Taking Risk is essential, but how much, when and why? Taking risks effectively is as much of an art as it is a science and we’ve asked some of the brightest folks in the community to tell us about how they think about risk taking.

Monetta Plassmeyer | Fractional Consultant -Organizing Operations

I like to think that I embody the phrase “Fortune favors the bold”. To me this means that one must take risks to live a full life. Also, the definition of fortune is not always monetary. It can mean rich in experiences, lessons, and insights. I’ve always leaned into risks since I was a kid. I was the only girl in high school that rode a motorcycle, at least to school. I joined the Navy after my 1st year of college to seek adventure and an education. For physical adventures, I’ve sky-dived, hang-glided, scuba-dive, rock-climbed and sailed some treacherous waters. I believe doing things that scare you, stretch you, challenge your limits and provide a unique perspective to look at your life. Of course, these are rich experiences provided the foundation to apply risk later on in my career decisions. My unusual career path has provide valuable lessons to help small business owners. Read more>>

Rachel and Eric de Koekkoek and Neilson | Co-Founders of DharmaDen Sessions

Every decision we make in our lives involves a degree of risk. What is important to us when pursuing a goal is not how great the risk, but how meaningful the challenge. Our project, DharmaDen Sessions, is still in its infancy. We are learning as we go. We’ve definitely encountered our fair share of doubt about whether or not the time and money spent on this project will pay off. It’s a lot of work without immediate reward. But that’s how all big pursuits are. This is a project driven by our love for art and community. If we keep the right intentions as we progress, the risks will only make us stronger. Read more>>

Kate Dorsey | Recruiter and Co-founder of How to Launch, Grow, & Scale your Recruiting Business

That doesn’t work. Life is messy. Let it be. Your life is meant to be lived. You have dreams inside of you. You regret what you didn’t do. I’m writing this from Mexico. It’s a risk I just took. I’ve dreamed of traveling and working remotely. I’m living it right now. Has it been easy and perfect? No. I can say I’ve had some hard moments along the way to where I am. And, it’s been worth it. I am really proud of myself and who I am. My point in sharing this is not to let those dreams die inside of you. Go out there and live them. Let yourself make mistakes. Trip up. It isn’t about being perfect. Life is full of experiences. You will feel badly at times. You will screw up or drop the ball. Let yourself LEARN. This already happened on this trip. Even though I’d perfectly set up my cell service ahead of time. Guess what, I get to Mexico and nada. I spent hours trying to resolve, My phone carrier wasn’t going to work. Read more>>

Tobias Platt | Music Producer, Engineer, Student

I think the biggest risk is not taking a risk in all honesty. The risks that I’ve taken in my life have been for the benefit of me, myself and I. I’m sure I’ll be taking more risks as my life goes on. Read more>>

Laura Lenhard | Small Business Owner & Practicing witch

I left an abusive home at the age of 14 with only a suitcase and box of school papers/memorabilia, and moved across the country from California to Connecticut to live with my grandparents. I ended up attending four different high schools in three time zones – always the new kid and never fitting in. I began modeling in my senior year and then “fitting in” didn’t mean much anymore. I learned very early that public opinion is fickle and what matters at the end of the day is that you like what you see in the mirror and can go to sleep with a clear conscience because you are honest, ethical and authentically YOU in every aspect of your life. I think that when you have nothing to lose, your life can go in two directions: You can sink or swim. You quickly learn you can’t pay your bills with other people’s opinions. When I opened Talisman and Cauldron LLC in 2007 (a year before the “Great Recession”). Read more>>

Joanna McCartney | CEO of Pyne and Smith Clothiers

Risk taking has been a bigger part of my business (Pyne & Smith) than I ever thought it would be. When I started dressmaking and selling them at a local market back in 2015, I thought it would be a very sedate way for me to make a living, but it definitely has involved far more risks that I had anticipated. From making the dresses myself to reaching out to hire local seamstresses, to working with small scale production locally in Los Angeles, making the jump to move into our own warehouse and office space from our home garage, hiring employees and all the small risks we make daily, I definitely think risk is necessary for growth – even though it can be very stressful. Read more>>

Cindy Macaranas | Island Product Creator

When I think about the idea of a risk, I think about challenges in my own life, whether personal or business. I was diagnosed with Chronic Kidney Disease and doing dialysis in 2006, which is when I started my business, so that itself was the first biggest risk I took to start my business while also going through treatment for my kidney. As a single mother, my disability income would not have been enough to raise three children, so that is what pushed me to take that risk. Later that year, I was blessed to have a kidney transplant. After two years, I had a stroke while still concentrating on my business, trying to have a steady income. In 2015, I was diagnosed with stage 3 breast cancer. For a full year, I had to halt my business due to my treatment. After a year of chemotherapy, I was so grateful to work again, participating in all the vendor events that I can do with my body still in recovery. In 2018, I was diagnosed with Mitral Valve Stenosis and Atrial Fibrillation. Read more>>

Marlon Amaro | Painter

Coming from a poor family and a favela resident, my life has always been risky, where i came from to die is a risk that everyone runs. living in such an environment brought me the idea that anything is worthwhile to get out of this social black hole because I have nothing to lose. my career was built on this idea, even when no one believed, I believed, I knew that everything was a a matter of time, even though I knew that time was a luxury that I couldn’t have. so risk is if you gamble on something indefinite, it is betting without being sure, it is living without fear, it is ignoring the chances of going wrong, risk is believing in yourself. Read more>>

