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.

Chris Hjerling | Business Projects. Speaker. Thinker. Creator.

There is a risk in everything. Risk is an unavoidable an inherent part of life. Every new and fulfilling adventure, relationship, business, and learned skill requires thoughts and actions in an unfamiliar territory. All we can do is decide what level of risk we are willing to face to achieve, create, or experience those new and fulfilling things. We have to be willing to risk being uncomfortable. Risk to be untalented. Risk being hurt. Risk failure. Read more>>

Jesse Biondi | Musician/Producer/CEO of Creative Global Entertainment

When you are a creative, risk taking is all you ever do. Is my song ready to be released? Can I make a sustainable income doing creative work? Will people actually take the time to engage with the content that I’m creating? These are just a few of the questions that our inner critic will shout into our ears as we are getting ready to do something that involves risk. My life has been defined by the risks that I was willing to take. I recently left a stable job of teaching to move to a new state and pursue a more creative endeavor. When I met my wife, she lived in Atlanta, GA while I was living in Spartanburg, SC. Read more>>

Ana Gonzalez | Licensed Esthetician

When it comes to risk taking I usually doubt and question my self where? or when? or how to start? I start thinking of what to eliminate in order to be a step ahead to make my dream into reality. It all has to start somewhere within your self. I was feeling helpless for not being able to provide enough for my family I knew I wanted something better for us. I was ready for the challenges and acknowledging that slow growth was going to be part of the process. Ive gone through so many emotions pushing my self after every bump on the road but at the end of the day I ask my self, if my family and I didn’t go thru this risk together would we be here where I am now? Read more>>

Breonna Vann | Intuitive Reiki Practitioner , Dancer/Choreographer , Oracle Reader

I think about taking risk, as a leap of faith into the unknown. You won’t know the full truth and outcome until you dive in. A lot of my life , I have taken multiple risks and not once have I ever regretted it. Because I know that even if it does not work out, at least I took a chance and tried with everything in me. I wouldn’t have known that til I dove in, and that is why I will always do it. I crave knowledge and wisdom from all vibrations of life. Taking a risk brings expansion into your life. If I never took a chance on myself and my reiki business, I would never know just how truly beautiful life could be in this specific way. Read more>>

Rachel Pizzolato | Model…Maker…Mythbuster

When we think about taking risks, we usually associate risk with possible failure and look at it as a bad thing. However, failure should be looked at as a good outcome. If we go into a project with an open mind, it allows us to analyze why something failed, make changes, and try again – That is how we learn! As a Mythbuster, one of our main themes is, “Failure is always an option!” The unknown can be a very scary thing, and fear of the unknown and failure tend to prevent us from reaching our goals and fulfilling our dreams. Read more>>

Regina Leigh | Tarot & Divination Practitioner

Taking risks can be a controversial topic to many. Some like to play it safe while others enjoy a good gamble. I am an advocate for “calculated” risks, healthy risks and strategic risks. Tarot has helped me lay all my cards on the table, asses all the players, situations and potential outcomes. This allows one to wisley evaluate their situation from a different perspective and encourages creative and integrative decision making. Read more>>

Xavier Ray | Youtuber and Videographer.

Risk taking is something I’ve grown accustomed to. You can’t start a new venture or a business without taking a few risks. Nothing in this life is guaranteed, so if you want to try something and it doesn’t hurt anyone, do it.
You either succeed or fail. Nothing wrong with failure. It’s a teaching moment and sometimes it’s the best learning experience you can ask for.
With my career, everything I’ve done was risk taking. Making videos? There’s a risk of being judged or a video comes out ugly and unpresentable. Read more>>

Monique Beskin | Reiki Master Practitioner Teacher – Sound Healer – Yoga Teacher

Until recent years, risk was something we had always shied away from. Raising a young family we tried to keep risk to a minimum and focus more so on security and stability, even if that meant we were not happy with what we were doing. We’ve both been working a regular 9-5 in corporate America most of our adult lives and I tried a few different multi-level marketing gigs that interested me, but ultimately there was no passion behind those ventures and in time they fizzled, and we pushed on, playing it “safe”. Read more>>

