18 Entrepreneurs Explain The Best Ways To Get Out Of One’s Comfort Zone

Want to get out of your comfort zone? Well, it’s not always natural or easy to be creative and get out of the comfort areas as a business owner due to fear of risk-taking, desire for perfection and clinging on to old ways of doing things. So how do you ignite your creative self and foster that in your team? It can be achieved.

Here's how entrepreneurs and business owners get out of their comfort zone.

#1- Discover the nuances with other responsibilities

Photo Credit: Reuben Yonatan

The best way to get out of your comfort zone is to find the person you feel you have least in common with, get to know them, and dive into one of their hobbies or professional responsibilities. On the home front, if you have a domestic partner, ask them to swap duties for a week – you'll quickly discover the nuances to their weekly household chores.

Thanks to Reuben Yonatan, GetVOIP!

#2- Get creative

Photo Credit: Alex Strathdee

It's the worst place to be. A place fueled by your ego. One tactic I implemented to get away from my own head is as follows: I would get into creative ruts. I wasn't inspired at all and I felt burned out by the work I was doing. To combat this, I would wake up every Saturday morning for almost 6+ weeks where I go up to several strangers and ask them if they wanted to grab lunch with me. I know it sounds easy, but it's extremely difficult in practice. I had to learn to let go of my biases, preconceived notions and go up to complete strangers to get them to trust me enough in 30 seconds to hang out with me for a couple of hours. Every yes felt like winning the lottery and this wasn't an environment similar to Humans of New York. I kept it very casual and did so on purpose. Notable highlights: sang Happy Birthday to a stranger, met an individual that grew up with Michael Jackson and played tennis with recent students from China living in Chicago. These casual conversations where my brain was just focused on getting to know these folks made it very relaxing and rejuvenating.

Thanks to Alex Strathdee, inPerson!

#3- Be accountable

Photo Credit: Daisy Jing

It's not enough to set a goal and challenge yourself. It's better to dare, do and be accountable WITH someone else. That person will check on your dare to do new stuff. You can also be accountable to each other. Get out of your comfort zone with an accountability partner.

Thanks to Daisy Jing, Banish!

#4- You have to be willing to give up control

Photo Credit: Tod Colbert

We all seek control even if you think we don't. Routine is control. Our morning routine, the route we take to work, even the way we set agendas for meetings. It is all designed to control our environment and avoid surprises. However, you can only grow or change if you are willing to relinquish that control and venture into the unknown. Think about the route you drive to work. Most likely the same route everyday. You know the coffee shop on the route, how to time the traffic signals, and the best time to leave to avoid the most traffic. It is possible that you have done this for years. So, as a first step to get out of your comfort zone change up your drive to work. Look at your city from a whole new perspective. Be open to new discoveries. Then when you are ready, apply your new-found adventurous side to a meeting or task at work. Driving your colleagues down the same road every time may be comfortable but it also might be hiding their true talents or your companies next great thing.

Thanks to Tod Colbert, Weather Tight!

#5- Ask for a discount

Photo Credit: Jordan Bishop

The best way I've found to push my comfort zone is by asking for a discount on everything that I buy. It may sound odd, but there's a good reason behind it: by asking for special treatment in places where it's definitely not expected, I'm giving myself a constant reminder that I can make things happen just by requesting them. The benefit of this is twofold: it pushes me way out of my comfort zone and keeps me sharp, and it also works more than you'd expect. Personally, I've got plenty of half-price meals and free coffees just because I asked for them, but our business has also received big discounts like fifty percent off of software and twenty-five percent off our payment processing just for asking as well. As an entrepreneur, I can't imagine a better way to continually strengthen both yourself and your business at the same time. If you don't ask, you won't receive!

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Thanks to Jordan Bishop, Yore Oyster!

#6- Learn Something New

Photo Credit: Nate Masterson

One of the best ways to step out of your comfort zone is to learn something totally new. Be it a sport, craft, or skill, all of your ego will go out the window when you're back to the beginner level and it can be a humbling experience. Stepping out of our comfort zone is a useful growth tool that enables us to try new approaches to decision making, fostering creativity and productivity. The real failure is not trying and knowing that many things don’t flow perfectly, but learning to try new ways and taking a few risks shows that you are all about the growth and the process which is often applicable in many other areas, it’s like a value-added trait.

