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.

Kelli Carlson | Artist & Producer

Risk and going for the unknown is the thrill, and taking calculated risks is what I try to get better at everyday. Every aspect of being an artist is a risk, there is only security if you create it. I go with the saying, “Opportunity dances with those already on the dance floor” (H. Jackson Brown). I practice separating risk from fear so I can take bigger leaps. Read more>>

Kat Trimarco | Evolutionary Thought Leader, Spiritual Quantum Teacher & Life Coach, Author & Speaker

There have been so many times in my life and career where those around me have thought I was crazy and questioned what I was doing. Often times from the outside many of my actions and decisions have looked like a risk, but I’ve always known I was following the path of my heart and soul’s calling. When we are actually willing to follow the path of our heart, our soul and our inner truth, it always requires trusting in the action we’re called to take BEFORE we can see a definitive outcome. Most people are relying on the physical world, what they can see, for their sense of security. I’ve learned to mostly derive and create my sense of certainty internally through my connection to myself and the Universe and of course my inner vision for where I’m headed and what I’m creating. Read more>>

Aalia Lanius | Award-Winning Novelist, Podcast Host & Founder

No great act has been accomplished that didn’t involve risk! Any dream or venture has risk involved and too often we are scared to take them when we need to most. I think the biggest piece of advice I’ve learned to give my own self, is that I am worth betting on. It doesn’t mean I always win what I want to, but I can tell you that I’ve always gained something of value—sometimes its monetary, but it’s also been relationships and connection that have brought such joy to living. In my personal life, taking risks is the entire reason I am who I am today as the founder of a media organization, podcast host, executive producer and award-winning writer. In my personal life, I’m selective with my risk-taking adventures, but it gives mystery to my life, which in turn, provides inspiration to give it all I’ve got with pages still unwritten. I was homeless at 14-years-old and have been supporting myself since then. Read more>>

Curt “Kirkee B.” Bisquera | Drummer, Musician & Producer

If you really have a desire and passion about what it is you want to BE, “risk” is everything! You must be willing to NOT look at the alternative and know that 100% focus is the way to be! Every aspect of the pursuance will add to your desire, wants and needs. Had I not taken all the risk I had for these past 30+ years, I would not be here to tell you about it! Read more>>

Suzanne Brosnan | Founder & Designer

When I think about taking a risk I think about how it makes me feel deep down. Am I truly excited by this? It’s ok if it scares me, but I should still have a feeling of pure excitement or exhilaration. If it passes that test then I like to have a backup plan for if/when things don’t go according to plan (because do they ever?). If I have a gut feeling that is not sitting quite right with me or I can tell I’m making a rash decision, I’ll try and steer clear of those situations, if possible. It has taken me awhile to get to this point though…I’d always heard other entrepreneurs say “If it’s not a hell yes it’s a hell no,” and not totally understood what they meant until recently. Risks are always a part of entrepreneurship. Putting yourself out there and investing in an idea is really hard. Every decision isn’t always as extreme as life or death, but it still feels like you are always walking on the edge, and a lot of the times you are doing it alone which makes it feel more extreme. Read more>>

Daniel Corey | Author, Comic Creator, Singer & Songwriter

Risk-taking is pretty much the logline of my life and career. Any working artist will tell you the same. So many of us uprooted ourselves from the security of our hometowns to make our way to Los Angeles, hoping to make something happen in an industry that is entirely oversaturated. The thing of it is, while the entertainment industry is overwhelmed with talent, every person who contributes has a unique voice with unique ideas, and there is room for A LOT of unique ideas in today’s media space. To join the landscape, it’s just a matter of spending time in the city, getting to know people, and continuing to work and work until that day when you finally start getting opportunities. That’s the only way to rise above the pack. In being a comic creator, the financial risk that you take is enormous. The comic industry is very unpredictable, and marketing a graphic novel is very difficult. Read more>>

Ashley Merrill | CEO & Founder

I’m not a natural risk-taker but I think it’s a muscle that I’ve built over the years. I think the key is taking risks that are mitigated and strategic. Over time and through a series of trials and errors, it’s becoming more clear when it’s the right time to play it safe and when it’s time to double down. It’s still a learning process and likely always will be. I’ve learned that you have to be ok with some failure or you won’t take any risks and there can be no success without them. Read more>>

