Risk is the most common topic that comes up in our conversations with entrepreneurs and so each week we ask entrepreneurs to talk to us on the record about how they think about risk.

Jahna Eichel | Founder The Creative Agency Co | Marketing Strategist + Digital Visibility Expert

Investing in your business is the first step to financial freedom through entrepreneurship. It’s easy to say you can’t or you shouldn’t. Risk is inevitable and until you make the bold move to start, you’ll most likely stay where you are. Covid-19 is a really incredible reminder of how important risk is when it comes to the growth of your brand and business- those that continued to invest in their visibility, their team, their process are keeping their heads above water- some are even scaling at a rate they never expected. The Creative Agency grew 325% in 2020. We hired a bigger team when we knew people in our community needed jobs, this allowed us to make space for growth. Our clients all expanded during 2020 by hiring more, advertising more and taking RISKS. Read more>>

Erin Jones | Online Reputation and Brand Consultant

I’ve been fortunate to always have a wonderful support system, from my parents and family to my friends and peers. At a time that I was really struggling with deciding if I were cut out for striking out on my own, a professional mentor that I’m now fortunate to call a friend sent me a message that said nothing more than “leap, and the net will appear”. I think of that message often, and when I find myself doubting my direction, it helps remind me how I’ve gotten to where I am. Often, taking a risk involves facing uncertainty. Weighing that uncertainty with the potential costs and benefits often helps me determine if a risk is worth taking. Typically, I find that big growth requires a fair amount of well thought out risk-taking. When you add strategy and reason, a risk can transform into a plan very quickly. I’d far rather learn from a mistake than look back and regret never trying. Read more>>

Dennis Sohocki | Sculptor

Being an artist is all about not just taking, but embracing risks and challenges. As I often tell people, there’s a reason all of your neighbors aren’t professional artists, novelists, etc. It’s because it is extremely difficult to create and maintain a career and lifestyle as a professional artist. While I am traditionally cautious in normal health and safety regards, such as motorcycles, viruses, gravity, diet, etc., I do believe, to be an artist, one has to have something to say and share that is meaningful across time and cultural barriers. This has to be based on a life of pushing boundaries and taking risks, of exploration, adventures, and seeking truth. It is through such a journey that one begins to understand and deeply feel the aspects of life and death that are so fundamental to all of us. For example, when I begin a carving in stone, I allow the child in me complete freedom to play, explore, and have an adventure without worrying about where it might lead. If in the process the stone breaks and eventually becomes gravel, so be it. Read more>>

Daniel Hopkins | Personal Trainer & Mindset Coach

Everywhere we look there is risk. Doing anything outside of our comfort zone is risky. Jim Rohn had a quote that went, “Everything is risky. The minute you were born it got risky. If you think trying is risky, wait till they hand you the bill for not trying. You know how risky life is? You’re not going to get out alive. Now that’s risky.” I replay this quote in my head every time I’m about to take a big risk in my life. Taking risks has become a massive contributor to the outcomes in my life. Without taking risk I’d be living the timid approach to life where I never had much because I lived too cautiously. There will always be some level of fear attached to risk. They go hand in hand. It’s the uncertainty factor of not knowing exactly what’s going to happen. The crazy part is, we know exactly what not taking risk will produce in our lives. Risk is the action that takes us from where we are to where we need to go. The balance of life, the yin and yang, applies to everything including risk. Without risk there is no reward. Sometimes, even with risk there is no reward. Atleast no direct reward. And when that happens we need to seek the indirect reward. Read more>>

Tammie Lane | Painter and Potter

You have to experiment and try new things. You will have a lot of things not go the way that you imagined, but the disasters are as important or more important even than the things that go without a hitch. You learn tons from the mistakes. Yes, sometimes it is that, this is not the direction I want to go! That is also unbelievably valuable. Getting too comfortable with one thing that sells, is a trap that will just kill your artwork. You have to keep experimenting and moving forward. If you don’t do that, you lose that messy vitality that comes with trying things that you want to just see where it will go. Read more>>

