“There’s nothing worse than getting to the top of the ladder only to realize it’s leaning against the wrong wall."

- Stephen Covey

Last week someone asked me a question that I didn’t have a crisp answer to.

I’m glad it happened because it forced me to think about and articulate what I’ve had trapped in my head for years.

I’ve changed jobs, industries, and companies several times.

Every time it’s worked out great.

It wasn’t until recently that I realized many of the things I processed intuitively were actually, at least in part, due to my ability to recall, pattern-match and synthesize information.

In other words, what is obvious to me, isn’t always obvious to other people.

Back to the question that stumped me…it was "How do you know it's time to move your ladder?"

Considering my goal is to positively impact as many lives as possible, I saw this as the perfect opportunity to codify how I’ve always thought about changing jobs, moving cities, and/or leaving relationships.

Hopefully you can find it useful too. In the era of AI, the costs of not having your ladder attached to the right wall or greater than ever.

So here are the 5 ways to know if it’s time for you to move your ladder to another wall.

1. If your ladder doesn’t lead to the thing you actually want.

This is the most obvious, yet non-obvious one. It’s because so many people never get crystal clear on what they actually want and fail to self-reflect on if the path they’re on is getting them there. It really is that simple. Most people don’t live intentional lives. They take the path of least resistance. They don’t think about whether they’re on a path worth climbing. They go through life on auto-pilot…drifting, hoping, and praying.

This is why Solomon’s Paradox exists and 60% of workers are unhappy with their jobs.

Unfortunately hope is not a strategy.

The world belongs to those that have the courage to create it.

And it takes courage to live an intentional life.

One of the reasons I left my job in Corporate America is because I knew I didn’t want my manager’s job, or his manager’s job. Continuing to climb the ladder would’ve been a form of cognitive dissonance, kinda like driving East and hoping to go North. The definition of insanity is doing the same thing over and over and expecting a different outcome.

I wanted to be an entrepreneur.
I wanted to be able to control my time.
I wanted to grow at a rate faster than my job would allow.

I wanted to be able to go snowboarding on a Tuesday because there was fresh snow on a Monday.

I had to move my ladder to get the prize that I wanted.

A book that really helped me get really clear on what I wanted is Vivid Vision. In 2021 I sat down and wrote my own 3 page vivid vision document. I wrote out my actual life, in explicit detail, present tense, three years out. It covers every area of life. Relationships. Health. Career. Finances. Spirituality. Not in fluffy, vague, non-descriptive language. For example, this is a line from my Vivid Vision document:

“I have the financial and time freedom to go snowboarding at Heavenly Mountain on a Tuesday because there was fresh snow on a Monday. I love using my season pass 30+ days a season. I get to miss the all the crowds, wait lines, traffic and have the mountain to myself. This is living!”

In January 2024, I made it happen. Pretty cool, no?

2. There's a more efficient ladder.

Sometimes the destination is right but the vehicle is slow.

Say the destination is making $250,000+ a year.

In 1990, or even 2000, becoming a medical doctor was one of the surest ladders to that number. Today there are ladders that didn't exist back then. You can buy a small business with little of your own money down. You can build an online audience with just your iPhone. You can build your own media company from your laptop and publish directly to the world.

In 2026, the possibilities with AI are unprecedented.
The $1M/year, one-person company is the new normal.

This is why medical school applicants have now declined three years in a row, down to the lowest level since 2017-18. Part of that story is simple math. When new ladders appear, the old ones lose their monopoly on the destination.

3. The wall moves.

Sometimes we don't leave the ladder. The wall leaves us.

Herb Caen named this feeling back in 1971: you work your whole life toward a goal, and "somebody moves the posts on you."

That's corporate America right now. So far this year 120,000 tech employees have been laid off. Some predict millions more jobs will be replaced by AI in the coming 3-5 years. Entire functions are being rewritten. Roles that felt permanent in 2019 quietly disappearing from org charts.

4. The juice isn't worth the squeeze.

Sometimes the ladder reaches the wall, but the prize no longer justifies the climb. For those in corporate America it may be the office politics, re-orgs, and unnecessary stress. For others it may be commute times or travel demands that prevent you from spending time with your loved ones. For others, like professional athletes in high-contact sports, such as Chris Borland, it may be the cost of physical injury, brain damage, or even potential death. Sometimes it’s better to walk away while you can; literally.

5. It's not a reasonable ladder (for you).

This one takes the most honesty and Intellectual Courage. Some ladders are real, and the view from the top is spectacular, but the climb isn’t for everyone. Becoming an NBA player, a Hollywood movie star, or the founder of a VC-backed unicorn start-up, are all reasonable and achievable goals; just not for everyone.

Some ladders are deceptively attractive. The lowest rungs are easy to climb, but then the spacing between the rungs starts to grow exponentially. Many aren’t aware of this until it’s too late.

According to NCAA data, about 3.6 percent of high school basketball players go on to play in college, and only around 1 percent of college players get drafted. The rungs aren't evenly spaced. Between "very good" and "professional," the gap becomes a leap most bodies can't make, no matter the work ethic.

This isn't a speech about abandoning dreams. Some people are built for those leaps, and the world needs them to jump. It's about measuring our reach against the rung spacing honestly, and asking whether a parallel ladder reaches a version of the same wall.

But if one of them is genuinely true for you, the research on waiting is clear. Psychologists Gilovich and Medvec found that in the short term we regret the bold things we did. In the long run, we overwhelmingly regret the things we didn't do. The pain of moving fades. The pain of inaction compounds.

Covey's warning was never really about ladders.

It was about the cost of climbing without being intentional.

Here’s to having the courage to be intentional. I’m wishing you all the best on your climb.

Here's your reflection for the week:

Assess your current situation. Is your ladder leaning on the right wall?

Here's your challenge for the week:

Pressure test your current ladder. Take 10 minutes to ask yourself (and/or AI) if you’re taking the most efficient path to that destination.

With courage,

Jonathan