By far, the topic that comes up most in our conversations with entrepreneurs and creatives is risk. We’ve had conversations about risks that worked out and risks that did not. We’ve seen eyes light eye sharing about career-trajectory changing risks as well as folks sigh about the risks they wish they had taken. Below, we’ve selected and shared some of those thoughtful conversations.

Kathy Phan | Bakery Owner

Most people see risk as something that should be avoided at all cost. They prefer to take the safer route, to more surely secure the outcome. But my take on risk is that it is unavoidable. There will always be some degree of risk in any decision we make. Before I decided whether I should pursue my dream of opening a bakery, I had to weigh the risks of quitting my job and putting my all into opening a bakery. What are the chances I could make it when statistics show that 60% of restaurants fail within the first year, going up to 80% within the first 5 years? I had no previous experience in the restaurant industry and no one but myself to start the business from scratch. But then I weighed the risk of staying in a career that I hated and being unhappy for several more decades just for a secure source of income. I was risking my happiness which I realized I was less willing to lose than money or ego. And as you learn, it is better to take higher risks while you’re young and more likely to recover than when you’re older and it is much more difficult to recover. Read more>>

Julie Roland | Naval Aviator, Entertainer, Producer

In the Navy, especially in aviation, we talk about risk all the time. Before every flight, we fill out sheets dedicated to Operational Risk Management. We examine what might present the greatest risks that day—live ordnance? bad weather? fatigue?—and discuss deliberately how we’ll address those risks before we even walk to the aircraft. Flying is always risky, but our missions often require accepting additional risk in time critical situations, so we develop techniques to swiftly and smartly identify our options, assess their unique risks, and then consider how we can mitigate those risks. We never accept unnecessary risks and we accept risks only when the benefits outweigh the costs. This may seem like common sense, but these kinds of principles turn risk analysis into an ingrained and continuous calculus. I do not have this discipline when it comes to risk management in my non-Navy life. Read more>>

Thiago Valdi | Muralist Urban Artist

I believe when we assume our dreams we are accepting a great risk. In my case the dream to become an urban artist, even without academic study or something. I was completely blind in the beginning and the only light i had to clarify my path was the shine of my dream. I had to face many difficult choices to incorpore it in my life, to transform an idea to reality. So, i had to learn how to live with risks all the time, in different ways. For example: To quit a job to have more time to paint: Risk. To go out in the streets with a spray can to create a name for yourself: Risk. To say in public that i’m urban artist, in that time urban artist was not a cool thing: Risk And to keep going in the darkness, everyday believing in art. So, to live with this feeling and this uncertainty is to accept risk as part of the artistic life. Not only me but all artists may face this dilema. Read more>>

Jevaughn Pinnock | Movement Specialist

At the end of summer August of 2018 is where my Ultimate Journey had begun. It started with a Heart break that hit me by surprise & when a man heart is broken it’s not easy to heal but most boys won’t admit the heartache but “Real Men” Will. In the back of my head I knew it was coming but the heart didn’t want to agree with the mind.. in the midst of that I was starting my 7 month Yoga Instructor Training and yet homelessness was upon me I still had a job at the time but sacrifices were going to have to be made. My question was do you stay where you feel unwanted and swallow my pride? or do I go get it from nothing. While seeking a positive in the midst of turmoil and Save money from the ground up for your Upcoming business (Movement Specialist) because nobody is going to give you a handout nor am I taking loans out, so something had to be scarified in order to reap the fruit in the future so I bet my last dollar on myself with the trust and Faith of GOD. Read more>>

Karen Meisels | Professional and Nutrition Coach and Behavioral Health Consultant

When I think about risk I think about Brené Brown’s book Daring Greatly. Being brave enough to be seen exactly as we are, with all of our fears and imperfections. For me, that is what risk is about. Feeling the fear and doing it anyway. My whole life I’ve learned by doing and figuring it out. I am unconventional, and that means I do things from the heart, with passion, verve, and a little bit of fear. I do not follow a formula nor emulate others. I have an understanding of how others before me have done things and I take what resonates with my spirit and leave the rest. The fear of not doing something is greater than the fear of staying the same and not evolving or growing. Risk has played a role in my resiliency, my continuous curiosity about life, myself, and others, and the courage to be vulnerable, to be seen, to have an impact. Read more>>

Laura Bashore | Career Coach & Resume Writer

I’m not afraid of failure. The best moves I’ve made for my life and career came from taking risks. I have an internal deal with myself which is if I’m presented with an opportunity, I go for it even when I don’t feel 100 percent prepared. When I was eight, I decided I wanted to move to San Diego, CA. At twenty, I was offered a part-time job in San Diego, so I packed one suitcase and moved. I’ve been in San Diego ever since – where I met my wonderful husband and am raising two beautiful boys. One example from my career was when I applied for a management position after being with the organization for only four months. I had no intention of getting the promotion but wanted to show my future intentions. Well, the person with 15+ years of experience was unable to accept the new role and I found myself promoted within four months!. Read more>>

Conner Farrell | Rockstar

If it’s something you care about, it’s worth the risk. All things in life are risky. It’s just a game of how risky it is and is it worth it. As a general rule, I don’t compromise my values to gain something I think I want. If I do, it ultimately eats at me and ruins whatever I gained for doing such. Usually something much better that I couldn’t or wouldn’t have predicted occurs when I turn down said opportunity. Risk is necessary. Obviously I don’t go adding unnecessary risk to my life, but there’s certainly a healthy amount to maintain. If I don’t feel like I’m putting something on the line, then I’m not doing it right. Absence of risk is an indicator that I’m either not doing something meaningful or I’m not giving it the energy or dedication it requires. At the heart of it all, I’d rather fail a thousand times than never try. All I’ve ever risked is being embarrassed and being seen as a failure. But honestly I really don’t care. Read more>>

