June 12, 2025

“I should be further along by now.” “I need to catch up.” “This isn’t where I’m supposed to be.”

If you’ve had these thoughts lately, you’re in good company.

We live in an age of quiet (or not so quiet) comparison, where our worth is measured against arbitrary timelines and invisible scoreboards. It’s subtle, but corrosive.

We begin to believe we’re behind—behind in our careers, our relationships, our own expectations. And with that belief comes shame, urgency, and decisions rooted in fear.

But what if that feeling isn’t truth… just distortion?

This week, I invite you to consider: What if your timeline isn’t broken—but perfectly unique to you?

MINDSET
Your Life isn’t a race. It’s a custom map 🧭

When a close friend had his second child, I felt a mix of joy and… something else.

Alongside pride and happiness, I felt a pang of fear that I was behind. Though I’ve made peace with the prospect of not having kids, a part of me still felt off-track, like I’d missed a key milestone.

That’s the power of milestone thinking—the idea that by a certain age, we should hit specific life markers: marriage, house, kids, career title. It’s a cultural GPS that tells us where we should be and when.

But here’s the thing: real life doesn’t follow that kind of rigid map. It unfolds more like a hand-drawn sketch—full of peaks, switchbacks, valleys, and unexpected turns that honestly make for a far more rewarding journey.

Milestones can offer general guidance, sure—but they can also pressure us into rushing big life decisions or feeling shame when our path veers. They make normal detours feel like failures.

What’s helped me is seeing my life as a landscape, not a ladder. The forest, the fog, the unexpected detours—they’re not wrong turns. They’re just part of the adventure.

Atomic Action: Mentally list one or two pivotal decisions or detours you’ve taken.

Then reflect: What did each one teach me that I wouldn’t have learned otherwise?

QUOTE
"You are right where you are supposed to be.”

I love this quote. A woman who coached me a few years back said it to me and I now repeat it to myself and to clients.

It’s not just a comforting phrase—it’s a statement of defiance to the noise of comparison and self-judgment.

You’re not late, you’re not lost, you are arriving precisely when you’re meant to. 🌱

COACHING QUESTION
What story am I telling myself about where I should be— and is it actually true?

At 42, I sometimes catch myself thinking: “I should be married by now.” Or “I should be farther along in my career.”

With many friends deep into marriages and established careers, that quiet voice creeps in—you’re behind, it’s too late.

But those aren’t facts. They’re stories—unexamined ones. And unexamined stories often breed panic, pressure, and rushed decisions.

When I slow down and question them, I create space for a better narrative—one grounded in truth and trust:

“I’ve waited for the right person.” “I’ve figured out what doesn’t work.” “There’s still time. Bro..chill.”

So I’ll ask you what I ask myself:

  • Where in your life do you feel “behind”?

  • What belief is fueling that feeling?

  • And what if... it’s not even true?

Perhaps you’re not behind at all—just on a path uniquely your own, right on time.

RECOMMENDATIONS
The Hotlist For the Week

Book: The Practicing Mind by Thomas Sterner. This is the second time I’ve recommended this book, because it’s that good. If you tend to focus too much on achievement rather than enjoying the process, this book is for you.
Playlist: Wild Ambience. This Spotify playlist brings so much calm to my overly anxious mind.
YouTube: Unreal Places: This video reveals some incredible places on our planet and is just so freaking calming.

REFERRAL SHOUT OUT
Calm Hustle Referral Shout Out!

Want to give a shout out to the MVP of the week Andrew Chrighton.

If you enjoy the newsletter and want to become a Calm Hustle Crew MVP, share the link below and hit the referral milestones.

CLOSING THOUGHTS
Thank you for reading..

In the chill moments—away from the chaos and measurement—we remember:

Life is not a race.

It’s a gradual unfolding, a series of small, meaningful steps taken at your own pace.

So wherever you are today… let it be enough. You are right where you’re supposed to be.

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