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.

Amanda Finney | Commercial & Residential Solar Broker

Risk is another word for opportunity. We bet on ourselves and more often than not we are pleased with the results. We avoid making costly mistakes, and taking frivolous risks however if the choice is safe and stagnant or risk and growth/loss we will choose risk everything. Business without risk is like a birthday without cake. It just doesn’t seem quite as sweet. Read more>>

Bakker Shields | Entrepreneur & Creative

I think as a group, entrepreneurs are very risk-tolerant. I would consider myself to fit into this group. I have noticed that I am definitely much more willing to take risks financially than most of my peers, but I also think it is important to note that the risks I take are calculated. For the most part, they aren’t risks that could make or break me or my companies. I have read about entrepreneurs who take that dive into owning their own business head first, with no safety nets in place, but that is definitely not the route I have taken. Read more>>

Amy Davis | Registered Dietitian & Content Creator

I think taking risks is one of the most important things you can do for growth in your business and in your personal life. Some risks pay off, and some risks you learn from. But swallowing your fear and taking that leap of faith is almost always essential to grow, learn and evolve as a person and in business. Read more>>

Justin Christopher | Songwriter/Artist

Anytime I feel myself at that familiar crossroads; one side sunny and vibrant with lush vegetation, and a fully paved softened path, the other side drastically darker, no clear direction to walk, and a rundown sign stating “DANGER”, I’m inherently drawn closer to the unexplored. Risks are the mirage-like lighthouses that beckon us to do something new, to be different and stand out and against whats expected. Read more>>

LanceBattalion | Answering as a band

If we never took risks we wouldn’t get anywhere. Trying to pursue a music career and taking risks go hand and hand. Read more>>

Jill Malouf | Abstract Artist

“Wow I wish I could do that!” … people told me when I recently announced I was now a full time artist. I hadn’t been in a dead end or meaningless job. I was a partner in a law firm with my name on the door. I loved my clients, my coworkers and even our beautiful offices. It was fulfilling and lucrative – and stressful – work. Read more>>

Cindy Podeschi | Artist

When I think about risk taking, I approach it in two ways. The first way is to limit the amount of risk by learning as much as I can before making a big decision. The second way is to list the Pro’s and Con’s. I think this is very helpful…the Pro’s have to surpass the Con’s before I jump. Most importantly though, I never want to approach life from a “fear” base. Sometimes, especially when it comes to love, you just have to take a leap of faith! Read more>>

Torie Wiley | CEO of Wiley Corporation & The Professor Of The Road- 18 Wheels

You have to take a risk to be an owner-operator contractor in the CDL industry. Sometimes you have to put your loved ones on hold to become a successful owner-operator. It doesn’t matter if you own one commercial vehicle or a fleet of trucks; they are three significant variables you need to meet to have a consistent flow of income and become successful in the business: 1. Hire a professional, qualified and reliable driver. Read more>>

Brittany Williams | Entrepreneur & Influencer

Living life as an entrepreneur, upcoming business owner, and inspiring influencer often comes with many risk. You’re (R)apidly making life changing decisions to better your circumstances. Constantly having to (I)magine your plans and goals while they unravel in front of you. Making daily (S)acrifices to ensure these risk are worth taking, while trying not to doubt yourself. Having the (K)nowledge to know whatever you put your mind to, you will succeed! I took a HUGE risk uprooting my life from Las Vegas, Nv to Houston, Tx with $1500.00 in my bank account. Read more>>

Leslie Boyce | Hair Stylist/business owner

I think of risk as a positive step in life. I definitely feel like risk has played a big part in my life since I was a little girl . But out of all risk I’ve taken, starting my own business and opening my own salon suite has been the best so far ! Read more>>

Damon Zen Drummer | Yoga Musician

I view my created career as The Zen Drummer as a huge risk. I am intentionally taking the risk of doing a passion based business based on the massive upside of a fulfilling life expressing my art, creativity. The fact that I have chosen the transformational yoga meditation realm makes it even more fulfilling. But also, spiritual value based businesses are even more difficult to monetize. Add to that, the music based businesses are difficult to monetize and you have a huge amount of risk when you invest time and money into this. Read more>>

Damarkus Bean | Artist/ business man

Risk taking is like getting out the bed b/c if you don’t get out the bed nothing will take place around the house n without taking a risk you’ll be stuck in the same spot, taking risk is what got half the world rich. Read more>>

Corea Elaine | Pro MUA

Taking risks can either make you or break you. I took a risk and moved me & my son to Dallas without ever visiting and it was the best decision of my life. Coming from a small city like Flint, Mi didn’t really allow me to grow or reach my fullest potential. But after taking the the risk and moving here I feel I’ve grown so much in a short amount of time and finally have a platform to expand my business and really be successful. Read more>>

Wellington Marinho | Architect, Interior Designer, Lighting Designer and Author

Taking risks is about having confidence in yourself. To step beyond your comfort zone require a good strategy and maturity enough to know that everything has 50% been right. But if you don’t try you will never know. I would regret looking at my past and knowing that I didn’t take risks because I was scared to try. My confidence teaches me that I can not always win, but I can learn with every single try. Read more>>

Cindy Olsen | Director of Business Development + Content Creator

I was risk-averse for most of my life due to the fear of failure. I put off a lot of things I wanted to do because I was scared of the unknown, of what people around me would think, and honestly due to expectations of what success is. In my mid-twenties, I realized that I could not continue to live that way. This started a series of changes that have changed my life for the better. Read more>>

Briana Haas | Senior Marketing Executive & Podcast Host

I look at risk as a requirement to truly living life to the fullest. Now, don’t get me wrong, I’ve never jumped out of an airplane or scaled a mountain, however, I have taken risks that have helped shape the woman I am today. From moving to NYC as a young woman – with no job or friends – to launching the Jobs Blow podcast while unemployed and in need of work, I try to live my life with a “no regrets” mentality. Read more>>

Emily Smith | Hair stylist, colorist, make up artist

Taking risks are fundamental in achieving the impossible. In my experience taking a risk gives you the motivation to work harder and provides a greater threshold to Learn and grow from all of the experience taking a risk provides. I left the medical field which was consistent and safe to achieve what I was truly passionate about. In my younger days I didn’t know if I had enough money for my rent, car payment or even food on a few occasions. Read more>>

Krystel Petite | Esthetician Instructor

Whenever people hear the word risk people have two thoughts behind it. One is omg no! They immediately feel fear and the other side of people jump right in. I personally think you should go all in. In life you shouldn’t always live by taking the backseat. In my career I wouldn’t have made it to where I am by not taking risk. I took a risk to leave my job. I took a risk to be a business owner. With taking risk their will be bumps in the road, however when you overcome them, it makes the risk so worthwhile. Never live on the end of fear because you will never experience life to the fullest extent. Read more>>