Risk Taking & Saying Goodbye To Comfort Zones

Taking risk is natural for some, but in our experience most successful risk takers gradually developed their ability to leave comfort zones and take risk and we’ve asked them to share their experiences and advice below.

Kelly Moon

The only way to improve at anything is through practice. As an immigrant, I was taught to prioritize stability—get into a good college and secure a stable job. I followed that path, graduating from Georgetown and landing a six-figure job in NYC. But I was deeply unhappy. Though I wanted to leave after just three months, I stayed nearly two years before finally quitting my job, with no plan in place. It was the most terrifying decision I’ve ever made, but that leap of faith left me feeling empowered and less afraid. About a year later, I took another risk, quit my second corporate job, and moved to Korea to pursue my passion for art. Now, I’m a full-time tattoo artist and content creator in Oahu. Read more>>

Nina Garcia

Living with ADHD, I had to confront my own emotionally turbulent landscape head-on, not just to survive, but to exist as my most authentic myself. Navigating the extremes of my emotions became an act of necessity — and eventually freedom. Each risk I took was a declaration that I wouldn’t be defined by the chaos within me. Today, I guide others through their own emotional landscapes, helping them engage with the parts of themselves that hold them captive or cause self-sabotage. Read more>>

Elienai Escudero

Since I was a child, my dad always taught me that life is about risks, you can’t live without taking risks. At first it’s terrifying, uncomfortable, then, with time you’ll start to have another perspective of the situation, you notice what you like/dislike, and when you least expect it, you find yourself growing from that experience and move on with another.
Once you accept and learn that life is a risk, you’re going to be happy. No matter what happens everything’s meant to be for your good. The word “risk” will no longer be scary. Read more>>

Nuohan Jiang

I believe that taking risks is essential for keeping creativity alive. When I paint, if I notice myself getting too comfortable with certain techniques, color palettes, or brushes, I actively try to do things differently. I usually start with small pencil sketches before painting. Some sketches are clear, and I know exactly how to execute them. Others are less resolved, with many uncertainties. I often choose the latter type of sketches to paint with because they offer more possibilities and uncertainty in the process. Even though it can be a struggle, I usually end up creating something unexpectedly rewarding. Read more>>

Han Swoish

I developed my ability to take risks by embracing the idea that you never truly know what you’re capable of until you try. I often find myself reflecting on the notion that I would regret not pursuing an opportunity more than I would regret trying something new, even if it doesn’t work out as planned. Read more>>

Robert Wright

When I was in college I had money to start investing in the stock market but I was always so afraid to put large sums of money in at a time because I was too afraid to watch my equity go down and possibly never recover. It wasn’t until Apple and Tesla issued a stock split for their stock in 2020 where I could start buying the stocks that were really appealing to me in bulk loads. At first I started to buy shares just a handful at a time, saw little gains, and thought to myself if I increased my holdings at the entry prices that I had them at I would’ve made a lot more money than before.  Read more>>

Tam & Jt

To us, the thought of risk is similar to solving a puzzle. There are a lot of scattered pieces with multiple starting points and end points. You might not solve it during the first try, but with each attempt, you will eventually reach the end goal. Read more>>

Lisa Coder

Risk is hard. It’s scary. It’s easy to want to stay in your comfort zone, but that’s not how you grow; staying safe is staying stagnant. You won’t know what you are capable of until you try. I saw a silly sign once that said, “be brave enough to suck at something new”, and that really changed my perspective on things. Read more>>

Brian Sumption

I’ve always believed that growth comes from stepping outside of your comfort zone, but it wasn’t until I faced significant adversity while acquiring Troubadour Wine Bar and Minnesota Bartending Services that I truly developed my ability to take risks. Early on, I realized that entrepreneurship is inherently uncertain, but I found that calculated risks are often necessary to achieve success. When I was acquiring Troubadour, I had to navigate financial hurdles, uncertainty about the future of the business, and even moments of doubt. The decision to move forward required me to assess the potential rewards against the challenges I’d face. Read more>>

Lindsey Howard

My ability to take risks has been shaped by a unique experience: I started racing cars at the age of 11 and continued through my early twenties. This sport requires quick decision-making and a comfort with uncertainty, teaching me to embrace challenges head-on. The thrill of racing instilled a mindset that sees risk as an essential part of growth – even when sometimes terrifying. I often remind myself that a “no” answer really isn’t the worst thing in the world which, in return, empowers me to pursue opportunities in both my professional and personal life with more confidence. Read more>>

Alberta Thomas

I developed my ability to take risks by embracing spiritual self-care practices that nurtured my inner peace and helped me find clarity in uncertain situations. By regularly engaging in activities like meditation, journaling, and spending time in nature, I learned to trust my intuition and connect with something greater than myself. These practices gave me the mental and emotional tools to handle challenges, reduce stress, and stay grounded, even when taking risks. Creating a sacred space and setting aside time for reflection allowed me to explore my fears, gain insights, and develop a sense of purpose and confidence. This holistic approach to spiritual self-care enabled me to embrace risks with a clearer mind and a balanced perspective, turning them into opportunities for growth. Read more>>

Justin Soleimani

I grew up in a community of immigrants, and as a first-generation American, I was surrounded by entrepreneurship from a young age. My father, aunts, uncles, and many friends were always their own bosses – whether running small businesses or managing larger ventures. Even my father, who was a doctor, owned his own practice and managed his own employees. This ingrained an entrepreneurial in me from early on. Read more>>