In our experience, most folks, including ourselves don’t have enough of an understanding of risk and the role it plays in our lives and careers and so we have made a concerted effort as a team to have conversations about risk with our interviewees. We’ve shared some highlights below.

Cassie Boettcher | Songwriter

Risk taking is so important. It’s one of the hardest and scariest things ever but also one of the most satisfying things one can do for themselves. If I wouldn’t have taken the risk to move to Los Angeles randomly without a job, I probably still would’ve been living in my same small hometown. Risk taking is essential, especially for creative people. When we’re willing to take risks to make the art that we make, we impact and inspire others. Read more>>

Maria Tornberg | Photographer Actor Writer

When I jumped out of my bedroom window during a home invasion a few years ago. As horrifying as that and my devastating injuries I suffered were, the following months of recovery triggered a profound self discovery journey that forced me to take a good look at my life. The vision of me jumping in blind faith, was showing me how brave I really am, and always have been. I realized that I have been taking huge risks my whole life. Even though, at times, the fear was overwhelming, it never stopped me from my true calling; to find freedom. I was always scared, but my desire to live was always greater. And for many artists, creating art is the way we breathe, feel free and feel alive. Choosing a life as an artist, is in itself a huge risk. It means risking financial stability, risking feeling exposed and rejected and also facing the risk that we may be misunderstood and isolated at times. Read more>>

Suzanne Redfearn | Suzanne is The Bestselling Author of Four Novels | Hush Little Baby, No Ordinary Life, In An Instant, and Hadley & Grace.

One of my favorite sayings is “You can’t win if you don’t try.” I have thrown a lot of mud on the wall. Most of it didn’t stick, but without the failure, I never would have found success. Risk comes in lots of forms: financial, personal, emotional. I put a lot on the line to pursue my dream of becoming an author. I gave up a lucrative career as an architect. I gave up time with my family, my friends, personal time. I exposed myself to ruthless criticism and rejection. The way I see it though is you can’t just look at the risk, you also have to look at the regret you’ll have if you don’t try. Life is short. You can either live it cowering in the shadows, or you can be bold and try to do something amazing. For me, the choice was easy. I’d rather spend a lifetime falling down in the mud than sitting dry and safe on the sideline. Read more>>

Braden Summers | Photographer & Director

The biggest risk I have ever taken in my career paid off with the biggest rewards. I created a personal series titled ‘ALL LOVE IS EQUAL’ in 2013, the project illustrated same-sex couples from different countries and cultures around the world. When the project launched on Valentine’s Day of 2014, it went viral and led to incredible opportunities and a nationwide campaign for Marriott International called “#LoveTravels. Deciding to believe in myself and the idea to change how gay romance was viewed by the general public was a risk! I had no idea that the work would be seen by as many eyes as it ultimately had. Since then, I have taken risks on other personal projects that have not had nearly as much success or attention – muddying my overall positive association with the idea of taking risks; but at the end of the day and to borrow a popular phrase, you will miss 100% of the risks you do not take. Read more>>

Yancy Perez (YAN) | Artist & Businessman

Ever since I started Acting I have been told that I am a risk taking actor by almost every director I have worked with. I have always wondered why they felt that way, but as I grew and have had the honor of working with other amazing actors from all over the world I noticed one thing that the majority shared that I was never able to comprehend. This barrier called “fear” has prevented many to not take risks whether it was in scene and someone was too scared to try something new or trust their instincts but there was always a cloud of fear following many other professionals I have met in my life. Fear is the preventative factor of risk taking, if you can find the cause of your fear you can disperse the effect it has in your life. I have always been willing to take risks and because of that I have gotten to where I am today and will continue to progress and reinvent things I do such as music, cinema and fashion. Risk is the gateway to achieving a full life. Read more>>

