The Uncomfortability of Success

Jason Bennett
5 min readSep 8, 2022

Ever wonder how some people just seem to get it done while others stagnate? Analyzing my own entrepreneurial journey and my role as a mentor, coach, and or fractional CGO for founders and businesses, here’s a brief on the personal side of startup and how that relates to building or scaling a business.

IBM CEO Ginni Rometty said it best, “Growth and comfort do not coexist.” When you decide to make a change, any change, embracing what is uncomfortable is a prerequisite. It doesn’t matter if it’s learning a new skill, growing a business or making a life change. Enduring the uncomfortable is necessary for learning what you need to learn so you can transform into who you’re capable of becoming.

“We learn in our discomfort zone”

The psychology of, and focus required to achieve personal and professional growth as an entrepreneur is a journey of highs and lows and not a comfortable ride. Dan Coyle, , best-selling author of Talent Code, said “We learn when we’re in our discomfort zone. When you’re struggling, that’s when you’re getting smarter. The more time you spend there, the faster you learn. It’s better to spend a very, very high quality ten minutes, or even ten seconds, than it is to spend a mediocre hour.”

If you’re not ready for that level of commitment, maybe, at this point in time, being an entrepreneur isn’t for you. But if you decide that it is, here are a few things that I have learned along the way that will help you in your journey.

“Growth and comfort do not coexist.”

Embracing a growth mindset

Based on the “Messy Middle” by Stephanie Quilao (stephaniequilao.com)

In a nutshell, a growth mindset, versus a fixed mindset, is the belief that challenges can be overcome. That one can elevate themselves to achieve more than their current state.

Alternatively, a fixed mindset is a belief that we are what we are and that won’t change.

Having a growth mindset is the essence of entrepreneurism. Don’t fret over the title, “entrepreneur”. You’re an entrepreneur when you are striving for change, or growth, in whatever you’re focused on.

Replace the word “fail” in your vocabulary with “learning” and go for it!

Embracing a growth mindset is a way of viewing challenges. Knowing that even if you struggle with certain things, your abilities aren’t set in stone. Your abilities will improve over time. Thrive in the challenges! Failure is not who you are, it is a jumping-off point. A chance to develop your skills. Every time you fail at something it is a learning experience that without it you would not be where you are today. So fail! Fail often and fast. Don’t listen to that voice in your head saying “what if I fail” or “If I don’t try, no one will see me fail”. Replace the word “fail” in your vocabulary with “learning” and go for it!

Find your lane and stay there

Clarity. It’s vital that you get super clear on what you want to create and what your values are and stick to it. Being clear about what your values are and who you are as an individual or a company gives you an attainable goal and a path to get there. Stay dedicated to your core premise and serve your target audience. Clay Clark from the Thrivetime podcast says this about finding your lane, “you should focus on that with a maniacal passion. You should check on the other lanes periodically but you should not be constantly weaving back and forth between everyone else’s lanes. When you leave your lane, you are taking time out of making progress in your lane and you are now going backwards. You must focus on your lane and keep your eye on the prize.”

“You should focus with a maniacal passion”

Learn how to focus

Learn to focus. It’s easy if you try.

Find your focus, getting to the next point is the only thing that matters. There are a few things you can do to help accomplish this. First, avoid Squirrel syndrome. Squirrel syndrome can cause sudden dashes from one idea to another or one project to the next. When this happens, you can easily become unfocused. This is likely to cause you to become frantic about not getting things accomplished.

The result is, you delay or never finish important projects that bring you closer to your goals. Second, focus on one big project at a time. Trying to start multiple projects at one time fragments your focus and time. This can be difficult as an entrepreneur. After all, having multiple great ideas is often how we become entrepreneurs in the first place. However, splitting your time between many big projects at a time can make it difficult to complete anything at all.

Consistency is key

Be consistent! It’s very hard to develop a stellar reputation without consistency. To be known for something you have to provide the same results enough times for people to notice. Inconsistency shows a level of unprofessionalism and untrustworthiness.

Consistency also makes it possible to measure your results. In his recent article, 4 Practical Reasons Why Consistency Is Important in Your Business, Dave Shoenbecyk, an accomplished business and executive coach, says “ If you’re providing consistent work in a consistent amount of time, it will be easier for you to track progress towards your goals”.

If you find yourself in the position of not being able to get where you want to be, start by changing your behavior. Ask yourself what can you do every single day to get closer to your goal, and whatever it is, follow through with consistency.

“If you’re providing consistent work in a consistent amount of time, it will be easier for you to track progress towards your goals”

This is not an easy road but gets easier as your journey progresses. Take the time to learn, reflect, and appreciate the discomfort while maintaining your mindest, focus, and discipline, things will fall into place.

I’m Jason Bennett, a RevOps expert and product-led growth strategist on a mission to help 000’s of Enterprise SaaS founders and teams thrive. I enjoy writing about FinTech and InsurTech SaaS, growth operations, and self-improvement.

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Jason Bennett

I’m an entrepreneur, advisor, and VR fitness nut who writes about SaaS growth tactics, the founder’s journey, and lifehacking.