Laidback Lee | Artist/Creative

I love taking risks now, I remember when I used to be afraid to take risks but now I’ve realized in order to get what you want you have to get uncomfortable and take a few risks. Read more>>

Rebecca Nowosielski | Couples & Individual Therapist

I think about risk as less of a gamble, and more as the process of making a decision. To me, making any decision includes three parts: educating myself, trusting in my abilities, and trusting my gut. If all of those things point me in a direction, that is the way I go. Making a decision becomes more difficult when there isn’t cohesion in direction between the three parts that help drive choice. When that’s the case, there are eight qualities I consider to help me gain more cohesion in direction: being calm, confident, clear, connected, curious, courageous, creative, and compassionate. I ask, which of these qualities do I feel will best serve me to make this decision, and work to cultivate more of that quality or qualities. I see life as a constant dance with risk. Big or small, we are always making decisions that impact the direction of our lives. I wonder, if a decision that feels riskier is one that simply feels most unfamiliar and is hardest to trust? If for a moment we say that is the case, the decisions that I make that feel the riskiest, are the ones that redirect my path. The decisions that feel less risky are the ones that I make to keep me on that path. Read more>>

Kendra Gilbert | OOAK Figurative and Mixed Media Artist

Taking risks is essential to true success. I don’t know of anyone who has never had to make a risky decision, or take a leap of faith, to get to where they are. I’m not exactly what you would call a “major” risk taker, but I do tend to push myself in order to test the boundaries of my abilities and comfort zones. Four years ago, I took the leap of faith, and left my home in Florida, to move nearly across the country to the Rocky Mountains of Colorado. I went from living at sea level surrounded by warm sunny beaches, to 8700 ft. in elevation, in some of the harshest winter weather conditions in the country. I had never even been to Colorado previously, but thankfully my husband is the “Thelma” to my “Louise”, and we decided to risk everything to experience a life we had always dreamed of. We now live that life, and have had many say it’s their “dream” too. We didn’t get here easily, but we had to take that initial risk, which lead us to other challenges, and then ultimately – home. I’ve also taken a quite a few risks in my creative journey as an artist, some paid off, others didn’t. That is just the nature of risk. Read more>>

Drew Button | Artist

I’ll preface this statement by saying, I’m not a huge risk-taker. When it comes to climbing the face of a wall or a rock, I typically won’t hesitate unless it seems beyond my skills as a scrambler. If I can measure something visually and feel confident beyond the shadow of a doubt that I’ll be able to surmount said wall or rock – I’ll do it. I take calculated risks. Risk taking in this way has been key in my development as a man and as an artist. Had I declined to take the risks that I have to this point in my life, I would not feel so handsomely rewarded as I do. As I weigh the possible losses and victories against each other with each calculated risk, I try to remember each time that there is a journey between where I’m standing and that eventual success or failure. That journey will teach you more about yourself and your environment than any moment or destination you’ll eventually arrive at. For the risks I’ve taken, I’ve been rewarded with better balance, communication skills, a career as an artist, and a thriving relationship with my partner. Each of these rewards was preceded by numerous, discouraging failures. Read more>>

Peter Laffin | Writing Coach & Educational Entrepreneur

I’ve always taught my students that writing is not the task of recording one’s thoughts, but rather the adventure of discovering one’s thoughts. So often in life we don’t know exactly what we think about things; the best we have are merely inclinations. But when we take the opportunity to match those inclinations to particular language–which is how I best understand the writing process–we finally, truly see our minds reflected back at us. This involves a tremendous amount of personal, intellectual, and emotional risk. It’s a great deal safer to remain disengaged and indifferent, because then nothing is demanded of us. To understand one’s own relationship with reality is to acquire moral responsibility. I’d like to think that I model this for my students each day, first by discovering myself on the page right alongside them, and then by holding myself responsible to the moral demands of my reason. Read more>>

