Career Ladders, Incline Walks & Rebranding Success

9/3/20252 min read

3 Things I'm Loving, Reading, Watching or Doing

1. The End of the Career Ladder

I came across a great piece on Sinéad Bovell’s Substack about what she calls the Independence Era of employment. The old idea of a neat, linear career ladder is crumbling. But instead of fearing that shift, I think it’s exciting, if we’re equipped with the right tools. We may be heading toward this new era faster than we imagine, and those who adapt will thrive. Good for our teens and college kids to think about.

2. Incline Walk for Zone 2 Cardio

As I’ve previously mentioned, I like doing my longer cardio (45-60 min) one day/week on a bike or walk/ruck. Sometimes I do this on a treadmill with full incline, but I get bored so I’ll mix in something like a set of dips every 5 min. The key, though, is a good walking playlist. Here’s a banger set that may surprise you. :)

3. Book Club?

My librarian wife just finished Fredrik Backman’s My Friends and loved it. So that’s next on my list. Anyone up for a super informal book club? Read it over the next month, then hop on a Zoom chat with some tea (or whiskey). I’ve never hosted a book club before, but I imagine that’s how these things work. Who’s in?

2 Quotes Worth Pondering


“Don’t prepare the path for the child. Prepare the child for the path.”
— Native American Proverb

“The ladder of success is best climbed by stepping on the rungs of opportunity.”
— Ayn Rand


1 Big Dad Idea

Redefining Success for Our Kids

If the “career ladder” is disappearing, what does that mean for how we talk to our kids about success? For decades, the formula was clear: work hard in school, get into a good college, land a secure job, climb the ladder. But that ladder is wobbling, and in some cases, disappearing altogether.

This is a hot topic in our household because we’ve got a high school senior. Having run my own business for the past 20 years, I’ve essentially preached to my kids: be builders, not just climbers. Entrepreneurship isn’t for everyone (as my wife will quickly remind them), but in a shifting job climate, they’ll need to get much better at creating opportunities, stacking skills, and adapting quickly. That can feel overwhelming, but it’s also liberating. It means success isn’t defined by a single path.

As dads, maybe the best gift we can give our kids is figure-it-out ability: the courage to take risks, even small ones, and the responsibility to own their outcomes without relying on a corporation or government safety net.

Also, there’s a deeper (and more positive) shift I see here.

It’s not just about moving from “How high will my kid climb?” to “What will my kid build?”

The better question is this: Who will they become in the process?