Past posts live here. Come 👋🏼 at me on FB, IG, Threads & Bluesky

Hello, friend,

You're reading The How to Live Newsletter—where psychology meets real life, offering practical wisdom for life's challenges. New insights weekly, with a full resource library available on our website to paid members.

As a paid member, you'll access all articles and archives, join our thoughtful community, and enjoy an ad-free experience.

Can’t afford $6 a month, but believe in this work and want to chip in—or-gasp-want to give more than $6? You can:

Necessary Questions: Seven Inquiries That Reveal the Hidden Self

The other night, I took Busy out for her last walk before bed—late, past midnight, in Birgu, Malta, a town dating back to the 3rd century. It’s quiet, safe, the kind of place where restaurants leave tables outside overnight without worry. Yet, I have lifelong anxiety. And I am alone in a stranger’s three-story house, in a secluded part of a secluded country.

So, naturally, stepping onto a dark, deserted street should have scared the hell out of me.

But it didn’t.

Instead, I felt entirely, utterly unafraid.

That absence of fear—the mythical ease an anxious person longs for—was so tangible it startled me. And in that space, I realized: fear is just a thought.

This, of course, is not new information, but like most things that catapult you forward, it struck me in a new way—I could feel this truth instead of intellectualizing it. Maybe because the thought occurred when I felt safe in a situation I’d typically feel afraid.

I asked myself: What if it could always be this easy to feel unafraid when I am already safe?

Anxiety makes us fear our own thoughts more than real danger. And sometimes, all it takes is the right question to shift our perspective.

So I started wondering: What other questions, answered honestly, might help close the gap between the person we are right now and the person we want to become?

Here are seven I came up with.

1. What am I avoiding, and why?

This question hits hardest in moments of crisis or transition. We stay in bad situations long past their expiration dates (ahem—me). We ignore or deny creative urges, dismiss medical advice, tune out therapists and friends—only to find ourselves in the same crisis again and again.

What we’re avoiding seems obvious: loneliness, judgment, the discomfort of discipline, confrontation, uncertainty. But the why is trickier—it’s always the same. We fear the unknown. We can’t sit with self-doubt. It’s easier to stay in misery than to risk change.

Yet within that broad fear is a personal truth, one we must uncover ourselves.

A man might abandon his career and family to care for his aging father—not out of selflessness, but because he’s terrified of growing old. Rather than marking time through his children’s growth, his wife’s graying hair, or younger colleagues superseding him, he retreats to the one place where he’s always young. But his father will die. And then what?

An artist trapped in a corporate job might not just fear failure but also the weight of success. A writer stuck on their novel might not just fear criticism, but what it means to tell the truth.

Someone clinging to a stagnant relationship may not just fear the pain of leaving but the possibility of real happiness.

Sometimes, I fear reaching my goals—not because of success itself, but because achieving them brings me closer to death. That’s my warped belief, at least. But within it lies what I’m avoiding—the possibility that I’m not broken, that the stories I was raised to believe—that I’m defective, not smart, not the right kind of person—are only true because I choose to keep believing them.

Asking what we’re avoiding is uncomfortable. But it’s also the seat of change. We can stay the same and complain—or we can face what we fear and move toward what we want.

2. Whose expectations am I living by?

This one sneaks up on you.

It drops just as you realize the life you’ve been living isn’t one you chose, but one imposed upon you.

A woman starting her fourth round of IVF wonders why she’s filled with dread—not that the treatments won’t work—but that they will. It’s only when the fourth one succeeds that she realizes she’s been chasing her mother’s dream of a big family, not her own.

This question often surfaces in moments of loss or change. A divorced woman might realize her fear of failure comes from her religious upbringing. A man hesitant to take antidepressants might trace his resistance to his father’s beliefs about mental health. An injured athlete pushing too hard might see that their timeline isn’t their own—it’s their coach’s.

Upgrade to read the remaining questions and how to answer them…

(Free preview of questions 3-5 for Non-Members)

• What does freedom look like to me?

• What would I do if fear weren't holding me back?

• What patterns in my life keep repeating, and what are they trying to teach me?

Join How to Live: Where Research Meets Real Life.