Risk is the most common topic that comes up in our conversations with entrepreneurs and so each week we ask entrepreneurs to talk to us on the record about how they think about risk.

Van Curaza | Program Founder of Operation Surf

I realized I was afraid of success in my own life as much as I was worried about failure. Ultimately it came down to making a choice and deciding to do what felt right, to get out of my comfort level and out of self. I decided to no longer worry about whether I failed or succeeded but rather focused on each experience as a learning opportunity. My recovery journey led to my career after the judgment of others focused on what I wasn’t, I took the risk to focus on what I was. I learned along the way that there is a bit of good and bad in each of us. So I chose to believe in the good of myself and started my own Surf School. I believed I was a good surf coach and focused on the positive aspect of surfing in my own life, and I wanted to share that experience with others. After recognizing the need for others, I started a non-profit, Amazing Surf Adventures, to reach at-risk and underserved youth. Using my own experiences to serve others. Furthermore, following my own journey of helping others, I had the opportunity to help a group of injured warriors in transition recovering from the Brooks Army Medical Facility in San Antonio, Texas, to experience surfing. Read more>>

Justine Nelson | YouTuber & Freelancer

There are moments in my life where risk was at play and I wasn’t even aware of it until after those moments had passed. I remember feeling the pull to leave corporate life to start my first business as an independent marketing consultant in 2016. In the moment, I was scared. The fear of not knowing how much money I’d make or how I would obtain clients was overwhelming. However, I realized that fear and risk was how I knew I was onto something. I made the choice to move forward with that business in spite of the risks and as a result, I was able to develop strong business and marketing skills as an entrepreneur which led me to build Debt Free Millennials. Read more>>

Mel Sage | Artist & Woodworker

I think about risk as a necessity in order to grow and succeed. Risk has played a monumental role in getting me to where I am today. I began my career in architecture, working as an associate at a firm in NYC. There came a time when I realized I needed a change. I felt myself wanting to shift my career and the risk of leaving the security of my desk job made me feel initially uncertain. I followed my gut and threw myself into starting my own business. This began my journey as an artist, an invaluable part of Sage Woodworks now. I learned so much of what I now do through my time in architecture and I wouldn’t change my path at all. If I never took the risk, I wouldn’t be nearly as happy as I am today. Read more>>

Marjorie Taylor | Artist

Throughout my life and career, I’ve taken risks. Whether quitting my job as a graphic designer in Boston to move across the country to become a West coast painter, or traveling half-way around the world to paint en plein air, the risks I’ve taken have made my life more interesting. Most recently I took a risk by signing a lease on a new studio in the middle of a pandemic. The economic impact from COVID-19 made it impossible for my two partners at my former studio to pay the rent and it was too much for just me. I found a cute space in North Park that I knew wouldn’t stay vacant for long, so I had to make a quick decision and made the commitment. Luckily the classes I’m teaching online, as well as painting commissions, and gallery sales, have enabled me to survive 2020 and I love my new studio space on Upas Street. Read more>>

Sabastiani Leon | Professional Tennis Player & Coach

Risk runs in my bloodline. Even before my existence, my family made high-risk decisions that would alter their lives forever, fortunately for the better. In the 1800s, my ancestors took the risk of migrating to Latin America for business opportunities. During WWII, my grandmother took the risk of immigrating to Mexico for survival. My parents took the leap of faith and moved to the United States to give my brother and I more opportunities. When I was thirteen years old, my parents asked me what my intentions were in regards to tennis. I told them I wanted to play at a Division I university and play professionally. I remember how uncertain they were, considering we did not have as much knowledge and experience as other top players. They told me that we would need to work hard, study more, and make sacrifices. I took their advice to heart- When I was 17 years old, I signed the National Letter of Intent to compete for San Jose State University under a fully funded athletic scholarship. I was filled with emotion; I could not believe that I achieved the goal that I set for myself four years prior. And now, ten years later, I am currently playing professional tournaments and have three professional doubles championship titles, all played in different countries. Read more>>

