Leaders, When Was the Last Time You Asked “Why”?

When was the last time you took inventory?

Not of your closet or your inbox or your quarterly goals. I mean a real inventory—of how you’re spending your time, your talent, and your treasure. Does it align with your core values? Does it bring you joy and fulfillment? Are you making a difference? Are you spending time with people who fill your energy jar, or with those who drain it drop by drop?

Here’s the harder question: How much are you doing out of guilt, obligation, or what you think is expected—versus what you actually want?

I used to think these questions were indulgent. Optional. Something to consider “someday” when life slows down. Except life never slows down if you keep saying yes to everything.

A Leadership Juggling Act Nobody Wins

For years, I said yes to everything.

Executive and owner in a family business? Yes. Mom of two active kids? Yes. Wife, daughter, sibling, friend, athlete, volunteer—yes, yes, yes, yes, yes. I believed I could do it all. More than that, I believed I should do it all.

But I never stopped and asked myself, “Why am I doing all this. And, at what cost?”

I didn’t look at the impact on me—physically, emotionally, intellectually, spiritually. I didn’t ask which version of me was showing up in each role, and whether any facet of my life was getting the best of me. I just kept juggling, even as I felt the weight of every ball in the air.

I knew I was out of balance. I knew it in multiple ways—in my energy, in my relationships, in my health, in the growing gap between who I was and who I wanted to be. But knowing you’re out of balance and doing something about it are two vastly different things.

Making Transformational Decisions

In 2022, I took a leave of absence from work. Crazy! For those who really know me, they were stunned. Heck, I barely even took parental leave, but I needed a break, and admitting that was one of the hardest things I’ve ever done. 

And it was the best thing I’ve ever done. 

When I announced my leave at a town hall meeting—my hands shook, I was crying, and felt so vulnerable. I felt like I was admitting defeat. Like I was raising my hand in the middle of the game and saying, “Take me out, coach. I can’t do this.”

At first, I thought I was a failure. I thought it meant I wasn’t strong enough, capable enough, resilient enough. If I just tried harder, organized better, slept less, pushed more—surely, I could juggle it all.

But here’s what I’ve learned since: That decision wasn’t a failure. It was a badge of courage.

It takes more strength to stop than to keep going when you’re depleting yourself. It takes more courage to say “this isn’t working” than to pretend everything is fine. It takes more wisdom to ask for what you need than to martyr yourself to what everyone else expects.

The Questions That Can Change Everything

Taking that leave forced me to sit with some uncomfortable questions:

Why was I saying yes to everything? Was it because these commitments genuinely aligned with my values, or because I was afraid of disappointing people? Was I filling my time with what mattered most, or just with what was most urgent and visible?

Why did I believe I had to do it all? Whose expectations was I trying to meet—my own, or some invisible standard of what a “successful” executive, parent, partner, and human should look like?

Why was I measuring my worth by how much I could juggle, rather than by the quality of what I was creating, the depth of my relationships, the alignment between my actions and my values?

These weren’t comfortable questions. But they were the right ones.

What Curiosity-Driven Leadership Looks Like

Here’s what taking inventory of my time, talent, and treasure has taught me:

• Balance isn’t about doing everything equally. It’s about being honest about what matters most right now, in this season, and having the courage to let other things go—even temporarily, even imperfectly.
• Your energy jar matters. You can’t pour from an empty vessel. Spending time with people and pursuing work that depletes you isn’t noble; it’s unsustainable. And the people who genuinely care about you don’t want your exhausted leftovers; they want you at your best.
• Guilt is a terrible compass. If you’re doing something primarily because you feel guilty saying no, it’s worth asking why. Guilt keeps us tethered to expectations that may no longer serve us—or may have never truly been ours to begin with.
• Courage looks like vulnerability. Admitting you need help, saying you’re out of balance, stepping back to recalibrate—these aren’t weaknesses. They’re the most powerful leadership moves you can make towards executive wellbeing, whether you’re leading an organization or just leading your own life.
• The inventory is ongoing. This isn’t a one-time assessment. Our values shift, our seasons change, our capacities ebb and flow. What aligned last year might not align today. What brought joy six months ago might now feel like an obligation. Asking “why” isn’t a destination; it’s a practice.

An Invitation to Wonder

So, I’m wondering: When was the last time you took inventory?

What would you discover if you honestly assessed how you’re spending your time, talent, and treasure? Would you find alignment—or would you find a gap between who you are and who you’re trying to be?

What are you doing out of joy and purpose, and what are you doing out of guilt and expectation? Who’s filling your energy jar, and who’s draining it? What would it take to have the courage to say, “Take me out, coach—not because I’m failing, but because I need to recalibrate”?

These aren’t easy questions. But they’re the ones that change everything.

Maybe the real failure isn’t stepping back when you need to. Maybe the real failure is never asking why you’re running so hard in the first place.

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I’d love to hear from you

What’s one commitment you’ve been holding that no longer aligns with your values? What would it take to let it go for a better work-life balance? 

Write it down. Sit with it. Take one small step toward releasing it.And if you’re a leader navigating this tension between expectations and authenticity, between doing it all and doing what matters—let’s talk. This is the work I do with executives and organizations: cultivating the curiosity and courage to ask “why” before burnout forces the question.