Risk is the most common topic that comes up in our conversations with entrepreneurs and so each week we ask entrepreneurs to talk to us on the record about how they think about risk.

Lynn Goldstein | Original Abstract Landscape Painter & Teacher

I’m generally a risk-averse person, influenced by my upbringing. However, whenever I’ve dared to take a leap, I’ve found it rewarding. One significant risk I took was moving to an unfamiliar area after college, rather than returning home or joining friends elsewhere. It wasn’t easy, but I’m grateful for the experience. Read more>>

Melissa Foote | Photo Organizer & Educator

Taking risks can be incredibly scary and uncomfortable, which is why I avoided them most of my life. Instead, I chose to stay in my comfort zone where my family, friends, home and job were safe and predictable. Read more>>

Annica Lydenberg | Creative Director and Mural Painter

I have always been a cautious person – shy, afraid of the spotlight, overly anxious about pleasing others. I didn’t celebrate risk. Goals of kindness, hard work and staying in my lane were what I thought mattered most to me, not bravery. I worked very hard, asked for very little and I was satisfied with that. It wasn’t until some friends introduced me to rock climbing in my late 30s that I learned how to become less afraid of failure and how to take risks. At first I would only climb routes I thought I could successfully complete, more of the same. But over time I began to go for holds that I might not make, I felt my fingers slip off of the wall as I fell. And it was the best feeling I had ever had. I started to feel more confident everywhere in my life and my career. Read more>>

Paula Freeman | Professional Artist

I truly believe risk is necessary and that we all take part in some form in our lives. Early on in my life and career the choices didn’t seem too risky. I had time to change direction if my choices didn’t work out but I still tended to make a safer choice or tried to balance my risk with a safety net. Art school felt risky but teaching art felt safe. For me it was a great place to begin. I graduated from Virginia Commonwealth University with a fine arts degree and teaching certificate in hand in the mid nineties. I loved teaching art because I got to do it all. I could explore painting, drawing, printmaking, ceramics and more right along with the students. I began a mural painting business and loved meeting new people and clients. I started a family and continued to teach and work my business for the next 20 years. Read more>>

Ty Taylor | Singer/Songwriter

Taking risks has played an extremely big role in my life and career these past few years! In 2019, I decided to quit my corporate job of 5 plus years to chase my dream of being an airline pilot. After graduating flight school in under a year during Covid and instructing for a few months, the realization hit me hard that flying planes was not my passion. I put myself into a ton of debt that I will be paying for 20 more years all for a passion I thought I had. Do I regret it? Not at all. I had to get an iPad for flight school, and that iPad allowed me to get back into playing and recording music- my true passion. I still write and record on that same iPad to this day, and I ended up taking another risk by moving halfway across the country (Atlanta to Denver) to chase my dream of being a musician! Risks get you out of your comfort zone, and they have helped me get clarity on a lot of things. Have a dream? Always chase it! Even if there is risk involved, what’s the worst that could happen? Life is short, and I think it is extremely important to find what makes you happiest and do everything that you can to make a career out of it. Read more>>

Pete Saloutos | commercial photographer

to be successful you have to be willing to risks! Read more>>

Jessica Montgomery | Photographer

Risks are an inevitable part of growth. With every risk, there is opportunity and you’re never going to find those opportunities from your comfort zone. If you take a risk, but don’t get the outcome you were hoping for, there is still the opportunity to learn from the experience. I think most people are afraid to take risks because they are afraid of failure, but failure is important too. Failure teaches you things and makes you better for next time. Read more>>

Rachel Eisenstat | Musician, Songwriter & Voice Teacher

In my late teens and 20s, I was a very risk-averse person when it came to my career. Even though I was always working on music and it was the only career I could really envision for myself, I didn’t trust I could make it work. So I was a double major in college, got my masters in political science, and prioritized my Plan B career path for far too long. Read more>>

Jasper Riddle | President Noisy Water Winery

In building my business I started with absolutely nothing. I heard no from over a dozen banks in trying to get things started before I was able to hear my first yes. Its grown from 4 people to over 100 in the past decade and when facing challenges I can understand the fear of “Oh no! what if I fail? What If I make a big mistake? What if it all goes away?” All small businesses are undercapitalilzed from day one and usually remain that way for the majority of their business life. When times get hard and it seems that any move could be of potential determent to the business I constantly joke with my wife about the worst case scenario.” I say to her well let’s just say this all goes away? I bet somebody would hire me for a lot more to run their company than I currently pay myself.” Risk reward scenarios are the backbone of small business you need to learn from the one that don’t work, build on those mistakes to shape ones that will and keep getting up when life knocks you down. I think the economic principal of “Sunk cost” is invaluable to a small business owner. Don’t worry about the past decisions you can’t change those and you’re in the leadership role. You need to keep moving, stagnation in more dangerous than bad decisions sometimes. Keep taking risks, keep failing and remember your building you business and if your business fails you’re building your resume for someones else’s business. Most of you came from nothing and built this from nothing, whats the real fear of starting back there again. You’ve already done it. I think if this is the backbone you have for your business than you’ll take the risks needed to be successful. Read more>>

Bekah O’Shea | Designer & Leather Artist

“My thoughts on taking risks are: it’s not gonna be easy, there’s always a chance of failing, but how you handle those challenges is really what defines success.
Truly, what’s worse, never taking the chance and finding yourself stuck doing what’s comfortable, not really pursuing your passion? That was me. I went to college to be a respiratory therapist and did that for many years, it was a good way to make a living, but in my heart of hearts, I always felt I should be doing something creative. Read more>>

Katrina Austin MA, NCC, LPC | Licensed Therapist and Podcast Host

Growing up in the south, I was quite comfortable with comfort, consistency, and predictability. When I left Oklahoma and moved out of the state, then out of the country, I learned some valuable lessons about risk taking. Read more>>