Sometimes You Have to Fail to Understand

(Even When the Advice Was Sound All Along)

There are so many things in life we’re warned about—advice we’re given, sometimes over and over, in the hopes that we might avoid pain, inefficiency, or burnout. But as much as we want to believe we’re rational and proactive, the truth is: sometimes we just have to experience it for ourselves before we truly understand.

This happens in small, everyday ways. And it happens in the big, life-defining ones, too.

The Hoodie Lesson

Take a recent moment in my own home.

My oldest daughter has entered the era of teenage independence—and that includes a fierce commitment to wearing hoodies and jeans in 90-degree heat. As a parent and a physician, I gently (and sometimes not-so-gently) reminded her: “You need to stay hydrated.” “Heat stroke is real.” “You’re going to feel awful if you don’t take care of yourself.”

Her reply? “I’m fine. That’s not going to happen to me.”

Until the day it did.

She came home lightheaded, fatigued, and miserable. After some water and rest, she perked back up—and the connection finally clicked for her. She’d ignored advice because it didn’t feel relevant… until it was.

And in that moment, I realized: this dynamic plays out constantly. In our homes, our clinics, our relationships, and most definitely in our careers.

You Can’t Always Hear It Until You’ve Lived It and Fail

I see this all the time in medicine.

I’ve told countless residents and colleagues the same golden rule of time management: Finish your charts before moving on to the next patient. Not because I love saying it. But because I’ve seen what happens when you don’t. The hours spent charting at night. The creeping resentment. The erosion of work-life boundaries that turns into burnout.

But for many, that advice feels impossible at first. “There’s no time.” “My clinic is too busy.” “That won’t work for me.” And so they wait—until the exhaustion sets in, they feel like they fail and they finally circle back, ready to try a new way.

It’s not that they didn’t believe me. It’s that they weren’t ready to hear it.

I’ve Failed Too

And I don’t just say this as someone who gives advice. I’ve been the one who had to learn the hard way, too.

For years, people told me to delegate. “You don’t have to do everything yourself,” they’d say. “Trust your team. Let go a little.” And I’d nod, but inside I thought, If I want it done right, I have to do it myself. I’ll just work faster. I’ll figure it out.

You can guess how that story ended.

I burned myself out. Completely. This made me feel like I was failing in my job. And without meaning to, I sent a message to my team that I didn’t trust them—or value their contributions. What I thought was dedication looked, to them, like exclusion.

I had to unlearn a lot and rebuild how I worked. And only after going through it myself did the advice finally stick.

Why Don’t We Listen?

There are so many reasons we don’t take in good advice when it’s first offered.

• We’re overwhelmed. The idea of adding one more thing feels impossible, even if that thing might help.

• We don’t think it applies to us. We assume we’re the exception—that we can handle it, that we’ll manage. That we won't fail.

• We’re afraid of change. Especially in high-stakes, high-performance environments like healthcare, the unfamiliar can feel riskier than the known.

• We don’t know how to start. Vague encouragements like “set boundaries” or “take time for yourself” sound good—but without tangible steps, they go nowhere.

And sometimes, we just aren’t ready yet. And that’s okay.

When Experience Becomes the Teacher

There’s no shame in needing the lesson to hit home before it changes us. But what we can do is make space for reflection—so when the moment comes, we’re more prepared to recognize it.

Experience is a powerful teacher. But it’s even more powerful when paired with curiosity and compassion.

Instead of beating ourselves up for not listening sooner, what if we simply asked:

• What do I know now that I didn’t before?

• What support would have helped me hear this advice earlier?

• What might I still be ignoring today?

Because chances are, there’s something in your life or career right now that’s quietly sending warning signs.

Maybe it’s your calendar packed with back-to-back meetings and no space to think.Maybe it’s the emails you can’t respond to because you’re still catching up from yesterday.Maybe it’s the low hum of dread before Monday morning.

You don’t have to wait for a full-blown crisis to take a different path.

Creating Space for New Choices

This is exactly why I created the work I now do with coaching clients, and the resources I build like the Pathway from Chaos to Calm masterclass and my 7-Day Boundaries Challenge. Because even if you’ve already felt the weight of burnout, you can still choose to build something different.

You can:

• Finish your notes on time—and still provide excellent care.

• Say no to things that don’t align—and still be seen as a team player.

• Delegate effectively—and show your team you believe in them.

• Protect your peace—and still be a committed, high-performing leader.

The key is recognizing that real change doesn’t start with a giant overhaul. It starts with one honest moment of reflection. One new choice. One step toward alignment.

Your Turn

If something in this post resonates—if you’ve been brushing off advice, or stuck in habits that no longer serve you—pause and ask:

What advice have I been resisting?

Letting the advice pass you buy

What might change if I gave myself permission to try something new—just for a week?What’s one thing I already know, deep down, but haven’t been ready to act on yet?

Because sometimes, yes, we have to experience it to truly understand.

But we don’t have to keep repeating the cycle.We can listen with new ears, act with new courage, and choose a path that honors both our purpose and our wellbeing.

Resources to Support You:

• 📘 Free Purpose & Priorities Workbook – Reflect on what really matters in this season of your life.

• 🎥 Free On-Demand Masterclass: Pathway from Chaos to Calm – Learn practical tools to protect your time and energy.

• 🧭 Join the 7-Day Boundaries Challenge – One small mindset shift and action step each day.