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.

Nashe Machiri | MachGang

Risk taking has been my new year resolution that I have been sticking to fully and I have fully embraced the mentality of not having any regrets. This mentality has brought me so many new opportunities and have revitalized my music career. Every successful young person has had to take a big risk and for me to think that I could be different is crazy, and for me to be in a position of having time, energy, and no dependents puts me in probably one of the only positions in my life to take on any risk and try to become as successful as possible. Risk is just something needed for success and I have no fear of failure because that’s just part of the risk just got to work hard and hope for the best. Read more>>

Tindal Muzic | RnB Pop Soul Duo

As a band we see risk as a way to push ourselves beyond our comfort zone. Taking risks has allowed us to imagine a broader scope of what we thought was possible and opened us up to new experiences that have been some of the best things we have done in our career to date. From deciding to become a band and recording our first studio album, to playing on stages we had previously dreamed of like Crescent Ballroom, to opening up for artists we admire like Giveon and Lindy Vision. Taking risks has shown us what we are capable of while allowing us to build the confidence we need to fully embrace our talents. Read more>>

Crystal Stark | Award Winning Vocalist & American Idol Semi-Finalist

I am inherently opposed to risk, but I’ve consistently jumped head first into many different experiences throughout my life and career. Risk taking has been at the core of the biggest experiences of my life. Whether it be jumping out of a plane or trying out for American Idol, every risk I’ve taken has paid off in experience, knowledge, and career advancement. I told my husband the other day “I am constantly terrified.” I explained that I wasn’t in any danger, but I’m constantly pushing myself into new things that scare me. Immediately before COVID hit, I had the opportunity to write, produce, rehearse, and perform one of the biggest one-woman shows of my life: A Tribute to Whitney Houston. Paying tribute to an icon is no small task, but paying tribute to Whitney is an overwhelming undertaking. I wanted every detail to be perfect so I practiced day and night, hand picked and tailored every outfit, planned stage backdrops and lighting, and painstakingly researched as many details of Whitney’s life as I could. Read more>>

Bridget Brooks | Facebook Ad Expert

I guess I would’ve considered myself a risk taker from a very young age. I was always outgoing and the girl who always sold the most candy bars on the softball team. So it didn’t come as any surprise when I told my family I wanted to start my own business. Actually I had started many businesses before but never really saw any of it through. I guess at that time I didn’t understand the importance of a coach. However now that I’ve built a multiple six-figure digital advertising agency, I can look back on each little risk that I took and see how much growth taking that risk gave me. Much like failure you get so much growth from risk. Now don’t get me wrong…. I am not talking about the risk like buying a $1000000 car all on credit. But the risk to believe in yourself to do something more… something bigger…. something better. I took that risk in June of 2019 and my life will forever look different because I believed in my ability to help businesses with their digital exposure. Read more>>

Dr. Vanessa Ruiz | Naturopathic Physician | Enliven Mental Health

This is such a great question because it fits so well with what I’m grappling with personally and professionally. I think about calculated risk as a necessary part of growth and stepping into your next level. Risk can help guide us to take on actions and mitigate damage/harm to ourselves or others. The downside is that it can keep us too safe or unable to act. In the past, risk used to delay me or stop me in my tracks from reaching my goals. Now, I’m used to having small and large successes (failures too!) so risk is just an inherent part of that growth process. Professionally, I’m creating a unique holistic approach in the field of behavioral health and complex trauma – one that encompasses mind, body and spirit in a community setting. It’s a different paradigm so there’s normative fear around what it could look like or how to execute it with success. The upside to this for me is that it’s incredibly exciting and I’ll be able to make a greater impact for others. The risk is there but the call to act is louder. Read more>>

Olivia Gaxiola | Fitness Studio Owner and Instructor

Boy if I had a dollar for every time I second guessed myself when taking risks! lol All jokes aside, taking risks is part of the recipe to success! honestly, you need risk taking in order to succeed. No one ever succeeded by playing it safe. It would be too easy. When I decided to open up my studio, I was given a 55 page lease. I was not ready for that, I felt as if I was giving my life away lol no really, I told myself “Olivia, do you really want to do this?” here I was trying to find a way how to get out of it. However, I knew I needed to be uncomfortable. I also knew if I didn’t take that risk, I would have lived with resentment my whole life. And that was not an option for me. When an opportunity presents itself – take it. So I decided to sign the lease. Here I am (1) year in, and having gone through the worst in these covid times. I wouldn’t have traded anything for it. I am learning so much as I go through challenges. Life is supposed to be uncomfortable, hard and beautiful all at the same time. Next time you find yourself in a difficult position, know that growth comes from being uncomfortable. Read more>>

