277 - You're Not Failing. You're Building a Toolkit

What if you haven't failed at something once or twice — you've been failing at the same thing for decades? Last week was public failure. This week it's private, repeated, long-term failure. And it's harder in a different way. For me, that thing is weight. I've been trying to lose it since I was a child. And what I eventually figured out about all those attempts changed the entire way I look at failure.

Private Failure Has Its Own Weight

No one sees you stepping on the scale at six in the morning. No one sees the attempt that was working until it stopped. The people in your corner see the headlines — a good week, twenty pounds gone — but not the daily private reality. Private failure is lonely. And the accumulation of it can start to feel like evidence that you are simply broken in this one particular way.

The Fresh Start Trap

Our culture loves the clean-slate story. But fresh starts often require throwing away everything learned from the last attempt. Jenny Craig out, Weight Watchers in — and you're back at the beginning, carrying nothing forward. After years of this, Jill realized: what if the knowledge from the last attempt was actually valuable? What if she didn't need to start over — she just needed to iterate?

Building a Toolkit from Every Attempt

Every attempt gave her something: the trainer fourteen years ago taught fitness science she still uses today. Weight Watchers gave her a food framework she still applies. Every time she thought she was starting over, she was actually carrying something forward — a principle that had become second nature, a piece of self-knowledge she didn't have before, a habit that had quietly snuck in.

The Wrong Question — and the Right One

'Why can't I make this happen?' assumes the problem is willpower or discipline. But what if something else is actually going wrong — something metabolic, hormonal, or structural — that no amount of grit can fix? Changing the question from 'what's wrong with me' to 'what is actually going wrong' opens a completely different door.

Iteration Is Not Failure on Repeat

Iteration is progress. It's what happens when you make small incremental adjustments and try again — not a complete overhaul, just a nudge here and a nudge there. Every attempt is a little better than the last. You're not the person who keeps failing at the same thing. You're the person who keeps iterating on a hard problem. And you are not done yet.

Closing

When you look at a long history of attempts, the thing that's actually happening is not an unbroken record of failure. It's an unbroken record of getting back up. That stubbornness — the quiet, unglamorous stubbornness of refusing to stay down — is actually the thing. Next week we talk about what happens when those iterations finally reach the right conditions.

Jill’s Links

http://jillfromthenorthwoods.com

https://www.youtube.com/@startwithsmallsteps

https://www.buymeacoffee.com/startwithsmallsteps

https://twitter.com/schmern

Email the podcast at [e-mail]

By choosing to watch this video or listen to this podcast, you acknowledge that you are doing so of your own free will. The content shared here reflects personal experiences and opinions and is intended for informational and inspirational purposes only. I am not a licensed therapist, life coach, or mental health professional. Any habits, strategies, or suggestions offered should not be considered a substitute for professional medical, psychological, or counseling advice. Results vary — small steps look different for everyone. You are solely responsible for any decisions or actions you take based on this content.