Why “Getting Ahead” isn’t what you think it is

Read time: 3 minutes

You ever catch yourself mid-sentence and realize, “Wow, I say this all the time… but do I actually believe it?”

That happened to me recently.

My wife and I were sitting on the floor of our son’s room—Hot Wheels scattered everywhere—when I caught myself mid-sentence.

I don’t remember the exact order of our conversation. We were just passing thoughts back and forth—about a future plan, a financial goal, something we needed to get done.

I looked up and said something like, “Once we get through this, we’ll finally start getting ahead…”

But then I paused.

I heard myself say it.

That phrase again: “Getting ahead.”

It’s one of those expressions that rolls off the tongue so easily—especially when you’re wired for growth, progress, or responsibility—and I’ve used it for years. In conversation with myself. In goals I’ve written down. In subtle ways I didn’t even notice.

And yet, I’m starting to realize something important:

We’ve been sold a version of success that sounds smart… but quietly keeps us stuck.

Let me explain.

What does it even mean to “get ahead”?

For most of us, it means reaching a point where we finally feel free.

Free to prioritize what matters.

Free to rest.

Free to stop sprinting.

We believe that once we make more money, pay off the debt, hit that income level, get the promotion, buy the house, or stack up enough in savings—then we’ll be ahead.

• Ahead of our peers (“status comparison”)
• Ahead of future hardship (“security”)
• Ahead of who we used to be (“self-improvement”)
• Ahead of a fear of not being enough (“validation”)

And then we’ll finally get to exhale.

But here’s the truth I’ve had to confront:

“Getting ahead” is a moving target.

Every time you inch closer, the finish line shifts.

The goal post keeps moving.

And the new raise becomes the new baseline.

The new lifestyle becomes the new standard.

We don’t feel ahead—at least not anymore—we feel behind in a fancier way.

I know this because I followed that path too.

I spent years in a corporate career, accepting promotions that looked great on paper but didn’t align with who I was becoming.

I wasn’t chasing status. I was chasing stability.

I wanted to be a good provider. To create options for my family. To get ahead so I could eventually step back.

But the job kept demanding more.

And I kept telling myself, “This is fine—for now.”

Until it wasn’t.

So I got serious. I paid off $23,000 in student loans in 12 months.

I used my income to cash flow my wife’s education so we wouldn’t go further into debt.

And then I made a decision to leave that job after eight years.

Not because I hated it.

But because I realized that getting ahead in a life that doesn’t feel like yours… isn’t really getting ahead at all.

(Hit reply and send me a 👍 if that struck a nerve.)

So what does it look like instead?

It looks like waking up with a calm mind instead of a racing one.

It looks like being present at dinner with your family instead of mentally sorting through your inbox.

It looks like choosing a career or business that may pay less at first—but gives you time to breathe, space to grow, and energy to build something meaningful.

It looks like setting boundaries. Saying no. Making trade-offs.

Not because you’re giving up on success.

But because you’re redefining it.

And here’s the shift that made the biggest difference for me:

Getting ahead isn’t about more.

It’s about alignment.

It’s not about reaching a finish line.

It’s about choosing the life you want while you’re still building it.

Oof. That hit.

You ever read something so true you just sit with it? Yeah. That.

Here’s the thing. The path I’m navigating on my journey is the path I want to help you step onto. Commit to. Trust.

So, the next time you catch yourself saying “once I get ahead…”

Pause.

Ask yourself:

What does getting ahead mean to me?

And is the path I’m on actually leading me there, or pulling me further away?

Because you don’t need to chase someone else’s version of progress.

You don’t have to earn the right to prioritize what matters.

You can start now.

Redefine “ahead” as the freedom to live aligned.

And take one small step in that direction today.

See you next Sunday, my friend.