Article by Cecilia Meis

Consider what life would be like if we only did the things we were already good at. We would never grow.

Learning happens outside of the familiar and the comfortable. This isn’t news for experienced entrepreneurs, many of whom know from firsthand experience that trying, failing, changing directions, and trying again is often the only way to succeed.

But is there such thing as venturing too far outside your comfort zone? When are you learning, and when are you simply inducing fear and anxiety just to say you did?

Imagine a person who is afraid of heights generally but willing to ride roller coasters. This person has a full understanding of — and trust in — the safety measures in place. They also have a learned expectation of their own physiological response. In other words, they know their limits, and they make preparations for the times when they are willing to push those limits.

The brain is primed for learning when dealing with uncertainty, which means learning requires at least a little risk. However, taking a risk isn’t always about facing your greatest fear. Small acts like trying a new restaurant or striking up a conversation with a stranger  can be valuable opportunities to learn and grow. Start small.

Best-selling author Brené Brown begins each day with the mantra, “Today, I’m going to choose courage over comfort.” Choosing courage, in all its forms, challenges our preconceived notions and expands our comfort zones. As your comfort zone increases, so does your willingness to tackle bigger risks.

Finding the sweet spot between total comfort and total discomfort requires preparation, honesty, and some risk. Start by asking yourself the following questions:

  1. Have you done the work to ensure you’re prepared for this type of risk?
  2. Is it worth it? Taking a risk for the simple pleasure of overcoming a fear or insecurity is great, but is your time better spent on something more personally or professionally gratifying?
  3. Is this the best time to leave your comfort zone? If you’re in a tough financial spot, for example, now may not be the time to launch a new business.
  4. Are there less risky options that would help build a foundation on which to expand your comfort zone?
  5. How will you respond to failure? Venturing too far from your comfort zone can drain your motivation to try again.
  6. Is there a trusted friend or colleague who can support you through this risk?

Need a little more help getting comfortable with discomfort? Check out some advice from three successful entrepreneurs who have been there before:

ColeCole Hernandez, Founder and Chief Storyteller of Pink Graffiti

Some take one vitamin a day. I take one dare a day. A dare is a courageous action packaged in play. It’s important for me not to allow fear to dictate my life. I choose play.

For more than 14 years, I’ve been helping boutique hotels and travel companies with their marketing and PR efforts. I was inspired to launch my business, Pink Graffiti, out of frustration. Many hotel owners focus only on profit. We all want to make money, but sometimes owners forget that customers don’t buy unless you’re solving their problem or fulfilling their desire. When a business stops caring about wooing its customers, everyone loses.

In late 2018, I launched a podcast, The Daring Kind. I wanted an outlet to speak to brave entrepreneurs, coaches, and professionals who were living in alignment with their personal missions.

There’s no one-size-fits-all approach to leaving your comfort zone. If you are someone who struggles with anxiety, it’s about taking small, incremental steps toward your personal mission through daily dares. I’m a recovering perfectionist, so I struggle with anxiety. This is my approach. For others, it might look more like leaps.

Either way, it’s important to remember to do no harm to yourself or others, and let your dares be guided by what feels energizing rather than depleting. The question I ask myself before I take any major leap is: Would I regret it if I didn’t try? If the answer is yes, I owe it to myself to step into the journey.

Not everything is going to work out. When you dare to take ownership of your life, you’ll never end up empty-handed. There’s always a lesson, an adventure, a friend, or a new opportunity that will come from the energy you’ve created by being more daring.

ShyamShyam K. Iyer, Founder of SKI Charities

I am a finance professional with a focus on international projects and emerging markets. I was inspired to launch SKI Charities in 2010 after the Great Recession. The finance industry was rightly scrutinized at the time, but I knew finance could also be used to support and empower people in the most isolated parts of our world.

To build SKI Charities from scratch, I dipped into savings and raised small donations through our website. Through careful financial management and the pro bono work of attorneys and professionals who shared our vision, we survived the first year, and we have been building upon that foundation ever since.

Although a single entrepreneur may drive early success, I have found long-term success to be a far more bottom-up affair. Ownership and buy-in at the local level will determine the success of any project or enterprise. Autonomy and control must devolve from the entrepreneur to the field. Making this change to my outlook was incredibly difficult for me, a type-A person, but with so many staff members and beneficiaries depending on me to get this balance right, I had no choice but to embrace this type of management.

Without having some knowledge of your limits, there is always a chance of pushing yourself too far too fast. The entrepreneurial path is full of challenges. At its core, it is about a person’s appetite for remaining outside their comfort zone. To leave the stability of a day job, you must be ready — professionally and financially — for a situation where two or three years of limited income and fitful progress are the norm. However, the most important factor is a very personal one: You must be ready to take responsibility for making your ideas into a reality.

RioRio Rocket, Artist, Actor, and Entrepreneur

I could draw before I could read or write. I would draw and sell my own comics to my family members. I began a career as a part-time graphic artist and web designer in the early stages of the modern internet. Through passion for my craft and delivering world-class service, I was able to grow into a full-service commercial graphic art, web development, and digital marketing service.

Today, our career paths are so affected by technology. What you did last year is completely antiquated in comparison with what is being done this year. I’ve had to learn and relearn how to deliver the highest-quality products and services to my clients over and over again. This has made me realize that I must dedicate myself to being a lifelong student of my craft.

I got too comfortable as a visual artist. As with any entrepreneur who eventually reaches the summit, I needed a bigger mountain to climb. So, I entered the acting arena as a voice artist. Eventually, I became a film and TV actor, commercial model, motivational speaker, and event host. I grew up saying I would likely never do those things, but I discovered that I loved the artistry of storytelling with your voice and body even more than I love storytelling with visual art alone.

If you are fearful of change, eliminate all intellectualization of what will or won’t happen. Take action immediately. Action cures fear, and motion creates emotion. You are important. Think and believe that you are an important person with important goals. Visualize yourself achieving those goals. Do this every single day. In most industries, 90 percent of people fail or give up right before they reach what they’re striving for. Be enthusiastic about your goals; never even consider the thought of giving up. You owe it to your future self.

Versions of this article originally appeared on and in the November/December 2019 issue of SUCCESS magazine.

Cecilia Meis is the integrated content editor for SUCCESS magazine and She recently earned a bachelor’s degree from the Missouri School of Journalism. A Kansas City native, Cecilia enjoys sand volleyball, new stationery, and a heaping plate of burnt ends.

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