We asked some brilliant entrepreneurs, artists and creatives to reflect on lessons they’ve learned at prior jobs. We’ve shared highlights below.
I learned that you might not get it right the first time (in fact, you probably won’t), and that is NORMAL. My first Head of Content position for a connected fitness startup involved my producing hundreds of on-camera workouts in a short amount of time. It was connected to wearable tech and a complicated CMS, and through the process of bringing that content live I learned the value of extensive product testing and quality control. It is better to launch a great product later than expected than to launch a subpar product on time. You only have one shot to make an impression. Read more>>
When I finished pediatric residency training, I started working at a busy insurance-driven primary care pediatrics practice. As a new physician with three young children, I was quickly frustrated by the day to day pace of seeing 20+ patients daily. I felt torn. The days were a blur of brief visits and rushed conversations, and I often went home wondering if I was really making a difference. I became a pediatrician because I wanted to help children thrive and families feel supported, but in that setting, it felt like I was simply moving patients through a conveyor belt of care. Read more>>
The most important lesson I learned from a job was that “perfection” is, at its core, an illusion. In many roles, I was required to give presentations regularly, and this part of my job began to trigger panic attacks. I found myself trapped in a destructive perfectionist spiral, consumed by fears of being judged for misspeaking or not being eloquent enough. The fear of imperfection left me paralyzed and prevented me from growing. Perfectionism convinced me that if something couldn’t be perfect, there was no point in trying. Read more>>
At a previous job, I was asked why I dedicated so much time to building relationships with my members—whether they were users, customers, or colleagues—and what tangible benefits I expected to achieve from that effort. To those asking, this investment in relationships didn’t seem like a priority or hold value in their eyes. Hearing this perspective, I couldn’t help but disagree. That moment became a pivotal reminder of the core value I hold in my work: always leading with a people-centered approach. I firmly believe that for any community to truly thrive, its people must remain at the heart and center of every effort. It’s never about the “I”—it’s about the “we.” Together, as a collective, we learn, grow, and achieve success that wouldn’t be possible individually. Read more>>
One of the most important lessons I’ve learned at a job that has helped me be a better leader is serving others with gratitude. My first job was a cashier position at Taco Bell for $6.15 an hour. I worked there for two years during my sophomore and junior year in high school. As a teenager, I was thrilled to be earning my own money considering my family background. My mother was a single parent of five who survived off government assistance. She was never able to afford the things I wanted however, tried her best to provide the things I needed. Although I was not making a ton on money, it felt good to have my own financial earnings. Read more>>
Luxury retailing set the stage for us as an interior design firm specializing in second homes and destination vacation residences in so many ways. The better part of my “work” day as a retail buyer was spent interfacing and collaborating with high profile creatives (designers, vendors, stylists) or hunting for unique treasures in design districts, long before “found items” became a buzz word you hear everyday. Rare or limited editions and one of a kind items are highly sought after by our clients today. Furnishings that set apart an interior can provide interesting conversation starters and are just fun to have. Everyone loves a good story. Read more>>
The best leaders I’ve worked for and supported were the ones who understood the organization at a granular level (i.e they could zoom in and out of the details if they needed to); they had an insatiable curiosity about the business and a general desire to study the issues at the forefront in great detail; yet, they never stayed in the granular, they never stayed in the weeds. They were always asking the overarching strategic question: what’s the bigger picture this detail has to nest in? They could zoom in to the trees but quickly zoom out to the forest ie vision, always keeping functional leads laser focused on the overarching strategic vision and trajectory of the organization. Read more>>
The most important lesson I learned from a previous job was to never get too comfortable because your job is never really solidified anywhere, most corporations see you as a placeholder that can be easily replaced when convenient for them. My last job had a company wide lay off/rebranding period where supervisors and superintendents who thought their place with the company was solidified were sadly mistaken because they were laid off without warning. Seeing this as an intern left a lasting impression on me by reinforcing the thought to never get too comfortable anywhere. Which is another reason why I decided to become an entrepreneur. Read more>>
Before going full time as a business owner, I worked in commercial banking. The bankers I worked under stressed importance of the high quality customer service. Quick replies, lots of ‘hand holding’, going the extra mile. Thank you notes, check in’s and Christmas gifts for clients. It wasn’t commercial banking anymore, it became relationship banking. The saying “It’s not about what you know, it’s about who you know.” Means more now as a full time entrepreneur than it ever did before. The relationships created and deepening those connections have been monumental in the growth of my business. I continue to write thank you cards, send Christmas gifts and follow up with past clients. It’s that extra mile that frequently gets skipped over that makes a customer a client. Read more>>
I run my own business as an independent filmmaker. Prior to jumping into directing, and for many years, I worked in retirement homes and long-term care. Working in a retirement home, surrounded by elderly people whose lives were filled with experiences, traumas, and stories, profoundly shifted my perspective on the power of film as a medium. It wasn’t just the stories of these individuals that stood out to me, but the way they recalled their pasts—the emotions, the laughter, the grief—often with a depth that surpassed words alone. In their eyes, I saw how much time shaped their identities, how recollection, both postive and negative, intertwined to form who they had become. Read more>>
I was a social worker in my former life before opening Wildflower Bridal in January 2014. I often say that my days as a social worker were the absolute best training I could have ever had for what I do now. As a social worker, my primary client-facing task was being a good listener and observer. That is also my primary task when working with brides and ultimately guiding a bride to her chosen gown. While the world at large generally perceives bridal stylists as retail workers, in reality it is 90% a service and hospitality-driven position. Read more>>
The most important lesson I’ve learned in nearly 20 years in the creative industry is that success doesn’t hinge on having the flashiest designs, the most groundbreaking ideas, or the perfect lighting setup. While technical skill and creativity are essential, the real differentiator is being someone people want to work with. It’s about cultivating authentic relationships, showing genuine care, and making every interaction count. Read more>>
I was a young corporal in the US Army just after my combat tour in Desert Storm, we were training at Fort Irwin and I was in charge of setting up a forward air refueling point. This was a way to configure refueling operations for helicopters in a combat situation from a couple of fuel trucks and hoses extending out from those trucks to points that were far enough from each other so that the helicopters could fly in, land, refuel and fly out without hitting each other and making the process quick to get them back to the fight. Read more>>
I was an electrical engineer before. The fun part of engineering was dealing with problems. You knew there were always exact answers to the questions as long as you devoted time and knowledge. Gradually, I got tired. I went to exhibitions, read books and learned to draw. I found myself indulged in the art world, feeling obsessed with the beauty of abstract, especially those illustrations based on text. Thanks to my prior job, I got to know myself better and finally set my career goal as an illustrator. Read more>>
The best lessons I’ve ever had to prepare me for running my own business and starting a non profit, came from being a food server during my college years. – I learned how to be a team player and to help out co-workers when they were overwhelmed, who helped me out in return. We all did better as a result of having each other’s backs. It gave me the values that I still have today where I see how supporting fellow human beings all over the world, raises us all up to do better. Read more>>
In 1984, I was a hardware engineer on the Lockheed team that built the Hubble Space Telescope (HST). My responsibilities included technical oversight of the design and construction of the reaction wheel assemblies (RWAs) that pointed the HST (there are no thrusters). For redundancy, there were 4 RWAs pointed in different directions such that any 3 of the RWAs could provide complete 3-axis (X-Y-Z) control of the pointing direction of the HST. The HST guidance software calculated the x-y-z torque that needed to point the HST and then converted this to 4 separate commands using a 3×4 conversion table that was based on the physical arrangement of the RWAs. Read more>>
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