The Career Ladder is Officially Broken. Enter The Monkey Bars.

By: Michael Youngblood, Unsettled Co-founder  

Artwork by Katie Rodgers, @paperfashion

As a child, did you visualize what getting a job and growing up would look like? I think many of us envisioned a staircase with a well-dressed business person making their way to the top.


Our education, parents, and the media embraced this idea that we would enter a career field and methodologically climb our way to the top; each step bringing with it better pay, benefits, an impressive job title, and retirement options galore.

If I was a social theorist, which I often pretend to be at cocktail parties, I would hypothesize that the very idea of a career ladder is a pacification tool to keep the masses in line, in check, and in control. The idea of it is that a methodological, step-by-step process will unfold over a lifetime.

The myth goes like this: Don’t make any drastic moves. You wouldn’t want to destabilize anything. Slowly inch your way up the ladder, one step at a time. Stay orderly. Don’t rock the boat.

The Career Ladder is Officially Broken

It turns out that the notion of a career has changed so much that we need to reorient all current and future generations about what life really looks like in the workforce today. For the majority, it is not a slow and steady climb upwards. It is a traverse, from one career and chapter in life to another. In between these chapters is where we find out what we are made of. It’s where we cultivate grit, form conclusions about our values and interests, and think deeply about what we want out of life.

As a society, we mock these “in between” moments as a midlife (or quarterlife) crises. When we fall off that career ladder, we enter into a life-defining crisis. We tell ourselves: stay on that career ladder. Keep looking up. Don’t take any risks that could end in failure. Climb, climb, climb.

In reality, I think we can agree that adulting looks more like this: We jump from school to school, job to job, apartment to apartment, city to city, and often for short durations. About 25% of millennials under 35 have already worked five jobs as an adult. According to the US Department of Labor, the average worker today spends less than 4 years in a career field before moving onto something new. We’re not talking about jobs here, but entire career change every 4 years.

We need to embrace this reality that our lives are in constant change and learning how to navigate through these moments of transition may be the greatest predictor of life-long satisfaction today.

Career paths today, if we can call them that, are more like monkey bars, those bars that your childhood self learned to swing across, one by one, gaining momentum, holding on for dear life at times, hoping to catch yourself on the other side, and often falling down embarrassingly in front of your playmates, hopefully to get back up, dust off, and pick up exactly where you left off.

Each year about 200,000 children in the US are treated in ERs for playground injuries, and, yes, the monkey bars are culprit numero uno.

It’s risky. It’s anything but a step-by-step process. It has a steep learning curve, but when you pick up momentum and get in the flow on the monkey bars, it begins to feel smooth, your confidence soars, and it’s actually fun to transition between one precipitous position to the next.

Like nearly everything, playing on the career monkey bars is a skill that can be learned and in learning it, you will unlock the key to navigating uncertainty. Let’s break it down.

Step 1: Build Momentum  

The career ladder is a step-by-step journey where you focus your effort on an upward trajectory and with each step, you get closer to your ultimate goal, higher status, better pay, and more responsibility. The problem with this journey is that it fails to understand the interests of the person, and rather lays out the goals as an upward progress towards success as defined by society (social status, pay, etc.).

If the career ladder is about a progressive journey towards success, then those precipitous monkey bars are about learning about how to propel yourself across the open spaces in life. You have to learn how to let go of one known position, reach across the void one-handed, and grab on as tightly as you can to the next without slipping or falling down.

Unlike a vertical ladder (where you can chill on a single step for 30+ years, get tenure, retire, and hope your pension fulfills your dreams before you die), when you’re swinging on those monkey bars, you are constantly in motion. You must learn to use this motion to your advantage.

The best way to develop this motion in our lives is to set goals that are truly connected to our interests and passions. In her book, Grit: The Power of Passion and Perseverance, this is the formula that Angela Duckworth discovers behind persistence, or our ability to keep moving through uncertainty in our lives.

Whatever it may be, work on building momentum and acceleration in your career because there will be unexpected moments of freefall that you can more easily navigate if you have hit that gap with speed. Remember, an object in motion stays in motion and an object at rest stays at rest. Careers today are more volatile than ever before and they will require sudden change. If you rest on your laurels, you’ll fall straight down. Instead, always build momentum.


Step 2: Prepare for Lateral Moves

The career ladder depicts a slow and steady upward climb. While we all want to feel forward progress in our careers and want to earn more year after year, don’t break your neck by looking up; opportunity for advancement may be beside you.

You need to be prepared to make lateral moves and see them as opportunities for you to get closer to your interests and passions, not a pie-in-the-sky goal like fortune and fame. There is possibility for this all around you, but you have to be willing to let go of a steady position you’re so tightly holding onto and grab onto a new position, even if it doesn’t feel like upward progress.


Step 3: Falling is Part of the Process

The monkey bars are all about learning by practice: falling off, getting back up, trying again. And fall you will. Our career counselors never told us this, or maybe they didn’t tell us enough, but no one gets anywhere without a few knee scrapes and possibly a broken arm. When you attempt the monkey bars, epic falls are a given.

And why shouldn’t they be? When you choose this path of defining your own goals, you are deciding to live differently. There is no clear map for success, but rather a process where you give yourself permission to embrace the unknown and follow your personal pathway towards the goals you have set. You will fall, but when you do, you will be one step closer to figuring out what works for you.


Step 4: Find Your Sandlot

In the cult classic film, The Sandlot, a group of playmates come together to collectively face down their fears (“The Beast”… a seemingly ferocious giant gorilla-dog who turns out to be a real softie) and realize that their greatest learnings in life come from each other. When you decide to branch out and follow your own path, you’re going to need a peer group that will support you when you fall off, help you understand how to do better, and give you feedback from a new perspective.

You need a group of peers who carry no judgement when you go through those transitions — the word midlife crisis is not in their vocab. They know that the path your on is the best one for you, and they’re not there to change that, only to help you up when you fall.


Step 5: Be Prepared to Take Chances

In the art of the monkey bars, you’re never going anywhere unless you take the risk to let go. But you can prepare for those moments of freefall by building up your capacity for resilience when confronted with change and uncertainty, which is ultimately the name of the game. When challenging moments are met with an embrace rather than a shove, the transitions themselves may feel like they are getting closer and closer than ever before.

In today’s world of constant career change, a risk averse career may be the most dangerous pathway out there. If you do not begin to master the swing, at some point the ladder will break and you will fall hard because you weren’t willing to take risks. In today’s career landscape, you need to be prepared for one wild ride across the transitions as much as the steady moments in life. Remember to build momentum by defining goals around your own interests and passions, look for opportunity beside you and not always above you, that failing is part of the process and you’ll learn a lot, to find your peer group on the sandlot, and be prepared to take chances.


When you join Unsettled, you are joining more than a travel experience; you join a traveling community of career swingers, job hoppers, and embracers of those open spaces from all around the world. Learn how to join us here.

Sources of inspiration from over the years:

The Four Year Career.

The Parable of the Trapeze.

The Sandlot. 




Unsettled is a global community for those who live and work differently. 

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