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 jill@startwithsmallsteps.com

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.

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 jill@startwithsmallsteps.com

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.

Have you ever failed publicly — in a way that everyone around you could see? I did. I walked away from a high-status, well-paying job with no backup plan, no other offer, and no real financial cushion. And everyone in my world was watching. This is the first episode in my Bouncing Forward mini-series, and it's about exactly that — not bouncing back to where you were, but bouncing forward to somewhere better.

Why Some People Don't Come Back

Public failure carries a specific kind of weight — the humiliation, the awareness that people are watching, the fear that what you did will define how they see you. I've watched people fold under that weight, cutting off friendships, avoiding eye contact, never recovering. This episode is about making sure that doesn't happen to you.

The Job She Left

A high-demand company, team awards (the hardest ones to win there), 100+ hour work weeks, and then a boss who made clear that the punishing pace was now the permanent expectation. Jill's best friend cleared out her entire office in one visit and said: you're done here. Three weeks later she walked out with no job lined up — and everyone knew it.

Resist the First Life Raft

The temptation in public failure is to grab whatever comes along first, just to stop the bleeding. Jill did the opposite. She analyzed what had made her miserable, what she had actually loved, and built a clear picture of what the next role needed to look like. New hire training, for example, had been one of the highlights of her month — that was going on the list.

The Shift: From Job-Seeker to Evaluator

The moment she got clear on what she actually wanted, the dynamic changed completely. She was no longer interviewing for jobs — they were auditioning for her. She needed to be convinced this company would make her happy. That shift in mindset changed everything about how she approached the search.

The Landing Is More Important Than the Fall

Three weeks after making her list, Jill found the job she spent the next fifteen years in. Everyone sees you fall. But everyone also sees where you land. If you can hold out long enough to aim the landing — to figure out what the next chapter actually needs to look like rather than just stopping the bleeding — the bounce forward becomes something real.

Closing

Whatever your situation looks like — a relationship, a city, a business, a role in your family — the fears are probably similar. What am I going to do? How will I pay for this? But if you can resist grabbing the first life raft and instead ask: what does the next chapter need to look like? — that's where the real bounce forward happens. Next week we talk about private, long-term failure. Different kind of hard.

Jill’s Links

http://jillfromthenorthwoods.com

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

https://www.buymeacoffee.com/startwithsmallsteps

https://twitter.com/schmern

Email the podcast at jill@startwithsmallsteps.com

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 healthcare provider, psychiatrist, or counselor. Any advice or suggestions offered should not be considered a substitute for professional medical or mental health advice. You are solely responsible for any decisions or actions you take based on this content.