Valerie Gill | Filmmaker & Writer

Even for people who never take any risks, whether its because their scared or anxious. By never taking a risk those people could be taking the biggest risk of all, and that is simply that their life could end up feeling so underwhelming you’d have to question whether that’s a life’s worth living. I simply don’t believe someone could be content with only having a life that had nothing in it that was worth taking a risk for. That being said I am also that same person who can be consumed by my own fears and anxieties that I can miss my own chance to take those same risks. I’ve lived my life for a very long time in fear of my own wants and desires because I had always played the cards that where dealt to me in life. But I’ve reached an age where I now get to have some say of what cards I want to be dealt and in doing so I have won some of my happiest memories. Read more>>

Neema Skye | On Air Talent/ Influencer / Entrepreneur

In order to measure the weight of your talent it’s important to put your self in positions that force you to become your best. Never taking chances and staying on the same level keeps you comfortable and stagnant. Risk show you what your made of and it helps you build character. So no matter what is thrown your way, you can withstand anything and position yourself to become one of the greatest. Read more>>

Hunter Nakazono | Vocalist/Guitarist For The Tens

Getting out of the “comfort zone” has defined the ethos of this LA band since its formation in 2014. Early on, no venue would book us. We didn’t have much to offer them in the form of experience or a fan-base (5 instagram followers…probably someone’s parents). So, the band bought a gas-powered generator and we unloaded our amplifiers, guitars and drum set out onto the streets of Los Angeles in search of a corner on which to busk (a worldly tradition where musicians play outside for tips). The band was chased out of everywhere by the authorities except for a busy, nightlife corner in Hollywood where we performed from 9pm-2am, 4 nights per week for a year. It was an immense risk to bring our favorite material objects onto the sidewalk and perform for rowdy nocturnals without any sort of security. There, the band witnessed a gun-fight, numerous brawls, direct threats and theft (our first generator was stolen). The physical danger was so prevalent that the ever-present, petty hecklers and social rejection didn’t even phase us. Read more>>

Vanessa Sanchez McCullough | Celebrity Manicurist and Nail Stylist

I have taken so many risks in my career(s) and each one of them brought me right to where I am now. At 16 years old, as a manicurist, there wasn’t much risk involved in the beginning. However, making a decision to not take over my family salon and go to college instead, that was my first risk. Because of it, I worked in TV and Film Production for about 10 years in NYC with an exciting career as an assistant editor and ultimately, Managing Director of a TV and Film Production Company. With a more business based job, my creativity was lagging. I longed for something else and missed my days of working in the salon, but I feared that I couldn’t have a career that would match the income I made in TV and Film. I took a risk and I did it anyway! I worked for a couple great salons in NY and was was signed on by the professional nail brand CND as an educator. Education gave me the ability to share my knowledge and hopefully inspire other nail professionals. Read more>>

Megan C Tinio | Wedding + Event Planner | Creator of Magical Moments

I think the concept of risk is something that we are often raised to be fearful of. “Be careful” or “be safe” are concepts we are more accustomed and more comfortable hearing. However, I believe that “without risk, there is no reward”. I have seen this play out in my personal and professional life. I moved out of my childhood home and went straight to a 4 year university immediately after my senior year in high school – I was 17. There were many risks involved: I was going to live alone for the first time in my life, I was going to be living hours away from my family and my comfort zone and I was venturing out to start “building my own life” and I had NO idea what that meant. Ultimately, that risk played out. I got an amazing education, I met wonderful people, and it set me on a path that has lead me to the life I live today. I think of the time that I was looking for my first internship. Read more>>

Erica Winn | Food Blogger

Both Justin, my husband, and I were certified public accountants in our prior careers. If that tells you anything, it’s that our nature is to be risk averse. At least we used to be. Over the last five years since we took the most gigantic leap of our lives and quit our corporate careers, moved to a smaller town and began working on our business full time, we’ve become more comfortable being uncomfortable and taking risks to build and grow our business and also ourselves. We think about risk and reward. There is often little reward with no risk. If you play safe all the time, you’re missing out. It’s that simple. That said, we don’t take a ton of totally blind risks, but rather we take calculated, strategic risks where we have some inclination or feeling that it’s the right direction for us. Our risk-taking is largely developed by learning to trust our instincts and intuition. Of course, we never know exactly what the outcome will be, but we’ve developed a learning mindset. Read more>>

