Taking Risk is essential, but how much, when and why? Taking risks effectively is as much of an art as it is a science and we’ve asked some of the brightest folks in the community to tell us about how they think about risk taking.

Tayler Simon

Starting my bookstore, Liberation is Lit, was the biggest risk I have taken in my life. Usually, I am risk averse. I hate uncertainty because it gives me a lot of anxiety. But when I decided to quit my full-time job to pursue this path, I felt like I had to make a choice for the sake of my mental health. I decided to bet everything on myself, and so far, it has been paying off. I continue to remember that betting on myself doesn’t have to be a risk, and as long as I believe in my mission, everything will be alright. Read more>>

Jessie Driver | Co-Founder of Canvas Studio & Nail Artist

When I think about risk, I see it as a leap of faith, trusting that my hard work will be enough to ensure I land on my feet. My career has been shaped by several pivotal moments, each requiring me to make difficult choices with no guarantees. I began my career in nails out of necessity, helping to support my immigrant parents and four younger sisters through challenging times. There were periods when we didn’t have enough food or money, and I know firsthand the reality of poverty and homelessness, relying on shelters and food banks. Fortunately, I had family mentors in the salon industry who taught me everything they knew about nails and salon management. Learning this trade wasn’t just practical but also empowering. It gave me a skill that would allow me to support myself anywhere. Read more>>

Ryann Morris | Radiologic Technologist & Influencer

All my life I’ve been the type of person to always play it safe, constantly scared of taking a risk for things to not play out in my favor. My outlook was ‘if you never take the chance, there’s not much to lose’. That was until I was faced with a once in a lifetime opportunity that I felt I couldn’t pass up. I was presented with the opportunity to participate in a reality TV love experiment with my partner of 7 years with this experience being a good distance away from everything I’ve ever know for a period of time. Read more>>

Kaitlin Popow-mark | Creative Director

I believe taking risks is essential, especially when you’re aiming to reach new heights. For example, when I started Leave Your Mark Social (LYM), I had to make a big decision. After being laid off due to budget cuts at my corporate job, I faced two choices: apply for new corporate roles or take a leap and start LYM full-time. Read more>>