When You Slip, Don’t Dump the Jar

Finding progress in the messy middle of change

So often we see progress as a straight line, measured by days without a setback. Real growth lives in the messy middle—the pauses, the slips, the lessons that follow. Even when we stumble, the pennies stay.

Recently, I met with a client who was feeling defeated. She had been working hard to change her relationship with food, and for a while, she was doing “so well” because she went a few weeks without a binge episode. Then, one night, she binged — and it continued for a few days, which was such a disappointment for her. She couldn’t understand why she’d “slipped” after making so much progress over the last few months.

As we talked, she mentioned she had just left a meaningful job, one that had given her a sense of purpose and connection. She started telling me stories about the growth and changes her clients made when she worked with them. She also worried about other clients’ outcomes, wondering how some of their situations would “turn out” over time. She feared she had made a hasty decision to leave this role.

When I gently asked if she might be grieving that change, she was initially confused. I explained that we grieve more than death — we also grieve change, even when it’s for the better. I hypothesized that she was using food as a way of self-soothing and escaping the discomfort. Her binge wasn’t a lack of willpower — it was a way of coping with loss.

I see this often, in my clients’ lives and in my own. We become frustrated that our patterns aren’t changing fast enough. We beat ourselves up and “should” ourselves into showing “more discipline.” We expect progress to move in a straight line, and when it doesn’t, we decide we’ve failed.

However, real change isn’t linear or clean. It’s messy — it loops, wobbles, and runs straight into roadblocks.

After my dad died in 2007, drinking and eating became the ways I coped. They numbed the grief, soothed the overwhelm, and dulled the ache that lingered for years. Despite my best efforts to eliminate those behaviors, the pattern stuck. I was doing all the “right” things — tracking streaks, counting wins, marking days on a calendar. However, no matter how many days I strung together, I kept finding myself back in the same place, returning to the coping skills I was trying so hard to eliminate.

I used to think progress meant stopping completely — collecting as many “X’s” as possible. Each time I slipped, I saw it as failure, proof that I’d been sent back to square one. I’d tell myself to “buckle down” and try harder next time.

What I didn’t realize then was that returning to the behavior wasn’t a failure at all — it was information. I began paying attention to what those behaviors were doing for me at the time.

There was a reason I kept going back: they offered comfort and escape when I felt overwhelmed by emotions I hadn’t yet learned to face.

That realization changed everything for me. I stopped trying to erase the behavior and started exploring the moments that activated it. Instead of seeing urges as proof of failure, I began to see them as signals — invitations to pause and check in with what I was actually feeling.

That’s when I started using the phrase “practice makes prepared.” Real growth wasn’t about perfection or streaks; it was about readiness. Each time I practiced staying with the discomfort instead of escaping it, I became a little more prepared for the next time it showed up. 

Another client I worked with recently was struggling with mornings. She wanted to get out of bed early enough to exercise, shower, do her makeup, and get to work on time. When we began, she could list her “failures” effortlessly — every day she didn’t work out, skipped makeup, or ran late to work. Her focus was entirely on what hadn’t happened.

Together, we decided to slow things down. Instead of tackling everything at once, we focused on one small step: simply getting out of bed. And rather than counting how many days she succeeded, we looked at what was happening before those mornings — the night before.

She began to notice patterns. Her late nights often came after social plans or long phone calls with friends. Those moments were important to her, yet they made it harder to follow through on her morning goals. Over time, she realized the problem wasn’t just about willpower or motivation — it was about alignment. How could she honor her social needs and care for her morning self?

That’s when we brought in the “pennies in a jar” metaphor. Early on, she judged herself harshly for not adding a penny each morning she overslept. It felt discouraging, like she’d emptied the whole jar and had to start over. Eventually, we shifted the focus: instead of counting pennies, she began noticing what helped her earn them. Was she winding down earlier? Saying no when she was drained? Leaving time to prepare for the next day?

And slowly, the jar began to fill. Not because she was perfect, and yet because she kept learning. Even on the mornings she overslept, she didn’t dump the pennies out. She looked at what happened with new eyes, applying what she learned the next day.

In the end, growth is rarely about eliminating the behavior altogether. It’s about understanding what it has been trying to do for us all along. Each time we pause, reflect, and approach ourselves with curiosity instead of criticism, we’re adding a penny to the jar.

Whether it’s reaching for food after a loss or oversleeping after a long night out, the point isn’t to collect perfect streaks — it’s to learn from each moment and apply it to the next. The urge, the stumble, the insight that follows… all of it counts.

Progress happens when we stop starting over and start paying attention.

The truth is, the pennies don’t disappear. Even when we stumble, they stay. Every reflection, every moment of awareness, every act of self-compassion is still in the jar — proof that we’re growing, even when it doesn’t feel like it.

If this speaks to you, take a moment to reflect: where are you on your road to progress? Are you hitting a wall of frustration because you keep “slipping up”? The next time you lose your footing, remember — this isn’t the end of your progress. It’s simply another chance to practice being prepared.

I’d love to hear what “pennies” you’re adding to your jar lately. Small wins count too — maybe especially those. What’s one lesson your “slip” taught you that you wouldn’t have learned otherwise?