Alexa Lowery | Actor & Teacher

I believe in taking risks. Being able to push past fears and take risks opens up new possibilities. It’s important when taking a risk to make a clear, strong & confident choice then execute. I first took a risk when I left my home-state of Ohio and moved across country to pursue an acting career in Los Angeles: 7years later and I’m still taking risks nearly every day. Signing with new agents, choosing which teacher to learn from, character choices, how to approach a script, taking on risqué or controversial roles, etc. Taking risks has helped to develop my self-confidence and has opened up new doors for me. Read more>>

Amir Levi | Entertainer & Activist

I don’t think about it in terms of risk-taking, I just think of it as what I need to do to either find fulfillment, or because my brain won’t let up until I do whatever it’s telling me to do. I’m very much someone who follows my instincts, and whenever I don’t listen to them, there Is usually some sort of consequence. As an artist, one of the biggest lessons I’ve kept with me has been to “Risk. Fail. Risk Again” (thank you National Theatre Institute). So when I had the instinct to start my own dance company in NYC, and then go back to training at conservatory, and then come out to LA for further training, and then to make the decision to stay… All those decisions in life could’ve definitely been considered high risk. And yes, I definitely thought about each of those decisions, but ultimately it was my instincts that had the final say. Also, the decision to live as a non-binary person in my day-to-day, and not just at special events. Read more>>

Ernie Steiner | Visual Artist

For me risk has been a necessity in pursuing a creative career. The trick has been balancing these risks with some aspects of stability and/or being very flexible and making adjustments on the fly. Read more>>

Chris Kostantewicz | CEO of Ck Media

I jokingly say that without risk nothing in my life I do would be possible. I have an all in or nothing mentality, often going all trading stocks or into new business ventures on impulse before I have second thoughts. This is both the reason why I’m successful, but definitely have had a bumpy ride along the way building my agency ck media and losing a TON of money trying to get proficient at trading stock options (still learning everyday). When I left my last desk job in 2019 at first I wanted this hybrid existence of running my agency from my phone but still having a social media marketing career in the industry at least part-time. Afraid to go all in out of fear that if I just worked on my agency, I’d risk becoming irrelevant on my resume, cause at the end of the day, who doesn’t have a side hustle from their phone? This side-hustle turned into a quarter-million dollar per year venture after working on it non-stop for 3 years straight, at times extremely broke and worried about the future. Read more>>

Keosha Griffiths | Owner/Baker & College Advisor

I would say the biggest risk I’ve taken so far, has been moving out of the state of California. I moved out of California in August 2012 to start my Graduate degree work at The University of San Antonio. I moved to San Antonio, knowing precisely 4 people in the city and starting graduate school work. Oh yeah, and I did not have a job at the time. I’m not sure if it was a leap of faith, a quarter life crisis or just a part of taking a huge risk. I was not sure if I would succeed in my graduate school work. I was not sure if I would find a job. If I would even like San Antonio, having only lived in California my whole life. And I look back now, so appreciative of myself for taking that risk. Sometimes we are so used to something, that the thought of taking a risk – is enough to stop us from even starting the steps to take that risk. However, I have learned that if you do not try, you’ll never know what you can do. Read more>>

Ariel McCleese | Director

It was thirty degrees, a dusting of snow making the Joshua trees in our wide shot look like weird alien beings. I called action, and the makeup artist dumped a gallon of fake blood on the body of a naked man lying on the concrete deck. I could see him shivering, hear his teeth chattering. But he was supposed to be dead, his guts ripped out. I called cut; we had to go again. I stood there thinking: What the hell am I doing? My background is in fine art, and I have no formal training in filmmaking. When I decided to direct my first movie, I didn’t know a thing about blocking, coverage, or shooting schedules. What I did know was that I no longer felt fulfilled making static art objects. I craved the urgency of a time-based medium that would allow me to more fully communicate the feminist politic that guides my work and my life. So I took a risk and spent all of my savings making a feminist horror movie. Read more>>

