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.

A. Marie Dingwall

I left one corporate job with a boss that was a micromanager and went to another job with a boss that trusted me. The second boss gave me training and then empowered me to apply that training on my own. I was able to make decisions that my boss backed me up on. I could ask questions and make suggestions. To see the glaring difference between the dehumanizing experience of being micromanaged and the liberation of being trusted and how that enhanced my manager’s work was very impactful for me. I felt like a partner and a collaborator instead of an incapable subordinate. Read more>>

Jamie Taber

I am a former special education teacher. I spent most of my 20 years teaching students with physical and health impairments but ended my teaching career teaching students with severe and profound intellectual disabilities. My students have taught me so many lessons! First, they have taught me the importance of kindness and joy (which has become the motto for my business!). So many students with special needs love unconditionally and find joy in the little things. Second, they have taught me resilience. Almost all of my former students had (and still do have) many surgeries and medical procedures. Read more>>

Nadgeena Jerome

One of the most important lessons I’ve learned throughout my career is that hard work alone doesn’t guarantee promotion. In fact, I’ve never been promoted in any job I’ve had. Instead, I’ve been fired, laid off due to restructuring, or left voluntarily because of uncomfortable work environments. However, that doesn’t mean I wasn’t valuable. It simply means that the decision-makers didn’t see my value the way I saw it. Read more>>

Meshanda King

One of the most important lessons I’ve learned came from a 9-to-5 job that I thought would be my “forever” role. I loved the projects, enjoyed the team, and thought it was where I was going to be. Then, as life often does, things shifted. Leadership changed, the dynamics weren’t the same, and suddenly, the space that once felt comfortable didn’t fit anymore. Read more>>

Michon Covington

One of the most pivotal experiences that shaped me as a business owner was my time as Vice President, where I worked alongside two incredible colleagues to manage the day-to-day operations and strategy of a multi-million-dollar software company for over a decade. That role taught me the fundamentals of running a business, including financial systems development, cash flow modeling, and recurring revenue management. I built financial frameworks from the ground up, such as a three-year rolling cash flow model and annual budgets that drove cost management and resource efficiency. I also gained extensive experience in contract negotiation, dynamic forecasting, and job costing, all of which prepared me for the challenges of business ownership. Read more>>

Tanner Partain

I spent several years working for a nonprofit called YoungLife. I loved my time there and learned a lot about consistency and courage in trying new things, as a large part of that job was going into junior highs and talking to students, which is still a terrifying thought. However, the more I showed up the better relationships with the school and students I was able to make, and I felt like I was really able to make a difference in my community as a result. Read more>>

Nadia Jarfi

Before starting my own business, I spent four years as a Community Manager for a locally-owned coworking space. Like many small businesses in their early days, “Community Manager” was really an umbrella for about ten other job titles. Lucky for me, I thrive on variety, so I embraced my role as the company’s “Swiss army knife.” Read more>>

Amya Bourgeois

Before launching my own business and mustering the bravery to follow a creative path, I worked as a security guard. It wasn’t elegant, but it covered the expenses. My shifts were lengthy—frequently at night, remaining in one position or making slow rounds in vacant structures. It was the sort of position that allowed plenty of time for reflection. Read more>>

Lisa Loop

In my twenties I worked as a story editor for a Hollywood studio. I came into the job armed with an English degree and some Indy screenplays under my belt, but I didn’t know what to expect. What I learned was that more important than talent or hard work, the best writers had a strong voice. It sounds counterintuitive, that someone trying to write for the marketplace needed a real point of view. But each screenplay that crossed our desks and moved forward to the higher levels had an extra sparkle that set it apart, a creative risk that felt unique. Great writers are story tellers, but what makes them rise above is a willingness to share their passion. There is no shortcut to admitting what you truly care about. Read more>>

Nora Sun

Throughout high school, I was interested in developing solutions to healthcare issues using technology. I was always drawn towards implementing the newest and most exciting discoveries, proposing projects to improve patient quality-of-life that involved artificial intelligence, brain-computer interfaces, and such. Over time, however, I recognized that my target audience showed a hesitancy to adopt the most complex, cutting edge innovations. What they wanted was not some fancy AI-powered gadget, but a simple tool they could incorporate into their lives with the minimal number of changes to their lifestyle possible. While the newest inventions were appealing to me as a scientist, I was metaphorically recommending a bulldozer for a job that could be done with a hammer. Thus, over time, I learned to instead place greater emphasis on researching the lifestyle of my target audience and develop the most convenient and effective solutions for them. Read more>>

Alicia Shevetone

Follow-Up is critical. No matter your product or service, you are likely fairly far down on your client’s list of priorities. The best way to ensure your success is to consistently follow up, which reinforces your resolve and embeds your brand’s footprint on their business. As many as 44% of corporate sellers fail to follow up after their first attempt. In most cases, a minimum of 5 outreach attempts is required to lock down interest – and up to 8 connects is needed to secure business (FitSmallBusiness.com November 2024). Read more>>

Elizabeth Dryden

Pre-Covid I worked in cosmetics for the flagship Neiman Marcus store in downtown Dallas promoting products and performing facials for clients by appointment. It was technically a sales job with very high goals and expectations. I worked hard to maintain clients and formed lasting relationships with them so I could help in any way possible through the years. I would follow up with notes and samples, and kept current files on everyone. Learning these basic fundamental business skills helped immensely when Covid came and my day job at NM was completely dissolved. Having created artwork professionally since college on the side, my dream was to be a full-time artist one day, but was never quite brave enough to make the leap. Read more>>

Shimon Braun

I found my way into the Batsheva Dance Company through a chance encounter. After finishing my university studies, I was on my way to visit my parents in Ramat Gan when I ran into my friend Ehud on Dizengoff Street in Tel Aviv. He told me that Martha Graham herself was in Israel auditioning dancers for a new branch of her New York company, which would later be known as the Batsheva Dance Company. Read more>>

Carly Giglio

I was an Account Executive for a beauty brand which meant running the business for over 25 retail accounts and management for about 10 makeup artists. The job consisted of sales, building and maintaining a successful business in my market, makeup artistry, product/brand education and more. Read more>>

Kendal Paley

I think the best experiences I’ve had at past jobs are all related to the worst bosses I’ve had! Strange, I know. Those are the experiences that have taught me the most about the type of person I want to be. How I want to treat others. What values are important to me. How to lead with kindness and respect. I’ve learned so much of what I DON’T want to do/be from the horrible people I’ve worked with and for in the past. Read more>>

Antonio Boswell

I think the most important lesson I learned from a job was, it doesn’t matter what I personally like, what matters is what will work. Before starting my business, I worked for a corporate investigations firm. I learned to gather and analyze information. Then develop a plan and make decisions that had the best chance of giving me the desired outcome. I had to lean on this process when I became head of the media department. The decisions I made not only impacted me, they impacted my team and the company. My ideas and plans had to be based on what had the best chance of working not what I liked. I use the same process when doing consultations for clients in my business. Read more>>

Isaiah Mcswain

In May 2023, I finally made it in mind. I had landed a role at Hearst Corporate in the newspaper division. Hearst is one of the largest cross media companies in the world. So while working on two of their top strategic teams, I learned a lot. I learned both soft & hard skills that I use in my business now.

However, the most important lesson I carried back to Zayam Design is catering to and nurturing your relationships with people. People truly do equal profit. But profit comes in both realized and unrealized gains. Your team, clients, and platonic relationships need morale and trust. Read more>>

Brenda Leshay

One of the most important lessons I’ve learned is that vulnerability is catalyst for positive growth and not a weakness! This lesson I learned through a culmination of experiences in becoming a psychotherapist. But there was one experience in particular that really solidified this message for me.

To give you a little background first, I was raised in an environment where mistakes were not tolerated. In my family, the consequence for messing up was either to be punished, teased, or humiliated. And sometimes, all three. As a result, I learned to either avoid doing things altogether or to hide my faults. This, as you can imagine, created many problems for me in my personal life. Read more>>

Shannon Price

I worked in the mental health field as a case manager and clinician before I worked in real estate. All of my clients had a mental illness, were low income, and many of them were homeless. The job was both extremely challenging and rewarding at the same time. The experience and insight I gained from working with my clients is something I carry with me everyday. I learned how compassion, empathy, and empowerment can change a person’s life. Read more>>

Erica Jones

The most significant lesson I learned in my previous job was the need to develop self-discipline and business acumen to succeed in my endeavors. While I consistently performed my job well, I often thought about pursuing entrepreneurship, especially given the volume of creative work I was producing. I thought I was ready to dive into my own business full-time, but I quickly realized that the experience of having someone else manage your tasks and set deadlines is very different from the responsibilities of being your own boss. As an entrepreneur, you have to establish and stick to your own standards—otherwise, the work won’t get done. For a long time, I struggled to understand this, but eventually. Read more>>

Leslie Woodward

The most important lessons I’ve learned that shaped me as a business owner came from two distinct career paths.

First, when I lived in Orlando, FL, I worked at the Orlando Convention and Visitors Bureau in membership and advertising sales. This role taught me the value of listening deeply to clients’ needs, confidently walking into diverse spaces—big and small—and fostering partnerships that create meaningful communities. It was a crash course in relationship-building and understanding how to bring people and ideas together effectively. Read more>>