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.

Zeinab Ghais | Lifestyle Designer

I think being a risk taker has made me the person I am today. Ever since I was a child, my mother said I had no fear. We moved from the US to Africa when I was seven, which wasn’t a choice but a huge change. After my parents divorced, my mother began to travel with her job and we would start over every year or twice a year at a new school. This limited my fear of change because it was constant in my life. My mother always instilled in us that taking a chance is an adventure. When you go into it with excitement then you lose the fear. During college I took some risks that may not have been the smartest choices, but I lived through it and learned from my mistakes. When internet dating became popular, I took a chance and met some good and not so good people, but it made me realize what I wanted in my life partner. Read more>>

Scott Duffy | Founder & Business Strategist

I used to think the most important job of any entrepreneur had something to do with leadership, management, team building, or some other functional skill. But what I’ve learned is the most important job of every business owner has “nothing to do with business”. Instead, it’s LEARNING HOW TO PROTECT YOURSELF. So if things don’t go as planned, take longer than planned, or go sideways, you can recover and bounce right back. How do you do it? By following these 3 steps to mitigate your risk every step of the way. 1. Separate your business and personal bank accounts: This is such an important place to start. Decide how much you are willing to risk in this venture. Then take that capital and put it into a separate business checking account (not just part of it, all of it). If that means you have to sell an asset, cash in on a retirement policy, redirect your auto pay, then do it. Read more>>

Jessica Richmond (JRich) | Writer, Actor & Producer

Quite frankly, I don’t know how not to take a risk. At 13, I auditioned for / was cast in my first paid theater performance gig. At 18, I moved from Los Angeles to Boston for conservatory training. At 21, I managed an independent band for 3 album releases & 3 national tours. At 25, I launched a summer residency comedy show in Los Angeles. At 28, I created live & digital content for Downtown Los Angeles’s growing arts district. At 30, I switched to production to immerse myself in set life. At 33, I produced an original short form narrative series ( – and proposed to my fiance). At 35, I’m releasing my book “Get Off: The Patriarchy” (out 2021). Read more>>

Kohle Heimlich | Entrepreneur & Corvette Guru

Risk and the ability to deal with risk are major factors in the sucess of any entrepreneur. Without Risk you have no sucess. You must risk your current comfort today to eventually have an elevated level of comfort in the future. Any true entrepreneur has had to deal with Risk head on. Its one of the key factors that must be considered when starting a business and then considered again and again every time you want to grow your business. What are you willing to loose, to trade in order to be more successful? Who are you willing to become to get to your goals? What are you willing to go through and persevere through to get to your goals? For most business owners risk is often tied directly to Finances and in short its often looked at as gambling but an educated, calculated gamble where your not putting your bet on the black jack table, Roulette wheel or a horse but instead your putting your money on yourself for the win. Read more>>

Jorge G. Camarena | Film Director

Risk has always been a fundamental part of my career. I constantly search for ways to get out of my comfort zone in order to keep learning and grow. The fear involved when taking risks is something that pushes me to stay sharp and focused. I recently left my commercial and music video director career in Mexico in order to get a Directing MFA at the American Film Institute. It was a tough decision, but I felt it was a risk worth taking due to the fact that I wanted to transition into narrative filmmaking. It has been a great experience so far and one of the best decisions I’ve ever made. Risk taking has also played major role in each film, music video or project that I’ve made because opportunities to enhance the concepts usually arise from these circumstances. Allowing me to see alternatives that I wouldn’t consider otherwise. Read more>>

Anna Azarov | Conceptual Portrait & Music Photographer

I think risk is an inherent part of life and the creative process (although I must admit that I did not always live by that philosophy). When I was growing up, pragmatism was encouraged in my family. My family and I emigrated from Russia when I was 8 years old and my parents worked very hard to rebuild their lives in the US. Although I always loved art and photography, the overall perspective was that you had to build a career that can give you stability in life. So I did. I went to college and studied International Politics, while always maintaining my love and study of photography. It wasn’t until I experienced real loss in my family, that I realized life is way too short not to do what you love. What followed was a whole lot of risks – I quit my job, moved to another country to study photography, came back to NYC and began building a career in photography from scratch. Read more>>

Kirby Mekler | Food Photographer & Stylist

I’ve never been big on risk. I’d spent my entire adult life chasing fulfillment in various “safe” jobs. Needless to say, none of them did it for me. When I found myself ready to start a family, I realized I couldn’t keep that up. I didn’t want my kids to grow up with a mom who was miserable, and perhaps more importantly, I didn’t want to be miserable. So I decided it was time to take a risk on a career I was actually passionate and excited about. Despite the inherent risk of pursuing self-employment in a creative field, however, I inched my way towards this change in the least risky capacity possible. I kept my day job while hustling off the clock. I wanted to retain some amount of control over the level of risk I had to take. Eventually I’ll have to up the ante, but it was helpful to me to have some financial stability while laying the groundwork for my business. Read more>>

Charley Izabella King | Wedding and Event Planner & Designer

I have always taken risks in my career and my life . I have never been the 9 to 5 girl with a steady paycheck and a 401 k being paid into every week. I wish I could be like that, but my life has been about following my dreams and making them a reality. The pro’s of that, is that I feel like I have never worked a day in my life, as I have loved every job I have ever had, but of course the cons are the risks of stability. Thankfully all the risks I took paid off! It was a risk at 16 years old to leave school and turn down a place at a theatre school because I wanted to see if I could get a West End show in London .Two weeks after leaving school, I got into 42nd Street the musical at the iconic Theatre Royal, Drury Lane in London. I would stay in a show for a year and then move on, taking more risks, sometimes leaving a show when I didn’t have another one to go too, but the biggest risk came when we decided to move to Los Angeles in 2000 to have an adventure. Read more>>

