We asked some brilliant folks from the community to talk to us about how they think about risk and the role risk has played in their lives and careers.

Jasinta Sanchez | Massage Therapist

I feel like being an true entrepreneur is all about the risk. You are choosing to take your passion/dream and invest a huge amount if not all of your resources, learnings, money/investment, time and energy into creating your own business. You are risking the a stable and secure job/career where you are making someone else dreams a reality, and putting it all on the line for your dream, and that is scary! The risk is what makes dreams a reality. Without the push of going all in its just a great idea. Even the thought of making that leap, to risk it all for your dream, can send people into a panic. At least that is how I see it for me. For years I worked for a spas or other massage practices where I was helping out others dreams come into reality and as lovely as it was most of the time to be apart of that process I was left with a unfulfilled urning for more. When COVID started I was at a crossroads. At the time I was working at a Med Spa that I wasn’t feeling appreciated and was not in alignment any longer so I decided to take the risk and go out on my own during the hardest time in recent history for a massage therapist. Mainly because there was a global pandemic that left people in a state of fear to even be around new people. But that didn’t matter, I believed in myself and I made it happen. With in 6 months I had about 15 clients a week and when I left Portland 3 years later I had around 28 clients a week with mainly only word of mouth referrals. And then life threw another curve ball at me. I had created this thriving business but then my daughter who was 12 at the time was experiencing racist name calling and threats of ignorant kids I knew that it was time to move from Portland when she asked if we could move somewhere else closer to home (New Mexico). Even though my business was thriving and had so much potential to grow even more I will of course put my daughters safety and well being first. So we decided that we would move to Phoenix, AZ when school started and moved in 2 months. This is a risk that I didn’t plan for and I pretty much lost a business I had worked so hard to create. However as a mother I truly feel like listening and putting my daughter first is my primary job and I would absolutely risk anything for her. That brings me to my current situation where I had to wait 4 months to transfer my massage license then start building my clientele from scratch. I soon realized that the massage world is very different in Phoenix compared to Portland. I freaked out a bit and got a part time job at a chiropractors office as well as a spa job at a chain membership company and then in desperate energy signed up with Groupon. Now all of these may be ok and work for some, no judgement, however the rate that I was getting paid was a 1/3 of what I was use to and it was completely out of alignment with me and my company. I had a Aww Ahh moment and knew that it was time to take the risk and risk it all again. So I rejoined a BNI group and quit my 2 jobs and did my best to use Groupon to lock in some new clients who your be willing and glad to pay my normal price. Taking this risk means that I have to go within and be positive, strategic and take the proper action to make my dream a reality once again. I have noticed every time I take a huge leap of faith and risk it all I discover so many amazing qualities such as inner strength, confidence in our skill and knowledge, relentless positivity, strategies, networking and all of the other qualities you tap into when you are a entrepreneur. Risk seems to be the magic ingredient in pushing your dream into reality. Read more>>

Kyle Lacy | Musician and Singer-Songwriter

Risk is the thing that keeps you going. When you look at an opportunity and say, I have 100% chance of succeeding at this, the opportunity becomes ultimately unsatisfying. You have to take risks and put yourself out there to have a career as an artist. You have to be willing to stand firm on your tastes and beliefs even when society tells you otherwise. Not counting all the financial risk you take as an independent artist, the risk of standing out on your own can also connect you to your true fans. Read more>>

Liz Fox Roseberry | Jewelry Designer & Small Business Owner

For me, taking risks has been absolutely essential to the success of my business. I’m kind of a procrastinator by nature, but once I build up real momentum, I become an unstoppable force. I once heard this great term called “Excited Accountability” that really resonates with me. Basically, it’s about intentionally putting myself in these intense, high-stakes situations where I have no choice but to follow through. A perfect example is when I first started my online store. I had all of $500 to my name and zero prior knowledge of running a small business or even shipping products. But I went ahead and took on 100 orders (which is A LOT), because I knew that the only way I was going to learn was by just diving in headfirst. Was it terrifying at the time? Absolutely. But looking back, that baptism by fire is what allowed me to develop the skills and problem-solving abilities that are the foundation of my business today.
I just find that when there’s real skin in the game and serious consequences on the line, that’s when I’m at my best. The risk-taking lights this fire under me and unlocks this relentless drive to figure things out and make it work, no matter what. Of course, I’m careful not to be reckless, but I’m definitely all about the calculated gambles. That willingness to take risks is what has allowed me to achieve the level of success I have today. Excited accountability. Read more>>

Jacob Cooledge | Musician & Concert Promoter

This question can have many different answers. If you are an entrepreneur, or an artist there is always risk involved. You really need to use your best judgement, and know what you can afford to risk. This does get easier to judge. If you keep the big picture in mind, and make the right steps to get there risks will get bigger. That being said the rewards also get bigger. Read more>>

Kelynn Z. Alder | Artist/Curator and Vice President of Latino Arts of Long Island

It’s interesting to consider the concept of “risk” and “risk taking.”

