How to address your insecurities

How to Address Your Insecurities in Retirement (and Life)

by David Smith, The Ultimate Retirement Coach

ONE IDEA: Everyone Feels It—You’re Not Alone

If you’ve ever looked around and thought, “Why does everyone else have it all together?”, let me offer you a gentle reality check:
Every confident person still feels insecure. Every successful person still fails. Every happy person still struggles.

Insecurity doesn’t disappear when you hit retirement. In fact, with all the identity shifts and life changes that come with it, those inner doubts can grow louder. But here’s the truth: feeling uncertain doesn’t mean you’re doing it wrong—it means you’re human.

3 Key Insights to Help You Positively Address Your Insecurities:

1. Accept That Insecurity Is Normal
   Confidence isn’t the absence of doubt—it’s moving forward despite it. Stop comparing your inner reality to someone else’s polished exterior. What you’re feeling is more common than you think.

2. Challenge the Voice of Perfectionism
   Unrealistic expectations are often at the root of insecurity. You don’t need to be endlessly productive or perpetually happy in retirement. Letting go of perfection opens the door to peace.

3. Treat Yourself Like You’d Treat a Friend
   Self-compassion quiets insecurity. When a friend feels unsure, you offer encouragement—not criticism. Why not offer yourself the same kindness?

ONE QUESTION: What If It’s Okay to Struggle?

Ask yourself:

“What if my struggles are normal and don’t mean something’s wrong with me?”

How would your day feel if you didn’t have to “fix” everything… and simply allowed yourself to be in progress?

You may want to journal with these bonus prompts throughout the week:

• Do I have unrealistic expectations for myself?

• What am I judging myself for that I’d never judge in someone else?

• What would self-acceptance look like today?

ONE EXERCISE: Drop an Unreasonable Expectation This Week

This week, I invite you to let go of one unrealistic expectation you’ve been holding over your head.

Maybe it’s “I should be busy all the time.”
Or “I must have all the answers about what to do in retirement.”
Or “I should never feel uncertain now that I’ve left work.”

Just drop it. Let yourself breathe.

To help, I’ve created a simple worksheet to guide your reflection:

📝 WORKSHEET: Letting Go of the Unreasonable

1. What’s one expectation I’ve been holding over myself?
(e.g., “I should have my retirement perfectly figured out.”)

2. Why is this expectation unreasonable or unhelpful?
(e.g., It assumes I should never feel confused or stuck.)

3. How has this belief made me feel? What has it stopped me from doing?

4. What new, more compassionate belief could I try instead?
(e.g., “I’m allowed to take my time adjusting.”)

5. What’s one small action I’ll take this week based on this new belief?