Arthur Yemchyk | Professional Dancer

I think this is one of the things what can to push you out of your comfort zone , which is helps you to grow up and achieve your goals! I’m from small town in Ukraine. I took a risk to move to the capital of Ukraine by myself in 17th years old. Literally with nothing start building my life and career from the beginning in big city. Which is pushed me to find the ways to grow up. And again after 7 years I decided to move by myself in Los Angeles. Take a risk to leave my career and everything what I had build in the past years and start from the beginning to follow my biggest dreams!. Read more>>

Alyssa Black | Founder, Drawn To Ecology She/Her

Risk-taking isn’t really about risk, in my opinion. We make decisions every day, small ones that only affect that day and big ones that can affect months and years of our lives. But the question is, is it really a risk? or is it presenting itself as a risk but is it really fear? The other personal aspect to risk-taking is how much of your decision-making process is steered by past trauma in your life? I know the question is about risk-taking but so much of what I have learned about it and decision-making is rooted in the experiences we have had across our entire lives. Here is the example I go back to whenever I am making a decision in my life and business. I have two degrees in Landscape Architecture. I was working at a firm in the field I loved and thought I would be doing for the rest of my life. A big life event came up, my mom was diagnosed with breast cancer. I lived 3,000 miles away and couldn’t take the time off that I needed in order to be with her. Read more>>

Alejandra Duarte | Makeup Artist & Business Owner

I love taking risks! I opened a whole new business during a world wide pandemic and it has been going better then expected. I think that if you don’t take risks in life you won’t get anywhere in life. Read more>>

Jeanette Wagner | Life coach & NLP Practitioner

Taking risks is something I’ve done my entire life! I left my country of birth at 18 (by myself) because I had a dream and I’ve lived in 4 different countries since then. I think, to take risks, you have to have a strong belief in yourself and what you’re wanting to achieve. I’ve always wanted to make a difference and I think I always knew that I had something to offer. And that I think is the driver to taking risks!!! You have to be willing to fail and not make it mean anything & keep going!. Read more>>

Brittany Lee | Personal Trainer & Fitness Influener

As Bruce Arians says..”No risk it, no biscuit” I think in life we need to take risks to level up in all aspects. We don’t thrive from our comfort zone or change. Ive been taking risks since I moved to Arizona in 2012 more so than ever. I up and left Oregon on a whim with a friend that moved here with work and invited me to start a new life here. I didn’t have a job, no friends, no family, nothing. It was all new to me. I struggled. I was lonely. I didn’t make great money in the bank job I had been in for years. But I wouldn’t change a thing. Leaving home and struggling, learning, being uncomfortable and growing has made me who I am today. I can look back and be grateful for the things I have gained and lost along the way. The biggest risk that I have taken lately was this past year. 2020 was hard for everyone in many ways but I think people really sank or swam. I didn’t sink… I took this year to find my self. I slowed down and was able to find the things I loved and I things that no longer served me. Read more>>

Nick Hailey aka N. Hail | Recording Artist, Producer, & Streamer

First of all, thanks so much for including me in the Shoutout series. Risk, to me, is absolutely essential to and inextricable from success. In order to get something no one else has, you have to do something no one else would do. In order to experience love, we must be vulnerable. In order to deliver a truly powerful performance, an artist must risk making mistakes. On a philosophical level, risk is what gives live value. Risk is the currency of our life force. If we lived forever, there would be no opportunity cost to our time. Because time is fleeting, we pay for success with risk, or we pay the interest of our mistakes. Since we cannot predict the future, we make plans and by following through or not, we are betting on ourselves (or not) in every decision we make, risking all the other opportunities we could have pursued. So belief and willpower are the driver and the fuel, and risk is the vehicle. Read more>>

Bentley Siimone | Content Creator & Boutique Owner

People who know me well know my best kept secret and I’m so grateful for this moment to share it with you. I think risk are the best thing that God has gifted us. I view risk as the caffeine of life. Something about defying fear that wakes you up. You need that certain mindset to keep you elevated. The biggest thing about my entire entertainment industry career is the fact that I took the risk. Two kids, one baby in each arm, I took the leap. Quit my 9-5 mail order phT position, I jumped off the ledge. Mind you, I had no updated portfolio photos, no guaranteed gigs, no website prepared, no mentor, no agent, no experience in hair or make up, just my big risk. Wow! Becoming a frequently booked not tall enough 5’2, considered “fat” petite model (according to typical upscale brick-and-motar agency standards) has been an experience I cherish so much. The thing about risk is, people think of their own hidden agendas and they figure risk to feel like…speed, rugged roads, friendships, harmony. When love has a whole ‘nother plan for you. Read more>>