Susanna Powell | Real Estate Professional

I think risk taking is an intrinsic part of life. Thirty plus years ago I took a major risk and came to Mexico at age 22 with my sister to open a restaurant and bar in Cabo San Lucas Mexico. Owning and operating this business while raising a family since 1989 is what has given me a leg up when I began real estate. I have seen Cabo change from A one stop light town to the leading luxury destination in Mexico. Read more>>

Patty Pancak3s | Artist

It may sound dramatic, but I think of risk as a matter of life or death: will this decision lead me down a path that will eventually kill me? It makes things incredibly black and white for me. Within this perspective, risks are judged on whether or not it’ll affect my cost of living (physically and mentally). Sure, I might be rejected, or I make mistakes in my creativity, or even just making a fool of myself in general; but I won’t die from any of these things. Rather, these are seen as opportunities with this perspective; and due to the journey it takes to get to that point in time: can be that much more rewarding once achieved. Read more>>

Empress Joshett | Tarot Reader. High Priestess, Spirit Medium , Root worker and spiritual advisor

Risk is mandatory on the road to greatness and success. Those who lead are the ones who are willing to take the risk others are not. There is a understanding that it is not about failure as you cannot fail without succeeding first, it is about discipline, perseverance, passion and drive. Risk is inevitably what helped me grow and see things with great clarity. I had to be willing to walk into the dark with a deep inner knowing that at the end of it I was going to end up at the destination I was reaching for. Read more>>

Heath Alan Farmer | Guitarist, Vocalist, Producer

I feel like the very idea of becoming a musician is a risk unto itself. When you pick up an instrument for the first time, you are coming to terms with the fact that you are holding an object that you know virtually nothing about, but you know that it can be mastered because you’ve seen a select group of other people do it. So right away the idea sinks it: just because I may not know how to make this thing sound good yet, it doesn’t mean that I won’t be able to one day if I put in some hard work. But you have to visualize yourself at that destination in order to know how to take your first step. Read more>>

Markeisha Brown | Digital Creator

You have to take them. Taking risks in life can open doors you’ve never imagined. Yes, taking risks means stepping into the unknown and possible failure. However, not doing so also means being stationary in life. A little over five years ago, I had to decide whether to accept a job offer in California or remain in Philadelphia and continue my job search. Some people would say that’s an easy decision, but the job offer came with a low salary and no help with moving expenses. Not to mention, I would have to move three thousand miles away from my family and friends. I would also have to make this move in under two weeks. Read more>>

Andrea Wild Botero | Entrepreneur

If you don’t risk, you don’t win. I learned over the years that the faster I test something, the faster I can see whether something is worth pursuing. On a scale of 1 to 10 in terms of how much risk I take I’d say I’m an 8. I enjoy the challenge of moving around, dominating a new city, having a new job, attempting new things, launching projects, never feeling 100% comfortable. I think the most beautiful thing about Pickled Pulp is that it didn’t start as a business. It started as a means of entertaining my 18 month-old son at the time during lockdown. Read more>>

Isaac Guerra | The Gravities Collaboration & Music Director

Following that innate feeling of uneasiness or the unknown has always been something that has fueled my career. Leading with that gut feeling has opened so many doors and opportunities not only for me but for The Gravities crew as well. Falling in love with the process of risk taking has made me a better person and a more confident Leader that I could ever dream of being. Dive into your goals and dreams, cause sure as heck no one else can do it for you. Read more>>

William Lita | Professional Auto Detailer

Overall starting a business and being part of the process of becoming a professional in auto detailing has been a risk itself. The life lessons, experiences, and obstacles through life and my career have led me to not settle down and to explore out of my comfort zone. One of the main risks that I had to take was to quit my job. With the intent of pursuing a career that involved auto detailing. Without this risk, I wouldn’t taste success nor gain knowledge of this craft. With certainty, I can say risk-taking has played a huge role in my growth not only in creating but as well as managing a business of my own. Read more>>