Devika

got my first job around age 15 and have been working ever since. For many years, none of the jobs I worked had even the slightest correlation to any of my passions, interests, or career goals. In retrospect, though, those jobs were, in many regards, the ones that taught me the most valuable lessons. They taught me the power of perseverance, regardless of environment. Read more>>