How to stretch beyond your comfort zone

To start your business, you’ll need to engage in some critical self-reflection. You’re about to embark on something incredible. How prepared are you for that journey? There are many essential skills you’ll need to master. But, I believe, one of the most challenging – and the most rewarding – is learning how to stretch beyond your comfort zone. 

And, yes, it is a skill you can learn. 


Here’s how author and inspirational thinker, Roy T. Bennett, defines the comfort zone: 

“The comfort zone is a psychological state in which one feels familiar, safe, at ease, and secure. If you always do what is easy and choose the path of least resistance, you never step outside your comfort zone. Great things don’t come from comfort zones.” 

Roy T. Bennett

There’s a lot to like about that quote, but the thing that resonates with me most is the word “choose.” Stretching beyond your comfort zone has to be an active choice. 

Unfortunately, the way we often talk about the “comfort zone” makes it sound like it’s fixed and unchanging territory. If we approach it with a growth mindset, however, we’ll see that we can push the boundaries and actually get comfortable with more over time. 

When I started 321 Liftoff, sharing my thoughts on a weekly blog was firmly outside my comfort zone. But, I was able to build confidence and comfort by running small experiments. Instead of immediately jumping into weekly posts, I started by writing the occasional article on LinkedIn. That was far less risky because (1) there was no commitment and I could walk away after one article, and (2) I shared it with a trusted network of peers and former colleagues who could give me feedback. Win-win. It was a safe experiment that helped me build some confidence. 

stretch beyond your comfort zone

Now, the boundaries of where your comfort zone begins and ends will be unique to you. It’s often based on your past experiences, assumptions, and the stories we tell ourselves about failure. 

At the end of the day, however, the process to stretch beyond your comfort zone is the same for everyone. 

To understand that process, let’s look at a model from Andy Molinsky. He’s the author of Reach and a professor of psychology and organizational behavior. 

Molinsky explains that the process of stretching beyond your comfort zone typically happens over five stages: avoid, consider, attempt, refine, and enjoy. 

Here’s an infographic I created to walk you through it:

stretch beyond your comfort zone


  • To push past the avoidance stage, you’ll need to have an ongoing conversation with yourself and engage in some critical self-reflection. There are practical steps you can take to deal with your inner-critic – find them here.
  • When you start moving into the attempt stage, you might have thoughts like “I can’t do this” or “this was a terrible idea.” That’s normal. Know that you may need multiple attempts over time before you really lean in and embrace the learning process. Be patient with yourself. 
  • When you do move to a new stage, don’t forget to celebrate. Moving from avoidance to consideration is a huge step, for example. 


Like I often mention to clients, starting a business is not a straight line – and neither is stretching beyond your comfort zone. Know that the zig-zag is normal. 

To succeed, you’ll need to hold an experimental mindset. Starting a business is about reinvention. It’s an opportunity to question everything, even the way you think. 

Over time, your comfort zone will grow to encapsulate more of your life, because you’ve grown in your skills and abilities. When you feel frustrated or stuck, remind yourself that you’re doing something new and that you’ve made an active choice to move forward. 

Remember, we learn and grow the most when we’re stretched, just beyond our comfort zone.

stretch beyond your comfort zone

Now, it’s your turn. 


Here are a few things to think about this week: 

  • How would you define your comfort zone today? Draw two circles on a piece of paper. In one, write down any activity, skill, or topic that you know or are already good at. In the other, write down any activity, skill, or topic that you need to grow or develop in. 
  • How comfortable are you with what falls in the second circle? 
  • If you had to prioritize, which activity, skill, or topic should you be stretching in right now?
  • How might you bridge the gap between the two circles? What small experiments could you run? Be specific. 

Share some of your reflections in the comments or send me a message. 


Starting and growing a business is not a straight line. It can feel messy. It zigs and zags. It starts and stops. It can feel frustrating ven for the most seasoned business owners. And, that’s ok. It’s also an exciting challenge. It’s going to stretch you. You’re going to learn a lot – not just about business, but about yourself. And, that’s why it’s worth it.

2 thoughts on “How to stretch beyond your comfort zone

  1. pambroekemeier May 13, 2020 — 9:58 pm

    I totally get the 5 Stages! I’ve always had a hard time speaking in front of groups and would always find a way to get out of it. And when I started my own side business, I had to come to terms with the fact that I would have to eventually speak in front of groups. So, I finally took the first step and taught a class. I felt it went ok, but I could have done better. I took that and the feedback from the students and made adjustments. I then taught another class, and another class. And then I actually put together a larger online course. The excitement I had when I had my first student sign up for it was exhilarating! I still have a long way to go, but it is the little steps that keep me moving forward. And I’ll keep on taking those steps to get to where my goals lie.

    1. Michael Schefman May 14, 2020 — 6:19 am

      That’s awesome! Great job stretching the boundaries of your comfort zone. 😎🚀

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