Amber Sullivan | Chef & Menu Consultant

My view on taking risks has evolved over the years. As I grew, I naturally took more risks and quickly realized that outside the comfort zone is where all of the personal growth (& fun) happens. I moved from Dallas, Texas to Los Angeles after college with very little money and no job lined up. I knew it would take some time to get acclimated and comfortable in this big new city but I also knew that it was exactly where I was supposed to be. That’s the thing about taking risks, they kind of force you to trust your gut, your intuition, & yourself. The first year I lived here I was working as a Teacher. Eight months later I had completely transitioned into a new career… working to become a chef. I didn’t go culinary school so this felt like a HUGE risk. It’s now almost five years later and I can confidently say that it was the best decision I’ve ever made. Taking that risk propelled me into a career that’s aligned with my passion and feeds my competitive & creative traits. It’s just as they say, you gotta risk it for the biscuit… and I love biscuits. Read more>>

Elthia | Singer-Songwriter

When I released my debut single, I changed my stage name, all of my social media handles, and deleted all my videos with millions of views so that I could showcase my new work with a clean slate. I worried beforehand that changing everything would relinquish the credibility that I made for myself online and make it increasingly difficult for my existing audience to find my future music. But, by doing so, I was able to find a new audience that really resonated with my new work, and I am so grateful for them. I felt that taking this step was necessary because, for me, creating art under a stage name felt more authentic to my music in a way that using my real name and identity didn’t. With a persona, I can have fun and be more experimental in my work. Taking this risk has been essential in my creative process, and also in the way that I relate to both my art and my audience. Read more>>

Laura Austin | Photographer, Writer, & Videographer

Most people would say that it is a risk to take something you love doing and try to make a living from it. However, I was incredibly lucky to be brought up by two parents who turned their passions into successful careers. So for me, making up your own job never seemed risky, it simply appeared to be the path I was supposed to take. By my early twenties I had already worked in three very different fields… starting as a graphic designer at Quiksilver when I was 18, then to the Online Editor of Snowboarder Magazine at 20, and dropping everything to pursue freelance photography at 22… each move I jumped off a cliff to follow what I was most passionate about at the time. A quote that sticks with me is that you can’t have one foot on the dock and one foot on the boat and expect to go anywhere. Anything truly fulfilling tends to involve risk. Read more>>

Sammy Jo | Cannabis Professional & Social Media Specialist

I believe, is essential in moving forward in just about any area of life. The choices we make can open so many doors for us, and if we learn to let go and trust (the universe, a higher power, ourselves, etc.) we can feel more comfortable taking those risks. The way I see it is, nothing that isn’t meant to be mine can be taken from me… so if I want it, I’ll go for it. I’ll take the risk. If it works out the way I hoped it would, that’s great! If it didn’t, it wasn’t meant to, and I always trust that something even better is waiting for me on the other side. Read more>>

Monica Leigh Rodriquez | Designer, Artist, & Entrepreneur

My creativity and drive comes from a deep place within: autonomous, strong willed, knowing my own. This internal force drives me to take risk because I listen to my instinct and I am confident acting on my ambition and vision. It takes a tenacious strength to drive through the noise of the everyday social traffic with uniqueness, remaining true to vision, sharing with those who who take interest that I have something to share of genuine personal aesthetic with the flare from history intertwined. The intrinsic belief in my creative vision is a force that I can not deny. It pushes me to take entrepreneurial risk. I have taken many risks, I have excelled, I have failed, I have rebuilt and I have succeeded again. The life cycle risk creates when taken from an inner volition is a road paved with difficulty and beauty. Read more>>


I’m not exactly sure when it started but, for as long as I can remember, risk taking has always just looked like opportunity to me. I’d hate to lean into the cliche of “no risk no reward”, so instead I’d put it like this: Risk offers a level of reward unseen along the safe route. I personally need a heavy amount of risk to face in order for my motivation to evolve into dedication. Over the years I’ve realized that without that level of challenge, and some doubt from my peers, I seem become uninspired to press on. The successes are much more fulfilling and the failures become strong lessons that help guide future endeavors. On a simpler note risking something is just a lot more fun for the kid in me. Read more>>

