Article | 12 min read

Get uncomfortable: the path to radically better relationships

By Chelsea Larsson

Last updated June 13, 2016

As a child, did you have a security blanket? A toy or bit of fabric that made you feel safe and comfortable. For most of us, we continue this habit as adults. Only in adulthood, security blankets look a bit different—a video game console, new TV, closet full of shoes, freezer stocked with ice cream, a certain relationship. The things, stuff, and people that keep us “comfortable” keep us from questioning what life could be because they tell us this is what life should be.

In 2012, Jonathan Munn decided he’d had enough of security blankets. He detonated his comfort zone by ridding himself of every possession he owned, save 100 items. Needless to say, it was very uncomfortable. Jonathan explored this discomfort for years and discovered something radical. Without the distraction of material comforts, he found a world of possibility and, as he puts it, magic. With unhindered openness, he built a stronger sense of self, rekindled friendships, and started a successful business, BoxedUp.

He now teaches other people how to be radical, get uncomfortable, and rid themselves of habits, possessions, or people who are clouding their path to happiness. Don’t worry, you don’t have to give everything away in order to gain a new perspective on life. Jonathan has a few tips on how small changes can have a big impact on better relationships.


On throwing off the shackles of comfort

You’ve said that once you got rid of all of your things, people became much more important to you. Did you explain your new circumstances when you started reaching back out to people?

Absolutely. I started to appear at people’s houses that I maybe hadn’t spoken to in three months. They were like, “What are you doing? Why are you here? What do you want?” Then I would explain, “Yeah, I gave away all my stuff, We went through a process of them going like, “Well, I’ve got stuff on,” or, “I want to watch this TV show,” and then I became really persistent. I just kept ringing them or knocking on the door.

It was a real kind of shell-shock for everyone, I think, because these days we don’t put an emphasis on friendships. It’s easy to fall into the trappings of yourself and your things, and other people who do exactly the same thing. When people try and break you out of that routine and habit, your natural defense is to go,” I don’t really want to do that.” When you’ve got someone, like me, persistently saying, “Come out. Let’s go play. Let’s go to the pub. Let’s go do something interesting,” it can bring people around pretty quickly, I’ve learned. Persistence pays.

Persistence pays when trying to rebuild relationships?

Yeah, I learned that If you ask (people) enough, eventually they’ll want to spend time with you. There’s a reason you’re friends in the first instance. It’s just re-finding that in a way. It’s sitting down with somebody and learning what it was that attracted you to them, or them to you, in the first place. Why are you friends? What are your common interests? They go further than a TV show or a game console or your stuff, right? Ordinarily, they do. They go a lot deeper.

When you weren’t watching TV, or relying on all of this pop culture knowledge that we fill our lives with, how did it change your conversations with your friends?

I moved from being an incredibly selfish person to incredibly selfless, and I became a listener. That was a really profound moment for me. Up until that point, I was a talker. I’d steal silences, and I couldn’t sit in silence. I couldn’t sit with the idea of emptiness. But, it’s alright to just sit in a room with someone and just be there with them. You can just be present, whether you’re eating food, or you’re watching a film, or you’re staring at the sky. It’s the process of being with somebody, and that was an incredibly powerful movement in myself—learning that sometimes you don’t need to speak. Sometimes you just need to be in each other’s presence.

I moved from being an incredibly selfish person to incredibly selfless, and I became a listener. That was a really profound moment for me. Up until that point, I was a talker. I’d steal silences, and I couldn’t sit in silence. – Jonathan Munn

Do you have any stories of forming new friendships during this time?

One of the best stories is that I met a guy at an event and we ended up founding a radio show together. It was the most surreal experience of my life. We had a late night radio show on a dodgy pirate station in the middle of the countryside in the U.K. We would do that from 11:00 at night to 1:00 in the morning, and we called it “New Potatoes.” The idea is we’d dig up new tracks.

This guy and me, we were from different worlds. I liked music, but I didn’t have an appreciation like he did, and that really took me out of my comfort zone. I would never have been given that opportunity had it not been for me getting outside of that routine, that habit, and that pattern of…I come home from work and I play computer games or I watch TV.

The Language of Fear

Not sure if you are stuck in a comfort zone or not? Jonathan Munn says to listen for these manifestations of fear.

  • Excuses: Do you hear yourself making excuses like, “I don’t deserve that promotion” or “It’s too hard”? The reasons we give ourself for not trying are holding us back. Find out what your excuse persona is and climb these obstacles.

  • Procrastination: We’re all guilty of this one, “I’ll do it tomorrow,” is a common manifestation of fear. It’s not easy to jump off that starting block but once you get going inertia will take you further and further.

  • Agreeing with a non-believer: Jonathan says this one is as common as it is dangerous. You tell a friend your wild idea and they immediately say, “That’s going to be too hard,” or “That’s a stupid idea, it won’t work.” If you let their sentiment feed your fear, you’ll have self-doubt, and never get started. Avoid these non-believers and instead surround yourself with supporters.

Why you should seek discomfort

Speaking of something outside of your comfort zone, why is it so important for someone to step outside of their comfort zone?

