Experience is often valued because of the lessons prior jobs have theoretically provided us with. While hearing about those lessons isn’t a replacement for actually experiencing it, we thought it would be very helpful to create a space where sharp and generous members of the community can come together to share stories and lessons learned at prior jobs for the benefit of others.

Dallas Jack

One of the most valuable lessons I learned in a prior job came from Stephen Woessner, owner of Predictive ROI, an outstanding podcast marketing agency. He often said, “We only do good business,” and he was willing to stand by that principle—no matter the cost. That meant turning away clients who weren’t operating above board and being transparent about our capabilities, so clients felt they could trust us completely. This unwavering commitment to integrity and honesty showed me that profitability and ethics aren’t mutually exclusive; in fact, they strengthen each other. Read more>>

Brandon Sharp

My first management job was at Restaurant August in New Orleans. When I buttoned up the embroidered jacket of the Executive Sous Chef for the first time and took command of that kitchen, here are some of the good habits I tried to get across to the riotously motley crew: Cook a timely and delicious family meal. Read more>>

Storyboard Casting

Tish Campbell – For me it’s two things – not trying to go it alone and making sure I have the right team members at my side. There’s no one experience in my past that taught me this lesson, rather many. I’ve owned two previous businesses – one where I was 100% solo and did everything myself. Long story short, I ended up completely burning out, though I did learn how to manage all aspects of business from product creation, to sales and marketing, to finance, and everything else that comes with a small business. After I shuttered that business I partnered with someone else and we worked together for 10 years and built up the company from a basement business to one that employed about a dozen people. Read more>>

Michael Bress

During the start up of my journey as a personal trainer I actively was pursuing a bachelor’s degree from Michigan State University in supply chain management. Fast forward a few years after starting up powerlifting coaching and personal training, I got my first real world job at DHL Express as an operations supervisor. Very grateful for the opportunity, I made GREAT money out of college and was given an opportunity to grow as a leader and prove myself. I worked for just under a year at DHL before I decided to ultimately leave my job. I had a lot of people doubt my decision and for a decent amount of time afterwards, I doubted my decision too. The most important less I learned is the importance of taking action > everything. Read more>>

Tia Barnett

I have been a dental assistant for over 19 years. I love what I do and I love teaching what I love.

Something that I learned at the school I attended was book work, paper charts, and 12 months of coming to classes. After I graduated, I was hired at a great dental office who was willing to train a new assistant. It was then I realized after 12 months of school, I knew nothing about the practical clinical workings of a dental office. I had a great office that was willing to teach me everything and anything dental related. I learned a lot of things at that first office. Read more>>

Nichole Kreps

I once worked for a woman who held incredibly high standards—not just in the service she provided but in the quality of work we delivered to our clients. She was intentional about who she hired, ensuring that we were all aligned in curating the salon culture we wanted to create. At times, it was challenging to meet her expectations, and it didn’t always feel good. But looking back, I realize how invaluable that lesson was. Read more>>

Svetlana Kandybovich

I’ve been a motion graphics designer since 2012, working in the TV industry and content creation world. My background is in arts—I have a classical education in fine art and a degree in animation. Horses, though, have always been my passion. A few years ago, I found myself craving a creative outlet where I could express that side of my life. That’s how my blog was born—it became the space where my professional skills and personal love for horses finally came together. Everything I’ve learned from my “day job” in design and storytelling now helps me build and shape my content as an equestrian influencer. It’s been such a rewarding way to merge two parts of myself. Read more>>

Amanda Evans

At my last job, I knew it would be my last. It was my final experience of trying to fit my creativity and ideas into a box that was never meant for me. Deep down, I always knew I wasn’t meant to fit in. I was meant to build something of my own. While that job didn’t align with my purpose, it did introduce me to core values like resilience, resourcefulness, and integrity. Ironically, those values weren’t fully reflected in that role, but they became the foundation of who I am as a business owner today. Read more>>

Melody Law

One of the most impactful experiences in my career was working as a kindergarten teacher after university. I learned the power of confidence and guidance in helping others realise their potential. I saw talents in children—whether in languages, creativity, or sports—and always encouraged their growth. This taught me that confidence is key to unlocking one’s abilities. Over time, I realised I needed to apply that same belief in myself and my own dream of becoming an actor. This experience not only shaped my approach to teaching but also fuelled my passion for performing. Read more>>

Angela Aguilar

My personal important lesson was “Don’t work for family or friends.” Things can get weird really quickly. Relationships can be ruined and it can affect other family members as well. It just isn’t worth it in the long run. I won’t go into all of the bad things that happened. I will say that I can see where I am to blame in how things played out for not having boundaries and speaking up for myself. I have since learned boundaries and I would never allow myself to be treated the same way today as I did back then. But everything that happens in our lives happens for a reason and is there to teach us a lesson if we will let it. I work for myself these days and I treat myself pretty great! Yay me! Read more>>

Tracie Root

I didn’t realize until recently how my prior (read: corporate) job had set me up for success as an entrepreneur. I was in charge of moving people from office to office and from building to building within large corporate office campuses, sometimes one at a time and sometimes hundreds at a time week over week.

A-ha! I discovered why I was a great relocation/project manager and why I’m a great coach and business owner now. Read more>>

Sophie Princeton

I’d say the last job I had before “quitting my career” to become self-employed was the one that taught me the most lessons that I’ve brought with me to my business now. I spent seven years there and while it was an international firm, the team I joined back in 2016 was very small – it was just me and my boss! Read more>>

Anna Yukevich

I worked for three years at the Johnson O’Connor Research Foundation, a 100-year old nonprofit, where I administered aptitude tests and helped people understand their natural talents. The work was fascinating and hands-on – I’d time clients while they put blocks together, arranged words in diagrams, etc, and then I’d spend 90 minutes going over the results with them, helping them understand how their scores might translate to a satisfying career. All told, I spent about four hours one-on-one with each person. Even with our tests being very different from school exams (they’re more like puzzles and games), many people, especially high achievers, came in with intense anxiety. Read more>>

Rachel Pipan

Before I started my firm, I had a defining experience about claiming territory and taking credit – one that still guides me today! In my previous job, I was responsible for curating and directing a high-level annual gathering of CEOs, nonprofit leaders, government officials, startup founders, and other impressive people. It fell under my remit because much of public relations and communications is about building relationships with diverse groups, not just people you pay you, like customers or investors. Still, it was a huge undertaking to ensure that all of these key stakeholders were happy while also running logistics. Read more>>