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.

Tim & Heather Kostka | Husband & Wife Team. Custom Furniture Builders. Entrepreneurs.

Risk is SCARY. I think it’s something that most people try to avoid. Comfort, security, stability are typically what we as human beings tend to cling to, and risk is the absolute opposite of that. I think we both were wannabe risk takers early in our careers and married life – we took promotions that lead us all over the country from Georgia to Las Vegas, Nevada, to Austin, San Antonio, and Dallas, Texas. But there was also the caveat of a very stable job opportunity, the security of a salary, and the promise of company growth. Read more>>

Danielle Marshman-Hall | Hairstylist & Product educator

A lot of people are afraid to take risks. As a hairstylist, once you graduate from school you don’t necessarily start making money right away. There are options like Great Clips and Supercuts where you can make an hourly wage and tips. If working in the salon is what you want to do, it is a huge risk to start booth renting fresh out of Cosmetology school. Read more>>

Eric Oberto | Singer, Composer, Producer, Actor, Director, & More…

Risk taking is the key to living your life to the fullest! The more risks you take- the more of life’s rewards you are likely to receive. All of my life people have told me to “play it safe” or “go with the flow”, and countless other useless statements that are born out of fear. Sometimes I’ve followed these pieces of advice and I’ve regretted it every single time! My biggest accomplishments and successes have all come from risk taking. Read more>>

Scott Gordon | Entertainment & Business Consultant

I’ve always takin risk since I was little. I grow up in a military family so my father was taken risks while I was growing up. So seeing my father & mother taking risks for there family strengthened who I am. I grew up in a small town in California “Vacaville “. I started doing parties in 83. 16 1/2. Managed my first teen night club in 84. I also had a breakdance group “GBC” & I managed 4 DJ’s. Went to school & had a full time job. It was all about taking risks to see if I could do it. Some ventures were successful some weren’t. Read more>>

Jasmine Rivera | Licensed Esthetician & PMU Artist

It’s simple if I didn’t take any risk I wouldn’t be doing what I am doing at this moment and where I see myself in the future. Taking risk and being extremely tactful in your “risk taking” is important to me my life and future. It helps me get out of my comfort zone , get uncomfortable but knowing that I am going to gain what I am working are for. Most importantly just having faith that by following my heart and taking risk God will guide my path. Read more>>

sweet bonezz | Model & Creator

Realizing in the last years that inhaling fresh air is a big risk itself has helped me take further steps into my career. Any young Hispanic female raised or living in a lower-middle-class neighborhood has never been safe. I learned the hazard starts when you put on the shoe, as one has to check if there are any bugs inside. My eyes have encountered a lot, anyone can be a model, photographer, musician, or dentist. Many try to roll the dice but get caught in scams forgetting any career is a game of chance. The only way to gain is by realizing who you can surround yourself with. In order to gain, conflicts are a must. Read more>>

Hunter Pricer | Owner of American Grit Fireplace and Grill

believe that risk is imperative to success! Initially, I took financial risks to get my business off the ground; creating an LLC, purchasing the tools necessary, etc. I had to bet on myself and the business and it paid off. Read more>>

Hassaan Arien | Realtor

I firmly believe, to succeed in real estate, you have to take risks. As we all know, “high risk… high reward, low-risk low reward” is one of the basic principles of finance and business. Since being a real estate agent and running a business go hand in hand I think this principle relates not only to my career but also to my life. When I first became an agent I was taking a risk by choosing real estate over going to school. Not knowing if I would be successful was a scary thought. Fast forward a little over a year and I think it was the best decision I ever made. I learned to be more confident and spontaneous, Ive met so many people who help me grow everyday, and lastly I’m able to do the thing I love most, help people. Without taking that risk I would’ve never gotten here. Read more>>