When Familiarity Fails: The Trap of Doing What Once Worked
We’ve all heard it: “The definition of insanity is doing the same thing over and over again and expecting different results.” It’s a quote commonly attributed to Albert Einstein—though there’s no evidence he actually said it. Regardless of its origin, the message resonates because it captures something essential about human behavior.
Still, it’s not always mindless repetition that trips us up. Often, the pattern that leads us astray is more subtle, and more dangerous: doing what once worked, over and over again, long after it stopped serving us.
The Comfort of What Used to Work
Most people aren’t blindly repeating failed attempts without realizing it. We’re generally smart, aware, and capable of course correction. If something brand new doesn’t go as planned, we learn quickly. We pivot, tweak the approach, or ditch it altogether. In that sense, even mice running a maze are wise—they’ll stop running into the same wall if it keeps yielding no cheese.
But when the thing we’re doing used to bring success, when it once worked reliably, that’s when the trouble begins. That’s when change becomes harder, and the line between perseverance and self-sabotage blurs.
It’s not insanity. It’s habit. It’s familiarity. It’s the belief that if it worked before, surely it can work again—maybe this time, if we just try a little harder.
The Invisible Decline
Let’s say you launched a product three years ago and it sold like crazy. Every time you promoted it with a certain email strategy, results followed. Naturally, you kept using that strategy. Why wouldn’t you?
But now the market’s changed. People are tired of that format. Attention spans have shifted. Your customers have evolved. And yet—you stick with what once worked. Not because you’re oblivious, but because you’re emotionally and mentally invested in the familiar. You tweak the subject line, resend to unopens, post a few more times. You’re not doing nothing, but you’re still circling the same well, hoping for water long after it’s gone dry.
Why is this so common? Because comfort is powerful. Success reinforces patterns, and those patterns are hard to break—especially when they once validated your efforts.
Conditioned by the Past
We’re conditioned by success. That’s the crux of it. We form attachments to behaviors, workflows, strategies, or even relationships that once served us well. The brain latches on to those patterns, tucking them into the “this is how we win” folder.
When those methods stop producing results, it’s not immediately obvious. We don’t think, this is no longer effective. We think, maybe I’m not trying hard enough. Maybe I need to do it again—one more push, one more email, one more round of effort.
This isn’t foolishness; it’s hope. It’s trust in past experience. But it can become a trap.
When It’s Time to Change the Playbook
There’s a moment in every effort when you need to step back and ask a hard question: Am I trying harder, or just repeating myself? The distinction matters.
Progress doesn’t always come from brute force. Sometimes it comes from stepping sideways rather than forward. Sometimes the smartest move is abandoning the method that used to work, not because it was bad, but because it no longer fits.
Changing your playbook doesn’t mean admitting failure. It means acknowledging change. It means being nimble, curious, and honest about your circumstances.
And this doesn’t just apply to work. It’s true in relationships, health routines, creative projects—any part of life where we develop habits and expectations.
Recognizing the Tipping Point
So how do you know when something’s no longer working? When is it time to stop tweaking and start transforming?
Here are a few signs:
- You’re seeing diminishing returns. What once worked easily now requires disproportionate effort for mediocre results.
- You’re stuck in a “just one more try” cycle. You keep thinking one small adjustment will fix everything, but nothing changes.
- You feel frustration, not progress. Your energy is being consumed by doubt and disappointment rather than motivation.
- You’re ignoring signs of change. Feedback, data, or even your own instincts are telling you something’s off, but you’re brushing it aside.
The moment you begin asking Why isn’t this working anymore? is often the moment you need to zoom out. It doesn’t mean your idea, your effort, or your intentions are wrong—it might just mean the strategy is outdated.
Letting Go of Familiar Success
Letting go of something that once brought success is emotionally hard. It feels like betrayal, like discarding a part of yourself. But clinging to expired methods keeps you stuck in the past. Growth demands new thinking, not recycled comfort.
The real wisdom isn’t in never repeating yourself. It’s in recognizing when repetition becomes resistance to change. It’s in knowing when to pause, re-evaluate, and reinvent. That’s not insanity—that’s maturity.
In Closing
The real danger isn’t trying new things that don’t work. It’s doing familiar things that no longer serve you and being too invested to notice. Success, ironically, can become the very thing that blinds us to new opportunities.
If you find yourself stuck, ask: Am I chasing yesterday’s success with today’s energy? If the answer is yes, maybe it’s time to stop pushing the same button—and start designing a new system entirely.
You don’t need to go insane to move forward. You just need to let go of the past, and make room for what’s next.
