I had coffee with an acquaintance yesterday.

We actually live in the same town, and it’s a small town, but our only connection was through social media.

He reached out and asked if I’d be up for coffee. The idea of meeting and chatting in real life is missing from my life.

We grabbed our coffees, found some seats, and dove right in.

Unfortunately, he’d lost his very high-profile C-level position the week before. He knew my story, that I’d been through some stuff, and wanted to chat.

We talked about the next steps, and I asked him,

“How do you define success?”

He answered along the lines of:

“I always thought it was more money and the next big thing, the next big job title.”

I nodded in total understanding and asked him,

“You achieved that definition of success, but let me ask you—did you feel successful?”

His answer was immediate:

“No, not even close. I wasn’t fulfilled.”

Professional and financial success are only two components of our lives, yet we tend to make them the only metrics we use to measure our lives.

Professional and financial success at the cost of personal fulfillment isn’t success; it’s half an existence desperately trying to pretend it’s a full existence.

It’s one of the biggest lies we tell ourselves. It’s the lie that it should be enough.

Because that’s what we’ve been conditioned to believe, you bust your ass, you move up the ranks, earn lots of money, and everything will fall into place.

Except it doesn’t.

For one simple reason: we may check all the boxes we believe will make us a “success” and make us happy, but nowhere in that success is the authentic you.

The boxes we check are hand-me-down beliefs, and those beliefs displace our authentic dreams.

We fall into another of the biggest lies we tell ourselves:

“When I achieve a certain level of success, then I’ll pursue my dreams.”

How many dreams have died in the clutches of the “When I…, then I…” trap?

“Then” never comes because “When” is infinite.

Maybe your “when” is:

“When I have X amount of dollars, then I can write my Civil War novel.”

What happens when you hit your target? Your target moves.

All of a sudden, you’re faced with multiple realizations.

One is—sure, X amount of dollars felt great, but… it’s not quite enough. X.5 sounds like an awesome number. Then, I’ll be secure enough to start pursuing my dreams.

Two—you reached your target, which means you have to pursue your dreams, and you realize how terrifying the work actually is.

You’ve never written a book. You don’t know where to begin. But you’ll feel a whole lot better when you have that X.5.

X.5 will make all the fear disappear (another tremendous lie).

This is how so many of us end up on the Golden Treadmill of Empty Success.

We chase an infinite “when,” so we’ll never get to “then.”

It’s the fastest path I know to create an empty life destined for regret.

So, how do we change course? How do we start down a new path—one that will actually bring us to the life we say we want but keep deferring to an unknown future?

In crystal-clear clarity, we write down our current definition of success.

We examine our current definition and ask questions:

🔹 Where did this definition come from?


🔹 If, like my acquaintance, you achieved your definition, ask yourself: Do I feel successful?


🔹 What’s missing from my current definition?

Redefine success authentically. No shoulds, outside opinions, or others’ expectations.

With your new definition, it’s time to break free from the “When I…, then I…” trap.

Identify the first, tiniest step you can take toward your dreams.

Put it in the calendar, and understand this:

This is non-negotiable. Commit to executing this first small step—no excuses, no BS, no distractions. Get it done.

When you execute the step, take a moment to feel how it feels to move toward your authentic definition of success.

It feels incredible, doesn’t it? That feeling is available to you all the time.

Celebrate yourself for making and keeping your commitment because you’re doing more than just feeling good.

When you make and keep meaningful commitments to yourself and celebrate your success, you cultivate deep self-trust and train yourself to want to keep going.

Once you’ve taken the first step, schedule the second. Wash, rinse, repeat—all the way through the entire process.

Inertia can be your foe or your ally.

Remember Newton’s First Law?

“An object at rest stays at rest, and an object in motion stays in motion with the same speed and in the same direction unless acted upon by an unbalanced force.”

Your authentic dreams are that object.

Taking the first step sets them in motion.