Jude & Gabe Adjei-barimah & Martin | Co-Founders

We look at risk as the only way to create greater opportunity. Growth comes outside of the comfort zone and the only way something special can come out of growth is by taking a chance in life. The great DBC once said that “Chances make champions” and that phrase has been a pillar of who we are ever since the first time hearing it. Without risk theres very little reward and without risk in life we wouldn’t be here. As athletes we took chances in order to make plays on the field, trusting our instincts to find greater success for our team. As entrepreneurs we took chances on ourselves knowing that we had the capabilities to do something for the greater good of others but more importantly something we could build to leave a lasting legacy of who we truly we are. Read more>>

Holly Rose | Founder/CEO of Check For a Lump

I think taking risks are what open up the possibilities to many different chapters in one’s life and the potential for growth. That is definitely the case for myself. However, in my opinion my risks were not indeed risks. They were merely actions I made with high enthusiasm and relentless optimistic thoughts of “I CAN.” My entire adult life has been a series of these actions and has given me many beautiful chapters in my life and a few I that were not so beautiful that I learned from. A few of my favorite risks that impacted my life immensely . . . I met my dream man on the beach at the age of twenty-two and I asked him to move in with me two weeks later – Risky? Yes! Twenty-nine years later he is still my dream man and father of our two beautiful girls. We then blindly moved to Las Vegas for a fresh start and opened our 1st vintage clothing store together while finishing college. That college summer we hopped in our car with $300 a trunk full of vintage clothing and stopped in cities along the way to sell our thrift store finds to other businesses. Read more>>

Michael Leto | Healthy Chef

I think risk is a necessary evil, that when approached correctly becomes a gift or blessing. I try to remain consciously aware of my current capabilities, and that has allowed me to grow at a great rate. I have taken small, baby step risks that have helped build my confidence, but not put me in a really tough spot. Read more>>

Rob Ballard | Photographer

I think about risk as part of everyday life, we need it to succeed. The role risk has taken in my career was at the time when I was going to jump head first into photography as a career and then the 2008 economic crash hit. Creative jobs were at risk and many companies did away with staff photographers, it was not a good time to start this career. This is were I decided to risk it all and go to photography school, the risk paid off!. Read more>>

Ali Gentry | Speaker & Founder of ARISE

When people get to the end of their life, they say their biggest regret in life is not taking more risks. Risks, in essence, is taking the chance of loss and danger. But for me, I see risk as the possibility to go an adventure that I never would have gone on otherwise. Every ‘yes’ we take even when we’re scared (or especially when we’re scared) but we see that saying ‘yes’ to the chance of receiving the reward is worth more than potentially being handed a ‘loss’. Risk has to be a prevalent characteristic of an entrepreneur, a leader, and any one who wants to move forward in life. It takes some level of risk to advance it anything we do but I believe that risk is required to achieve our wildest dreams. If we knew it was attainable, the risk wouldn’t be high. If we are pushing past our comfort zone for the chance of something amazing happening, something beyond our current place, no matter the outcome, I truly believe you will still achieve more than you could have if you stayed still, stagnate or stuck. Read more>>

Shae Freeman-Caimitte, EMCTP | CEO and Lead Educator of Community Responders LLC

I believe risks are meant to be taken if you want to make the dreams you have come true. Reaching for your goals and chasing your dreams can be scary, and it takes you out of your comfort zone. By staying in your comfort zone, you will never really reach your full potential, and I want to live as full a life as possible without ever wondering “what if” when it comes to my dreams. The biggest risk so far that I’ve taken in my career when it comes to my business would be the day I decided to leave my employer, and my dream job in EMS….and work for myself full time. I had people who would constantly tell me how much they believed in my potential and would even say that they believed that one day I would take a leap of Faith, and focus on my business full time. Of course, initially I would laugh this off, because I worked for a department that I was in love with, and a Community that I saw myself retiring with. Read more>>

Patherine (Panther) Charoenmins | Food, Travel, & Lifestyle Blogger

I think of risk as necessary for growth. If I didn’t take any risks, I would not be where I am today. At one point I had turned down a consulting role with a Fortune 500 company and left corporate life behind. I consider myself an entrepreneur and taking risks is something you have to be comfortable with. As for my personal life, one risk I took that paid off big time was when I went on a blind date and ended up meeting the love of my life, who is now my fiancé. As a result of some of these risks I took, I get to live my best life. My approach towards risk has evolved over the years. I want to leave your readers with this: Risk can be positive. Don’t allow the thought of taking risks to cripple you from taking action. Consider your intent behind whatever risk you were planning to take. If you’re doing it for yourself and your growth, that is worth it (no matter the outcome, there’s always a lesson to be learned). If it’s to seek validation or means you have to rely on someone else for that so-called risk to pay off, stop right there. Read more>>

