Prompt: Write about the difference between winning and succeeding.
The prompt for today, July 25, 2026, is: Write about the difference between winning and succeeding.
I guess, on the face of it, winning is in competition with somebody else, while succeeding is in competition with yourself. I think that’s probably the simplest breakdown I can offer.
Even if you win a game, unless your goal was to win that game, I don’t know that it’s really a success. Well, I suppose winning is a success if winning was your objective. Maybe that’s what it comes down to. Success is something we define for ourselves, whereas winning is defined by rules that come from outside of us.
In school, we talk a lot about success criteria.
Part of teaching is showing students how they’ll know they’ve achieved the learning objective by giving them markers they can refer to. For this audio journal, for example, my success criteria might be posting every day for a month, making each post at least three minutes long, and so on. You might have four or five criteria, and if you meet them all, you’ve succeeded. If you meet some of them, you’ve made progress. If you meet none of them, then there’s room to improve.
I don’t know how I feel about success criteria, though, because everybody’s learning is different. In life, we don’t usually get handed a checklist that tells us whether we’ve succeeded.
Then again, maybe that’s part of what school is trying to do. Maybe we’re giving students examples of how to define success for themselves later in life.
This flips things around for me a little bit because it makes me think about how I measure success with SANA Stationery & Gifts, or what it even means to be financially successful. When we look at someone and say they’re successful, what do we really mean?
Oftentimes, we mean they have a lot of money.
But does that mean they’ve succeeded, or does it just mean they’ve won the game of making money?
I’m remembering a podcast episode—though I can’t remember which one—where a psychologist who worked with the ultra-wealthy talked about how they have their own unique problems. They even need specialized psychologists because it’s difficult for most people to empathize with someone who owns a $500 million yacht.
And, honestly, it is hard for me to empathize with somebody who owns a $500 million yacht.
I don’t know. Maybe I didn’t arrive anywhere with this one.
Or maybe that’s the point.
Winning is easy to measure because someone else keeps score.
Success is harder because we have to decide what we’re aiming for in the first place.
You can find this post and more at Letters’ Lounge, www.letterslounge.com. I’d love to hear your thoughts on this one—or any of the others—so please leave a comment or a link to your own blog or audio journal, and I’ll be sure to check it out.
Right on, 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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