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Tracy Sheen


There is something visceral about feeling uncomfortable that is good for the business soul.

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The question though is how do you maintain a sense of wonder and discomfort when you’ve been out on your own for a while? How do you keep things fresh when you can do what you do with your eyes closed? Questions I have wondered about as I stare down my first decade of being in business for myself.

I explored and questioned and came up with three ways I make myself get ‘uncomfortable’ regularly in business that you may find helpful also:


Yep, I’m putting it out there. I’m leading with the very thing that I have found the most challenging, and the most rewarding. We are all so connected all the time. Our smartphones are never far from reach, and God helps us if we can’t quickly put our hand on that phone. That sinking, panicked feeling that you get for the 15 seconds you run through all the places you could’ve possibly left your phone.

After doing the missing phone dance one too many times, I decided I needed to set aside time in my calendar each day to step away from all forms of technology. For a minimum of 30 minutes every day, I walk out of my office, away from my phone, my laptop, and any other ‘tech’ temptation that may be around and pick up a book, or go and sit outside with my dog, or go for a walk. Something, anything to disconnect.

A wonderful thing started to happen when I made this part of my daily routine. My brain found a pocket of freedom, space where it could exhale and not have to concern itself with the next thought. From there, I started to notice ideas, solutions, and creative concepts pop in. I don’t do anything with them in the moment, but I allow them to bubble up to the surface.

Try it … I’m sure you’ll find yourself surprised by how quickly you become addicted to being disconnected.


Most people I know in business have a small panic attack if they hear from a customer. They assume a quiet customer is a happy customer. I invite you to flip that on its head and think a little about reaching out to your customers on a regular basis and seek feedback on their experiences in dealing with you and the business.

Asking for feedback can be scary, especially if they say something we didn’t want to hear, but, it’s far safer hearing it directly from a customer than to read about it on your social media and then have to figure out the best way to deal with the aftermath of negative publicity.

Make a point to pick up the phone (you, not one of your team) and call a few clients each week. Ask them how things are going, how their last interaction with your business was, what worked well and where you could improve. While you’re at it ask them if there is any other product or service you could be offering which would make life just a little bit easier.


This one follows on from the last point and can be the most uncomfortable thing you can do in business. When someone offers feedback, our usual default position is to justify our own position, creating sides and preparing for battle.

Instead, try to shut up and listen. Remember, the purpose of this is to seek ways you can improve as a business and as a person. This means, potentially, you are going to hear things you may not want to hear. It’s a tough thing to offer critical feedback, so allow them the courtesy of speaking. Sure, you can ask questions to clarify your understanding or their positioning, but for the most part, you are going to want to shut up and let them do the talking.

In doing so, you will find ways that you can tweak a process, implement a new service, or, just alter the way you or the business do things. The point is, we always learn something when we take the time to listen.

I understand that it is a big temptation to reach a stage in your business where you can kick back, set the cruise control and watch the world go by. Doing that though is a recipe for disaster. It’s a recipe for your business to completely disconnect from you and your clients. It’s a recipe for boredom and stagnation.

Instead, why not step up to the plate, jump in the deep end without your floatation device and get yourself ‘comfortable’ with being out of your depth once again. It’ll strengthen your business muscle and keep you feeling engaged.