Andrew Utt | Museum Director

After pondering this question for a few days, I came to the realization that everything I do is take a risk. While I leverage experience and learn from mistakes (and there have been many) I would not have gained had I not taken the risk. Rather than describing each action I’ve taken as a risk, I would imagine each action as a step on a giant staircase. The steps have treads, there are rails to hold on to, and I’ve got a harness that prevents me from falling backwards. Onwards and upwards. The top of the staircase is not visible, and that is what drives me. It’s not that I want to see the end, but simply that there is no end at all. This metaphor is not meant to prove that I want more, rather, it is meant to show that risks should be a natural phenomenon in our lives and if we stop taking risks, we become complacent. Complacency shouldn’t be equated with satisfaction. Satisfaction with what we have and what we do comes with an approval of your actions. We should be satisfied that a risk has been taken, you have learned, and that you continue to climb the staircase. Read more>>

Monika Kupiec | Intuitive Painter & Reiki Practitioner

Risk is a game of self-acceptance and inner trust. Over the years I’ve come to terms that taking a whole-hearted risk on my life and career have given me an immense amount of joy. A whole-hearted risk is what I call my heart’s deepest desire. When I was in 8th grade, after a trip to Hawaii, I made it a goal to live there. During my second year in college, one professor advised to finish college wherever I wanted to live as it would make finding a job easier. Little did I know my move to Hawaii was the best whole-hearted risk I took on my life. When I listen to my intuition, I find myself advancing in the quality of my life. Each risk has led me to a grander awakening of my abilities. For example, after my move to Hawaii, I took a break from college to attend a yoga teacher training that led me to iRest Yoga Nidra meditation training in Australia. I even flew to New Zealand to backpack for over a month which was another childhood dream of mine. Before my travels to Australia, I had a high-paying sales job at a retail store. Read more>>

Ashley Yandle | One on One Personal Trainer & Online Trainer via Ashley Lane App

Taking risks and being an entrepreneur go hand and hand. You no longer have the security of someone else paying your paycheck, making sure you have health insurance, helping retirement contributions, and all the other perks of working for a company. I knew in 2012, when I quit my corporate sales job that I was taking a risk. But, my belief in myself, and my passion for helping women become strong and confident through health and fitness was bigger than my fear. I have always been someone who likes change and likes to take risks. My biggest successes have come when I took the risk and jumped. I love planning, and spend lots of time mapping out what and how I am going to do something. But, at the end of the day you can only plan so much. There are only so many safeguards you can put into place to ensure everything goes as planned. Ultimately, you need to take the risk, trust in your abilities, and know that you are capable of anything you put your mind to. That being said, I have absolutely fallen on my face in the almost 10 years owning, Ashley Lane. Read more>>

Anaili Galindo | Digital Content Creator & International Relations Student

Risk taking: how do you think about risk ? Taking a risk could be the push you needed to start living that life you always wanted. Take the risk or lose the chance. The “risks” do not always need to put in danger your health or even your life it just could be an exit of your comfort zone, set aside the overthinking, let the fear and give the next step because eventually, the ordinary is gonna bore you. Be dreamer, realistic, and brave, wish, decrees, and act. All we have is now. A lot of times we’re self-sabotaging, and we limit ourselves by putting up an imaginary barrier based on foolish prejudices. If you take the risk, be conscious. And if it didn’t turn out the way as you expected, look forward, be thankful, learn about it and focus on the good. But hey! Remember something “The what if’s & the should-have’s will eat your brain” –John O’Callaghan. If you feel that your decision it´s going to change your life, Make an analysis and any positive resulting impact take it as a win, the negative aspects then can be a guide and a way of learning. Read more>>

Symone Carpenter | Business Woman & Model

The way I view risk now is a lot different than how I used to. Risk was something I tried my best to avoid because I associated it with all things negative. I like to think of risk as a challenge or an opportunity now. Don’t get me wrong, I’m not going to go out and be reckless! I just believe that if you are passionate about something and you do the proper planning, risks won’t seem so scary. I am in the process of building my own business and it’s crazy to think how the old me wouldn’t have even started! I would have thought of all the possible things that could go wrong and stopped before giving the idea a chance. I made the decision to start my business almost a year ago and the journey has been amazing. I’ve learned so much in a small amount of time and everything feels right. I took another risk last year and started modeling even though “everyone was doing it” and “I’m not tall/skinny”. Deciding to model has been one of the best decisions I’ve ever made; I’ve found something I’m extremely passionate about, I’ve made some amazing relationship, and I’ve cultivated a community for myself. Read more>>

