Let’s play 20 questions

Digging into your values when you're at a crossroad

Jun 22, 2026

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Most of us think we know what matters to us. We say we value creativity, freedom, family, adventure, growth, contribution, authenticity—etc., etc. But, when push comes to shove, how many of the decisions we’re making (or avoiding) every day are telling a different story about what’s most important?

The problem isn’t that we’re lying to ourselves or even necessarily acting in opposition to our values. It’s more like…modern life conspires, pretty efficiently, to keep us stuck in patterns, dynamics, and straight-up needs that mean our priorities are necessarily elsewhere.

We can also, understandably, mistake our goals for values, our obligations for values, and sometimes even our anxieties for values. We may also inherit values that aren’t authentically ours, or absorb them from our social group, colleagues, or the culture at large.

We’ve found, in talking to mid-career coaching clients and in sessions at our retreats, that a sneaky cause of feeling stuck, restless, burned out, or unsure what comes next is simply: your values and your actions have drifted apart.

If that’s relatable, we have some resources! What can be helpful is to take stock of what your values actually are, whether or not you’re able to live them or if they feel aspirational, and consider ways to incorporate them or realign yourself with them.

One way to do that is to come to our free event on June 24th, all about discovering and defining your values. This is a tried-and-tested exercise we’ve used for years, and you’ll come away with a succinct list of your authentic values and personal definitions for each. It’s quite fun! (And we’ve even made it into an app for you! 🎉)

Another resource? The 20 slightly spicy, maybe-uncomfortable questions below, designed to poke you about the things you say you care about...and where your choices may not align. No need to answer all of them! But give the list a scan and notice which ones elicit a little “Oof…”

Those are usually the interesting ones. :)

20 questions that help reveal what you truly value

What do you keep complaining about but never change?
What part of your life would completely fall apart if you stopped trying so hard?
What do you spend money on without hesitation?
What do you secretly judge other people for?
Whose approval are you still trying to earn?
If someone followed you around for a month, what would they conclude you value most?
What do you envy that you don’t admit that you want?
What are you willing to disappoint people in order to protect?
What dream have you abandoned not because you wanted to, but because you “had” to?
If nobody could ever know you were doing it, what would you still choose to spend your time on?
What are you optimizing for that you don’t even enjoy?
What’s something true about you that you keep discovering over and over again?
What do you consistently make time for, no matter how busy you are?
What do you say you want, but repeatedly avoid when it gets close or feels unsatisfying once you have it?
What kind of pain are you most willing to tolerate?
What part of yourself comes alive when nobody is watching?
What would the people closest to you say you value more than you admit?
If your current life continued unchanged for the next 10 years, what would you regret most?
If your current life continued unchanged for the next 10 years, what would you be most proud of?
What is one thing you know matters deeply to you that isn’t getting enough space in your life right now?

These questions aren’t going to give you a list of your values, but the choices, tradeoffs, frustrations, envies, and how you spend your time and dedicate your attention will surface some commonalities and patterns that can point you in the right direction!

If you do want to dive deeper into this topic and define your own list of values, join us for The Hidden Rules Running Your Life: Discover and Define Your Values on June 24th!

Because when your values become clearer, decisions become easier. And sometimes the fastest way forward is understanding what really matters to you.

Over to you…

What moments in your life—either one-off or recurring—cause you to confront your values? Are there any situations in which you have to repeatedly reaffirm them?

But wait! There’s more…

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