Chance Calloway | Filmmaker & Author

I have a “no net:” policy. I take the leap, whether I fly or fall. And what I mean by that is that if the net’s there, I’m more comfortable with embracing the fall because I know there’s protection before the crash landing. With no net, I start calculating all of the various ways I can engineer a result that isn’t a crash. Have I crashed before? Yes, I’ve plummeted. But the times I’ve soared, I can guarantee they would not have occurred if I had the cushion of a net waiting below. Plus, my name is synonymous with risk. It’s a part of my essence. Read more>>

Iesha Irene | DJ

I’ve been on both ends of the spectrum of being fearful and fearless. You truly never know what can happen until you try! Taking a risk to make a career switch was very scary at first but honestly, I’m so pleased that I went through with it. The universe really opened up for me as far as community and resources because people in my life actually believed in what I was doing. I had no clue that I had so many folks rooting for my wins. I know what it’s like to be afraid of risks, but I also know what it’s like to watch your gift and time pass you by; and the regret is far worse! I’d like to say that I’m making calculated risks, I’ll ‘jump’ but I have a parachute with me. There’s always something to fall back on if it doesn’t work out, but what if it does?. Read more>>

Joseline Mejia | Psychotherapist & Founder of Konnect Counseling Services and Stream Konnections, Inc

During my childhood growing up I played it safe most of the time, even during my adolescence, can you believe it? yes! even then I never took risks, I didn’t give myself permission to explore and experiment. I would always be terrified of the “consequences’” from doing something out of the norm. The “uncertainty” and the “unknown” always caused fear in me. However, I got to a point in my life that I started questioning my behaviors, beliefs and started a self discovery journey that helped me redefined limiting beliefs and emotions that weren’t letting me grow and get out of my comfort zone. The first time that I tool a risk in my career was not due to my inner work was due to circumstances of burnt out and personal things going on in my life. I knew that I could not continue as a clinical supervisor so I decided to start my own business in private practice called Konnect Counseling Services, that allowed me to continue with my inner work, have more freedom in a sense of time with my family and self care. Read more>>

Jenny March | Artist/Musician/Songwriter

I first chose to take a risk when I decided I wanted to move to Los Angeles to work in the entertainment business. Both the acting and music business are not always consistent and so by making the decision to move away from home at an early age, I had to face many difficulties, therefore taking many risks. Jobs aren’t always consistent so you may not have a lot of money at times, and you are left with your faith and your belief in yourself, which is not always easy. I believe that without risks, you won’t ever succeed in life because you won’t experience failure, which means you won’t be able to learn and grow from it. Over the past few years I have focused more on my music career than acting. As an artist you never know what the reaction is going to be to your songs that are released or who is going to see it. You put countless hours and your heart and soul into something and it could ultimately flop. Read more>>

Anna Elise Johnson | Artist

As an artist, I admit that I rarely risk life or limb, but risk taking is an essential part of my work. My creative modus operandi is the invention and establishment of conceptual and physical processes that are immediately subject to revision, restructuring, and possibly subsequent reconstruction. In fact, I feel a bit like Lord Shiva, working in a continuous cycle of creation and destruction. I destroy to create and create only to destroy. For me, being risk averse or “playing it safe” by relying upon obvious, old, or borrowed solutions to the problems that I set for myself is the antithesis of art making. Read more>>

AJ Watkins | Founder/CEO All Natural Kinks

“The comfort zone is a beautiful place, but nothing ever grows there.” This quote always comes to mind when I think of risk taking, because without risk, growth cannot occur. I took a huge risk when deciding to be a full time entrepreneur. At the time I started my All Natural Kinks haircare line, I was working a full-time corporate job at an IT Consulting firm in Washington, DC. Because this job was taking up most of my time, I could only work on growing my business on nights and weekends. I knew the corporate job was not my passion but was terrified to leave it and commit to All Natural Kinks full time. I feared if I left my cozy corporate job, I would not have the means to support myself financially. Despite my fear, I still felt in my gut that this was the best time in my life to take a chance on myself because I had not yet started a family and I knew where I wanted to take my business. In September of 2017, I decided to take the leap of faith and go for it. Read more>>