Thanks to Nate Masterson

#7- Be proactive

Photo Credit: Jon Hill

You have to be proactive when you want to push yourself beyond your current comfort limits. Comfort comes from familiarity. This is why I feel the opportunities you happen upon in your daily life usually won’t do the trick—the more familiar it is, the less it will push your comfort boundaries. If thinking about a new opportunity scares you, that’s when you know it’s a chance to expand your horizons. Seek out these moments then be decisive in taking advantage of them.

Thanks to Jon Hill, The Energists!

#8-Do the opposite of your preference

Photo Credit: John Moss

One of the best ways to get out of your comfort zone is to do the exact opposite of what your preferences or instincts tell you, within a controlled and managed situation. Whether that be trying a new food that you think sounds vile or going camping for the weekend when you're more of a five-star spa kind of a person, being bold enough to push yourself when your senses are screaming at you to run away is a really valuable skill to possess. I'm not going to promise you're going to love it, and you might well find out you were totally right in the first place, but the experience itself is vital. So too is learning and developing the courage to go ahead with something when you're not fully sure about it. You can then apply this to your work, to help you to make more effective choices in the future and to prevent yourself from becoming overly risk-averse.

Thanks to John Moss, English Blinds!

#9-Several ways

Photo Credit: Jimmy Nathan Zarate

As many kids do, I started out in life full of optimism and ambition but as life does… it has it's way of beating you down and you lose site of these characteristics. I lost my mother when I was 16 and I quickly turned to anything, like food, friends, alcohol and even drugs, that would provide that similar feeling of motherly comfort. After going to jail and hitting rock bottom, I knew something had to change and that thing that had to change was me. I don't know if I would have ever changed, if the superficial comfort hadn't quickly turned to pain. The answer became clear as mud, I needed to do something different but what was it? I first turned to God, and asked Him why he spared me and not just killed me too. His answer was clearly that He needed me to do some work for Him down the road. I had to better my skill set to go to work. I picked up every book I could find that talked about self help or motivation, including the Bible. They all said the same thing in different ways. Mindset, mindset, mindset… it all starts here. We all have that little voice inside and we have about 5 seconds to pick which one we want to listen to. The good or the bad, the easy or the hard, the comfortable or the unknown. The unknown can be scary and people tend to shy away from scary or fear but the truth is that on the other side of scary or fear is greatness. If you can conquer your mindset then you can conquer anything. Just know that eventhough it is your mind, you typically can't do it alone, you will need help. Call it God, call it a higher power, or call it a coach/mentor… call it what you will. Don't do it alone! So as I said to begin, there are several ways I found to step outside my comfort zone… none of them more important than mindset and none of them more important than having someone to help you along the way.

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Thanks to Jimmy Nathan Zarate, TakeActionAgent at eXp Realty!

#10- Recognize that you can't grow without doing so

Photo Credit: Tiffinie Morton

One of the most important skills to develop is to not be so concerned with what others think about us. When we are able to let go of the need to impress and please everyone, our vision and our path becomes clearer and we can recognize our own wants and needs. I think people tend to hide behind pleasing others and being what others need from them so they can avoid leaving their comfort zone. When you can blame everything you do on doing it for someone else, you don't have to rationalize actions that were taken to pursue your own desires.

Thanks to Tiffinie Morton, Hey Pretty Girl!

#11- Learn more about it

Photo Credit: Bri Bell

If you're holding yourself back from something because it's outside your comfort zone, try learning more about it first. I find tasks often seem a lot harder in my head than then end up being. I look up a tutorial on YouTube or talk to a mentor about it to see if I can gain some insight into the situation from someone who has already done it! Knowing that it has been done before and having a framework to follow can help you step outside your comfort zone and move passed the hesitation you're feeling.

Thanks to Bri Bell, Frugal Minimalist Kitchen!

#12- Know why does it matter

Photo Credit: Daniel Demoss

Every action is backed by a reason, a thought, or a goal. Know why does it matter to you. What will be its impact if you do or don’t? When you know it, then your mind will be more focused to accomplish the task effectively. This approach will boost your confidence and motivate you to stick to your aim and take action to pursue it. Getting out of your comfort zone is a tricky business. Unless your mind not cooperates, you can’t deal with it. You need to tell your mind all the benefits of leaving the comfort zone. Then, only you will able to deal with it effectively and efficiently.

Thanks to Daniel Demoss, Dumbbell Reviews!

