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.

Caitlin Alexander | Doctor of Physical Therapy & Biomechanics Specialist

The reason why I am where I am today is because of the risks I’ve taken. From moving to New York City after college with no job, to making a complete career change in my mid-20s, to qualifying for my professional card in triathlon, the risks I’ve taken have shaped who I am today. But they haven’t been without a lot of hard work and heartache. I’ve held jobs that I’ve hated. And I quit them to find something more fulfilling. Notoriously, I’ve chosen the most difficult paths, the ones that require the most work. I don’t know what it is about it, but challenges are incredibly motivating for me. Great things have never come from comfort zones. I thrive outside of my comfort zone. I think that’s why I gravitate towards Ironman-distance triathlons. Read more>>

Rebecca Baack | Owner, Mecha Fitness; Co-Owner Level 4 Yoga (a franchise of CorePower Yoga), Co-Owner Ape Co Movement School

Risk and the fears associated with taking risks are just as difficult for me as for anyone. It was a huge risk for me to open my first fitness concept, a CorePower Yoga franchise back in 2006 when I had no cash savings at all. I had to take out a loan against my condo and take on a lot of credit card debt and just barely pulled it off. There were many sleepless nights and a lot of penny pinching those first few years. Read more>>

Ashley Onley | Mountaineer & Content Creator

Risk is something you have to learn. Taking risks is scary – we’re always taught not to do things that seem too “risky”. I had always loved photography, but always worked conventional jobs. When I took my last semester of college to study abroad, I realized that decision, dropping my life to take off for another country for half a year, was quite the risk. I didn’t know what would be waiting for me when I got back – and it was probably the best decision I have ever made for myself. So I started wondering: what’s the worst that could happen if I just did that thing I wanted to do, took the risk and chased what made me happy? Read more>>

Melissa Estepp | Owner of Premier Events By Melissa

I think risk is definitely apart of my job description as an owner of a business! I would say that it is a risk to start your own business . It is a risk to step out and start selling a product or service that your giving your all to. There are tons of risks in starting your own business. Especially for me this last year there has been even greater risk with my business doubling in size, to then take the necessary steps of hiring staff to maintain the next levels of growth. Read more>>

Darrah Reese | Photographer and Sound Designer

In my opinion, risk taking can be a controversial topic. It’s a trial and error type of thing and I believe taking risks requires a large amount of determination. It seems that when we’re young, we’re encouraged to take risks and the older we get, we become discouraged. After all, you have to be prepared for any consequences that come after whether it be positive or negative. In my experience, Read more>>

Michael Belochi | Owner, BOCO Cider

Many call me a risk taker and/or entrepreneur, but I don’t look at it that way. I just don’t want to be boring or bored. I’ve been just clever enough to get off the paycheck hamster wheel and allow myself the luxury of trying to build a start-up from scratch while not mortgaging the house or putting my family at risk. With the loving support of my wife, I now have the pleasure of working 60 hours a week towards an unknown future learning many hard lessons on the way without a single boring moment. Read more>>

Shannon Jackson | Bar Manager ( Black Bear Distillery) Admin Assistant/Guest Instructor ( Paragon Culinary School), & Director ( Colorado Springs Bartenders Guild)

Ultimately everything you do in life is taking a risk because you don’t know the outcome, but to be called ‘ Risky” is different. Risky is defined as the possibility of failure or loss. In my personal life, I take risks, but would not be called or considered Risky. As for my career, I have been what is considered risky. I believe in the hospitality world you have to be a little risky to be successful or make an impact. Over the last few years, some might consider me a little too risky. Read more>>

Christina Dyer | Professional Entrepreneur

For me risk taking corelates to curiosity and being receptive to trying new things in my business as much as my personal development. It is most definitely framed around a growth mindset and how we view perceived challenges before we take the first step. This has been a consistent, life-long attribute of mine, to always be reaching and stretching into new territories and never settling for stagnation. There is no going backwards, only forward momentum. Of course, there are instances throughout life that can and will deter the acceleration of progress. Read more>>

Sandy Priester | Executive Director of LifeSpark Cancer Resources

To some looking in on the outside, it may look like I have taken big risks. I am working in a field that has been dismissed by many as not real. But from my perspective, I have always known that energy therapies (Reiki and Healing Touch) are wonderful healing tools with incredible potential and that someday, they would be accepted as part of mainstream healthcare. Read more>>

Hannah Trim | Owner, Sew Alpine

My professional background is in Outdoor Education and Mountain Guiding, where I routinely assessed very tangible and often life-or-death risks for myself and my team. This experience has proved invaluable in my business venture and I’m very grateful to have familiar frameworks to lean on for analyzing risks. Working in the mountains always gave me great perspective and helped me focus my priorities. In the rest of life, I think we live in a relatively risk-averse culture. Read more>>

Tiffany Brizendine | Jewelry Blogger & Crisis/Emergency Manager

When I started Inspired Antiquity, I was unemployed and suffering from depression related to a career-ending injury that I went through as a search and recovery canine handler. For me, it was a dark time but I needed something to hold onto that would focus another side of brain – the creative side. Risk taking is much easier when you feel there is nothing more that you can loose. And, that is where I was at. As my life has changed and evolved, so has Inspired Antiquity and with that so too has how I view risk. Read more>>

Sashi Gerzon-Rose, MA, LPC | Psychotherapist, Coach, Yoga + Meditation Instructor

I think everything that truly matters comes with risk. To love someone or something- be it a person, animal, idea, or the natural world- means risking the devastation and heartbreak of loss. To pursue something that actually matters, like being vulnerable in relationship or pursuing a meaningful career means taking a risk. To be nakedly honest can be risky. It means expressing what is, rather than attempting to present the safe or approved of sentiment. Read more>>

Sonia Jumaquio | Certified Meditation Teacher & Etsy Seller

I’ll start by saying that I used to live in fear. Fear of the future and the unknown. I was doing a prep session for a Lessons Learned for Vets Podcast, and as I’m talking to the host, we came to the realization, that I dive head first into every aspect of my life. I served in the military for 12 years, and the decision to leave was not one I took lightly. As a single mother, being active duty did not align with me being a more present parent. I put everything I had learned from the military as I transitioned, and that was still not enough. Read more>>

April Waugh | Engineer, Runner, Model, Mental Illness Warrior

It used to be that when left alone to my devices, I would always gravitate to being extremely risk-averse. Mental illness definitely changed that for me. Coming so close to suicide was both terrifying and (later on) emboldening. When you get to that brink you realize just how bad things can get… and yet I still survived. Imagine the amazing things I can do now that I’ve experienced the “worst case scenario?” Read more>>

Stefan Nicolae | Performer/Song writer

Overall, everything about my musical journey has been and will be a risk, from what I write, to shows I perform to the people I work with. However when it comes to my team, that’s a risk I’m happy I took because they never let me down. Read more>>

Sharon Glassman | Designer/Songwriter, Smile Songs musical greeting cards and gifts

As an introvert, I’m a deep listener. Listening to what folks say – and don’t – has led me to take a lot of risks in my life and career. Because I pick up on the things folks are craving. And want to be of service, to address that problem, to deliver that thing. So far, so awesome, right? But there’s thing challenge: I tend create things a few years before they become trendy to a larger population. Read more>>