Today I’d like to recycle a Troy Story that wrote about in my 2020 lookback. A story that has been a consistent theme and reminder in my life ever since that fateful day. A story that has become a core tenant of my life philosophy, and thus it deserves a post of it’s own.

Let’s dive right into Comfort = Risk.


Summer 2020. I’m at a friend’s place where he has a highline rigged in his backyard. A smaller line of about 35 meters long, good for practicing and training.

At this point in my highlining career, I’m still very much so a beginner. While I’ve entered a handful of times, I’m still learning the ropes of the trade (pun intended😛 ).

My first run of the day was magical. Calmly walked back and forth. Practiced turning around, exposure, bouncing, you name it. I was on fire and in flow. One of the few times in my life I can say this on the highline.

After I finished I descended the tree and went to relax and rejoice in one of the best runs of my life.

An hour or so passes, I smoke a joint or two, a few of my friends had their runs, and lo and behold, it’s my turn again.

I didn’t feel like going out there for a second run quite yet, but my buddy encouraged me to get out there. Told me that the 2nd run of the day is always better as you’re more relaxed.

Fuck it, let’s do it. I put the fear and anxiety I always have when getting out there to the side, and I got ready for another session.

I climbed up the tree, clipped myself into the line, and started to tie my leash.

This is where the story gets a bit strange…

For some reason I couldn’t tie the 8 knot in my leash properly. Every time that I did it, something was off. I tried about 3-4 times and was doing something wrong each time.

Keep in mind I’m still a beginner and I’m also all the way up on this tree alone. My friends would do a double check for me from below once I was ready, but there was no one to help me tie my 8 knot. I still wasn’t completely confident in tying the knot, and thus, I kept making a mistake I couldn’t put my finger on.

After a few attempts the need to pee arose in my bladder as well. So here I am at the top of the tree, trying to tie my knot, getting anxious, and now I need to pee on top of it.

Call it intuition, but I felt that something was off. I decided to call the run off. Wasn’t feeling right. I decided to descend the tree, take a piss, take a breather, and then return again with more calm.

As I started to climb down the tree like I had done some 20 times before, something strange happened.

I describe it like climbing down a ladder. As you descend your mind expects your foot to hit the next rung of the ladder. For me on that fateful day, there was no rung to be found…

Before I knew it, my body turned and twisted to the left. I found myself spinning outward and away from the tree…fast.

Thank god there was a piece of 6mm chord on the tree. Instincts took hold and I grabbed on for safety.

Unfortunately, my only option now was to repel down 10m (30-40 feet) by bare hand. And I did.

Next thing I know I’m sliding down the rope to my safety. I luckily land calmly on the ground.

As I’m overwhelmed with relief that I didn’t just die or get severely injured, I can see everyone running towards me screaming “what happened?!?!”

I can also feel my hands burning. I look down and they are SMOKED. Severely injured and on fire.

(Here’s what they looked like the day after…)

Overall while it was a nearly severe accident, everything was fine. My hands and the strength in my grip/arms saved my life and allowed me to repel to safety. My hands were quite fucked, but the rest of my body and mind were completely fine.

Serious accident avoided – but what did I have to learn from this experience?

Fast forward a few days as I am recovering. I went to a friends house who is also a highliner and climber to smoke a few and watch a movie. My hands were fully wrapped and bandaged, and we talked about the accident.

In that moment he taught me a lesson that I will never forget. The lesson that is the purpose of this article today.

He said to me “in the world of climbing and altitude sports, the greatest risk is comfort. Most of the accidents happen to very experienced climbers. Climbers who are so comfortable that they don’t follow proper safety protocol”.

It hit me like a ton of bricks. It was true. I got comfortable and made a grave mistake. There was a key safety protocol I forgot to follow because I felt safe already.

That 6mm piece of chord that I grabbed onto and descended by bare hand? I should have clipped myself into it while descending the tree. I had the proper equipment – I didn’t use it because I didn’t feel like I needed to. It felt redundant. If I would have clipped into the chord, the situation wouldn’t have happened.

