We've been brainwashed.
For decades, we've been told that career success looks like climbing a ladder—one rung at a time, always moving up, never looking back. But that's not how careers actually work anymore. And honestly? It's not how they're supposed to work.
The ladder is gone. It doesn't exist anymore.
What we need is a complete mindset shift: Your career isn't a ladder. It's a jungle gym.
The Problem with the Ladder Mentality
When we think of careers as ladders, we create unnecessary pressure and missed opportunities. We focus so intently on the rung directly above us that we miss the dozens of other possibilities surrounding us.
The ladder mentality suggests there's only one way to succeed: up. But what happens when "up" isn't available? What happens when "up" isn't even what you need right now?
That's where the jungle gym comes in.
Why the Jungle Gym Changes Everything
Christine Bragale, a seasoned marketing professional, put it perfectly during our conversation: "A career is not a ladder. It's a jungle gym. And I think if people can approach their careers that way, they'll find so much more fulfillment."
She's absolutely right. The jungle gym approach reduces stress and opens possibilities. Sometimes you're better off going sideways. Sometimes you need to climb down to position yourself for a bigger leap later.
Every move on the jungle gym teaches you something new:
- New doors open
- You create fresh relationships
- You learn different skills
- You gain knowledge that serves you in unexpected ways
Real Stories from the Jungle Gym
The Wandering Path That Led to Success
Eric Nehrlich's story is a perfect example of jungle gym thinking. While his MIT classmates launched straight into tech careers, becoming VPs by 30, Eric was still an individual contributor software engineer. He felt behind, like he was doing something wrong.
But his broader, more wandering path set him up for something his linear-thinking peers couldn't access. That breadth of experience—mixing engineering, product management, business strategy, and finance—made him uniquely qualified for roles like chief of staff that required diverse skills.
"It's okay to take a different path," Eric reflects. "Figure out what's going to lean into your superpowers, what makes you great, what makes you different. That's going to be what eventually separates you."
The Reality of Modern Careers
Mark Beal brings another crucial perspective: "Nothing is linear anymore. There are going to be on ramps, there are going to be off ramps, there's going to be obstacles, challenges, step backs."
This isn't a bug in the system—it's a feature. The key is embracing these challenges rather than fighting them. When clients pushed him harder, demanding more, Mark had a choice: resent the pressure or use it to level up.
"You can be like, 'I can't stand this client.' Or you can be like, 'Okay, they're pushing us. Let's see if we can respond. Let's see how we can be smarter, more strategic, more creative.'"
The Experimental Approach
Kara Silverman emphasizes that careers don't follow straight paths, and that's perfectly fine. The trick is being able to tell your story—connecting the dots between seemingly unrelated experiences.
"Even if it feels like one job isn't connected to another job, or maybe you have a gap, or you're being experimental, as long as you can connect the dots and help an employer understand what your career path looked like and how you got from A to Z, that's what matters."
The New Rules of Career Navigation
1. Embrace Non-Linear Movement
Your next move doesn't have to be "up." It can be sideways, diagonal, or even down if it positions you for future growth.
2. Focus on Your Superpowers
Instead of following someone else's path, identify what makes you unique and lean into those strengths.
3. Every Experience Adds Value
That "detour" you took? That sideways move that confused people? It's probably giving you skills and perspectives that will pay off later.
4. Tell Your Story
Learn to connect the dots between your experiences. Show how each move contributed to who you are today.
5. Run Your Own Race
Stop comparing your timeline to others. We're all on different paths, and that's exactly how it should be.
Making the Mental Shift
The jungle gym mindset requires a fundamental shift in how we think about success. Instead of asking "How do I get to the next level?" ask:
- What do I need to learn right now?
- What experience would serve me best?
- Where can I add the most value?
- What move aligns with my current life situation?
Sometimes you might move step by step up a traditional ladder. But sometimes you need to swing to the side, drop down to build new skills, or take a completely different path altogether.
The Bottom Line
Career fulfillment comes from the jungle gym approach, not the ladder climb. By only focusing on one direction—up—we miss out on amazing experiences and opportunities that could transform our lives.
So look around. See all the rungs available to you. Consider your options. Then swing to the one that feels right for this moment in your life.
Your career is not a race to the top. It's an exploration of possibilities.
And the jungle gym? It's where the real adventure begins.
What rung are you considering swinging to next? Remember: there's no right or wrong move, only the move that's right for you, right now.