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.

Omar Davila | Co-Founder, Owner of Hope 4 Hip Hop, Brand Ambassador for Red Bull

I would like to think of myself as a calculated risk taker. I weigh out my options, analyze what the pros and cons are, factor in my experience and then decide if I will take the risk or not. One thing I learned very early on is that you cannot shy away from failure. Success typically takes risks, failure, and the ability to bounce back and learn from those failures. Taking risks has definitely put me into some uncomfortable and stressful situations. However these also gave me the opportunity to grow and mature both as a person and as a professional. Since I was a teenager I had people telling me what I couldn’t do, had I not taken any risks I wouldn’t be where I am today. Read more>>

Lucy Li | Visual Artist

I’ve come to realize that for me, living a creative life calls for a very intimate relationship with my fears. Taking risks naturally becomes an integral part of growing within my creative practice. There’s a lot that I’m afraid of — starting a new painting that could fail, experimenting with new ways of working, showing my work to others. But I see strength in admitting that, and being open to myself and others about my fears is what allows me to make space to overcome them. Read more>>

Sam Matthews | Artist, instructor, & entrepreneur

With both of my businesses, Art Across Borders and Propagate Studio, I have thought a lot about risk. With both of them I felt more angst at the thought of not taking a risk and going for it in terms of starting the businesses than I did fear of failing from taking that risk. While I am a very emotional and feelings based person I do think through the risks, best and worst case scenarios for different choices and can rationalize a reason behind the choices I make. Read more>>

Sergei Fish | Artist, Tattooer, Biker

Risk taking is an essential part of any success story, in my opinion. Courage to start and just a little luck are key factors in achieving goals. Taking risk will eliminate chances of you looking back and asking yourself “What if I tried and it worked out?” Even if you try and it does not work out, you will walk away with new knowledge and experience, that can help with your future projects. Fear of failure is normal, but only those stand out who overcome it. Read more>>

Carla Ross | Small business owner and maker of handcrafted goods

I have always jumped first and asked questions later. This can be detrimental but there is no adventure without risk. I never wanted to have a boring life so I made a pact to never do what was expected and always follow my heart. It got me into trouble a few times but that all led me to right here right now, and I couldn’t be happier. I’m from South Africa and I always wanted to expand my horizons. So, I lived in London for a bit and have been here in California for 10 years! I tried many different jobs, some because I needed to pay the bills and some because I wanted get them out my system. Read more>>

Kate Kerns | Kate Kerns Creative | Entrepreneur | Digital Marketing For Derm

I’m a risk taker as long it’s not a death-defying attempt at something. I have no desire to send myself over the edge to get a thrill, but where I take most of my calculated and uncalculated risks in my life has to do with making moves in my business, trying new things that I know will one way or another grow my brain, going for things I want, seeing ‘that’ end destination (aka goal) and taking a machete to clear the path to get there. Read more>>

Andrew Horn | Business Owner, National Sales Director, Entrepreneur

We think about risk probably a little differently than most others. To us, the risk of NOT moving forward, NOT saying yes to yourself, and NOT jumping wholeheartedly into your life is a bigger risk than attempting something new. If we hadn’t taken risks like changing jobs when we were already comfortable where we were, moving to California (in Alex’s case), taking positions with new/startup brands, etc., Read more>>

Julie Jenkins | Silversmith

I have always wanted to live a big, beautiful life full of adventure and I think taking risks is essential to an adventurous life. It takes a lot of blind faith to leap and wait for the net to appear but in my opinion, it’s always worth it. By taking the risk of opening my own small business, I have learned a lot about myself and what I can accomplish, as well as just how hard you have to work to be self employed. I began my adult life in the Rocky Mountains of Colorado after having moved from Chicagoland, Read more>>

Star Quinones | CPT/PN1 Nutrition Coach

The motto on my IG page is.. No risk, no reward. I started my page because I joined a challenge. That challenge was only supposed to help me stay accountable as I got back into shape after my baby. Had I not started that IG page, I would have never discovered powerlifting and the amazing people in that community. Had I not started lifting heavy, I would have never thought of competing… twice while pregnant. Although the delivery of my 3rd baby put a halt to competitive strength sports- it didn’t put out the fire to do more. Read more>>

Sarah Amenta | Owner of SoCal Weightlifting

Risk is relative. People have various levels of risk they are comfortable with and as far as I’m concerned, running a business is not risky at all. I know what I’m capable of and I know what I can achieve, which isn’t risky at all. Success is guaranteed when I put myself into the mix so I don’t view running my own business as risky at all. Read more>>

Cesar Torres | Digital Wallet App for Small Businesses

In the beginning, I don’t think I ever put too much thought into it. What ultimately changed the way my life would end up heading was my wife going through cancer. At the time of my wife’s illness, I was working for IBM. I was in my 10th year when going through the treatments and caring for my wife. Taking care of our twin boys was also challenging when going to these treatments and trying to manage home life. Soon after my wife’s last treatment, we discovered we were losing our home; this impacted me significantly.  Read more>>

Jerry Danielsen | Music Producer/composer and writer of words

For me, risk taking was necessary. In my 20’s I was woking at a job I didn’t like, and longed to get out of it, and into a career in music. Writing, performing and recording. Over time, I saved enough money to life for a few months, and started to also gain side work as a musician. I had gone to Sound master recording engineering school, and started my own home based studio. Read more>>