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.

Alexa Berman | Certified Ayurvedic Practitioner & Accountant

Risk taking has played a huge part in my life overall and I would say having a business in Ayurveda is a direct result of taking a risk. I was dead set on moving to Thailand after college, which I did for two years, and being there led me to my first knowledge of Ayurveda and then led me to pursue it as a lifestyle. Taking risks can be tough to do because of the unpredictability — sometimes they pan out sometimes they don’t, but I would always rather take the risk to pursue an adventure rather than always look back on that “what if.” My life would be immeasurably different if I hadn’t taken risks, and I don’t think for the better. Read more>>

Helen Williams | Founder & Flavor Master

People like to look at starting a business as a risk, but to me it’s just a more obvious one. Because everything about life and being alive is a risk, at all times. Whether you put it all out there and try to create something or if you hang back and don’t ever put yourself out there at all, both choices have inherent risk. Could you lose everything trying? Maybe. Could you never gain or learn anything by not trying at all? Also possible. Perspective is everything. It’s worth it to try something that feels important or meaningful to you. Read more>>

Radhika Mukhija Sud | Coach and Mentor for Busy Women

“Life shrinks or expands in proportion to one’s courage.” – Anais Nin I believe we all have the power to listen to our heart – our inner intelligence – also known as intuition. The wisdom of the heart is powerful and reveals the greatest truth. Oftentimes, it’s not easy and it can remove us from comfort into the unknown. But the risk that we take when it arises from our heart’s wisdom – is the path that leads us to perhaps the most beautiful outcomes, we would have otherwise not realised. That is what happened in my life/career as I took on to risks – small and big. Some that meant leaving the comfort of my home country, credibility at work and loved ones – and landing into a foreign land along with a new relationship and new responsibilities. Had I not taken that leap of faith, I would not have been in a place to take a pause from my fast paced work life and shifted gears. Being in a new country, led me through a series of life experiences, losing my mother along the way – led me back to school and I changed my career from executive/corporate to health optimization, mindfulness and coaching- and to a path of continuous self discovery and education. Read more>>

Caleb McFadden | Musician & Content Writer

I find myself in a lot of situations in which I’m too timid to take the risk — whether it’s out of fear of the unknown or fear of leaving behind comfortability. But because of these fears, I think it’s crucial for any artist or businessperson to take leaps, big and small. Every time I’ve taken some sort of risk, I’ve at the very least learned something about myself or others or my environment. Even when the outcome has turned out to be less than desirable (or just genuinely terrible), I always have an easier time saying, “I shouldn’t have done that”, as opposed to, “I wish I would’ve tried”. Read more>>

Kelsey Lee | Founding Designer & Creative Director at Shakti Creative

Growing up, I was almost always a risk-taker when it came to trying new things. I am 100% an experiential learner, so in order to find my place in the world, I knew I had to to absorb as much experience as I could when it came to friends, hobbies, sports, spirituality and travel. My family was a huge catalyst for this and I have them to thank for always giving me the support to follow my dreams – even if that meant trading my ballet shoes for hockey equipment within a day’s notice! As an adult, my fire for adventure has not gone out, but I have become more mindful about taking risks, especially when it comes to my business. I have spent a long time relearning how to listen to and trust my intuition and knowing what’s worth taking a risk for. I firmly believe the biggest risk we can take is not taking one at all, and on a deeper level I trust that going after what truly aligns with my goals and my beliefs is far worth taking risks for. But that doesn’t mean taking big leaps is always easy for me. Starting Shakti Creative and diving into it full-time in 2019 was a huge risk in itself. Read more>>

Rachel Taulbee | Creative Chameleon

I like to think of risk as an opportunity to step into a part of myself that I have yet to discover. My first big career risk was to leave my amazing job as an elementary music teacher in my hometown and become a Top 40 singer on a cruise ship. It was terrifying and exhilarating and I learned so much about myself and what I’m truly capable of. I spent the next four years traveling around the world using my voice as my ticket, meeting incredible people along the way. I’ve continued to take big risks, leaving the the cruise ship to become a holistic life coach, then a professional princess, and now a corporate event emcee, a singing telegram deliverer, a songwriter, a visual artist, and a creator of original characters. I have created a life that I never could have imagined when I was an elementary music teacher. Even when my life is challenging, I am so grateful I have followed my heart, and I know if I continue to listen to it, it will keep taking me on a ride that will blow my mind. Read more>>

