Cultivating Discomfort

Earlier this year I gave a talk at Thelesis Oasis in Philadelphia on Strategic Sorcery for a Volatile World. I talked, as I often do, about Set Point. Afterwards, at dinner, I was having a chat with a Therapist who commented that my advice for people who want to move their set point is exactly the opposite of what he does. He attempts to make people feel comfortable with their life, and it sounded to him like I was advising people to actively feel uncomfortable. 

I thought about it for a minute and confirmed: “Yes. That is what I am advocating. Active discomfort.”

Now don’t get me wrong, I believe in appreciating what you have. Most of the time our net-happiness would be improved by appreciating what we have rather than lusting after what we don’t. But there are some things in your life that you really do want to move and you have to make a choice: you can choose to feel good about your current circumstance, or you can change your circumstances so that you feel good.

It’s just that simple.|

Maybe you are not happy with your emotional state but you have gotten used to being afraid, anxious, and not taking chances. You dream of a bolder and braver self but have grown used to the patterns you have developed.

Maybe you’re not happy with your income even though its around what most of your friends make and are roughly the same economic level you were raised in. You desire improvement, but what you have is comfortable. Even the fact that you struggle is somehow comfortable because you are used to it.

Maybe, like me, you are unhappy with your weight, but have grown comfortable being the way you are. You have to decide: am I going to cultivate comfort and feel ok being how I am, or am I going to cultivate discomfort, so that I go out and do something about it.

You could say the same about love, or health, or emotional disposition, or even your level of spiritual realization: but I brought these three up because they are the ghosts that have haunted me personally. I am not speaking from some lofty tower, I am right down in the muck with everyone else.

When I was a teenager I was a wuss. No reason to beat around the bush, I was a complete wuss and scared of the world. Around the age 15 I contracted measles, which is pretty serious at that age, at one point I could have died. Something inside me shifted. I decided to start confronting things head on, one at a time. I was scared of heights, so I went to Pt Pleasant and spent the night in one of the light towers on the inlet. Knocked it right out of me. I was scared of relating to people I thought were cooler than me, so I started inserting myself into conversations, and developed friendships. That kind of thing.

When I was in my late 30’s and was staring 40 in the face, I realized that if I did not do something to change the career path that I was on, which paid meh but was comfortable as hell for a guy that came of age in the era of the GenX Slacker, I decided to make myself uncomfortable. I would meditate in the morning, than look in the mirror and literally tell myself – “If you stay like this, its gonna make you unhappy and be a fucking disaster”. It worked. I got off my ass and started a company. The first time I saw 10,000 in a bank account after bills, I meditated then told myself – “If you ever see less than five figures in this account again, something is seriously fucking wrong and you need to fix it”. I now do the same thing but with have added my brokerage account and others facets.

Now I am in my mid-40’s and weight not quite as much as my top weight, but close to it. I can see the effects its having on my energy, and now have started looking myself in the mirror and saying “If you get comfortable here, you will literally die before you do the things you want to do.” I have worked out a litany to say before every meal, but instead of a blessing, it is a reminder that what I am consuming should be fuel for transformation – not comfort.

I’ll chime in next year and let you know how it goes. In the meantime, as yourself the following questions:

  • What in my life have I been forcing myself to feel happy with but have dreams of improving?
  • What is the number one thing that I am comfortable with, but shouldn’t be?
  • What makes me happy or comforts me in the short-term, but harms me in the long run?
  • At the end of your life, what will you regret not changing because you were comfortable as you were?
  • How can I cultivate discomfort in this area to cultivate change, but not destabilize my whole life?

A word of warning: many of you reading this suffer from clinical depression, anxiety, and other disabilities that might be impacted if you were to actively seek discomfort. Others of you have walked a long road and overcome many obstacles to accept yourself as you are. This advice, like all advice, is not for everyone. Please keep your own situation in mind.

Click Here to Leave a Comment Below 2 comments
Bunny Boswell

I have been doing a version of this for over 40 years. I define myself as a performance artist, and a rather large part of my work included (not intentionally and not as a focal point) discomfort or rather, as I like to see it, experimenting with new ways od living. I am going to send you a FB friend request and reread this later and dwell on it. Have you read Charles Foster’s BEING A BEAST? Talk about experimenting with discomfort in order to learn something new!!


Comfort is balance. Balance is stagnation, inertia. Movement is imbalance, a force acting stronger than resistance, pushing in a given direction. If you can direct that force, you can choose where you’re going. “Constructive imbalance”, as another author called it. “Getting comfortable with being uncomfortable”, as someone else told me once. Success lies on the other side of that discomfort.


Leave a Reply: