By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Devon Sedrick

Risk it for the biscuit! Or whatever the saying is. It’s all about risk. I love feeling nervous, scared, like I’m jumping into the void. It’s what makes me feel alive and I think it’s the only way to really move forward. I think planning can be a good thing, but the best things come on the other side of a big fat risk. My parent’s instilled that in me very young and my whole life has been one big risk. Thankfully I’m still going so… I think it’s worth it. Read More>>

Tyler (Seps) Seppala

I think risk is a complicated concept, because there are often multiple opposing and sometimes hidden risks that come with every decision. The ability to identify these risks and weigh them against each other is absolutely crucial to succeeding in business, and accomplishing great things in general. Read More>>

Louis Goodman

Risk is everything. For real change it requires risk. Risk is what life is all about. I wouldn’t be where I am today without risk. Read More>>

Kelly Cloud

Risk, my middle name. Risk is everything. When I think of the word risk, I think: take it. Life is meant to be lived fully and truly living means stepping into the unknown, even when it feels a little insane. Read More>>

Mo Stewart

For me, risk has always been tied to belief—belief in the work, the craft, and the community around it. BBQ itself is a risk. You’re investing 10–16 hours into a brisket before you even know if it’s going to sell. That mindset carries over into the business side too. Read More>>

Bradley Palermo

I try to looks at risks like ‘what’s the worst outcome?’ and ‘has anyone less equipped pull this off before me’. Usually the worst outcome isn’t sudden death, and someone with less preparation or experience has made it work in the past. That’s not to say there isn’t still a risk in whatever hypothetical situation we’re talking about, but it is what pushes me to act on it or not. Read More>>

Vanessa Blaho

I think if you don’t take risks, you often end up living the same life over and over. Looking back, I feel like I’ve lived so many different versions of my life, and every decade I’ve become a different person. Read More>>

Tracee Dunblazier

I don’t think I believe in “risks”, just valuable consequences. Some choices create more impactful results. What I do believe to my core? I believe there is a right choice for every individual in every situation, and to be mindful in making those choices by being thoughtful in their execution, and recognizing who and how others will be effected. Read More>>

Arsen Misakyan

I don’t look at risk as something to chase—I look at it as something to manage. In this business, every decision has trade-offs, so I focus on calculated risks where the upside makes sense and the downside is controlled. That usually means testing things in smaller steps before fully committing. Read More>>

Valentin Thomas

In high school I just enjoyed music naturally, took the class, learned guitar, got Ableton, started recording beats that ended up getting over a million plays. It felt casual, accidental almost. When I graduated I wasn’t sure I could commit to it fully. Read More>>

Jewelzz Patrick

I took risk by betting on myself and going all in this time with my brand monetarily it was a big risk with the money especially with a small budget but it was definitely worth the risk I have substantially made more ground than I ever have with my brand and achieving shooting an video that is well industry polished amongst other various career achievements that I hadn’t achieved before, and gaining more impact on my audience fan base. Read More>>