I spent a lot of time thinking about this. Our comfort zone is built on fear. We live in a world of opportunity, but fear is what stops us from seeing the big picture. Also, we just exist for a moment. A really fleeting moment. We have a life of needs: eat, sleep, work, etc. If you can get outside of that—that amygdala—that lizard brain that’s scared, and get outside of that and see the opportunity, that’s where the magic happens.

How do you define ‘the magic’?

That’s a bloody good question. What is the magic? The magic is the opportunity and possibility. It’s what lies outside of your fear.

What does finding ‘the magic’ look like in someone’s life?

The magic is in reconnecting with people and reconnecting with the stuff we put into our lives. It’s redefining the relationships with our things, with people, and with ourselves. It’s your relationship with your friends, your family, your loved ones. It’s all of those relationships, but they have a bit more clarity around them and you can see a possibility in all of those things. You’re sort of dusting it off a little bit, and you’re kind of going, “Ah, I can see this for something different now.” I would say that’s the main crux of it— It’s the new relationship that you would have with everything.

You have relationships with everything, and you define how that relationship will work. But sometimes we’re so entrenched in our habits with our relationships that we stop understanding what they are.

We have to get out of it to be able to see it for what it is.

You have relationships with everything, and you define how that relationship will work. But sometimes we’re so entrenched in our habits with our relationships that we stop understanding what they are. We have to get out of it to be able to see it for what it is. – Jonathan Munn

What do you think keeps us inside of our comfort zones?

Above all else, the thing that keeps you in your comfort zone is fear. It’s our reptile brain. It’s the bit inside of us saying, “Don’t do that because you don’t know what’s going to happen. Stick within the confines of what you know,” and I think that kind of comfort zone is almost like a really dangerous place to be. But a lot of us don’t even realize we’re in it.

Why is it dangerous to stay in the safety of our comfort zone?

It’s dangerous because you’re missing out on opportunities. You miss out on relationships. You miss out on reconnecting with people. You miss out on experiences. You miss out on living life.

3 steps to radical relationships

Ready to exit your comfort zone? Jonathan says to focus on these three steps:

  • Get started: Fight the internal battle (the excuses, procrastination, and negative feedback) and just start. Whether that means scheduling a coffee date with someone new at work or building the website for your side hustle, just start. It won’t be perfect right away and failure is better than inaction.

  • Be present: Focus on where you are right now. Not on the past and all of the relationships, things, and actions that defined your life up until now. Stay in the present and make decisions based on what you’d like to do and be in this moment.

  • Be accountable: You don’t want to let people down, especially people that you love. Tell a supportive friend or loved one about your plans. Give them your start dates and your goal dates. Ask them to check up on you in three months to see what progress you’ve made.

Being radical at work

You speak a lot about the stepping out of your comfort zone in our personal lives. How about in our professional lives—does the same apply at work?

We get into cliques at work, don’t we? You have your work spouse and that’s the person you’ll go to lunch with, the person you’ll confide all your problems. That’s a great relationship to have. But, the problem is that you’ll never see another perspective other than that persons. That can be damaging and limited, especially in the kind of work of customer service—you’re only going to have one opinion and one outlook.

The person three cubicles down, or three floors over might have this golden nugget of information that’s stopping you from being the best that you can be within your work. Yeah, your comfort zone really does get into every part of your life, including your work. And work is, for a lot of us, the biggest part of our lives. That’s where we have most of our relationships.

Do you feel like people get stuck thinking about themselves a certain way at work?

Absolutely. In customer service roles, for example, oftentimes our comfort zone is to be reactive. People ring up and go, “It’s broken,” so we react. In customer success, though, it’s proactive. Customer success people think, “I can see that something is about to go wrong. I’m going to reach out to you before it happens.”

Customer service could, and is in some instances, learn a lot from customer success. That kind of learning doesn’t happen unless you get outside of your comfort zone, outside of your department, and go have conversations with people. You must have a willingness to form new relationships with different parts of the business. If you don’t, what you end up with is just your department’s siloed opinion.

You must have a willingness to form new relationships with different parts of the business. If you don’t, what you end up with is just your department’s siloed opinion. – Jonathan Munn

What are small ways people can get outside of their comfort zones at work?

Here’s the easiest way—go and find someone in a different department and have a conversation. Go buy a tray of donuts, come back to your office, walk to another department, find the head of that department, put the tray of donuts on their desk, and start a conversation. Everyone loves donuts.


Jonathan’s actions were extreme; he admits that getting rid of all of your things isn’t the best idea, but this desire to eliminate extra baggage is not unique. In the past year, “elimination movements” have gained popularity across the world. From food-based diets like Whole 30 to the phenomenal success of a book about eliminating meaningless possessions, The Magic Art of Tidying Up by Marie Kondo. People are keen to own less. To be weighed down by less. To only have what is needed and what brings them joy.

This life we have is a great opportunity. Let’s not live it with the blinders on and TVs turned up. Let’s eliminate fear, go out of our comfort zones, and see what life has to offer. Even if it’s just a tray of donuts.

Chelsea Larsson is a content marketer for Zendesk and a frequent contributor to Relate. She believes any problem can be solved with a pen, paper, and Pimm’s cup. Find her on Twitter: @ChelseaLarsson.