Carrie Davich | Small Business Owner

This is an intriguing question to me because I was a painfully shy kid that took no risks whatsoever; I barely left the house other than going to school. I was a very organized, rule follower that gravitated to friends that pushed me outside of my comfort zone. As the years went on my shyness fell away and I became braver and more willing to go after what I wanted and recognize opportunities as they presented themselves. My first big risk was walking away from a stable job to start a small clothing company with a friend in my mid 20’s; we grew to be represented in showrooms all across the country. I continued with this company until I had a second child and decided to stay home and which turned into raising 3 kids. As these kids grew and became more and more independent I suddenly found myself with a lot of time on my hands and felt the pull to try something new. Read more>>

Rock Jacobs | Writer, Director & Producer

Risk Taking – this is the most important factor in becoming successful as an entrepreneur, soloprenuer, director, writer, anyone who is in the driver seat or wants to be in control of their own destiny has to be willing to take risks. I put it all on the line daily to achieve the results I want. There are massive wins at times, there are also times in which you don’t win, but you live to fight another day. If you are not willing to take risks you will never jump to the next level. You have to be willing to fail and willing to try again, not only in your career but in life. Read more>>

Sarah Sohn | Business Owner & Esthetician

I think risk is an important factor to success. When I started my business it was probably the biggest risk I took on in my life. In the beginning, I used all of my savings, took out a loan for beauty school, and every dollar I earned was being reinvested back into my business. Before I invested my savings, I was under the impression I had a backup source of income just in case I wasn’t any good doing eyelash extensions, but it fell through. So when that happened, I told myself “I have no choice but to be great” You have to release a bit of vulnerability and believe you got this. Once I started seeing the demand and appreciation of my work, I became more confident in myself and more confident in taking on bigger risks. However, over the years I’ve learned to never risk more than what I am willing to lose. Read more>>

Courtney Casgraux | Entrepreneur

I think NOT taking risk in life is wayyyy more risky than what society or the conventional crowed looks on as “ Risky “ For young creatives, entrepreneurs, future entrepreneurs, or anyone rather that’s too scared, imitated or are busy comparing; measuring the difference between what they have to offer vs someone else or “ has been done “ to understand all things tangible, all Technology, Art, Film, Brand, everything we use and value was once a persons thought and what followed was creation – then risk. In my personal life and even career I’m pulled into all my projects through my heart, my heart runs my life which is shortly followed by risk. My heart together with risk has gotten me where I’m today. So take more risk, you’ll be surprised by the adventures that follow. Read more>>

Jill & Stanley

We create stuff for a living, so from that standpoint, it is ALL a risk. As independent, freelance, creative folks there are some signposts and industry standards to follow along the way but other than that, it is all risk, chance, luck. Did I mention risk? I don’t think we have ever looked at life or our career choices through the lens of risk. We don’t see it that way. We explore new ideas, experiment, collaborate to meet opportunity. Everything that we have ever accomplished both personally and professionally has been a series of various risks. Our mantra: “If Your Dreams Don’t Scare You, They’re Not Big Enough.” The element of the unknown always exists in life, so why not embrace it and take a risk? You never know what you might discover on the other side. Read more>>

Terrie Huberman | Intuitive Coach & Energy Healer

What risk taking does is change up your energy. If your energy is the same or stagnant there’s no room for something NEW & EXCITING to happen to you. So when you take a risk, you’ve just created in your reality, a window for opportunity to show up for you. I personally understand the scary factor in risk taking. In September of 2017 I was let go from a day job and I decided to take a risk and not go back to the familiarity of a 9 to 5, taking my own business from part time to full time. It was financially and emotionally scary and I had no idea what to expect as an entrepreneur. And now because i took that risk, I am my own boss, all of the money I make goes to me (and not someone else), and I make my own schedule. It has given me a sense of freedom, which is one of my biggest values. Read more>>

Lori Zuker Briller | Co-Owner

To me, while “risk” is scary, it is also exciting! My whole current career was based on the notion of risk — because I risked it all on a gamble. Having spent many years in the film development world, I came to the conclusion that I was not passionate about what I was doing. However, I had no idea what I should be doing. A friend made an introduction and I was hired in a company similar to mine currently, where I learned the world of staffing — both in homes and in companies. I took a huge risk leaving the world of entertainment as I knew it. I took a chance that somehow I would still utilize the relationships I had made over the previous 5 years. I learned how to recruit, what it meant to interview people and get a sense of how matches were made in this line of work. A few years later, I had been told that Rachel, my now partner, was starting The Grapevine Agency. Read more>>

Andrea michaelson | Environmental & Interior Designer

risk taking for me meant going with my vision, instinct, and not letting what others think influence my aesthetic. when i do work for clients, my vision/ aesthetic is used as one of the filters for my client’s vision/aesthetic. Read more>>

Jaime Whitton | Tequila, Music & Artisanal Originator

I have 5 major risks factors or rules that I have applied to my life and career. 1. BE… PATIENCE It’s a long process! Nothing happens over night. Our team has decades of experience in the spirits industry, we built an expert team, and still took us three years to launch. 2. BE FLEXIBLE Building a brand is climbing a ladder, after each step there’s another – Being a creative, that’s the fun part. Sometimes we get stuck on an idea, but you’re going to be evolving all the time. Things change. And sometimes… it’s everyday. 3. YOU NEED EXPERTS It’s okay to not know things. Arm yourself with experts outside your wheelhouse. When your product is finish and ready for the world to see, make sure you’re equipped financially and have enough cushion for mistakes because things are always more expensive than you think. Read more>>