Jim Riley | Business Consultant, Life Coach & Podcast Host

I have always been risk adverse as a business leader. This comes from my background as a professional off-road race truck driver and life long surfer. I once read many years ago that “Big wave Surfers make better CEO’s”. The point made was that due to the split second decision that must be made on a wave to take off or let the wave go by leads to quick decision making. If you took off on the wrong wave it could literally cost you your life, or if you put yourself in a dangerous situation you would have to live with that decision and figure out how to survive. The alternative is you would never know if that would have been the best wave of your life. The lesson is – having the ability to make quick, split second decisions and then living with the consequences either way helps CEO’s to make firm choices and realize that the worse thing that can happen would be less then death… I run hard and fast as a CEO and a business leader and place a lot of trust in my instinct. Read more>>

Cat LaCohie aka Vixen DeVille | Actor, Variety Performer & Body Confidence Burlesque Coach

Whenever someone mentions risk, I think of the front cover of “The Big Leap”, by Gay Hendricks, the fish jumping from the small bowl into the larger bowl. There is no way you are ever going to progress in any aspect of life if you don’t ever take a risk. Not taking a risk means you stay in your comfort zone and life is just going to be ‘more of the same’. I can think of two major risks I’ve taken in life which have been integral to putting me where I am now. Firstly, deciding to move to the US in 2012. Back in London, UK, I was making an OK wage, with an OK career, living an OK lifestyle. But that was it…… JUST ‘OK’. Not ‘amazing’, not ‘exceptional’, not ‘better than I ever could have imagined’… but.. ‘OK’. I looked around at my life and thought if I don’t make some big changes then the next five, ten, fifteen years is just going to be more of the same. Read more>>

Jordyn Torres | Actress, Photographer, Writer, Producer & Director

Taking risks is one of the most essential actions you must do in life. Most people don’t even reach almost all of their potential, and I don’t want to be one of those people. Every second is extremely valuable because life flies by. There’s an example I heard once, about how if you got a million dollars a day, but you couldn’t carry over the money to another day and you only had 24 hours to spend it before it is reset, that is how life an minutes are. That really put things into perspective for me. Or Cleo Wade’s quote, “lose your fear and gain your whole life.” Or Allan Watt’s “what would you do if money were no object?” Read more>>

Kayindae James | Photographer

Well, believe it or not, risk-taking is important. Taking risks is the only way you learn and grow as a person and an artist. I take chances on people, places and things because you never know when your next lesson will arrive or where your next boost will come from. I know a lot of people afraid to make the next move in life because they don’t know what will happen next. But, that is the beauty of life! You do not need to be in control all the time, so, take the chance to do whatever it is you need or want to do, life is too short. In life I take chances because it keeps life interesting and so far it’s been entirely rewarding. I’ve created a space to create my images and earn money simply because I said “Why not”. Soon I will be starting up a podcast which can be pricey to do but I believe the rewards are worth the risk. Risks and chances have lead me to meeting the love of my life, to buying my first home, and to dedicating my time to my passions. Read more>>

Andrea Kelsey | Web Designer & Developer

I seek experiences and growth in life and you can’t get those without taking risks. I’d like to say I make informed risks, but more often I go by what I feel like I must do. I admit to having a large amount of FOMO that directs me, I have put myself in all sorts of situations in order to have the experiences I want. I don’t think about myself as a risk taker, but when I look back at my life and the really big choices I’ve made like moving alone to Brooklyn, trying different careers, pursuing a Media Studies grad degree, moving to Los Angeles, becoming a full time freelancer, those were all incredibly risky moves! For each one I was betting on myself to make these things happen and work out in my favor, to fight through the hard times and keep working toward the things I want. Read more>>

Oliver Boon | Actor & Theatre Critic

In terms of my role as a theatre critic, I believe there are plenty of elements of risk involved in reviewing a show. To have an opinion is to take a risk and one that I believe is always worth taking. When you review a play, objectiveness is sacred. You can’t let your relationships with those that are a part of a production dictate your sensitivity to your writing, otherwise you risk writing a flawed review and that does nobody any good. I have written reviews where those involved with the production have resonated from what I’ve said and thanked me for my honesty. Not everyone is going to like what you write but you can’t let yourself be bullied into writing fluff! As an actor myself, it can be difficult at times when reviewing the work of my friends. I have friends that were a part of productions reviewed by me, that either ask for an early look at my review or request changes. Most of the time, this will be out of ego rather than anything factual. Read more>>

Ginger “Gigi” Damon | Designer & Protective Motorcycle Couture

How do I think about risk? Risk is provocative. It changes you, it compliments who you have become. I think risk brings your life into focus and propels you forward. Risk takers are unconventional imaginative people. I analyze and fantasize about how things can be better or advocate forward thinking for a cause, idea or philosophy. I feel risk is about change. What role has taking risks played in your life/career? My personal experience with risk has been “why?” Why this? why that? I have always questioned the status quo and then acted upon it. Trendsetters, innovators, disruptor are by definition “risk takers”. I believe with Gigi Montrose Moto Couture it is not about just selling products, it is about changing peoples minds and opinions. I am creating a new lifestyle and culture for women motorcyclist, bicyclist, scooters, e-bikes etc. I am advocating positive role models for women and myself. Read more>>

