The Motivation Trap: Why Your Goals Might Be Setting You Up to Fail
How smaller targets lead to bigger wins (and why your brain prefers it that way)
Welcome to The Evolving Leader's Guide. Each week, I share one mindset, framework, or toolkit designed to help you become a more effective leader—so you can lead with confidence, inspire your team, and build a career you're proud of.
This week's tool: The Right-Sized Goal
You're staring at your to-do list. That big project you've been meaning to tackle is still sitting there, untouched.
Maybe it's updating your resume. Or finishing that online course. Or deep cleaning your house.
Every time you look at it, you feel a mix of dread and guilt. So you avoid it. And the cycle continues.
Here's what's really happening: Your goals aren't motivating you—they're paralyzing you.
I discovered this the hard way recently. I signed up for an online class and quickly fell behind—four weeks behind, to be exact. And now I've hit a mental block about even starting to catch up.
Why? Because in my mind, making a tiny dent in those four weeks of material doesn't feel worth it. I've convinced myself I need a massive chunk of time to make "real progress." And since that perfect block of time never materializes, I fall further behind each week.
This is a pattern I see constantly with myself and my clients.
We set ourselves up to be in a motivation trap. And today, I'll show you how to escape it.
When identical progress feels completely different
Let me tell you about two of my coaching clients.
James set a goal to work on her resume five times a week for 30 minutes each session. Maya committed to just three 30-minute sessions weekly.
After one week, both had worked on their resumes exactly four times.
James was disappointed and frustrated with himself. He’d failed to meet his goal, and now he associated working on his resume with failure and inadequacy. Leading to even less motivation to work on it then following week.
Maya was ecstatic. She'd exceeded her goal by one session and felt accomplished, motivated, and eager to continue the momentum. She couldn’t wait to work on her resume even more.
Same exact output. Wildly different emotional outcomes.
This isn't just anecdotal. Research from psychology professor Teresa Amabile at Harvard Business School shows that perceived progress is one of the most powerful motivators in our work. Her research found that of all the things that can boost emotions, motivation, and perceptions during a workday, the single most important is making progress in meaningful work. (The Progress Principle or here is a talk she gave at Google on the topic)
The flip side is also true: The most powerful demotivator is the feeling of spinning your wheels without making progress.
The backward math of motivation
We've been taught to set ambitious goals that "stretch" us. Push harder. Aim higher. Go big or go home.
But there's a critical flaw in this approach. It fails to account for how our brains actually process success and failure.
Psychologist BJ Fogg, founder of the Behavior Design Lab at Stanford University, argues in his book Tiny Habits that the key to behavior change isn't motivation—it's making the behavior so small that you can't fail.
"When you succeed at something, even if it's tiny, your brain releases dopamine," Fogg writes. "This creates a feeling of success and increases your motivation to do that behavior again."
In other words, success breeds success. Failure breeds avoidance.
This explains why James started avoiding his resume work while Maya embraced it. It wasn't about discipline or character. It was brain chemistry.
The power of right-sized goals
The solution isn't lowering your ambitions. It's restructuring how you pursue them.
When I work with leaders feeling stuck on big initiatives, I ask them a simple question: "What's the smallest version of this that would still feel like progress?"
For my online course dilemma, the answer isn't "catch up on all four weeks this weekend." It's "complete one lesson today."
This approach works because:
It makes starting easier. The mental barrier to doing one small thing is much lower than tackling a mountain.
It creates momentum. Each small win triggers a positive emotional response that motivates the next step.
It builds confidence. Regular success reinforces your belief that you can handle bigger challenges.
The math often works out in surprising ways. If I commit to completing 2 lessons per week, I'll be caught up within a month. That's far better than trying to find time this week to do 5 lessons, which will become 6 by next week, and my current approach of waiting for the perfect time to do everything at once (which, spoiler alert, never comes).
How to rescue yourself from demotivating goals
Here's how to apply this in practice:
1. Catch the trap. Notice when you're avoiding something important. The avoidance itself is your clue that your goal might be sized wrong.
2. Resize ruthlessly. Ask yourself: "What's the smallest version of this that I could complete today?" Then cut that in half.
Behavioral economist Dan Ariely calls this the "dashboard light principle." When your car's gas light turns on, you don't need to fill the tank—you just need enough gas to reach the next station. (Predictably Irrational or here is his TED talk)
3. Celebrate completion, not perfection. Did you do the small thing? Great! You've succeeded. Your brain doesn't distinguish between small wins and big ones when it comes to releasing dopamine.
4. Stack your successes. Use the momentum from small wins to gradually increase your goal size—but only after you've established a consistent pattern of success.
This isn't about lowering standards. It's about understanding how your brain's motivation systems actually work, then designing goals that work with your psychology instead of against it.
Coach's Challenge
This week, identify one important task you've been avoiding. Now:
Resize it to something so small it seems almost ridiculous. Can't commit to a 30-minute workout? Start with five minutes. Can't face organizing your entire inbox? Just sort 10 emails.
Complete this micro-goal at least three times this week.
Document how you feel after each completion. Note any changes in your willingness to return to the task.
As for me, I'm going to take my own advice. Right after finishing this article, I'm going to complete exactly one lesson from my four-weeks-behind course. Not all four weeks. Just one lesson.
Because sometimes, the path to big achievements is paved with deliberately tiny steps.