Cynthia Soto | Graphic Artist & Screen Printer

In the very early stages of my business I just jumped. I did not analyze things or organize myself as I do now. You don’t realize that you are taking risks until you have accomplished something, whether it’s a success or a failure. As I continue to work and grow risks have become easier to take. At first I was scared to do anything, I was scared to quit my job , I was scared to to rank up too much credit, I was scared to commit to anything because I feared failure. I think most people starting their own business were scared at some point. We all don’t want to fail, without realizing that failures are our biggest success in business. In some aspects of the business I just dove in and in others I was pushed but all have tremendously affected my life in such a positive way. Now the way I think about risk can be a bit methodical. I put a lot of effort into what I want out of life, what I want out of my business and I think about what is feasible now and what makes sense for my business and from that I make a decision to take risks. Read more>>

Malcolm Alexander Brinkley | Creator & Host of On The Brink

A friend told me recently that people only regret the leaps they didn’t take over the leaps they actually took. And on the other side of the risks we take are some of the greatest rewards. On the other side of every risk I have taken with On The Brink and beyond, has been some of the greatest breakthroughs for my growth. The most painful or scariest part of risk taking is the process of abandoning the outdated thought processes that guided previous decisions. Whether shooting my shot at larger profile interview subjects or choosing the topics and stories I want to share with the world are risks from where I am standing. The hardest part of the execution for me is fighting the negative thoughts that are trying to keep me comfortable. And there is NO GROWTH IN COMFORT! Embracing and truly believing in the reality that there is something better for me is not easy but one of the greatest opportunities God gives us to choose into a better life. Read more>>

Lily Soleil Correa Lewites | Photographer, Model, Makeup Artist and Event Coordinator

I’d like to think risk has been a choice I have always tried to include in my life. However, a lot of it was probably accidental. The reason I like to think that I have chosen risk, is because I thrive off it. When I make a risky decision, like everyone else, I second guess it and experience anxiety over the it. When the anxiety settles though, those become the rewarding choices. I often create the best work when I have chosen to be strange, to embrace the obstacle rather than pushing it away. My styling, angles, makeup, hair, and location decision are always outside of what I know. It’s where I produce the best outcomes, and perhaps thats not an objective truth but I’d still embrace risk over getting used to how I create, even if its never objectively better than staying the same. Read more>>

Hannah Kwon | Spatial Experience Designer

Growing up in vastly different environments, from Korea, to China, to Germany, and to the United States, I constantly had to evolve and adjust to my surroundings. I had to courageously confront the unknowns every day. Many of these challenges forced me to switch into ‘survival mode’, when I had no option but to face my fears head on in sink or swim scenarios. This came with countless challenges of feeling unsettled, disoriented, and self doubt. From a young age, I learned to put forth the effort to meet the needs to survive the challenges set in my environments. The constant change helped me to understand the growth that results from stepping into an unknown. During my stay in Berlin for study abroad, I felt challenged as a foreign woman in a place where everyone seemed so strong and independent. In the beginning, I was in survival mode, navigating through each day. Read more>>

Erin Alls | Owner of Silicon Beach Homes and Queen of All Things Silicon Beach.

Like most people, I have had to take risks throughout my life and my career to find what works and what does not. How will we know what we CAN achieve if we don’t try? There is a quote by Frank Scully that sums this up perfectly for me: Why not go out on a limb? Isn’t that where the fruit is? I risked moving to California from New York and I risked moving to New York from Virginia. Risk has been a part of my business plan from day one and I look forward to helping my clients navigate any risk they may see in purchasing their dream home here in California. I welcome it. Read more>>

