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.

Emily Grant | Real Estate Agent | Staging SoCo Owner

I am not afraid of taking risks. As an entrepreneur, you must be willing to fail in order to succeed. It requires discipline, a plan, and then execution. You miss all opportunities you don’t pursue. Starting a business isn’t easy, but every journey starts with a first step. I focus on the lessons learned, and not the “failures.” Read more>>

Amy S. Werhane | Bakeshop Owner | EdTech Project Manager

Opportunities always come with a healthy amount of risk. I figure you can either practice avoiding risk, or, you can practice exploring opportunity. There’s nothing wrong with avoiding risk, but that goes hand-in-hand with avoiding opportunity. Read more>>

Hanna Gomez | Owner of Sunrise Charcuterie (charcuterie boards and grazing tables)

In my life thus far every ‘risk’ I have taken it has led me to some unexpected and beautiful experiences. I believe that fear can stop us from taking risk however facing that fear and jumping in head first or even gradually can really lead to something special and can even change your life. Read more>>

Stefanie Tacata | CEO and Co-Founder – Stateless

Risk-taking is necessary in business, and in life in general. Looking back on our company’s history, every time we “leveled-up” was a direct result of taking a significant risk. When we signed the lease on our first office in downtown Manhattan, when we hired our first W2 employee, when we signed our first contract with a Fortune 500 company, all of these were risks that ultimately lead to the next level of success for Stateless. Read more>>

Ethan LaPlante-Dube | Photographer

Risk for me at the start of my journey was terrifying, and I wasn’t sure what risks were worth it or what was worth taking a risk on. I was constantly tiptoeing around opportunities. I later learned that everything and anything is worth taking a risk on. I have taken many risks in my life that led me to Photography; some paid off, and some did not. Read more>>

Savanah DeCourcey | Stylist, barber, esthetician

Taking risks is the reason my career and my life are what they are today. Moving to a new city with no foundation or connections forced me to hustle hard and make a name for myself in the beauty industry here in Denver. It wasn’t easy at first but so very worth it. I have a level of happiness I didn’t think was achievable and have zero regrets about the risks I took to get to this point. Read more>>

Nancy Stohlman | Flash FIction Writer, Performer, Teacher

In order to make art, one must become comfortable with ambiguity and uncertainty. Real art is made inside the gap of uncertainty–we cannot “think” ourselves there. We have to move. Certainty comes from action. We embark on an idea…and only once we are in motion does the art take over. Read more>>