Prompt: Write about something that didn’t work.
All right, the prompt for today, June 8, 2026, is: Write about something that didn’t work.
I think failure is a huge part of learning.
I remember when I got my first contract job—my first full-time teaching job. It was with a Grade 6 gifted class, or I should say students who had been identified as gifted. I remember telling them, and telling their parents, that my job was not to give them assignments and tasks they could complete, but to challenge them to the point of failure.
I think how I should have phrased it was that students need to engage in productive struggle. They need to be given tasks that they have to work toward. Because my thinking was, and still is, that if you can already do the task, then what is the point of me teaching it to you?
So I had to give you something just beyond your capacity, just beyond your capability. Essentially, my goal was to make you fail.
And I think, for me, this rings incredibly true. I don’t think I found my footing seriously until I failed seriously.
School, for whatever reason, came fairly easily to me. So when I got to university, it was a real struggle because I didn’t have the skills I needed when things didn’t just make sense. Studying was not something I was accustomed to. I thought I could just party and I’d be okay, and that’s not true.
So I did a lot of failing in my first couple of years of university, and it wasn’t until third year that I finally found my footing and turned things around. But then, to be frank, it was a little late. The goals I had after that sort of fell through because I just hadn’t set myself up properly.
I think, too, even in terms of my working life, I kind of fell into a job and I hated it, but I did it for a few years. Then it wasn’t until I was fired from several jobs in succession that I finally went to teachers’ college and worked through that process.
After that, I had to work through the process of getting a teaching job on my own in a new city, without my parents’ direct assistance. They supported me financially, but they weren’t making things happen for me.
So yes, it was important for me to go through a lot of failure in order to meet with some success.
Now, I’m saying all of this, and I’m thinking about my current situation with SANA Stationery & Gifts and how I feel like that’s a failure. But I think that’s only because I’m the one standing in my way.
I’m not working against somebody else.
And I think that’s a learning for me, really—that I can be the challenge to myself. It doesn’t need to be external.
Maybe that’s how I have to re-envision my approach or reassess my approach to SANA Stationery & Gifts in order to make it a success.
Because right now it does feel like a failure. I’m not making progress. I’m not really making sales. It’s just eating up a lot of money. And, yeah, I just don’t have the time to invest—or maybe I’m not investing the time.
So I think failure is really important. And I think we need to destigmatize it in some ways.
Yeah. Right on.
Anyway, you can find this prompt and more at Letters’ Lounge, www.letterslounge.com. I’d love to hear your thoughts on this or any of the other prompts, so please leave a comment with a link to your own reflections, comments, or suggestions.
I’ll talk to you tomorrow, folks.
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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