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.

Rachel Hubbard | Licensed Clinical Social Worker

When I think about risk, I think about the phrase “calculated risk.” In other words, how big is the risk, and what makes this risk worth it, if anything? For me, both these questions come back to values. Is taking this risk going to lead me closer to, or father away from, my core values. If I value things like contribution, genuineness, creativity, etc then will having that difficult conversation, or taking that big swing with an idea, or starting my own business bring me closer to these values? If the answer is yes, the risk is usually worth it. Read more>>

JAYETEEE | Photographer/Videographer & Entrepreneur

No risk, no reward! I’m a firm believer in taking calculated risks! You can never achieve optimal successful or even discover who you truly are, otherwise. Most people spend their whole lives inside of a comfort zone they’ve created based on personal experience and perception of the world, over time. I’ve always wanted so much more than the conventional American lifestyle.. trust me, I’ve tried it! I don’t want to work a regular 9-5, I don’t want to climb any corporate ladder. I want the freedom to be able to create! Read more>>

Stephanie Mier | Founder of Persephone’s Sanctuary

The truth of the matter is that life is a risk but something truly magical always happens when you face your fears and challenge yourself to step out of your comfort zone. You either learn a valuable life lesson or you get catapulted into success, either way you end up closer to achieving your goals. Overcoming my fear of failure and the unknown has given me the confidence to stop working towards someone else’s goals and begin working towards mine and the birth of Persephone’s Sanctuary. Read more>>

Jeff Dume | Business Consultant, Recruiter & Investor

Risk is essential for all opportunities in life. I wouldn’t be where I am today if I didn’t take a risk to push outside my comfort zone. The risk can be big or small, it just depends on what would be the outcome. Risk has allowed me to move 4 hours away from home to college and graduate. Risk allowed me to move halfway across the country to Houston with no friends or family. Without risk, I wouldn’t have made it past 30 miles radius of my hometown. It has allowed me to grow into myself, not on as a professional but as a man. Every day do something new, cause at the end of the day it will be a day you won’t get back. Read more>>

Vanessa Perry | Credit Expert

Becoming a full-time entrepreneur is one of the biggest risks that anyone can take. You must not only believe in your business, but also yourself and your values. As an entrepreneur, you risk everything for your business. In the beginning, you do not know if your business is going to survive. You have to put your personal credit on the line, any assets, along with your time. Working another job just to keep your business afloat is not uncommon for entrepreneurs. The first thing that people think when they hear entrepreneurs is freedom. It is in fact the exact opposite, you live to work. Read more>>

Dominique Vicedomine | Bartender and Owner of Bartenders The Art Show

Failure is not something to fear ever and taking risks is the only way to push yourself to grow and pile drive your goals. Any success I’ve found is due to facing my biggest fears, closing my eyes, and making the jump despite judgement and failure. Read more>>

Maria Estela Duarte | Online Business Entrepreneur

Getting ahead in your career means taking risks. There’s really not many ways around it. What’s important is that the risks you take are informed and that you have a clear vision of what you want, and why. Business isn’t always about playing it safe. A conservative approach can protect your business’s position, of course. But that’s not necessarily what matters most in the long run. Success requires taking risks and gambling a little along the way. Read more>>

Sandra Murray | Graphic designer / potter

I am risk averse. Rather than jump into the unknown with both feet, I tend to wait for the tide to reveal my opportunity. While I wait, I work on my craft— which is what I love. The opportunities will come. It seems they always do (for me) when the craft and commitment are there. Read more>>

Aye Baker Bizzy Bee | Songwriter, Recording Artist, Home Organizer

Taking risks is scary. But true success never came from being comfortable. You can’t fully discover yourself if you don’t push your own boundaries. What feels safe could hinder your purpose. I tried things the “normal” way until I realized nothing about me is normal. If you trap me in an office… you are confining a creative mind to a fixed process. It’s imprisonment for a steady check off someone else’s idea. But many make it fit, because it’s “normal”. Read more>>