Bar Dahan | Musician

I find that it’s very hard to push myself to take big risks when I’m not so sure about my decisions. I’ve met amazing musicians who became close friends thanks to risks I took along the way in my music career. Their support and motivation pushes me to take even bigger risks today. For me, investing time and money into this musical journey of mine has been life changing. Even if it didn’t always pay off the way I had originally hoped. After spending many years in bands and ensembles, I decided to attempt to make a name for myself as a solo artist. Creatively, that was a big risk for me. I always felt like I thrived when bouncing ideas off of people I worked with, Chasing West is my personal narrative. Sharing the stories, the emotions, the naïve nature of youth, and the impact of adulthood. Risks and all. Read more>>

Damien Evans | Personal Trainer, Group Fitness Instructor and Franchise Owner of Eat the Frog Fitness

A risk can be large, like selling everything you own except what can fit in your car and drive to a place where you know almost no one. With no job lined up or no real place to live. I’ve taken both of these risks. In my experience, it seems the bigger the risk the more exciting the journey, and the larger your potential reward becomes. As a no named kid from a small town, who lived out in the middle of the forests in Oregon. There are not a whole lot of options presented to you. There is no exposure of the big city living potential. No real consciousness of what kind of money there is to be made, or what kind of impact one person can make on the world. These visions were not even in my realm of possibility growing up. Most of my friends back home work very hard and physically demanding jobs, while living very honest and simple lives. Read more>>

Saige Rouze | Jewelry Designer & Reiki Master Healer

Sometimes, to me, risk feels like the safest thing to do. The idea of being fueled by what I love and not wanting to be like any other brand I’ve seen before is a risk in itself. Once I made the inevitable decision to follow the yearnings of my heart, risk is all I know. My name is Saige Rouze, the owner and founder of Arid Collective. I am a soul-inspired, reiki infused, one-of-a-kind, brass and crystal jewelry and mala maker. I am a reiki master healer who enjoys infusing reiki energy into all that I create with my hands. It’s the intuitive process, crystal readings, and in-depth intention I provide that gives life to Arid Collective. I haven’t known any other business who works in the way that I do. There’s no way to condense what I do down into a box as it sits on a foundation that is free and flowing, yet detailed and concise. I fully believe that running your own business based on your passion is a huge risk, because your heart is at stake. I find it risky to choose to do what you love for money. Read more>>

Helena Holleran | Singer-Songwriter/Musician

Risk is a friend of mine. Over the past 4 years of performing out live and striving to make music my full time career, I have learned that a healthy serving of risk on a regular basis can actually improve your quality of life in every capacity. I used to fear failure or embarrassment just as much as the next human, but as I have continuously put myself in vulnerable and uncomfortable situations – such as performing for a live audience or voicing my ideas in a writing session – I have given myself the opportunity to learn by doing through a form of exposure therapy. I’m not the best musician, there is always room for improvement. The road of growth requires risk. At this point I have given myself enough evidence to know that failing isn’t nearly as scary as willfully inhibiting my own growth and living with the monotony of it. I’m looking forward to my next big failure because I know I will be one step closer to my next big success. Read more>>

Kimberli Weeks | Founder & Lead Dog Runner

I strongly believe risk taking is essential to success in business and life. Taking the easy approach of, “Yeah, but…” will not lead to success. Diving in head first, with a new business AND a new and untapped market, was definitely a risk. I had no one to model off of in San Diego, and having a Dog Running business as opposed to numerous dog walking businesses, was a challenge. I have a strong personality and positive outlook on life, and this helped when most people had the “Yeah, but…” questions regarding my new dog running business. Fast forward almost five years later, and my determination turned into knowledge. One client turned into five, turned into ten, turned into forming a team of Dog Runner’s and led to my rebrand last year. Now we are rapidly growing throughout most of San Diego, and very much a mission-based dog business. My determination and continued experience has led to numerous appearances in media, national brand partnerships and accolades in the Canine Wellness sector. Read more>>

Tamiel McKee Bey | Multidisciplinary Artist, Educator and Healer

Taking risks is at the core of the work that has made Black Voices Artists Collective everything that it is today. The leaders of BVU were Black, Queer, Women who organized people to make amazing art, to create long lasting connections and love that extends so far beyond all of us. This is risky, revolutionary, RADICAL. Risk looks like courage in the face of sometimes being your only supporter. Being the only person who can see the vision. I had the be vision for this organization for a long time, people don’t always know how to show up for your business or work, I gave people the opportunity to show up as themselves. What ever you have, where ever you’re at. Come, exist, take the risk to be all of yourself. Read more>>

Leslie Rivera and Mercedes Ayala Rivera and Ayala | Small Business Owner

We started our business in 2020 in the middle of a pandemic and without a loan. We are building our business from scratch with our own money from our pockets. We did not ask for help from family or friends we decided to become our own bosses and make a decision that during this time is very scary and edgy due to financial uncertainties. We both have full time jobs, plan on pursuing careers, and have children to feed, We knew that starting a business was going to be rough for a while but surprisingly business picked up very fast. For us in our career at the moment this was taking a risk, not sure if it would or will work out. There have been those thoughts “what if we are doing this for no reason?” but without taking that blind step willingly pushing ourselves into deep endeavors we would never know what success may come from this. Read more>>