Someone asked me over dinner to walk them through my career path. I laughed. "Path" suggests a straight line. Mine looks like a kid's scribble on the back of a napkin.
Army first. Then engineering. Then leading engineers. Then leading the people who lead engineers. Now writing and speaking about why so many bosses are so bad at all of it. Nobody handed me a map for a single step of it.
And the scribble beat every plan I ever wrote down.
The ladder has one rule, and it belongs to someone else
A career ladder is an org chart with ambition painted on it. It exists so finance knows what to pay you and so your boss knows who reports to whom. Nobody designed it around your life.
Look at how it works. One direction: up. One winner per rung. Your growth gets rationed by how often the person above you quits, retires, or gets fired.
You control none of those three events. So you wait. You take the extra project, the extra hours, the extra swallowed complaint, hoping someone notices, hoping the rung opens before your patience runs out.
It is a cage with a nice paint job.
Worse, the ladder tells you what to want. Manage more people. Own a bigger budget. Get a longer title. I have watched brilliant engineers climb into management, hate every minute, and stay there anyway... because stepping back down reads as failure on a ladder. On a ladder there is only one shameful direction.
Most people never get the rung anyway
The numbers here are grim.
Pew Research Center found 63% of workers who quit a job in 2021 named "no opportunities for advancement" as a reason for leaving. At least a third called it a major reason. Same share as low pay. People walk out of the building over a rung.
Now look at the people holding the ladder. LinkedIn's 2025 Workplace Learning Report found only 15% of employees said their manager helped them build a career plan in the past six months, down five points from the year before. Only 36% of organizations run career development well enough to earn the label "champion".
Read those two findings side by side. Most people leave over growth. Most managers never open the subject. Then everyone acts shocked at the exit interview.
If your growth depends on a system with those odds, your growth is a lottery ticket.
Sideways is a real move, not a consolation prize
Here is the part nobody explains at your first job.
Xin Jin and Michael Waldman published a study in the Journal of Law, Economics, and Organization on lateral moves inside firms. Workers moved sideways in one period turned out more likely to be promoted afterwards, with stronger wage growth than peers who stayed put. Their evidence came from linked employer-employee data on senior management roles in large US companies.
Sideways is not a detour from the promotion. Sideways is often the thing causing the promotion.
The mechanism is obvious once you say it out loud. Every sideways move buys you a new set of problems, a new set of colleagues, and a new set of skills. Three moves later you hold something rare: you understand how four parts of the business fit together. Nobody climbing one leg of the ladder ever learns it.
I got my biggest lift from a move with no title attached at all. I took on a mess nobody wanted, in an area I knew nothing about, and spent six months feeling like the dumbest person in the room. The stuff I learned in those six months paid me back for a decade.
My scribble, in hindsight
Every good thing in my working life arrived from a sideways step.
The Army taught me how people behave under pressure. Writing software taught me how systems break at the seams. Leading teams taught me how much of "technical" failure is human failure wearing a hard hat. Writing and speaking about bad bosses came from all three, and none of it appeared on any career framework I was ever shown.
At the time, each move looked like a wobble. My CV looked untidy next to people with one clean vertical line. I felt behind.
I was not behind. I was collecting.
Playground rules
A playground has no single top. It has bars, ropes, tunnels, and a dozen routes across. Here is how to build one where you work.
1. Chase skills, not titles
Write down the four or five things you want to be good at in five years. Not the job you want. The abilities. Then check every opportunity against the list. "Head of Something" tells you nothing. "The person who fixes broken supply chains" tells you everything.
2. Borrow the work before you ask for the job
Want to know whether product management suits you? Go help the product team for two hours a week. Nobody has to approve a career change. People approve small favors all the time. Do the borrowed work well and the formal move becomes a formality.
3. Keep a file of things you have done
Not a CV. A running list, updated monthly, of the problems you solved and the messes you cleaned up. It takes ten minutes. When a sideways door opens, you will have your evidence ready instead of scrambling to remember last February.
4. Ask the question most people avoid
Lee Woollsey puts three words at the heart of every one-to-one: "What aren't you getting from me?" Turn it around and ask your own boss the same thing about your growth. Most managers have never been asked. The awkward silence you get is information all by itself.
5. Move toward people, not org boxes
The best thing you learn from a job is often a person. Pick your next move by who you will sit next to. I have learned more from two bosses and one stubborn colleague than from every training course combined.
6. Treat a step down as a legal move
Reskilling looks like a demotion on a ladder. On a playground it is a rope you grab to reach a different bar. Some of the strongest leaders I know spent a year as a beginner in their forties.
Managers, you are selling a ladder you do not own
If you lead people, this next bit is on you.
You promise progression at interview. You then spend the year with no rungs to hand out, because headcount got frozen, or the org chart got flattened, or your own boss went quiet. So you say "next year" and hope nobody counts the years.
Stop selling a thing outside your control. Start handing out what sits inside it: the interesting problem, the introduction, the secondment, the two hours a week with another team, the project with a skill attached rather than a title. You own all of those. None of them needs a budget line.
My research on bad bosses found 99.5% of respondents had suffered one or more types of bad boss. Almost nobody escapes. A large slice of the damage comes from managers who make promises about progression with no authority behind them. Broken promises breed cynicism faster than honest limits ever will.
Try honesty instead. "I have no rung for you this year. Here are three things I will get you, starting Monday." People forgive a shortage of promotions. They do not forgive being strung along.
The scribble is the point
Your career is not a ladder in a building owned by a company with a five-year plan and a quarterly reorg. It is yours. It goes with you when the building changes hands.
So stop asking how to reach the next rung. Start asking what you want to be able to do, and which sideways step gets you closer.
The tidy vertical CV impresses nobody worth impressing. The person who has been around the whole playground, who understands four parts of the business and knows people in all of them, never runs out of options.
What sideways move have you been talking yourself out of?