Shanelle Crankshaw | Salon Owner/ Master Stylist

I believe in most things we do in life realistically we are taking a risk! Whether applying for that new job or promotion. Moving, buying, selling. Making any REAL decision is a risk. That being said not all people have the faith or drive with THEMSELVES to risk ONLY their assets and be willing to take on the liability, responsibility or accountability it takes to put in to start their own journey. We’re afraid of the “what-if’s”. I have always marched to the beat of my own drum. I personally never wanted to regret the “what-if’s”. I’m genuinely risking EVERYTHING I have! An opportunity presented itself and I went for it! I’m confident even when I’m scared. Your foundation and what your capable of doing will openly come from your confidence and how you treat yourself! Give yourself permission to live a big life. Stop playing small. It’s constant hustle and learning my own strengths and weaknesses that continue to drive me. Read more>>

Aaron Anderson | Commercial Photographer | Director

This career is pretty risky in general, most commercial photographers I know don’t really have any idea where the next paycheck is coming from (especially with the current climate of things). When I quit my job over six years ago to become a full-time freelancer we’d just had our first kiddo, and shortly after I quit we found out the second was on the way! There are definitely moments when the risk feels extreme, that was one of those moments, but you kind of get used to the fact that it’s not a normal life. Fast forward to the beginning of 2020 and we made the second most extreme decision of my career, we sold everything and moved into an RV with 3 kids. Our idea was to alleviate the burdens of mortgages, bills and debts, while making a way to move closer to clients in California without actually moving to California. While these choices are extreme, they are also pivotal, it allows me to grow as an artist and a business person, it also allow us to grow closer and have adventures as a family. I’m not trying to make it sound like these aren’t scary decisions, and there are times when I feel like a genuine crazy person. Read more>>

Patrick Marold | Artist

Risk is fundamental in what I do as an artist, as I think it is with most every artist. Inevitably it spills over into my family life and the decisions I make about how I live, and where I focus my attention. Risk is integral in my process of creative development and over time Ive grown familiar with the dynamics of making decisions that push me beyond comfortable paths of exploration and expression. Read more>>

Jill Kristin Berkana | Education Entreprenuer and Holistic Healthcare Passionista

If you do not take calculated risks you risk staying stagnant and missing an opportunity to expand, learn and grow! If the potential only exists for success, then it is not a risk. That’s a guarantee. A risk means you may fail, you may not make it and you may get damaged. This is something to sign up for if you have a solid plan and fully understand what you may lose if it does not work out, if you can sustain that damage and the potential win is far grater than the damage you may suffer. That is the difference between a calculated risk and just risk. If the potential win outweighs the risk of loss it may be worth it to jump off that cliff! Othertimes the juice is just not worth the squeeze. After considering everything, I will often bring in an advisor to bounce everythign off of. They may advise me not to take the risk but I still may decide to. Speaking the risk out loud to another person and trying to convince someone it will work is a great way to convince yourself it will work or figure out why it won’t and explore what can be changed to make it work out better. Read more>>

Sadie McAdams | Freelance Photographer / Videographer

Taking a risk is always a hard decision for me to make. The best piece of advice I ever got was to imagine the (realistic) absolute worst case scenario. Where does that leave you? Would you be okay? If so, then take the risk. Honestly, I am a naturally very cautious person. The last five years I’ve taken more risks than I could have possibly imagined whether that be applying for a job I wasn’t “qualified” for (and getting it!) to moving to Europe. I think risk has to come with the comfort of failure. I’d say in both my life and my career I’ve turned into a bit of a risk junkie. I’ve never regretted a single one. Read more>>

Katherine Frost | CEO & Founder

I never thought of myself as a risk taker until I saw this question. I was 27 when I decided to start my first company, a luxury event planning company. I started working for a Destination Management Company or DMC, when I was 24 and wanted to shake up how local corporate and nonprofits were planning their events. I also wanted to get into the wedding market and loved listening to all my clients and planning the smallest of details to make their event special. Along the way of building my company with employees and clients, I started to think to myself, there has to be an easier way to plan all of these events rather than the systems I have been using. So I started thinking to myself, what would I want from an app as a planner so I can access all of my event details in one central location. The light bulb went off and ORO was born. It took two years to get it off the ground but my planning platform and app are everything a planner needs to plan extraordinary events more efficiently than ever before. I took a risk not only jumping a corporate planning job to start my own, but half way through I decided to jump into tech, because this is what the industry is demanding. Read more>>

