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.

Deborah Young | Blogger/Writer

First of all, I just want to say I really think this question is super cool. It’s so different from some of the other questions I’ve had in the past, so this one really stands out. When I think about taking risks, especially over the last four years as a blogger, it’s definitely been about writing on topics that are different. Initially, I was a beauty blogger, writing about that, and I also had some book-related content that I had written very early on. Read more>>

Devon Dubois Certified Emotionally Focused Therapist And Supervisor | Psychotherapist and Relationship Expert

It was the fall of 2010 and I was an enthusiastic and eager grad-school student, sitting in the first class of my grad-school journey, with my new Marriage and Family Therapy (MFT) cohort. I was taking a “psychotherapy: interventions and techniques” course when my professor led with a very important and thought-provoking question; one, that I am certain will stick with me. Read more>>

Joaquin Hernandez | Cumbia Machin

Taking risks is essential in the music industry. As Cumbia Machin, I embraced a significant challenge by attempting to perform again with a new instrument called the Zendrum. Discovering the Zendrum allowed me to play despite my neurological condition, focal dystonia. Read more>>

Veronica Quirino | Boutique Owner & Stylist

Risk taking plays a huge part within my career. It’s actually one of my favorite parts. I take a risk in every aspect within my business. From taking a risk on what clothes to sell to opening up my own storefront. It’s always a gamble and I love it. Sometimes, it’s a failure, but I learn from it. Sometimes it’s a success! The success is what motivates to keep taking risks! Read more>>

Kres Mersky | actress/ playwright/ filmmaker

I try to follow creative impulse and trust that it will take me where I need to go. If a project is exciting me , I like to think that’s the path to follow. I’ve left projects and in my case, left a working career as a an actress in film nd television because I couldn’t express myself fully there. I have to say it reduced my income, but the creative freedom that came with that decision was well worth it. Read more>>

Lara Lavery | Fragrance Content Creator & Olfactiv Enthusiast

I believe that life is a gamble, a Roulette if you will, And a big part of that are taking a chances and taking risks , which is very important because opportunities could only knock once and it would be a big loss if you miss that window. Always follow your gut after a complete thought about a big decision, especially if it’s something you are truly passionate about. I’ve taken this risks a few months back when I started making content about fragrances, a passion that I truly love and enjoy since I was young. I always have loved scents as it always takes me back to a certain memory, it gives me a chance to relieve a moment in time and evoke feelings of that certain memory, whether it be joy, pain, triumph, or even disappointment, which all are a part of us and our history as a person and made who we are as a whole in the present. Read more>> 

Preston Dubreville | Real Estate Designer & Developer

No risk, no reward. It’s as simple as that. The opportunities that carry the greatest risk are often the ones that will yield the greatest results. It may not be an easy thing to stomach and not something everyone is built for; however, it is the ability to take risks and to keep taking risks after experiencing loss that separates the winners from simply the survivors. My entire career is built off of risk. While every entrepreneur takes this on, the game I have chosen to play in ultra luxury residential real estate is high stakes. Read more>>

Brian Bowersock | CEO, West Automotive Group

Great Question, I learned very early in the start of my business that people that excel in business are willing to take risks, those that do not take risk usually do not excel. I was taught to not get analysis paralysis, if it looks and feels good, then Pull trigger, do not over think it as calculated risk is how you get reward. Read more>>