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.

Kristin Gibby | Artist

Being wrong forces you to explore; transform error into insight. I’m not sure who said it, but it’s a principle I try to apply in art and life. Failure happens. We all get things wrong even when working hard to get them ‘right.’ Reframing the discomfort felt in those moments keeps me working toward improvement. It’s a reminder that my time and efforts aren’t wasted, and to move from self criticism to self compassion. Read more>>

Avi Steinhardt | Psychotherapist and Puppeteer

Many important moments in psychotherapy involve risks. When the therapist steps outside of being purely empathic or supportive, there are implicit risks- of pushing someone to a place they’re not willing to go, risk of losing their business, risk of offending- and it’s often in these risks that a new level can be reached. And of course I also took a big creative risk when I started my Instagram account, @monsteright. Read more>>

Colby Lefebvre | Chef and Owner

Risk is a very interesting topic amongst individuals. Risk can be seen in so many ways that are both qualitative and quantitative. These are the categories that I like to put my risk assessment into to. Quantitative risk is easier for myself to digest. I’ve always been a numbers guy. When I began my business plan for Alpine Pizza Company I first began with the numbers and based 3 sets of financial documents off the experience I had from running restaurants in the area for 14 years. Read more>>

Noah Catapano | Owner / U Call-We Haul Junk Removal

My favorite business quote is from renowned author Dale Carnegie, “You never achieve real success unless you like what you are doing”. The reason this quote sticks with me so much is the relevancy it has to myself and business. I have had countless sales jobs since high school, some worked better than others. Read more>>

Taylor Vacca | PhD Student & Aspiring Professor and Author

I love this question, as it has helped me (and I hope it helps you too) during some of my life’s toughest, most challenging moments. “You are enough.” This affirmation has been spoken many times in the last three years, while in graduate school, providing executive consulting, and serving my community by practicing individual psychotherapy. I know this may sound silly, but this quote became my go-to mindfulness-mantra technique that would help fill me up after frustrations, failures and lost fantasies that never fostered. Read more>>

Rebecca Simonson | Licensed Massage Therapist & Entrepreneur

“Choose a job you love, and you will never have to work a day in your life” -Confucius; This quote was one that I was introduced to me at the massage school I attended. It is my favorite because it’s a quote that really resonates with me and my passion for massage. When I have to take time off work, I am always excited to go back to work. Read more>>

John Peters | Spouse, Father, Firefighter and Distiller

In my job as a firefighter risk is directly associated with benefit. “Risk alot to save alot,” is a guiding principle. Straight forward, and not hard to mess up. With the distillery business the risk was being accepted as worthy of putting a product into another human. Does it taste good, does it burn, is it worth it? Yes, no, and I think it is. Read more>>

 

Liz Zorn | Model & Photographer

Risk taking has been the baseline of my entire career. In order to get to where I am today, I have had to take many risks that have left me wondering if I was really doing the right thing or if I was making a big mistake. Taking a huge risk to get to where you want to be in life is all about remembering why you’re taking it, Read more>>

Cora Aversano | Wardrobe & Product Stylist

I believe risk is a very important part of your life. It gives you an opportunity to grow in a different way and really pushes you to get out of your comfort zone. Risk is an important factor in achieving the life that you dream of. A lot of times you don’t know the outcome of a decision you have to make and to choose involves a risk. Sometimes without risking it all we may never truly know what we are really made of and if you really want the life you’re dreaming of. Read more>>

Susie Crosby | Teacher and Author

I am not by nature a risk-taker, but I have taken a few significant risks that have definitely changed my life for the better. One risk was leaving the only school I had ever taught in. After 28 years and with deep and strong connections to that community, I accepted a job at an all-kindergarten school near my home, and I joined the leadership team. Read more>>

Hannah Riccio and Alex Turner | Restaurant Enthusiasts & Dog Parents

We moved blindly across the country from Rhode Island to Trinidad, in the midst of the pandemic with plans to start not only just a business but a restaurant. The entire decision was a risk. We knew it would be difficult but the risk makes it all the more with it. No risk = no reward. Read more>>

Torin and Paige Rouse | Walking America Couple

Safety doesn’t necessarily lead to happiness and certainly not satisfaction. Walking America is an enormous risk whether walking into traffic or sleeping in a stranger’s home. But we’ve never been happier. If you’re not taking risks, you’re not challenging yourself. And if you’re not challenging yourself, you’re not going to grow. Read more>>

Jim Beatty | Founder, Zell’s Panini & Crepes

If I take a step back and look at all of the risks I have taken over my life so far, impartially, I would have to say that I have a high tolerance for risk. However, if I look at each of those decisions taken one at a time weighing the risk vs reward, they never seemed so risky. I always start by gaming “what is the worst thing that can happen” and try to understand if I can except that outcome and work through it. Read more>>

Wayne Rodgers | Owner, Batch & Trowel

was going places. But I was definitely addicted to the paycheck, and felt somewhat trapped. I mean in the way I felt unable to take major risks for fear of losing everything. Then I had a series of personal tragedies strike all at once. I lost my brother and my dad suddenly, while going through a divorce. It’s kind of difficult to explain how much my life changed. Read more>>

Indigo General | Songwriter, Recording Artist , Model , Actor , Entrepreneur

If you can see it in your mind , you can hold it in your hand – bob proctor . Who was actually a personal and director mentor of mine , who I’ve have the privilege of receiving great personal development methods for success . What I like about this affirmation is the Suttles yet direct message that says you can truly do anything you put your mind to if you just believe , envision and allow your imagination to flow Read more>>

Amy Feiman | Graphic Designer and Letterpress printer that specializes in personal, event and corporate branding.

My favorite quote is by Maya Angelou, an American poet, author and civil rights activist, it reads, “I have learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” I have tried to embody this quote not only in my life, but in my work. As a graphic designer with an emphasis on event branding, I know that it is more than just how things look and feel. Read more>>

Logan DeCicco | Parks and Recreation Communications and Marketing Supervisor

Taking risks is what got me to where I am today. In 2015, I made my first placement with a NY Recruitment Agency and took my earning to go back to school. At the time, I was training U-8 to U-12 soccer teams, waitressing, and working as a recruiter with a bachelor’s Degree in Communications. My passion has always been soccer, so working with students of the game is where I could be where my feet were and it never felt like work. Hence, the financial risk of going into debt for a career in Sports Administration and Coaching. Read more>>