One of the best things about video games is the ability to restart – you can use your learnings to move faster and avoid obstacles. We often think about what we would do differently if we were starting over in business and we figured others probably think about this as well and so we asked the community to share their thoughts with us.

Rachel Walters

When I was starting my womenswear brand, Rachel Walters Collection, there was a ton of hype around taking the e-commerce consumer direct approach. I fell into the trap of believing it would be easy to put up a website and instagram and easily generate sales. After trying to exclusively sell online for a year, I knew I needed a different tactic. So I started having in-person pop ups at markets so my customer could shop IRL. It turns out sales far surpassed my expectations and blew the e-comm approach out of the water. If I started over today, pop-ups would be my first priority from the very beginning. Read more>>

Jill Devine

I’m a St. Louis native and best known for being an on-air radio personality. I spent over 20 years at numerous radio stations in the St. Louis market. Once I became a mom, I started noticing all these things about being a working mom, things no one was talking about. It led me to create and host my own podcast, Two Kids and A Career. The podcast is an outlet to talk openly and without fear of being judged or shamed. The conversations are real, raw, emotional, and knowledgeable. Read more>>

Joleen Thomas

Time. If I had the opportunity to start over I would dedicate my time to truly learn specific skills and take more time to listen to business leaders, through podcasts and meeting with other small business owners. I think I have finally reached a period in my life where I can focus on my art. I am able to map out my commissions, try new mediums, and work to build my social media. Read more>>

Alexis Maddin

Looking back I definitely would have chosen to go to film school instead of pursuing a medical path. I feel like I would be much further along in my career, because I had to learn the art and skills on my on. Read more>>

Shackisha Clark

If I were to start over things would be extremely different today. As a tax practitioner and licensed insurance advisor, I would have started my entrepreneurial journey at 18 years of age. When you are an adolescent, it is much easier to retain knowledge. With the knowledge, I retained over the past 5 years I could have probably retained that same knowledge within one year as an adolescent. I would have been enthusiastic about fundraisers, saving personal, & investing funds. However, I have no regrets. Everything happens when it is supposed to at the perfect time. Read more>>

Mike Byrd

Honestly, If I had to start over, I would jump straight to ownership of a studio space. This is inherently an expensive industry to get into with the cost of equipment and software, so I would save myself an expense on constantly renting out spaces and having to stress about availability of those spaces and just have my own. I know that’s not typical, especially starting out, but if you are sure this is what you want to do, I would encourage anybody to make that investment. Read more>>

Kate Zills.

Oof, this question gets me. We as creatives and business owners always think of things we would have done differently if we knew this or that or had more money, etc. I think it’s helpful to think that way at times, but I also think it’s important to recognize that you did your best with the resources and knowledge that you had at the time. I always remind myself of this before criticizing my past self and decisions. Read more>>

Deborah Sheppard

I would glean longer from my peers, and mentor’s. I would educate myself in psychology because most of it mental than physical strength. I would strengthen my business skills and develop mental techniques. I can’t say I would want to get here faster, everything takes time, purpose is not gain without the wisdom, and knowledge of process. Listen, if you want to destroy your purpose take the process away, and your purpose will be destroyed. Read more>>

Nia Knowles

Hindsight is 20/20 so being a visionary, working with the end in mind and being willing to venture out afraid is how I would have gotten here faster and with less cash. When I became a licensed Realtor 2007, I relocated my family into the Historic West End community. I had visions of living within a community similar to what I left behind in Brooklyn. The brownstones, the cultural diversity and accessibility. Read more>>