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.

Grace-Anne Matocha | Lifestyle and Wedding Photographer

I’ve always been a risk-taker growing up. But a career risk packs a different type of punch compared to other risks. One of my mantras in life is, “You don’t know what you don’t know.” I’m a recent small-town implant that now resides in Houston, Texas. I moved to the city back in July, excited for the unknown. But with this excitement also came a lot of fear as well. Read more>>

Caroline Guntur | Organizing & Productivity Coach

As an entrepreneur, risk-taking is built into my DNA. It has had a massive impact on my life and career, and I wouldn’t be where I am today without it. A great example is my decision to move to a new country on my own at 18. I had no money and no idea how things would work out – I just knew they would. And they did. I enjoy taking risks because I know that very often I will get a big reward in return, and I don’t always know what it will be Read more>>

Rootsman Fender | Artist & Wholistic Health Therapist

Risks are necessary. It’s essential to living. Taking chances is truly what helps us to grow. It challenges us in ways that may seem difficult but it’s a part of the journey. Taking a rest also teach you about risk management. For example, once you lost more than you were willing to, you become more protective and aware of your values and your valuables. If you’re investing a whole paycheck in stocks and it goes down in value, it could teach you an essential lesson In maintaining your assets. Not just the physical, but the mental and spiritual. Read more>>

Wrecka | Artist

The way I see it when it comes to taking risks is you won’t ever figure out what you are capable of or who you can become without the challenges you’ve never or to afraid to take that’s what helps us evolve as humans you have tonbe willing to take the risk and the possible l to get to the w or the next level. Read more>>

Jamal Gaylor | Reckless Ambition- Owner and Creative director

I think risk plays a big part in everyday life. I think everyone takes risks and that’s inevitable. The greater the risk, the bigger return, The ability to manage risk will helps people act more confidently on decisions. I can say that risk in my life and career has helped me exponentially. Without it, I don’t think I would be where I am today. I’ve personally took a lot of risks myself that people would look at and think its crazy. When I wait my job to pursue my business full time while being a father, people thought that was a big risk too. Once you take risks regularly, then it becomes easier to manage. Read more>>

Megan DeCicco | Helping Small Businesses Do Big Things

I like to think of every risk as really an opportunity to take something amazing and make it my own. There’s a great quote by John A. Shedd that I think applies here; “A ship in harbor is safe, but that is not what ships are built for.” Sometimes something can look like a risk, but is really an opportunity to believe in yourself and your abilities. You have to stop and ask yourself honestly: is it the risk itself that gives me pause – or is the belief that I can do it is missing? Read more>>

Scotty Lindsey | Wellness Coach/Entrepreneur

When the word (Risk) cross my mind, I always think reward. When most people think about the word Risk, they think run. What people fail to understand is, life is a risk, marriage is a risk, jobs are a risk etc. Everything in life is a risk. If i’m going to live the way I expect to live in this thing called life, I must be willing to take risks. I didn’t won’t to be ordinary, I wanted to be extraordinary. The only difference between the two is, one is willing to go the extra mile to live the way most could only dream about. Read more>>

Mel Branker | Entrepreneur & Business Owner

“There’s no reward without work, no victory without effort, no battle won without risk.” Our lives are the accumulation of a series of choices that we make; no choice, no decision is ever “easy.” It’s impossible to grow in a space that is comfortable; for someone like myself, stagnancy kills my creative growth process. I pray before every decision I make, and have full confidence that what is for me will be for me, as cliche as it sounds. Read more>>

Jose Dimas | Entrepreneur

I feel like risk is a huge factor in one’s success when it comes to starting your own business or brand. You have to be able to get out of your comfort zone in order to be able to achieve results in what you are trying to do. You can’t expect your business to get started on its own or for it to grow without you putting in any work. I took a risk when I decided to try out the business I started, I invested all the money I had to my name which at the time was about $600 into 2 small machines to be able to start making vinyl t-shirts, without knowing if I was able to make a living out of this or even get the money I invested back. Read more>>

Stacey Sappington | Broker Owner of Red Shoe Realty

In life AND in business, you’ve got to take some risks! But, I think you have to be calculated. You can’t just jump off the edge of the canyon. Pack the parachute. Plan. Research. Learn always. Make connections. Find a mentor. But once you’ve prepared yourself, JUMP! We have one life to live and we have this assumption that we will have tomorrow to live our lives to it’s fullest. But today is the most important day. We all seem to be in our own way. Read more>>

Adrienne Carrington | Self-published poet

Risk is something that is terrifying, but gratifying. I’ve written poetry my whole life, but if I had never took a risk to share my work with peers and teachers, I would’ve never gotten the encouragement to share my poetry to all. If I had never taken the risk to create a book of poetry, I wouldn’t have found the ability to self-publish. If I had never taken the risk to self-publish my books, I would have never known there were people who wanted and needed to read my poems. Read more>>