Entrepreneurs: If You’re Comfortable, Change Something

Jayson DeMers
4 min readSep 29, 2020
Photo by Austin Distel on Unsplash

I would include myself in the camp that claims entrepreneurship is one of the most challenging jobs there is. You’ll wear many different hats, make tough decisions every day, and work long hours for lower pay (at least at the start of your venture). Of course, the benefits of being your own boss and having unlimited income potential balance these challenges, but even so, entrepreneurship is volatile and exciting.

Here’s the strange thing; even in such a volatile position, it’s painfully easy to get comfortable.

Your “comfort zone” as an entrepreneur might be different from the comfort zone of an employed professional — for example, you’ll get comfortable with cutting deadlines close and tense negotiations with certain vendors rather than getting comfortable with a 9 to 5 work schedule — but that comfort zone is as dangerous as any other. If you want to be successful as an entrepreneur, you have to break out of that comfort zone.

Why Being Uncomfortable Leads to Growth

Putting yourself in an uncomfortable position — such as meeting a new type of client or making a new type of product — does a number of things that can lead your business to growth. First, it forces you to try new things. History is ripe with successful innovators who moved forward only because they were willing to do things that other people either didn’t want to do or couldn’t think to do. The more novel and unconventional your ideas are, the more likely you’ll be to break out from the norm and find success. Doing so is also a risk — but without risk, there can be no reward.

Second, trying new things keeps you sharper. The majority of auto accidents happen within five miles of home in part because people are less likely to pay close attention to their surroundings when they are familiar with them. Driving to new locations forces drivers to pay more attention to what’s going on, and taking your business to new locations (physical or otherwise) will similarly force you to pay closer attention to your surroundings.

Third, putting yourself in a new environment stimulates your creative juices. You’ll be able to think more freely and more critically about circumstances surrounding your business, which will open the door to new innovations and new initiatives.

Why It’s Hard to Leave Your Comfort Zone

Even knowing the benefits of leaving your comfort zone, it can be hard to do so. As humans, we naturally seek out “comfort zones” because they minimize risk to us, and therefore minimize stress. Predictability is an important quality when it comes to survival — if you know a predator lurks in certain types of bushes but not others, you’ll become comfortable with “safe” bushes and never venture beyond them. If a third type of bush emerges, which may or may not contain predators, it’s evolutionarily favorable to avoid it and stick with what you’re comfortable with.

This principle, because it’s so hard-wired into our brains, applies to business as well. You become overly familiar and comfortable with the routines that have kept you safe, and you become unwilling to make decisions with the possibility of being unsafe. The difference is that there aren’t any predators looking to kill you — there are risks in making a bad decision, but the promise of what the “unknown third bush” might contain far outweighs those risks.

How to Break Out and Change Something

For some entrepreneurs, this risk taking approach comes naturally. For others, there’s a mass of anxiety that must be overcome to accomplish this. If you find yourself in the latter group, try using one or more of these strategies to help you break out of your comfort zone and change something:

· Don’t overthink it. First, try not to wrack your brain over it. Think things through, but don’t spend so much time on a topic that you psych yourself out of it.

· Talk to other people. Find a support system who will help you through the decision making (and execution) process — even if it’s your own team.

· Start small. Don’t start with huge, business-changing decisions. Start with smaller applications and work your way up.

· Create a failsafe. Build in safety nets to protect yourself in case something does go wrong.

The great thing about changing things to make yourself less comfortable is that it becomes easier over time. The first time you step out of your comfort zone, you might experience fear and anxiety, but by the tenth time, it will come naturally to you, and you’ll still get all the benefits of breaking out.

The next time you start feeling yourself becoming comfortable with your business and your position in it, force yourself to change something. Keep the pressure on, and there’s no limit to how great you’ll be able to grow.

For more content like this, be sure to check out my podcast, The Entrepreneur Cast!

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Jayson DeMers

CEO of EmailAnalytics (emailanalytics.com), a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!