Nadiya Jackson | Filmmaker, Writer, Actress

Risk taking has taken on a new role in my life. It has been simplified to everyday me and other people taking a risk by going to work in essential public institutions in the middle of a pandemic. When I speak for myself, I’ll acknowledge that I have become more timid of taking risks because of the uncertainty we’re currently experiencing. However, it doesn’t completely stop me from believing in taking 2 steps of faith that could transform my life. In terms of the art work I have shared, being authentic and staying true to my voice is a risk in itself. There are those who may not agree with my artwork, that doesn’t stop me. I possess the courage to stand by my work and the messages I spread. I practice taking risks with intention and I do confess that during these times I am filled with doubt. However, if I were to refrain from taking particular risks, I will be cutting myself off from exuberant experiences. I have taken risks and the outcome may have not been what I was hoping for, but I can go to sleep at night knowing that I still took a chance and learned something I wouldn’t have discovered had I not taken a risk. Read more>>

3lack | Recording Artist

I feel like risk taking is the center of any breakthrough. Those that take risks get ahead and lead the pack, while those that don’t have to sit with regret and watch others keep moving forward. Taking risks has elevated my life in multiple ways. I’ve learned from my experiences (both successes and failures). Without taking risks I don’t know where I would be but I know for a fact that I wouldn’t be who I am today. Especially taking risks and being vulnerable with my expression in my music. Read more>>

Bekah Lynn Broas | Portrait & Event Photographer

I love the quote from my favorite movie, Elizabethtown: “Those who risk, win.” It just says ‘win’, not necessarily “have great success”. So then, what is winning? Well, to me — winning isn’t really all about beating someone else. It has more to do with the race within myself. See, when I started out a few years ago to venture into the world of owning my craft, that move was indeed seen by others (and initially by myself) as –risk. Up until that point, I saw risk as a negative thing: it’s the sock that gets thrown into the dirty laundry basket, or even the Goodwill bag. Something to quickly discard. But the crazy thing is, like how Claire said it at the end of that movie, it is only through risking that you truly win. And I’ve found that winning, is actually about becoming victorious – not on the outside, but from within. It wasn’t until I risked quitting my 9-5 day job and stepping off the cliff of opening an LLC, building a brand and trying to “do the thing”, that I actually experienced that free-fall-feeling of being truly alive. I’m not gonna lie, stepping off the cliff is scary. Risk is scary. Read more>>

Leah Martin | Business Owner & Friend

I know I’m more of a risk-taker than some of my fellow business owners. I don’t take risks lightly, but I tend to be confident in making those decisions that others might shy away from, or hesitate to make for fear of failure. In my mind, it’s ok to fail at something; failure can be a way to gain important experience and learn valuable lessons. I think I was raised in such a way that I was confident enough to try new things. I’ve always been unafraid to jump in and try things out. Some people see that as risky, where I see it as opportunity. I took the risk of starting a business with my friend. I worked as much as I could on the business while still working full-time. As soon as I could, I took a leap of faith and quit my successful career and moved full-time to our business. That risk has paid off, and has put me on a completely different life path than I ever envisioned. One full of purpose and meaning. Read more>>

Bria Henson Valdez | Holiday and Event Design

Risk taking is an important part to personal growth and business growth. It requires being vulnerable and accepting failures along with the success. Every time I decided to take on a new concept for an event or holiday design that was over my head, it was a risk. I was scared to disappoint a client, but knew if we didn’t take a chance we could miss out on something beautiful. More times than not, it paid off. I would learn from that risk which broadened my skill set. If the risk didn’t succeed, it became a teachable moment. Learning from the failures is as important as the success. It helps you grown in wisdom and experience. I am still taking risks, and those risks still make my stomach turn until a project is complete. There is no greater joy then watching my hard work, success or failures, come together. Read more>>