#13- Ask yourself three questions

Photo Credit: Heather Vickery

As a success coach, I tell every client I work with that “everything you really want is just on the other side of uncomfortable.” That doesn’t always make it easy but asking three simple questions and answering them fully and honestly can powerfully motivate you into the uncomfortable. 1.) what’s the worst thing that can happen? 2.) what the best thing that can happen? 3.) is it worth risk?

Thanks to Heather Vickery, Vickery and Co!

#14- Change your surroundings

Photo Credit: Sean Weisbrot

As entrepreneurs, we tend to settle down in one physical place in order to develop a routine that allows us to fully focus on the business we're building. After some time, the space we inhabit feels so comfortable that it can make us stir crazy and lose our sense of creativity. The best way to get out of our comfort zone is literally packed a bag and hop on a plane to a different country nearby for a week or two. The mere act of changing our surroundings replenishes our energy levels and gets us thinking creatively again. While in this new place, we must take some time to relax, but also to network. The people we meet in these places may challenge us, be curious about what we're building, may want to even partner with us. We never know what will happen when we step out of our comfort zone, and that's why we must do it more often.

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Thanks to Sean Weisbrot, SideKick!

#15- Adventure with a small group

The “Comfort Zone” can suck all the meaning and purpose out of your life. It lures you in and tricks your mind into thinking that it is where you want to be, then traps you into a mediocre existence. In my 30 years of work, I discovered that my most fond and joyful memories occurred outside my comfort zone, under harsh conditions with my friends. This is when I experienced the most purpose and meaning in my life. It was when I was a Marine within a 40-man platoon, a Homicide Detective in a 20-man unit, a SWAT officer on a 40-man team or a Security Contractor on a 12-man protective detail. What did all of these roles have in common? Conditions that humans were designed to live in, specifically: Belonging to a Group (A tribe), Interdependency (Everyone fills a vital role) Risk / Challenge / Danger (The element that creates camaraderie and brotherhood). Going out to have a drink with your friends won’t cut it. Team sports can possibly help. However, I suggest going on an adventure with a small group. For example, book a 3-5 day excursion that includes roughing-it in the wilderness. Get some friends together and go out and tackle something that puts you in direct conflict with your comfort zone. There you will find that special thing you're searching for.

Thanks to Charles K. Redlinger,  MissionX!

#16- Do the things that scare you

Photo Credit: Jerry Brown

The best way for a person to get out of their comfort zone is to say yes to opportunities that scare them. For example, since I am terrified of speaking on a podcast, I don't hesitate to say yes when someone invites me on. Many people share my fear and for some, it prevents them from achieving their goals. The key to winning in life is to feel the fear and then do the very thing that scares you to death. That is how you escape
your comfort zone!

Thanks to Jerry Brown, Peerless Money Mentor!

#17- Two ways

Photo Credit: Katie Jones

I believe that the best way to get out of your comfort zone is by asking a lot of questions and finding out what other people find important. I keep a list of interesting questions to ask people at networking events. Some of these questions include What is one thing you are extremely passionate about? What makes you angry? What are 5 things you want to be remembered for? If you could deliver a speech to the entire world, what would you say? Through asking these questions, I have learned a lot about topics I had never thought about before. It has helped gain a new perspective as well as relate to people on a new level.

Thanks to Katie Jones, Agape Investing!

#18- Open up

Photo Credit: Kristine Thorndyke

Because I work from home, the majority of the time by myself, I participate in Toastmasters on a weekly basis as a way to still force myself in front of an audience to speak. If you’ve ever been to a Toastmaster’s meeting, you know it’s all based on giving speeches to a group of people. The types of speeches you must complete are already predetermined, meaning you are on the hook for giving a “humorous speech” as well as joining in on activities including Table Topics, which is essentially random questions you read up on stage and have to give a 2-minute speech on-the-fly about. I find this group extremely challenging and it forces me to open myself up to making mistakes or, in the case of the Table Topics, saying something that I didn’t get to think about much ahead of time. I love having control over things and tend to lean towards introversion, so this forces me to learn how to be myself on stage and to be more vulnerable.

Thanks to Kristine Thorndyke, Test Prep Nerds!

What's the best way to get out of your comfort zone? Tell us in the comments below. Don’t forget to join our #IamCEO Community.

Mercy - CBNation Team

This is a post from a CBNation team member. CBNation is a Business to Business (B2B) Brand. We are focused on increasing the success rate. We create content and information focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts, ( and videos ( CBNation is proudly powered by Blue16 Media.

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