Katherine Sleadd | Trauma Informed Life Coach and Friend Breakup Expert

I think of risk as choosing to stay present and vulnerable while navigating what’s unknown. While risk is involved in building one’s business (the decision to quit your day job, renting a space, hiring your first employee etc.), I am drawn to how it shows up in my work as a Coach. When we seek to create a new narrative with our lives, it is a process of discovery that involves risk. I partner with my clients on this journey and we become explorers together of their story and inner world. Risk taking to me plays a role in every session because if I ever think I know the answer, I’m actually the one who is lost. Each time I sit with a client, I say yes to staying present in the unknown, and having shown up to that work in my own story allows me to serve others who desire to do the same. A colleague and friend of mine once said, “Business is risk after risk after risk”, and she is not wrong. I believe it is the same in Coaching as well, you take risk after risk after risk to step closer with your client towards the freedom they desire. To be present in the unknown, whether that’s the future of your business or what’s next for someone’s story, is the essence of vulnerability; and that’s something you cannot do without risk. Read more>>

Amanda Hill | Dance Studio Owner and Dance Teacher

Risk is everything. It is the single most important function for success. It’s terrifying and sometimes you eat dirt, but if you don’t jump into unknown from time to time you will either stagnate where you are or dwindle away what you have. Like they say, “good is the enemy of great.” So take that leap. The day before I signed the lease for any first dance studio, I called my dad in a total panic. I asked him, “What if I fail?” He just replied with, “What if you do?” It took me a while to see the wisdom in that question. At first I said something about how I would be embarrassed. He let me run around these thoughts for a bit until I realized what he was saying. I could try and fail or I could never try… The outcome was exactly the same. But one path at least held the possibilities of me fulfilling my dreams. Read more>>

Amy Kear | Home stager/Interior Designer and Home Organizer

I am a huge believer in taking risks when it comes to my career. The universe loves to support those who take a leap/risk for something they love! Life is too short. You miss 100% of the shots you don’t take! What’s the worst thing that could happen? You fail? Well then get up and try again. If you combine your passions and your talents to serve others, you WILL succeed. Read more>>

Claudia Roulier | Artist

I am a risk taker at least to some degree, maybe not the all in 101% but I think I’m at least 90-95% in. This probably happened because early in my life I was presented situations where I had no where to go but to go forward, suck in a deep breath, say a short prayer, and step off the metaphorical ledge. I had a rough time in my twenties but with two small kids I had to think of them and move forward. I have found that with risk there is often reward, the unknown is also exciting, so I like to keep peeking around the next corner. Eventually all things work out, some better than others but that’s life…….. taking risk is better than complaining all the time and spinning your wheels and going no where fast. Read more>>

Jen Pastalo Dacpano | Creatrix

People who take risks tend to be happier. I read that in a Psychology Today article several years ago. I believe it too. Risk lies at the edge of you becoming something more, at the edge of your ideas manifesting, changing, growing, and shifting. When you take a risk, be it small or large, you feel your heart race a little faster, maybe you have a smile on your face, maybe you furrow your brows, but you’re definitely in for something new, a ride, a journey. Taking a risk means you’ve taken a step. And that’s brave. Read more>>

Josiah Holwick | Digital Filmmaker

“Life shrinks and expands on the proportion of your willingness to take risks and try new things.” – Gary Vaynerchuk Creative endeavors are by their nature are uncertain. Starting a freelance business carries substantial risk; however, embracing the inherent stress of fluctuating income pays dividends. It is the price you pay for opportunity, providing you freedom of a flexible lifestyle where you are in control over your own outcome. A critical component in keeping your sanity is to understand how much risk you are willing and able to absorb. “No worthwhile life can be lived without risks. There will be disappointments and failures and disasters as a result of taking these risks. But, in the long run, it will work out.”  – Alan Watts. Read more>>