Why didn’t I clip in? Comfort.

It’s a relatively easy tree to climb. After climbing up and down 20 or so times I felt comfortable and felt that I didn’t need to clip in anymore. I also followed the example of my friends – and none of them clipped in when ascending/descending the tree as well.

Lo and behold, I got into the habit of climbing up and down without clipping myself in. I got comfortable with the process, normalized the risk, and in doing so, got a severe injury.

Comfort = risk.

In the world of climbing, highlining, and extreme sports in general, human error is the number one cause of accident and death. Very rarely does the equipment and safety gear fail people. The gear itself is safe. People though, we’re not so safe. We make basic mistakes. Mistakes that can often be fatal.

Even more interesting, very rarely do these accidents happen with a beginner. No, it’s ironic that these accidents happen with the most experienced people.

Beginners? They’re scared as hell. They take every safety precaution imaginable. The people helping them as well do the same. They want to show proper safety protocol, and in doing so complete every minor detail. Even at the risk of being redundant.

Veterans on the other hand? They can often get a bit too comfortable. They stop doing the same things they did as a beginner. Stop crossing the same items off the checklist. Leapfrog steps because it’s not 100% necessary.

I see it all the time with highliners. People who don’t clip themselves in while tying their leash. People who don’t get a double check. People who go out without a piece of equipment called a “hangover” or “rollex” because they think they won’t use it.

While there is a very low chance they will actually suffer an accident, the same principle applies. The people who are the most experienced stop doing the same things they did when they were a beginner because they are now comfortable. They stop following the safety checklist.

Atul Gawande talks about this in the book “The Checklist Manifesto”.

In professions with the highest risk – think of people like pilots and surgeons – following a checklist is mandatory. Skip something from the checklist? Chances of error skyrocket. Follow the checklist? Improved results and safety.

Let’s take this to the next level now. Next I want to explore how this principle presents itself in more subtle ways. Comfort is risky in any area of life – especially when the consequences aren’t as obvious.

Let’s look at some examples.

The first and most obvious example I like to use is the example of starting a new job. Whenever we begin a new role, we are hyper aware of our actions. We want to make sure that we do everything perfectly. Show up on time, go above and beyond on our work, cross all the T’s and dot all of the I’s.

Spend 2-3 years in that same role? I GUARANTEE you are no longer doing the same things that you did during your first month on the job.

Over time we relax. We let the reigns loose a bit. As we see that we don’t have the oversight we thought we would have, as we see the 80/20 of what is actually essential and what isn’t, we slowly do less and less. We relax and get comfortable getting by with the bare minimum that is absolutely necessary, and let the rest slip.

Maybe that translates to answering emails in 48 hours instead of 24 hours (or even immediately like you did when you first began). Maybe that means that the reports you write aren’t as detailed as they were in the beginning. Maybe it’s the way that you talk to your peers and superiors. It can creep in a variety of ways.

I know I am guilty of this 1000%. I’ve been at my current role for over 3.5 years. The way I talk to my superiors has drastically changed. I will often say things and express myself in ways now that I never would have when I first started my role. Those ways of expressing myself bluntly can often get me into trouble.

Another example? When I first started my role I would diligently follow up with every single person who didn’t enroll over the phone on the first call. Now? I know that the vast majority of people who don’t enroll on the first call won’t enroll at all and will probably ghost me – so I don’t follow up with nearly the same intensity. I’ve lost deals as a result of that.

The point here? As I got more comfortable, as I relaxed, I stopped doing my work with the same intensity as when I was a beginner who needed to prove myself. I found the 80/20 of what actually drives results, focused on what is most important, and let the other pieces fall by the wayside. In losing that intensity, there is risk I won’t see the same results any longer.

I now need to consciously follow my checklist of activities, because if I don’t explicitly write it out, I know I probably won’t do it. The comfort in my role has made it risky.

