“Context has a real influence on how we experience ourselves. Paying attention to it is often the first step toward understanding it.”
Hey Rollers,
I’ve been thinking about shirts lately.
Not fashion exactly, but what wearing one — or not wearing one — seems to do to how we feel about ourselves.
About ten days ago I went out for a run. It was hot, properly Cape Town summer hot, and I enjoy running without a shirt when the weather is like that. There’s something about it that feels simple and free.
About seven kilometres in I tweaked my calf.
Not badly enough to call an emergency Uber, but badly enough that the run was over and the only option left was a two-kilometre walk back home.
Running shirtless felt great.
Walking next to a busy 5pm road, limping, suddenly felt like a very different experience. Cars passing, people glancing across as they drove by — well, in my mind at least. The same “no shirt” that had felt free ten minutes earlier now made me strangely self-conscious.
Same person, body and lack of shirt, but a completely different feeling.
Then on Wednesday evening I went into town for dinner with a couple of international guests and a few other entrepreneurs. We were seated at a private table in a wine cellar.
I’m usually a black t-shirt kind of guy, but I thought I’d make a bit of an effort. Smart pants, no sneakers, and a long-sleeve button-up shirt. Baby blue, in 36-degree heat (genius Justin).
When I arrived, it quickly became clear that I had overshot the dress code.
Everyone else was relaxed and casual. Meanwhile I was sitting there looking like the most formally dressed person in the room.
No one said anything. But I noticed it, and it made me realise that simply showing up as myself had always been an option.
Then on Thursday morning, Emma and I welcomed our beautiful son Harrison into the world — a little earlier than expected.
While in the labour ward I found myself doing something I’d never really thought about before. I took off the scrubs they’d given me so I could hold him skin-to-skin.
No shirt.
Over the next couple of days I’ve done the same thing several times while holding him. Not once did it cross my mind how it looked, whether it was appropriate, or what anyone else might think.
Some moments simply remove the space for self-consciousness.
Looking back on the last ten days, its amazing how the same thing — wearing a shirt or not wearing one — can feel completely different depending on the context.
Running freely.
Strolling beside traffic.
Sitting slightly overdressed in a wine cellar.
Holding a newborn in a hospital room.
Me every time, but a completely different experience.
It’s the reminder I needed that a lot of what we feel about ourselves isn’t fixed. Often it’s just the context we happen to be standing in.
And interestingly, it’s usually the moments that matter most that remove the overthinking — while the moments that matter least are the ones where we get caught in our own heads.
Until next week.
Keep rolling.
Justin 👊
Take Action in 3 Minutes:
Take a moment today and notice the context you’re in.
Where are you?
Who’s around you?
What version of yourself tends to show up in that environment?
Then ask yourself one simple question:
👉 Is this the version of me I want this environment to bring out?
If the answer is yes, take note of what’s working.
If the answer is no, consider what might shift the feeling. Sometimes it’s the room, sometimes the people, and sometimes it’s simply giving yourself permission to show up as yourself.