What My High School Art Teacher Taught Me About Permission
It’s grade 10. I am sitting in art class.
That might be an exaggeration. I am probably standing or moving around, talking loudly over others, arguing over what something means, or obsessing over a painting I am working on.
And, in the corner, at her desk, is Ms. Lottering. A somewhat frazzled, very kind and funny South African woman who used to refer to me as her “gogga” (which I later came to learn meant “bug” in Afrikaans).
Ms. Lottering was the best. She passed away in 2020. She went too early.
We kept in touch well beyond when I think most high school students keep in touch with their high school art teacher. She supported me in my photography work, and kept me up to date on what was happening in her life. Unfortunately, we lost touch.
She also questioned my decisions. To not go to art school. To go to law school. To practice law. To abandon a path that she saw me being completely right for.
I think of her often.
I think of her most often when I am considering my next move, or my next creative “thing” - what would she say?
Most likely, “Oh stop thinking about it and just do it gogga,” in her delightful accent.
Ms. Lottering (Deline to those who knew her outside of school) had an interesting life. She was married to a man named Willy. They were both artists who moved to Canada at some point in the 80s or 90s (I’m not entirely sure). They had children, both of whom I met and came to know at one point or another. I heard that she had a really cool house north of the city where every surface was painted.
She had an uncanny ability to draw things out of you. If you were stuck with a question of what colour to use in your work, or what subject matter to cover, or who to go to the prom with (I think we may have discussed this) - she knew how to help you arrive at the most truthful answer to your question.
In short, she was able to get you to let your guard down and give yourself permission to be sincere - with her and with yourself. And it turns out, we’re wired this way. We take risks - emotional or otherwise - only when we feel safe enough to do so.
In grade 11 (when I was again in her class), we had an assignment to paint a series of self-portraits over the course of the year. This was an interesting project - one that required quite a bit of vulnerability actually. I mean, trying to paint yourself - or your innermost thoughts, wishes and secrets - onto canvas at age 16 isn’t exactly a walk in the park.1
This is where Ms. Lottering’s skill really came in. She would ask questions - not about the portrait, but about you. She would challenge you to make a picture that was about something. A story we had to tell about ourselves, or a truth we had to confront, or an idea about our personalities that we wanted to dispel through our work.
She gave us the permission that, I think, we were so often looking for to be brutally, totally, and even perhaps disappointingly, honest.
There’s a growing body of research that suggests we don’t actually change because we’re hard on ourselves - we change when we feel safe enough to be honest.
As we roll into 2026, I am prompted by a recent conversation I had with someone around allowing herself to do what she had always secretly wanted to this coming year, but was afraid she would chicken out unless she really committed.
In other words, she was being honest that she was looking for permission to do this thing. To take a risk. Or to ask for something she wanted or needed. Or simply to do the thing that she knew she could, but had been too reluctant to do.
Why is it so hard for us to give ourselves permission?
I’ve come to think it isn’t because we’re incapable of giving it - it’s because we’re conditioned not to.
It’s easy to name a million reasons not to give yourself permission. Here are just a few:
The unrelenting march of productivity. The inevitable comparisons to others. The ways we hold back as a form prioritizing the needs or feelings of others.
We rarely need permission to work harder. Or to push through. Or to take on more. Those things feel virtuous. Productive. Safe. We’re far more comfortable being driven to action than deciding on an action.
But choosing? Choosing means owning the direction - and that can feel terrifying.
And that’s why it’s just easier not to give yourself permission to do the things that you know are likely good for you but will come at some sort of cost or discomfort or even - gasp - honesty.
Of course, we don’t struggle with all kinds of permission equally.
I’d bet you don’t give yourself permission to go to the dentist - in fact, I’ll double down and bet you don’t even feel a need to permit yourself that treatment. Unless you are one, you probably have no idea how to clean your teeth properly or fill a cavity. And so, once we’re over the financial cost of it, most of us have no problem booking the appointment.
Dental problems feel technical. Skill-based. We don’t take them personally. And, so, we have no problem giving ourselves permission to hire someone else to take care of it.
But, permission to slow down?
To change your mind?
To want something that doesn’t look impressive on paper?
Those kinds of permissions don’t gain you any followers or any applauding pats on the back. They come with discomfort. With the risk of being misunderstood. With the chance that, if the performance stops, then something else, something more honest about you, might be exposed - that you are the only one who can make this happen.
And that is absolutely terrifying.
Going back to our earlier discussion. The self-portrait. For me, this is a really hard one to get done.
But does it require permission?
Yes. Absolutely.
It requires allowing (i.e. permitting) myself to feel the weirdness of sitting in front of the camera.
But, can it be forced?
Not if we want it to be an honest self-portrait. It can only be truthful if I (the only one who can make it happen) lets myself make it happen.2
Here’s another one: telling that old friend that you lost touch with years ago that you miss them.
Do you force that? Or do you give yourself permission instead to be vulnerable - to be open to the awkwardness and the feeling of rejection and do it anyway?
What about asking for help?
For many of us, this is the real test - to say to ourselves, “You need to allow that you can’t do this on your own and, yes, you can request that someone provide some assistance.”
Unlike the dentist, asking for help with this “harder stuff” feels different. This kind of permission doesn’t just say something about what we don’t know. It feels like it says something about who we are.
Why Does Any of this Matter?
Because most of us aren’t stuck due to a lack of ability or opportunity. We’re stuck because we’re waiting for permission that no one is actually withholding. We’re waiting to feel “ready,” or certain, or justified - when the truth is, growth and change rarely need anyone’s permission at all. They come when we’re willing to tolerate discomfort, uncertainty & honesty. When we’re ready and willing to play.
Maybe that’s what Ms. Lottering really gave me permission to do. To experiment without needing to justify it and try something without knowing where it would lead.
So, Ms. Lottering, wherever you are - consider this the start of a self-portrait.
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I still find making self- portraits cringeworthy - which is why I don’t make them. The level of openness you need to not only set up a camera to focus on yourself, but then, look into the lens and be captured - it’s hard. Maybe that’s the reason I should be doing more of them. But, I digress…
For you lawyers - yes, technically, it can be forced. Put a gun to my head and, sure - you can get a self portrait. But how good is that really going to look?
