Legend holds that Cornelius Vanderbilt had built a massive fortune in the steamboat shipping industry, but then realized the railroads were the way of the future and invested almost his entire net worth into railroads. The gamble paid off and made Vanderbilt one of the wealthiest entrepreneurs ever. But risks are inherently…risky. How do you think about risk and how has it affected your life and career? Some of our community favorites share their perspective below.

Kim Grennan | Founder & CEO of Axle Eight

I have always been willing to take on a little more risk than say the average person. But I am an overthinker. Something that may seem like a big risk for most people is usually something that I have spent countless hours on evaluating risk and modeling out scenarios of personal and financial impact. I consider myself a fast learner and someone who will dive deep into understanding a topic I have interest in, but it took me 3 years to get the individual marketing knowledge and foundation that I thought was key enough to build an agency. So I went from doing M&A and venture capital to owning my own marketing agency with no “formal” training on the subject in a matter of 3 years. And to many, they thought I was taking a huge risk and that I was crazy for doing something COMPLETELY different than what my education and career experience had been up until that point. I had to learn all new skillsets and build the trust through positive results to the clients I was bringing on, and ultimately it paid off. I believe that you create your own luck. Read more>>

Tracy | Danielle Rouviere | Travel Advisor

Before I ventured out on my own, I had an office job as a travel agent. I was making a salary and it provided me with the stability I needed for my three young children. I had already been in the business for 16 years, so I felt like I had a good pulse on the industry. I was spending a large amount of my salary on childcare, so I decided it made sense to take the risk and start my own travel business from home. I had a few established clients that I was able to take with me, but it took around a year before I felt comfortable, and a few years before I really felt I had “made it”. I faced plenty of rejection and the industry was not always stable. I think with any small business you must keep in mind that there are going to be highs and lows. I had plenty! But I always tried to be prepared as best I could, even when business was good, I knew it was only a matter of time until a lull came. Read more>>

Mikayla Cunningham | Artist & Poet

My art is a direct reflection of who I am. To put my innermost thoughts and feelings on display for the judgment and interpretation of random strangers is always a scary thing, especially when the subject matter is so personal. As a queer artist who hasn’t always been out, it used to be a juggling act deciding which pieces I could post without “outing” myself and which were safe. I think much of that internal struggle is reflected in my artwork. I’ve identified as bisexual for a while now, but only in the past few years have I finally felt comfortable revealing some of my more queer-coded artwork, and just this past year came out to my family. I’m happy to finally be in a place where I can be my authentic self, despite the risk of harassment and hate. Read more>>

Izzy Salazar | Founder of Shameless Burger & Entrepreneur

I think that taking risks often leads to prosperous outcomes. Something I have learned is that when you put yourself into challenging situations, situations that require you to grow and feel uncomfortable, those moments are when really great things start to happen! For example, we decided to start Shameless Burger right in the middle of COVID. That presented many challenges but, it forced us to adapt and to know with certainty we were on to something special. Read more>>

Mary Fisher | Author and DJ

“My dear, you are here, now but for onc, let yourself get lost, let your heart swell & explode. Want to see the red of you love stained on your clothes. We are here, now, but once, let yourself love unashamed. Let yourself lose, win, and risk loss again, then emerge, new, & loving again.” -Mary K Fisher I use to be on a road with no destination, I was just driving with hope that I would find a place with peace, safety, and growth. I left everything packed in the back of my Dodge Caliber car to go up the coast of California. I didn’t know what I was looking for, but i believe it was more of a feeling of self discovery and new life I was pursing. A new environment that changed my perspective and with that, I found the self, through healing and understanding, while encountering the patience behind what time does for one. Without movement, there was only moss growing on the rolling stone. In order to avoid stagnancy in my life, I personally believe in movement and networking. Shaking new hands and looking into strangers eyes. Take the risk, and say yes more, while protecting your boundaries. Read more>>

Tina Arvizu | Aesthetics Educator & Aesthetician

A risk to me is doing something that will stretch you out of your comfort zone, taking risks gives us a chance to explore new opportunities and experience failure as well as growth. When I think about life I can’t help to view it as one big risk. As a child I took risks daily but without fear because I hadn’t grasped the concept of failure yet, and there was always someone around to catch me if I fell. As an adult taking a risk meant something different to me, I had questions such as, Would I fail and more importantly, how would it affect my daughters? I truly believe without risks we aren’t stretched out of our comfort zone, we miss opportunity for growth even failure which can be a blessing. It seems as though many risks aren’t taken out of fear, fear of failure, and fear of judgement from others. Taking risks have definitely played a role in both my life and career. I wouldn’t be where I am today had I not taken risks. I have three major risks I have taken in my life and career. Read more>>

Kristina Parrish | Screen Printer

Part of success in any area of life (Not just business) requires some form of comfort in the ability to take on a risk & be fully prepared to deal with failure. In fact, its the failures that that either break us or make us. We have a choice when faced with failure: Learn & grow and try again or try something new & keep going after it, or give up, quit, & throw in the towel. Starting a screen printing business was a leap of faith, a risk, & a big financial gamble. However, it was well thought out & weighed. The risk taking continues even now. There were more times than we can count of moments where I wanted to pull out my hair and have a complete & utter emotional meltdown. And I actually did! Very briefly! After some rest, we would take a few steps back and reroute in a similar but different direction that, ultimately, led us to a solution. It’s these continued risks that made our business better, stronger, stealthy, & in turn, successful. And guess what? More of these steps back and rerouting are in our foreseeable future. Read more>>