When Winning Doesn’t Feel Like Winning

You can be doing everything “right” and still feel like you’re losing.

I know that tension—not as a theory, but as something I keep bumping into. I’m a professional speaker. I started in 2007. By 2011, my calendar looked like a highlight reel. I was fully loaded with speaking and training opportunities, moving from hotels to airports, from resorts to hotels, and conducting workshops in far-flung areas. One stretch still sounds unreal when I say it out loud: Baguio, Subic, Cebu, Davao, Koronadal, Agusan del Sur, Butuan, Makati, Vigan, Samar, Palawan—then Indonesia, Malaysia, Singapore.

It felt like winning.

People were booking me. Projects kept coming. I was “in demand.”

But I was also burning out.

Not the dramatic kind where you collapse on the floor. The quiet kind. You can still deliver, but you’re not okay. You can still smile, but you’re running on fumes. And when you’re good at what you do, you can hide that for a long time—even from yourself.

That experience taught me something I wish I had learned earlier: a life can appear to be a win and still be a slow loss.

The Invisible Loss Problem

Most people think losing looks like failure.

But the real losing often looks like functioning.

You’re responsible. You show up. You keep things together. You do what needs to be done. And yet deep inside, something feels off. Not because you’re ungrateful. Not because you’re weak. But because you’re leaking.

Energy leaks. Time leaks. Attention leaks. Boundary leaks.

Nothing is exploding. But you’re slowly getting drained.

And the tricky part is this: leaks don’t feel urgent. They feel normal. Until you wake up one day and realize you don’t feel like yourself anymore.

The Autopilot Trap

My default was autopilot with good intentions.

I’d wake up with a plan, then spend the day reacting. Messages. Requests. Last-minute changes. “Sir Jef, can we add one more session?” “Can you also speak here?” “Can you adjust the program?” And because I was grateful—and because I wanted to deliver—I kept saying yes.

By the end of the day, I wasn’t proud. I was just relieved.

Then I’d promise myself I’d rest “soon.” You know how that story goes. Soon becomes later. Later becomes never. And the autopilot becomes your lifestyle.

That’s when even good work starts to feel like a burden.

Why I Needed Something Simpler Than a Mantra

For years, I’ve been sharing my personal mantra: All-in, A-game, Always.

I still believe in it. It’s personal. It has power.

But here’s the honest part: a mantra like that needs explaining. People want to know, “What does All-in look like in real life?” “What does A-game mean when I’m tired?” “Always… as in always? Paano yun?”

And when someone is already overwhelmed, too many questions can feel like homework.

So I needed a tool that didn’t need a long lecture.

Something people could start using in five minutes.

Where Nine Life Circles Came From

Nine Life Circles didn’t start as a “life system.”

It started as a team building activity.

I first encountered the idea inside Sessions Lab. We used it in team building. The goal was to help people see their whole life in one page so they could talk about it honestly without turning it into a therapy session.

And it worked.

Every time I ran it, people would look at their page and say something like, “Ah. Ito pala.” They didn’t need a long explanation. The visual did the work. It gave them language. It gave them permission to admit what’s okay, what’s not, and what they’ve been ignoring.

I kept using it because the feedback was consistent: useful, simple, clear.

I refined it.

Not to make it fancy.

To make it easier to use again and again.

And somewhere along the way, I realized I needed it for myself—not just for teams.

Why This Tool Works

Nine Life Circles works because it does three things most people don’t do:

First, it makes your life visible. You can’t fix what you can’t see.

Second, it reduces overthinking. You’re not writing essays. You’re not answering ten deep questions. You’re doing a quick, honest scan.

Third, it helps you choose one shift. Not nine. One. The whole point is focus.

That’s why it’s simpler than my mantra. You don’t need to “understand” it first. You just use it. Then insight follows.

And yes—being visual matters. When you see the circles, your brain stops arguing and starts noticing.

Pause Here: Do the 5-Minute Reality Check

Don’t just read this and nod.

Do the thing.

Download the Win in Life Starter and color your Nine Life Circles.

Use these labels:

I’m crushing it! I need to work on this a little. I need to work on this a lot. This is not a priority right now.

No overthinking. No guilt. No explanations.

Just honest coloring.

Then look at your page and ask, quietly: Where am I leaking right now?

The One Shift Question

Now choose one circle.

Just one.

And write this line:

For the next 30 days, I will play to win in ______.

That’s it.

Small shift. Real difference.

If you want, tell me what you picked. Seriously. Message me. I want to know what people discover when they finally see their life on one page.

Not because I’m collecting stories.

Because we learn faster when we compare notes.

And because I’m still practicing this too.

Download the Win in Life Starter, color your Nine Life Circles, and choose one circle to play to win in for the next 30 days. Then tell me what surprised you.

If this article helped you see why life feels off, the next step is deciding what to do about it.

Clarity is not the finish line. It’s the starting point.

Once you’ve colored your Nine Life Circles, the question changes. It’s no longer “What’s wrong with my life?” It becomes:

Where do I want to win next?

That’s what the next article is about.