By Dave Smith, The Ultimate Retirement Coach
Here’s the truth: most people aren’t paying attention to what you’re doing. Your loudest critics? They’re probably too afraid to try themselves. Yet many of us let the fear of being seen failing hold us back from pursuing what really matters—whether it’s a new career move, a business idea, or a bold retirement lifestyle shift.
Failure isn’t the enemy. It’s the doorway to growth. But the fear of judgment—that heavy, invisible weight—can stop us before we even start.
So, what are you really afraid of?
Is it the stumble itself?
Or is it someone else noticing that stumble?
Here are two journaling prompts to guide your reflection this week:
What are you putting off because you don’t want to be seen failing?
What is it, really, that you fear?
Write your answers down. Be honest, even if the truth surprises you.
This week, I challenge you to do one thing you’re afraid to fail at. It doesn’t have to be huge—it could be sharing your opinion in a meeting, trying a new fitness class, or finally launching that blog you’ve been thinking about.
To make it easier, here’s a simple worksheet:
Step 1: Name the Fear
What’s the thing you’ve been avoiding?
Step 2: Identify the Real Fear
Are you afraid of the failure itself—or being seen failing?
Step 3: Small Bold Step
What’s one small action you can take this week that edges you closer, even if it’s uncomfortable?
Step 4: Reflection
After you take the step, write down how it felt. Did the outcome matter as much as you thought?
Courage in retirement—or in any stage of life—isn’t about never failing. It’s about refusing to let the fear of visibility hold you back.
Take the step. Then let me know how it goes.
👉 If you found this helpful, share it with a friend who might need the reminder today.