Tina White | Leatherista AKA Leather Smith

I consider taking risks everyday in my career, from deciding which belts to make for a shop to picking out a new design as a staple. Should I spend more time on custom orders or creating inventory? My everyday tasks in running this business leads to the overall “risk factor” of trying to grow a business. Leaving the bartending industry to fully focus on creating this brand was one of the biggest risks I’ve taken. Building your own small business is a huge risk in inself, but being able to do something you love is worth it all. Read more>>

Ilse Hendrix | Singer, Composer & Producer

For me risk is everything. If you want to succeed and grow, you have to try new things and go out of your comfort zone, otherwise how do you know you are doing it wright? how can you compare your work to your own work if you dont risk? or if what youre doing is the most convenient way for you to keep doing it. Risk its been super important role in my own personal carrer because ive been able to discover other ways of working and knowing how things work better for me and how can i be better. Read more>>

Alkyshia McDonald | Sailor & CEO

Risk is the degree of probability of loss. We all know that In order to win big, you have to play big. Risks have recently played a huge role in my career as I’ve decided to retire from the military. The Navy is the only career I’ve had and now I’m choosing to take a leap of faith and take my business to the next level. It requires you to be restricted and make crucial sacrifices. Although the military has taught me so many things about my passion for cooking, it takes me away from my business which I love more than the military. Once I moved to San Diego, I took a risk starting my business with no support or guidance on how to operate. But as I said earlier, in order to win big, you have to play big. Read more>

Aileen Brandt Merling | Artist

Early on in my life, I always had the “bug” to have my own business. Ask my sisters. I was known for my “next money making plan”. If it wasn’t the Gold Nugget cookies, it was the make-up based on your season colors. Or writing letters for people who needed to send a Dear John/Betty letter. Or using our acre property to park cars during the 4th of July nearby park location. You get the idea, I came up with fantastic ideas as a kid. But no one took me seriously. Little wonder. Being my own boss and taking risks was calling me much like the 49er’s hunt for gold in California. I just had no idea about what my gold nugget would look like as my income source. Even though I would have liked to sell cookies out of my mother’s oven nationwide, deep down inside, I knew that plan was too risky. My DNA makeup is 2 parts adventure and 1 part risk, 4 Tablespoons of logical planning, and a cup of enthusiasm with a sprinkling of fear. Read more>>

Diana Benavidez | Visual Artist & Nonprofit Professional

I didn’t become comfortable with risk-taking until my mid-twenties. For a long time, my anxiety held me back from stepping out of my comfort zone. So I came up with an exercise that involved committing a whole year to accept every project, collaboration, or exhibit opportunity offered, regardless of how challenging they might seem. I promised myself I would give it a try! After a short period, I was impressed with myself because I was getting involved in things I had no previous experience with. Yet, I slowly became comfortable with challenging myself to try new things. This exercise brought a myriad of opportunities that subsequently had a significant impact on my professional development. Read more>>

Sabrina Fabi | Cosmetic Dermatologist

I think we all have to take risks sometimes if we hope to grow personally and professionally. The easy thing is to go with what we already know and feel safe or comfortable doing, but from that place there is no growth. Ultimately it is fear of the unknown (whether outcome or other) or fear of our own greatness that holds us back from not taking risk. But one has to really evaluate what they have to lose, because sometimes it is not as big as we may think, and the reward from taking the risk could be much bigger. As the saying goes, sometimes the greatest risk we take in life is taking no risk at all. I took the risk of letting down a great position in Chicago, and going back to my home town, where I was being offered a guaranteed salary and a position to open up an entire Cosmetic Dermatology division to a large, well established, Dermatology practice, in order to take a position as an independent contractor, with no guaranteed salary or benefits, in San Diego. Read more>>

Lauren Hensgens | Commercial Lifestyle Photographer specializing in Adventure and Water

I’d like to think that taking risks has gotten me where I am today. But to me it really doesn’t feel like a risk if you have a vision in mind. It’s just creating a new path with lessons to learn from and if you get to a dead end, you find another way. In doing that, there’s always opportunities or rewards you wouldn’t have seen otherwise and it works out one way or the other. Some of my biggest risks I’ve taken was moving to start a new life. (A couple of different times. Haha.) One move was out of the country to Costa Rica and the other was to California. Both times, I didn’t know anyone, nor have a plan, a place to live, or even a job. I just followed a feeling and knew if it was something I really wanted I’d find a way to make it work. People often ask if I was scared and my reply is always “Of course, I was terrified but it seemed even scarier to continue doing the same thing and not chase what I truly wanted.” Read more>>

Melissa Strother | Athletic Trainer & Professional Football Player

Sometimes the biggest risk we perceive in life is believing we are worth taking the risk. So many people avoid risks because they are afraid of failure, but all that is really saying is they don’t believe they are worth the risk or that they don’t think they will be successful in that risk. I have always seen risk as something that is essential in life, if you want to live big and make an impact in this world then you will have to take risks along the way. I quit my steady job in a Division I Athletics program for a complete unknown. I didn’t know what my income would be. I didn’t know how I was going to pay my bills. I didn’t even know what my steps to success were going to be. What I did know was that I wanted to make a positive impact in the world and change the way people looked at their fitness and health. When I quit my job of 7 days a week 70-80 hour days, I realized how much I wasn’t actually living. Read more>>