Chareonski Gray | Owner and Creator of Traces of Flavor LLC

I have been a risk to taker for as long as I can remember. I’ve always been the type of person that pushes the envelope. Taking risks can be extremely scary but I’m a firm believer in the statement “you miss 100% of the shots you don’t take”. I’ve taken risks in my life as well as my career that didn’t work out as well as I had hoped, but that’s the risk you take, no pun intended lol. But on the flip side, I have taken risks that have been the best decision of my life. Traces of Flavor being the biggest one. I literally had an idea and decided to take a chance on myself. I used my own money and spent countless hours developing a product, in an industry that I had very little knowledge about. Not to mention we were in the middle of a pandemic. I was so afraid that nobody would buy it, or even be interested in it. I had no idea that I’d be here less than a year later having shipped to over 26 states. Traces of Flavor is well on its way to becoming a national brand all because I wasn’t afraid to take a risk. Read more>>

Patrick Gramm | Filmmaker

I’m not risk averse — and that’s probably equally a good thing and a bad thing. I’ve certainly paid the price with taking risks in my life and career, but I’ve also reaped the benefits. My ‘career’ isn’t so much an occupation as it is the winding path of my pursuits — and, behind every great success I’ve had on that path, real risks had to be taken to get there. Neither of my companies, Salt and Lime Agency or Red Volcanic Film Company, would be thriving today had I been risk averse. “No risk, no reward” is a true statement. Read more>>

Anthony Smith Chaigneau | International Creative Director, Artist, Entrepreneur

I have never been risk averse. It is all too easy to not take up a challenge and simply stay in one’s comfort zone, That is not me. I have embraced risk, I have engineered it (created opportunity) and looked at it as a learning curve and a positive element in both my life and career. At the same time I am not cavalier about it. The risks taken are calculated risks that have ultimately paid off so far. I remember, many, many years ago now, being stood at the end of the pier in Key West (on vacation from France) watching the sunset. Three British guys were there also on vacation and we got talking. They offered me an opportunity to join them in a real-estate venture in Palm Springs. It was a serious offer. I had 12 hours to think about it. It was a mad, risky opportunity that was just what I was looking for at that time in my life. I slept on it, dreamy about it all night. Thought it over and over and the next day it was leave with them or go back to my other world. Read more>>

Bailey Crawford Patterson | Photographer + Filmmaker

Without risk, life doesn’t advance. Risk is the momentum that pushes us outside of our comfort zones and forces us to grow. For me, there was a part in my life where I was faced with making a tough decision. Should I keep my reliable 9-5? Or, should I quit that stability and put all of my efforts towards honing my skill, chasing my passion, and growing my business? I took the leap, quit the job, and haven’t spent a single moment regretting that decision. My story is not a unique one. Take a look at all of the people you truly admire in life. At one point, or another, they were faced with that same decision. It is a terrifying, yet liberating experience. If you are ever faced with the same decision I was and you find yourself stuck in an unhappy situation, it is never too late to make the change. My advice to you is: Take The Leap. Read more>>

Ben & Jack DeUrso & FU | Artist Representatives & Production Managers

Jack FU: Taking risks is everything, from the start of a project to the night of the performance or album release. We are as forgiving to ourselves as the friends and family of Citizens’ Loft are; but by taking risks, we inspire others to take similar creative leaps of faith and often, this leads to collaborations that otherwise would not have occurred. Ben DeUrso: Taking risks is important in business and life, yet more important is the factor of knowing which risks you can afford to take. Calculation and risk reconcile each other to make progress. The greatest creations can often come from taking risks, yet sometimes this leads to extended due dates, and delays, especially when it comes to artistic materials. However, as Jack says, if we don’t take risks ever, we close the doors on opportunities. In this regard, we often must take risks on ourselves as well as others. And taking risks or trusting that a risk I took was the right move has often led me to the greatest band members and collaborators of my life. Read more>>

Desiree Hardge | Founder/ CEO

The way I respond to taking risk is that it is inevitable if you want to maximize your success in life. Whatever that looks like for a person as there are various degrees of taking risk. It truly depends on if “the end justifies the means,” ethically and morally of course. I would not be where I am today if I listened to others telling me, ” you cannot…, it’s going to be difficult, you need to stay in your lane, you’re this you’re that etc.” Or even dealing with imposter syndrome and not having the confidence based on previous experiences. Or supportive and knowledgeable people in your inner circle. Whether it was a person who I trusted and by all means had good intentions or a person that wanted me to fail, I always bet on myself and God first and foremost. I have learned that in anything I do, risk is a part of my professional and personal growth and development of pushing the envelope, if you will, to become more into my purpose on this journey called Life. Read more>>