In the earlier part of my life, I unconsciously trained a lot of skills that allowed me to cope with the things in life I couldn’t be with.

For example, I trained the ability to be comfortable by myself, as this allowed me to avoid rejection. If I’m fine by myself, then I don’t need to invite people to do things and or ask if they’ll come to my party, and then I don’t have to deal with them saying “No, not interested”. 

Once I found transformational work, I became conscious of the cost of a lot of these skills. 

While I could avoid rejection by having a fine time by myself, I often felt kind of lonely underneath the surface. It also became harder and harder to show up to social gatherings, or hold my own party.

Consequently, on the other side of transformational work, I’ve spent a lot of time consciously training new skills that serve me differently. Some of these skills might support you. 

Here’s a list of eight that might be helpful for you:

  1. Sitting With Silence in Conversation

This has been really hard fought territory. I had a lot of concerns about feeling or creating awkwardness when in social situations, and so I took on 200% of the responsibility for how a conversation went. This meant that I would talk your ear off until I could end the conversation and take a break.

Conversations were exhausting for me, even though you would assume I was an extreme extrovert.

Learning how to sit in silence was life-changing. Suddenly conversations, social situations and most of all, networking events stopped feeling like work. They actually resourced me instead of draining my energy.

The way I learned this skill was a very simple, very excruciating practice: Any time I was in conversation, say what I have to say, and then pause. Count to ten in my head before I say anything else.

Initially I thought I would die or the person across from me would scream “You’re awkward and weird!!”. Instead, as I was counting, they’d say something, and the conversation would carry forward. How odd.

  1. Forget People’s Name

I hated the idea that people might feel forgotten by me, so I would make a point of remembering everyone one’s name. This was great, until I, being a human, would forget someone’s name.

Imagine that fear that would quell up inside me when I would come into a party, greet four acquaintances by name, and then forget the fifth one. My coping strategy was to simply avoid or ignore that person, as I couldn’t bear the thought of not knowing their name.

Learning to give myself permission to be human and just ask people to remind me of their name has made a huge difference for me.

I learned this skill at a Christmas party once, when a co-worker of my wife was taking a drink order, and asked me for my drink order. I told him, and reminded him my name was Adam. He smiled and said “Yes, I don’t remember your name, but I definitely remember you.”

How artful — I felt appreciated and remembered, and now he knew my name again.

These days I have permission to forget peoples names, and more importantly, for my own humanity to exist. It’s okay that I forget someone’s name. It doesn’t need to mean anything about me or them.

“Sorry, my brain must have mis-stored your name. Can you remind me?”

  1. Breathe and Smile

I had a lot of trouble being with bad humour. Like, if someone told a bad joke, and it was just sitting like a fart in the middle of the room, I would make a point of laughing and heightening the joke.

If someone was trying to make jokes to make themselves a feel a little more ease (like when they’re giving a presentation and they’re trying to make you like them, or something like that), I would make a point of laughing.

I did this, because I couldn’t handle my own jokes falling flat, and consequently, couldn’t handle anyone else having the same experience.

I had a hard time hanging out with anyone for very long if they didn’t “have a good sense of humour”. Hanging out would feel like work, because I had to put on a false show that I was laughing at all these jokes, or whatever.

These days, I give myself permission to not laugh. Instead, I take a breath and smile.

The smile is an indication of me loving the person in front of me, even if their humour isn’t grabbing me. I can look at what else I appreciate about them, or simply appreciate their courage doing something uncomfortable.

Ironically, my need to jump in, laugh, heighten and ease someone else’s tension had me take up some of the spotlight and possibly make them more nervous.

This skill has also allowed me to keep myself out of the space, so that the person in question can find their footing and learn to trust themselves.

  1. End a Conversation

I used to experience conversation as a timebomb waiting to go off. 

It was only a matter of time before I believed you’d grow tired of me and make up an excuse to leave.

Because I couldn’t handle the idea of that excuse, I would do one of two things — I would awkwardly end the conversation prematurely, or I would sit in the conversation with someone forever.

The latter we would probably call introvert behaviour these days. Even though I was finding the conversation draining, I didn’t know how to end it, and I didn’t want to make the person I was talking to feel bad, so I’d just sit in the conversation forever.

These days, I’ve practised training the permission to simply end a conversation when I’ve had enough of it.

“Hey, it’s been great chatting with you, I’m going to stand over here for a bit now,” or “Thanks for sharing all of that, I’m going to go fill up my drink,” or even, “This has been great, there are a few other people I want to chat with so I’m going to mingle.”

Of course, people might still feel like I’m ditching them, but this practise has really been about giving myself permission to trust how I feel, and to allow other people to have whatever experience they may have about that.

  1. DNF Books, Video Games, Movies and TV Shows 

Growing up, I would often reach a point in video games or books where I was no longer interested in continuing with them. I often felt really bad about this moment, feeling like I should push through.