Sofia Silva | Visual Artist

I would say that risk in my life has played the role of a shadow, it is there always following me, and it is accentuated every time there is more light in my path. But then I just try to make the shadow mine and go on. I think we can all set a goal and analyze the pros and cons, but I feel that by facing the path day by day to reach that goal, the real challenge and risk lurk. Personally, taking risks has led to precious experiences in my life. And yes, before making a decision, of course, I am dying of fear because I do not know the path that awaits me, but I try to enjoy it once the fear phase is overcome. It is always lovely to look at the whole experience because it leaves you with a rich lesson. Read more>>

Maria Von Losch | Digital Content Coach & Brand Strategist

Risk taking aka leap of faith is really the only thing that got me to where I’m at today in business and life. If I doubted or worried about the outcome, then I would’ve never opened my clothing store at age 22 (my first business) or created a popular novelty product at age 28 that was made in another country (had to learn everything about import/export business), or opened my PR/Media agency at age 34 and then starting all over with digital influencing and marketing at age 41, All these businesses started with little money and having my family doubt all my choices. That’s especially hard when you don’t have support but you believe in what you’re doing to the depths of your soul. As I got older, risk is harder to take because there’s more responsibility in life but I still go for it if my gut is telling me too. Read more>>

Ashwin Salvi | Clean Energy Technologist & Travel Photographer

Risk is an interesting concept. I don’t tend to agree with “risk”, I view it more as opportunity. Risk has a negative connotation and might deter action whereas viewing things as an opportunity promotes growth, exploration, and learning. I’ve found that changing my mindset from risk to opportunity has enabled life and career moves I never imagined. I’m a Ph.D. Mechanical Engineer by training and was set for a career in a traditional engineering role until I discovered an opportunity in Washington D.C. that would significantly expand my technological background and add in a commercialization perspective. It was a “risky” move since it was a limited term position that enabled a skillset that future employers didn’t know how to value, but it was also the reason that I secured a position that combines my interest in science and technology commercialization and relocated me to San Diego. This opportunity mindset is exactly why I also launched my photography business. I was told by friends and family that my photos were good – a common trap many people fall into when you take photos with a “real” camera. Read more>>

Sandy Yeh | Foodie/Blogger, Wander & Adventure, Fitness, & Healthcare Provider

I wholeheartedly believe that statement to be true! Most people fear risk or want to weigh the risks before deciding to step into the unknown, but you will never know the glory and wonderment of life without taking chances and pushing yourself out of your comfort zone! It is easy to stay comfortable, but if people are honest with themselves, most have always learned and gained the most from the situations that challenged them, where they felt some level of risk or discomfort. Every decision or choice in life that doesn’t work out exactly as you hoped or planned can be seen as failures, but I think of them as lessons, stepping stones to teach you about yourself, about life, and about others, if you’re willing to learn from those experiences. In any endeavor you pursue, getting an education, a new job or career, a new friendship or relationship, moving, having kids, etc., there are no guarantees on the outcome. It is what you gain from the journey. Read more>>

Peter Eide | Visual Artist

It took me a long time to cultivate the ability to be able to speak visually in a way that was unapologetic in order to make work that was the most sincerely in my own language. It is incredibly easy to make work that fits into a particular niche or lane, especially with the omnipresence of social media, and as I’ve continued drawing and painting over the years, I’ve striven to make work that is uncompromising, no matter how transgressive the subject matter. It has been my main priority to produce imagery derived from a simultaneously personal and objective standpoint. Many of the subjects that manifest in my work are included based on their effects on the senses. Subjects may contain an overwhelming amount of explicit content, but the work is not intended to be gratuitous, but rather poetic in the greater overarching theme of my work. While a lot of the images in my work are readily identifiable, they stand alongside my personal invented visual language that has evolved its own themes and narratives concurrent with the more traditional approach to recognizable subject matter. Read more>>