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.

Christen/Audrey Griffis/Herrera | (Christen G.) Wedding Hair Stylist /(Audrey H.) Wedding Hair and Makeup Artist

Audrey: “Risks are scary, but without risk there is no reward. I would not be Co-owner of Bride Meets Glam without taking that risk. Risks have played a huge part in my career, but I owe my success to those risks and I’ve met many great people who have helped me along my career. Overcoming your fear to do something or meet someone new can open and has opened many doors for my career. I think it’s always good to take those chances and see where your journey can take you. The alternative is scarier to me: being complacent and never learning or doing anything better. I’d much rather take the risk!” Read more>>

Seth Hansard | Immigration Lawyer focused on Growth

I try to gauge how much time, money, and energy I risk on any project. I adjust my expectations accordingly. In my first year, I guarded my money more carefully than my time. That strategy was necessary, but I passed up on some good opportunities as a result. That approach worked for me because I wasn’t trying to knock the industry on its rear – I was trying to build a foundation. Read more>>

James Barrett | Songwriter and barista

As long as I could remember I have had one goal in life: to be able to write my own songs and play them for a living. The idea alone would give my teachers a lot of stress early on. I knew from the beginning that I never wanted to go to college. To me being stuck in another place for four years after feeling stuck in public school didn’t make sense to me when I could be driving anywhere I want to play a show. So after I graduated high school I got a job and started my life as an actual person in the real world. It was terrible and a huge reality check but never once did I think I made the wrong choice. Read more>>

Ashley Joyner | Owner and Creative Director of Cinched Collections

I believe that becoming an entrepreneur is the biggest act of faith. You have to believe in your product or service enough to bring it to life and see the process through. Entrepreneurship is a journey full of highs and lows which requires endurance and perseverance. Starting Cinched Collections has been one of the most significant risks I’ve ever taken. Developing a clothing line from the ground up requires a lot of upfront capital and brand awareness, but with the brand strategies I have put into place Cinched Collections is set to make a strong return on investment in the near future. It’s a major risk but one that I would never regret. Read more>>

Amia Jackson | Vistionary, Author, Motivational Speaker and Artist

Risks play a major role in my life and career. I understand the importance of risk. Risk helps me truly discover who Amia Jackson is. If you don’t allow yourself to try new ideas and take risks, there’s a chance you will stay stagnant in life. Risk allows you to gain more faith in yourself and your beliefs. Faith often leads to confidence. Having confidence in yourself and your dreams is one of the most important traits a person can develop. Read more>>

Glenn Gordon | Veteran, musician, songwriter, singer, Inventor

I truly believe if you never take a risk in life, you’re not living and enjoying life to it’s fullest potential. To me that is not living life that is surviving life. I have been a risk taker all my life because I wanted the respect of my older brothers. When one of my brothers was drafted for Vietnam in 1966 i volunteered in 1973 simply because I wanted to show I was just as much man as he was and that was a very big risk to take at that time. I learned alot when I takes risk in life and I grow with a much better understanding of my life and my purpose of being here. Read more>>

Kaleia Hardeman | CEO/Founder of Pure Magic Aesthetics & The Post-Op Queen

I do consider myself a risk taker! Getting into the beauty industry was a big risk. No one in my immediate family was in the beauty industry nor at the time running their own business so me taking that leap of faith (risk) was big! When I told my family that I was going to take a lash class (I had to borrow some of the money from my Grandma Minnie which I paid her back in full) and eventually would quite my job, some of them laughed, said I was crazy but that didn’t deter me. It was my vision, not theirs so I didn’t expect them to understand! I was thankful to my Mom who was by my side and encouraged me from day one! I feel that taking risks are all a part of life and growing. Read more>>

Lakisha Patterson | Visionary, Creative Director, Motivational Speaker, Healer

Risk.. I think is one of the main reasons many of us never even Try, Or the reason we just put a toe in the water knowing damn well all we want to do is learn to swim. I can openly say that risk that has been my biggest bully these past few years, especially when it came to starting my business. There were so many risks, the biggest seeming to be whether or not to attach my face to my brand… it’s crazy because for whatever reason, Read more>>

Kevin Johnson | Aka KJ Da Assassin engineer , producer and writer

No risk no reward , entrepreneurship is a risk ! Your business plan to the first partnership is a risk ! As a creative there’s no rules the creation it self is a risk ! Read more>>

Amarachi Ibe | Master Reiki Practitioner & Self Development Coach

Prior to who I am now, I was a stranger to risk taking. I typically played it safe until it got to a point where I realized playing it safe was actually holding me back. I was limiting myself because I believed that there were only a few acceptable career or life paths. Although I was passionate about health, I struggled with how people may not take me or my craft seriously since I did not have a medical or nursing degree. If I had become a MD, I know I would’ve received more praise and been less fearful. However, if I had become an MD I would have been dishonoring myself and relying on external validation to keep me afloat. Read more>>

Brandon Lee | Owner of Smell Guddz Fragrance Oilz & More

I believe proper research and risk are key to entreprenuership and staying ahead of the curve in business. Taking risk has played a major role in the start of my business as well as throughout my journey of expanding business as well. From investing in myself to trying out new products or setting up for vending events and more. I can say all havent been successful risk but the lessons i learned have taught me how to come back and make better calculated risk… Read more>>