Risk is defined as “a situation involving exposure to danger, harm or loss.” But it also implies you have a choice to weigh your odds against failure or success for your chosen path. Read more>>

Austin Kelly | Podcast host

Life is about risks. If you play it safe in life, you’re never going to live up to your true potential. That’s how I look at it. Most people don’t like being uncomfortable but that’s where you grow and learn about yourself the most. I started investing in myself with my podcast and other ventures a long time ago. But as of a year ago is where I finally felt like people started taking me more serious. Before I started my podcast in the studio I’m in currently, I was filming interviews inside coffee shops and music venues. I had my friend at the time do camera work with me and when we would film at the coffee shop it would be an outdoor setting to avoid the loud music or people inside. At times that led to lighting issues but more so audio issues if it ended up being windy that day. If I wanted people to look at my interviews in a more serious light then I knew I had to avoid those problems at all costs. They were still fun to do at the time but that format wasn’t long term. Fast forward years later and transitioning into a podcast style format inside a beautiful studio ended up being the best decision I could’ve made to continue my growth as an “on camera personality.” Which leads me to this. Putting yourself out there on camera and trying to get better than your last interview each and every time takes a different mindset and is a risk I continue to choose to do. Especially the more recognizable my show or myself will become, the more eyes and critiques I can expect. That’s something I’m willing to endure and put myself through because I love what I do. Read more>>

Candice Eaton | Photographer and budding professional philanthropist

I think about risk as a necessary part of everyday life. We don’t often think of the risk of going to the store or getting in the shower, because those things are mundane and relatively low risk. I think the mundane is the most important part of the equation, though. The repetitiveness of the task or the risk-taking makes it more acceptable each time. Take skydiving for instance, jumping out of a perfectly good airplane. The first time you do it, it will be a rush so big that you think it might kill you. Maybe even the 2nd and 10th time that happens too. However, I know people who do it several times every week. They step out of a plane like I step off of a curb. They do flips and tricks and wait to open their chute longer than recommended. It could be argued that because of complacency and the added difficulty of what they do, their risk is equal to, if not even greater than, that of the first-timers, but because the task has become common-place, they no longer dwell on the risk, just like you and I don’t consider the risk of going grocery shopping. Read more>>

Ashleigh Alexandria Sampson | Visual Artist, Curator & Herbalist

At the beginning of 2024 a friend of mine and I chose our ‘word’ for the year that we would use to keep ourselves centered on our life and career goals. They chose the word risks. It resonated with me because it is exactly what’s needed in life, if you want to yield tangible results. I know that risks, when done intentionally, can create positive change. When starting my business I realized I needed to put myself out there in a new way that at first was outside of my comfort zone. Personally, I have always had incredible stage fright and speaking infront of crowds would shake me to my core. However, It was imperative that I lean into this fear if I wanted to make my brand known on a larger scale. Recently, I curated a art show for my collective and I was the key person to spearhead the programs and engage with new clients and community members. This role put me in a position to take up space and show up for myself. Since this exhibition I have found more comfortability in speaking in front of people. Taking a risk for me was shedding the lack of confidence I had in my abilities to connect to a large group of people at once. Since then it has become easier for me to do so and I have garnered more opportunities and made meaningful connections for it. Read more>>

Erin Frank | Pelvic Floor Physical Therapist & Yoga Instructor

Risk is all about balance. There is risk in everything we do and what we don’t do. But really in terms of my professional life, risk doesn’t play a factor. I only pursue things that I am truly passionate about. And when I have that drive, things fall into place. As cheesy as it sounds, the only risk that would exist in my career choices would be to not follow my heart. Read more>>

Omega Smalls | Investor & Multi-Business Owner

Of course, “taking risks” is something that a lot of people encourage & I can concur. I think early in my career I took a lot of creative risks, which allowed me to build and improve on my skillset. These days, while I still take risks occasionally it is less of a “risk” because my experience and expertise has been solidified. Although, there will always be more oppurtunity to learn and progress, which I am eager to do. Read more>>