Prompt: Write about trying something without certainty.
Okay, the prompt for today, June 14, 2026, is: write about trying something without certainty.
I think this is an interesting one because I was raised to avoid risk, really. You know: do well in school, get a good job, and you’ll be set. Things will be good.
That didn’t quite happen.
Eventually, I followed that path, but it took me a while to get there. And I wasn’t taking risks—I was being stupid.
Now, as I feel more secure in my life, I’m more willing to try things and take risks that I otherwise wouldn’t have. Most notably, starting SANA Stationery & Gifts. Starting a woodworking business is probably the greatest, or at least the longest-lasting, risk I’ve taken.
And other than the financial aspect of it, I’m not harmed. So I didn’t really lose.
I suppose finances are where risk seems to challenge me the most these days.
Even thinking back to girls and dating, I never really took risks by asking people out. It came down to a fear of failure. I didn’t have the confidence in myself that was needed to do that.
The same thing happened with work. I usually took the easiest path when it came to finding a job. I didn’t push myself toward difficult interviews or particularly challenging opportunities. What was easiest, and what came to me naturally, was what I wanted—or at least what I thought I wanted.
In some ways, becoming a teacher was different.
I think part of the reason I’ve stayed with it for so long, and care so much about it, is because I had to work for it. I had to go to Teachers College for a year. At the time, it was only a one-year program. Then I spent years driving between cities for work, interviews, and opportunities before eventually returning to Toronto and settling here.
There was no guarantee any of it was going to work out.
I needed help along the way, certainly, but there was still uncertainty. Looking back, if I had been a little more adventurous, I probably would have gone overseas to teach for a while before returning to Canada and trying my hand at finding a position here.
So I think I’ve led a life largely avoiding risk, even if it didn’t always look that way from the outside.
And when I think about what I want for my daughter, I want her to know that she is safe to take risks. I want her to know that if she falls, there is a net beneath her that will catch her, no matter how far she falls.
How do I teach that?
I suppose by encouraging her to take risks herself, and by helping her learn that when she stumbles, she’ll be able to pick herself back up. And if she can’t, our hands will be there behind her.
Risk is something you have to learn how to manage.
Actually, thinking about it now, I’m hesitant to advertise this audio journal because I don’t want to take the risk. I don’t want to take the risk of somebody telling me it’s shit.
So there’s that.
You can find this prompt and more at Letters’ Lounge. I’d love to hear your thoughts on this prompt—or any of the others. Feel free to leave a comment, or share a link to your own blog or audio journal.
All right, folks. I’ll talk to you tomorrow.
This transcript was lightly cleaned up with the help of AI to improve readability while preserving the original voice and intent of the recording.
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