I had a story that I wasn’t a finisher, and never really stuck through until the end of what I was pursuing, and as a result, I should make myself push hard to change this habit.

On the one hand, I’ve discovered, as I’ve built a career in coaching, that there’s been a lot of uncomfortable places where I’ve had to finish in the face of my resistance to quit, because quitting would be easier. Overcoming this threshold has been challenging.

But, I’ve also learned that we don’t have to be the same everywhere. While it’s important to me that I deepen my ability to be my commitment in professional and relational areas, my hobbies — not so much.

I read books, watch TV and play video games for pleasure, fun and enjoyment. If I’m no longer getting those things from the particular pursuit in front of me, I’ve learned to trust that part of myself. I set aside the book, game, show or movie, and move on to the next.

  1. Allow Myself to Suck

Letting myself suck at things I don’t care about improving at is easy. But there are other hobbies I like to pursue that I do care about. 

I want to improve at pickleball. I’m competitive, to an extent, and stagnation is boring. I want to see my skill improve over time, and I’m willing to practise to do so.

However, I’ve noticed that as soon as you put me in a tournament or a league where points and winning have some significance, I stop having fun and I start playing poorly.

The same thing happened when I was a squash player. I could play great, right up until the tournament began, and then everything fell away. I stopped having fun, and my forehead became a mess of consternation and wrinkles.

I would try and tell myself, “You’re a coach, you should bring this to your coach and work through this. This is just like everything else. You should take this on.”

But over time, I’ve realized that I don’t want to turn everything into my life as a coachable moment. I take on a lot of transformational work — it’s okay that some things are simply the way they are. 

The process of practising this has been one of surrender. I’ve fought with this tendency for many years, trying to push through it in tournaments, trying to force to play in leagues that would ensure I got practise letting go of this. And yet it remains.

Surrender isn’t something we can intellectually create for ourselves. We don’t tell ourselves “Just surrender” and then it happens. Instead, it comes about as we do everything in our power to avoid surrendering until there’s nothing left to fight with.

Hard fought territory.

7. Get Curious About the Light Over There

I used to filter people rapidly into categories of “Interesting to Me” and “Boring as Shit”. Most people fell into the second category.

I was fixated largely on my judgments of people and what was annoying or dismissible about them, as this provided me a way to ensure that I was only ever around people that I found stimulating.

Of course, everyone falls short eventually, so there’s no dodging this. I was just getting better and better at contracting from life.

Against my own insistence for how I related to people, my training invited me to consider that everyone was interesting, beautiful, creative, brilliant, and so on — I just had to look beyond my own prejudices and biases to see it.

Practising this skill has been and remains challenging — it’s really a lifelong practise. It’s most challenging because the time to practise is not when I’m open and feeling receptive.

The time to practise is when I’m feeling closed and judgmental. (The time to practise opening is when you’re closing, obviously, right?)

So when I notice myself categorize someone into “BaS” territory, I instead ask myself, “What is distinct or unique about this person? What is beneath the surface? What might I be overlooking?”

This skill has opened up life to me in so many ways I never imagined possible. I used to find it imperative to drink at social events, because this provided a way for me to get over my social anxiety and mitigate my inevitable boredom.

Now, that’s not necessary — even when I’m bored, I can get curious about what is having me be bored. “What is it about this conversation that is switching me off — and where is that coming from? What about our interaction is boring. What about this person is secretly fascinating? I wonder what secrets they have?”

8. Generate instead of Stimulate

One of my early coaches suggested that a good goal for me might be: “Create a Life Free From Boredom”.

I shrugged my shoulders and started saying “Well, I guess I could look to how I could take coaching calls in theme parks and stuff. And maybe find a way to make my chores fun, like while watching movies…?”

She interrupted and said “Well, it sounds like you’re relating to boredom as a lack of stimulation. I invite you to relate to it as a lack of generation on your part.”

Generating requires that I generate something, internally, in the moment, to create a new experience.

Stimulation requires that I consume something, externally, in the moment, to bypass my existing experience.

Learning the skill of generating requires a willingness to sit in boredom. As soon as I start to manage for my boredom (play a video game, read a book, pace around, watch TV, eat food, etc.), then the opportunity to generate goes away.

This is territory I’m continually working with, and it’s very challenging for me. I love to self-stimulate, and I’m good at it. Being willing to deepen my ability to generate requires building the muscle of sitting still with my thoughts, and my anxious need to do something to alter my experience.

(This whole post was written as a result of sitting in that silence).

All of these skills have been hard fought territory for me, in the sense that /understanding/ what I needed to do to train them was the easy part. The hard part is practising something new in the face of my resistance to doing so.

Creating something new in our circumstances is almost always available. Creating something new in our ontology — our way of being — will always be done in the face of our resistance.