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

Ashley Brown

One of the most important lessons I learned came from my time in the military. I had a mentor who drilled into me that you cannot complain about a problem without providing a solution as well. It’s a mindset that has been instilled in me ever since, and it’s played a huge role in how I approach business today. The backstory is that during my service, we often faced high-pressure situations where things didn’t go as planned. My mentor made it clear that complaining about the problem wasn’t going to change anything. Instead, we were expected to assess the situation, identify potential solutions, and act on them. It wasn’t always about finding the perfect solution on the first try—it was about doing something productive rather than getting stuck in frustration. Read more>>

Horatio Jay

The most important lesson I’ve learned from my last job is to follow the voice of The Holy Spirit even without all the details. When He told me to step down from the position, I didn’t know I had character issues hidden by pride. Now on the other side I can appreciate the growth and development and how it is preparing me for all future endeavors. Read more>>

Gabriel Abrams

Working in the emergency room is not for everyone, but the lessons you learn there certainly can apply to everyone. It is a whole new perspective on life’s challenges. Every day, hundreds of people fly through the ER doors having “emergencies.” While many people are having true life or death emergencies, the vast majority of people are not. Everyone thinks they are having an emergency, and you cannot see everyone at once so what do you do? Part of your job is called “triage” where you assess the acuity of the patient, or how emergent this really is. Patients with the highest acuity are seen first and patients with the lowest acuity are seen last. In order for the ER to function, you have to prioritize care; otherwise, you will be rapidly overwhelmed. There are many lessons one can pull from the ER, but this is one of the greatest because of its important applications to life. The ability to know what a real emergency looks like and prioritize accordingly. Read more>>

Mesbelle

One of the most important lessons I’ve learned as both an artist and entrepreneur is that you have to be proactive in building yourself, especially your brand. While there’s a lot of emphasis on living in the moment, what truly shapes your future is the consistent work and focus you put in today. Being a creative entrepreneur isn’t always sunshine and rainbows. There will be days when you don’t feel inspired, or moments when things don’t sell, and self-doubt creeps in. But that’s when you need to push harder. If you want success badly enough, you have to be willing to block out distractions that don’t add value. The key is to become valuable yourself, when people start recognizing that, you become the brand. Read more>>

Allen Penn

One of the truisms about owning a business is that ‘every problem is your problem.’ Fortunately, I didn’t have to wait until I actually did own my business (Framework) to learn this lesson, as start-ups teach the same. I was an early employee at Uber and helped launch and run it’s 4th market, as the GM of Chicago. We had a 3 person team responsible for the business and when I joined I was told (and subsequently came to view) everything that happened in the city relating to Uber as my problem. Regulatory heat? My problem (even though we have lawyers and government relations personnel). Drivers not get paid? My problem (even though the system that managed payments was run by the engineering team). Dispute between driver and rider? My problem (even though I was nowhere near the car).  Read more>>

Maria Baer

As the founder of an organizing firm, I am as Type A as they come. I desperately wanted to start my own business helping individuals create organized spaces as early as 2010, but felt like I needed to have “all of the answers” prior to exiting my corporate career. I spent my first 10 years, post college, honing my skills in marketing and sales jobs. In 2015, I took a leap from a large publicly-traded company to a start-up company in the tech sphere where I would be able to serve as a Sales Director.  It was while I was sitting on a sales call with our CEO and CMO that I heard them stating that our platform would be able to check all of the boxes needed, as a means to make the sale. We got off the call and they turned to our developers and said, “Let’s figure out how to make this happen.”  Read more>>

Alexis Dougherty

Every job I’ve had has shaped me into the professional I am today. Before transitioning to massage therapy, I worked in the food industry, starting from the bottom and eventually moving into management. These roles taught me invaluable lessons in work ethic, customer service, and handling unexpected challenges, like resolving conflicts without making them worse. However, it was waiting tables that most closely parallels massage therapy. Both require you to take personal accountability for your client’s experience, guiding them from start to finish, ensuring their needs are met, and making their experience as smooth and enjoyable as possible. Read more>>