Ellen Ma | Ink Artist & Crafter

I’ve been a pretty big risk taker throughout my art journey. Risk taking has taught me how to set real expectations and that failure is natural, especially since I’m a creative who does a lot of exploration. For example, if I start to think about taking my art in a completely new direction or I thought about picking up a new medium, it’s a lot of time, money, and effort that I need organize my thoughts around. I also think about commitment and passion, and it’s generally those two qualities that will tell me if I’m ready to take the risk. With failure, I think I’ve grown from “this idea didn’t work so I’m going to drop it and move on” to “this didn’t work so let me think about how to refine it before giving up on it” and somehow that process actually makes me really excited. I think it’s a big signifier (and reminder) that I want to learn how to improve and be better. Read more>>

Marianne Steinborn | Founder, indre Ceramics

I always thought of myself being one of the most risk-averse persons in the universe. In everyday life I try to minimize risk whenever I can, although I know taking risk, even in the tiniest situations, spices up your life and takes you forward. But, I would be the one who always picks the same dish on the menu just to avoid disappointment. Stock markets are not for me, I fear losing to much money. I really never asked myself what role risks played in my life. So, you can imagine my surprise when, triggered by your question, I realized, looking back to the major milestones in my life, that I have used to choose the most different and risky path in every case. For example: While everyone of my peer group stayed, I left my small hometown right after high school to work in Frankfurt. I quit my first job not knowing if the university I applied for would except me (it did not). Read more>>

Lisa Loyd | Co-Founder JJwinks

I think risk is an essential part of life, without taking risks how would you know what you are capable of, to take a risky path is scary, yet exciting at the same time. To achieve great successes and even failures you have to put yourself out there and take the risk. I realize risks don’t always pay off and can be damaging, but when that happens you just need to get up and brush yourself off and start over. I have never wanted to live my personal or professional life without challenges and risks. I took a risk when I moved from my hometown of Ann Arbor, Mi. and headed off to the Windy City without a job. I was hired by a company that transferred me out to CA. It was an adventurous risk I was willing to take, I figured if it didn’t pan out I could pack my car and drive back to the Midwest. That was a little over 30 years ago, you could say the move worked out. When Kelly, my business partner and I started talking about JJwinks, I was leading a successful real estate career. Read more>>

Matt Landes | Founder & CEO of Cocktail Academy

Before the pandemic started we were an events and strategy-driven company. When live events went away we had to rethink our business model, and fast! We have a great team around us and we knew we had to figure this new world out. We risked it all and moved our business into building bar experience in a box and delivered direct to door. It paid off! Our team has grown, our clients new and old alike are treated to creative and imaginative cocktail solutions and now we have even more to show for our passion of the cocktail industry. Read more>>

Anthony Shea | Musician and Lead Singer of The Lovepools

I think of risk-taking more-so like thinking outside-the-box. This year I made a goal to make more income from music so seeking new avenues of creative income is absolutely necessary for that. One new avenue for me has been live-streaming music performances on this newer phone-app called LIVIT. Last year I would not have really considered consistent streaming as a way to further my career as an artist. I am now finding there are many streaming talent agencies and some streamers are quitting their serving jobs to pursue streaming more heavily. I believe that trying new things always presents some sort of risk, as you are risking your time and possibly money out of what your normal practices are. Without taking the risks of trying new things, you may miss out on more opportunities and also risk subjecting yourself to monotony. Not taking a risk is a risk in and of itself. Read more>>

Chyenne “Chy” Roan-Santini | Model, Activist, and Author

The concept of taking risks has become an idea that I’ve learned to become homies with. As a kid, I always thought of myself as a star. I loved the arts and anything that involved creating. I remember there was a talent agent that approached my foster mom about me when we were in a toy store. I’m not sure how legitimate it was, and I don’t think my foster mom contacted the lady because she probably was skeptical but from then on, I could picture myself on the walls of malls and stores. I thought, “I could be up there one day, and everyone would recognize my face.” I didn’t get into the industry until much later, and independently at first.. but I believe that there is power in picturing exactly who & where you want to be, because that part came true for me later. The risk in following that vision is equally as important. People may call you crazy or doubt your path, but I’ve found that the more I take risks, the more I end up with results I could have never imagined for myself. Read more>>