Ryan Richko | Composer & Mix Engineer

I believe risk taking is the only way to truly succeed in running your own business. If you aren’t willing to take risks, invest money into your craft, and expand your network in clever ways, then you will ultimately fail. Perseverance is everything. My entire business and lifestyle is based on one big risk that I took back in 2010. I decided to move to Los Angeles from my hometown of Chicago. I wanted to pursue new opportunities as a session guitarist, and energetically I felt that I needed a fresh start. Chicago didn’t really have anything for me anymore. I saved up some money, packed everything up, and drove to California over the span of four days. 10 years later I am now running my own business. Not so much as a session guitarist (though I do still do that from time to time, I just did some guitar for the new Bill and Ted trailer campaign), but now my main gig is composition for film, video games, and television. Read more>>

Rohitash Rao | Artist

Risk is a funny word. Often we hear that and suddenly an anxiety attack kicks in. But I’ve found a new way to look at risk. Years ago when I was in Little League I used to be really scared of the ball when I was up to bat. I used to just stand there, frozen, as the pitch came in. I was really just hoping for a “walk.” And often times I struck out. And I did nothing to earn that “strike out.” My coach would yell at me and say, “At least you could have swung. You had a 50/50 shot if you just swung the bat. And if you strike out, so what, at least you go down swinging.” And that stuck with me: “Go down swinging.” That’s how I approach everything now. I may not know how to pull off a specific project, but dammit, I’m gonna try my best. I’m gonna go down swinging. Read more>>

Szilvia Campbell Bakos | Medicine Woman, Pelvic Core Specialist & Level 3 Forrest Yoga Teacher

Patience has been my biggest challenge. When the pandemics started I was supposed to go on a big USA/European teaching tour. I had to let all of that go and refocus my business towards something new. Instead of being sad or panicked for too long, I worked on developing simple healing body movements (exercises) to bring the body into ‘healing mode’. I am about to launch TWO online training programs from what I have learnt in my ‘body lab’ the past year and a half and as a result of working with so many people in the past 9 years of my yoga teaching carrier! ONE OF MY NEW PROJECTS is to teach people how to bring the pelvis and jaw into alignment and coherent communication. Combining beauty fitness (face yoga and BLAFit) with functional movement and body liberation somatic workout. Read more>>

Dean Morash | Owner & President

Risk taking is a significant consideration for every entrepreneur. Before I launched my business, I gathered as much data as I could to determine the demand for my concierge car storage business. I wanted to ensure that there was sufficient demand to be profitable. But at some point in this process, before I was sure, a building was presented to me putting me in a position to make a decision. At this point, it was important to allow my previous professional and life experiences to guide my decision making as well as this incomplete analysis. Obviously, I decided to move forward and we have had similar expansion decisions to make in the last three years that are very similar. I am super thankful that I took these risks as the community has responded favorably to our services and permitted us to expand. Read more>>

Amber Padgett | Stop Motion Artist & Adventurer

Risk taking is central to my career as an artist and fulfillment as a person. It’s terrifying, it’s thrilling, it’s heartbreaking, and it’s essential to creating authentic work and living a life rich with passion. It’s found in every corner from bidding a large job, to reaching out to an admired artist on Instagram; from traveling abroad alone, to respectfully trespassing for the sake of art; and from speaking up against injustice, to being vulnerable with a partner. My brother and I grew up crippled with shyness. We joke now that it gave us the super hero power of ‘sucking it up.’ Meaning, everything felt like a risk back then, and I learned to not only get comfortable with it, but require it to grow. These days, most of my personal art is done in public spaces. I’m open to being judged, interrupted, kicked out, losing my gear, getting hurt, wasting time, and being rejected, but this is how I’ve made my favorite work! Read more>>

Mark Indig | Photographer, Unit Production Manager & Producer

The dictionary defines risk (the noun) as “a possibility of loss or injury” and (as a verb) as “to expose to hazard or danger.” Personally, I prefer to follow a path of “managed” risk. I’ll never be an Alex Hannold, free-climbing Yosemite (or Yo-Semite), but as mostly a freelancer for decades in film production and photography, the beginning of each job is a leap into the unknown. And the end of each job can be even more unnerving. But being thoughtful about your options and actions helps manage the risk. Read more>>