Be Comfortable with being Uncomfortable.

Dewyngaert Design

I looked over the severance package. Stood up. Shook my former boss’s hand, and walked out into the unknown. This was about three years ago, the first time I had been laid off in my career. But also, it was a time that the path I had been following became derailed, causing everything to be different. This was an uncomfortable time in my life that would turn out to be fortunate.

It’s never easy to confront life’s obstacles. At times we think we have it all figured out, but in this particular scenario, it can erupt right in front of you, leaving us with an uneasy feeling of what tomorrow will hold. To the many that don’t handle change well, this presents a large hurdle to overcome. Rather than sway you from avoiding these times, I encourage you to take these situations head on. In Ryan Holliday’s book The Obstacle is the Way, he discusses the how the challenges we face become our greatest benefit.

Since starting a business, I have found myself in several uneasy junctures. Times where it was necessary for me to step out of the ordinary routine, and change the way I was operating. After reflecting on these situations and seeking advice from others, I’ve come up with some principles to help cope & embrace the idea of being uncomfortable.

  1. No time is the right time.

It’s called a leap of faith for a reason. As a business owner, you have to keep altering your day-to-day, continuing taking risks, scaling, and discovering what this idea you have created will become. I am a firm believer in having peace with a decision, however, there are times you may miss a progressive opportunity because of the fear of stepping forward. Whether it’s renting a commercial space, hiring your first employee, or simply investing income into marketing efforts, these are the challenging hurdles, defining why being a business owner is not for the feint of heart.

2. You aren’t alone.

When I struggle with failure, I search & read stories of how successful business owners overcame their times of opposition. Steve Jobs & Henry Ford, well-known and respected tycoons, have found themselves failing multiple times before finding the best solutions. Go to, find a good roundtable discussion with fellow entrepreneurs in your area, and discover how each person in attendance struggles with the same feelings. I find benefit growing my network of similar minds chasing similar goals, and talking through the fears and discomfort of the day to day. Don’t let your pride force you to not cope, but yet be vulnerable to the feelings. Share them with others around you. The solutions and advice you receive can make the day-to-day a bit easier to take on, and you will feel more confident having a circle of support around you.

3. Trust the process.

When beginning a business, or in the first few years of being live, we tend to focus so much on the future. Rather, place emphasis on the present day-to-day achievements. Every day that the business is open is another day of success you should celebrate. Whether you operate from the coffee table in your living room, or manage a team of fifty employees in a high-rise, you are thriving in the competitive world of owning a business. With this comes the need to take uncomfortable steps to continue advancing. The restless nights, the morning anxiety, these all should be part of the fuel that empowers you.

4. Change is necessary.

Being complacent will lead to nowhere. You may find that things haven’t changed with your business, but how much are you changing as the leader?Ask yourself what uncomfortable risks and decisions am I making to continue the forward motion. Change has its challenges. Today you may be running a service-based business, but could possibly find yourself developing a product that transforms the overall concept. It can be uncomfortable, but change is necessary. Once you accept it, learn from it, and follow it, you’ll learn to appreciate the benefits it offers.

5. Don’t see money as value.

You offer a product or service to your clients, and you get paid for doing so. That’s the model of standard business. Try and not let this process define your business’s success. Many times we pass through a season of minimal to no work, and I take the typical trip into my headspace, considering next career steps. I focus on worst-case scenarios. This the wrong mindset to have. Clients are important to a business, but your growth is the most important part. When things slow down, use the time to read and educate yourself on things that were missed when things were busy. Reconnect with past colleagues and clients. Go to museums, conferences or even travel to look for new inspiration. Don’t look at slow as negative, but a time to reflect on yourself; where you’ve been and what has been accomplished, and to set goals for moving forward.

Venturing into the world of entrepreneurship isn’t an easy task. More often than not, you will feel that its you versus the world. And once you accept the challenge, you can learn to handle the obstacles constructively, growing as a confident entrepreneur, and a person.

Dewyngaert Design

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A creative firm in Atlanta, GA. These are stories of business, design & personal growth. // Check us out at

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