Next let’s look at the example of a relationship –

When we first start dating someone, we want to present the best version of ourselves to that other person. We are hyper aware of how we talk to them, how we treat them, what we talk about, how we dress, so on and so forth.

Over time as we relax, our real selves slowly start to show. People often joke that you don’t really know someone until you live with them, because THAT is when people finally start to see the real you.

Essentially as we relax, as we become more vulnerable, we are more likely to make mistakes and fall into bad habits. This is why the beginning of a relationship is always the easiest phase. The comfort of the relationship can be risky.

What about outside of work and relationships though? Where else does this principle show up in life?

For our next example I want to take this to a different level – the comfort of not needing to make a change at all. The risk associated with the comfort of life.

I see this a lot because well, life is very comfortable for many people. They have a good job, make good money, are more or less in good health, so they don’t really NEED to make a change. They can keep operating exactly how they are with little to no consequences.

I see this most often with questions of passion, fulfillment, and meaning in life. Things that aren’t really essential. People might have some goals related to a passion project that they just never create the time for. A hobby that they want to explore but just never do. They can endlessly avoid it because there is no consequence other than the nagging inner critic.

If I asked you the question, “what happens if you don’t take action”, the answer might be, “well, life just continues on as is.”

What I try to highlight with people is that THIS IS RISKY!

It is risky because of what you are missing out on if you DID take those actions. You are missing out on the potential of what your life would look like, had you actually taken those actions. You could be in a different place, happier and more fulfilled. You could stay at your comfortable 7, or you could have taken actions to bring yourself to a 8,9, or even 10.

What if you did build your art? What if you did build that side project? What if you did start that hobby or diet or exercise routine? What if you did finally stop partying and drinking on the weekends? Where would that take you? What impact would that have on your life?

I think Bitcoin and Cryptocurrencies are a good example here. Let’s say 5 years ago you had $500 you were able to invest into something. If someone approached you to invest in Bitcoin and you didn’t invest, it wouldn’t have affected you. You could have remained comfortable with your $500 in the bank.

What if you did invest that $500 though? It would now be worth 100’s of thousands of dollars! (or more – I’m too lazy to calculate, but you get the point). The risk was what you lost out on by NOT investing. If you invested, you would now be rich. But if you didn’t invest, you stay in exactly the same place you are. The opportunity cost.

I tell this story because 5 years ago I had a friend of mine try to send me $500 in Ethereum. At the time I was like “What the fuck is Ethereum, fuck your Ethereum, send me my $500.” I didn’t even really need the $500 either. I just wanted my comfortable, reliable, $500, in the bank.

If I would have accepted that money? Yep, same principle applies. I missed out on the opportunity. My inaction cost me…big time.

Thus, inaction of staying in the same place – is inherently risky.

My point? If you are at a comfortable point in life where you don’t need to be taking actions to consciously improve your life – well, that’s a fucking risky place to be.

Rounding this long meandering exploration up – I hope you are beginning to see how comfort is risky.

At first we started with the example of extreme sports. Then we touched on work and relationships. Then the opportunity cost of not taking action and staying in comfort land. There’s more examples here too.

Finally – as always 😉 – Flip the lens on yourself!

How does this theme show up in your life? How has this affected you in the past? Have you ever made mistakes as a result of being too comfortable and letting the attention slip? Are there areas of your life right now where you might be a bit too comfortable? What is that potentially costing you?

Journal it all down as a reflection point. If you feel open and vulnerable, let me know in the comments below, or reply to my email here. I’m not some crazy famous author (yet😛), so I genuinely read all of your comments and will always reply.

Overall like always, I hope that this resonated and struck a chord with you in some way. Helped you to gain some insights into your own life.

Or, I hope that you enjoyed reading and exploring this tangent with me as much as I enjoyed writing this with my dog in my lap on a relaxing Sunday afternoon🙂

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