Somebody asked me last week where I see myself in ten years.
I laughed. Not at her. At the question.
I am 60-something, a grandfather, a former US Army soldier, a tech leader, a writer, a speaker, and a guy who straps a motor to his back and flies a parachute over the countryside for fun. If you had asked me at 25 where I would be at 60, none of those would have been on the list. None.
Ten-year plans are fiction. We tell them to ourselves because the alternative... admitting we have no idea... feels terrifying. So we draw the ladder. Step one, step two, step three. Tidy. Safe. Predictable.
And then life happens.
The Ladder Lie
The career ladder was invented in an era when men worked for one company until they got a gold watch at 65. My grandfather had one job his whole life. My dad changed roles a handful of times inside the same industry.
Me? I have lost count.
Research from Zippia citing the US Bureau of Labor Statistics says the average American holds about 12 jobs in their working life. Twelve. Men average 12.5. Women 12.1. The career ladder model assumes you climb one ladder. The data says most of us are scrambling across a dozen.
The average age for a full career change... not a job switch, but a career switch... sits around 39. And 80% of those who pivot say they are happier afterward.
Ladders do not predict this. Spaghetti does.
My Own Plate of Noodles
Here is how my career went.
I joined the US Army out of school. I served. I learned what it means to be useful to people who give zero attention to your feelings and only weigh your results.
I left, taught myself to code, and spent years writing software. Then more years leading teams who wrote software. Then more years leading the leaders who led the teams. CTO. Consultant. Advisor. Each transition was its own kind of weird.
Somewhere in there I moved to England, married a woman named Peggi, raised kids, and watched those kids grow into adults I love being around. I am now a grandfather, and my grandson thinks I am the funniest person alive. I will take the win.
A few years ago I started writing about leadership. Then speaking about it. Then helping other people who had been burned by terrible bosses figure out how to be the leader they wished they had themselves. Some of the work shows up over at Step It Up HR.
I also fly paramotors. Not because it advances my career. Because I like being a thousand feet above a field on a sunny afternoon with nothing but the sound of wind and a small engine for company.
If I had been working a ladder, half of those experiences would have been forbidden by the plan.
Why Spaghetti Wins
Spaghetti careers look messy from the outside. From the inside, they make more sense than ladders do, for three reasons.
One: Resilience
When your identity is hooked to one rung of one ladder, losing the rung becomes an existential event. People who have changed direction more than once know how to lose a job without losing themselves. They have done it before. The ground does not feel as far away.
Two: Optionality
Every weird detour I took gave me a skill the next job needed. The Army taught me how to keep my head when other people were losing theirs. Coding taught me how to break a problem into pieces small enough to solve. Leadership taught me how to build a team better than I am alone. Writing taught me how to think clearly enough to put words on a page without lying.
Ladders give you depth. Spaghetti gives you weird, unfair combinations of skills nobody else has. With AI eating predictable work, the weird combinations are the ones with a future.
Three: Life Happens
People get sick. Parents need care. Kids need you home. Industries collapse. Wars start. Pandemics arrive. The neat ten-year plan does not survive any of those events, but a spaghetti career bends without breaking, because nothing about it was ever rigid to begin with.
The Dirty Secret About Plans
I am not saying skip the planning. I am saying do not lie to yourself about what the plan is doing for you.
A ten-year plan is a story you tell yourself to feel less afraid. It does not predict the future. It calms your nervous system today.
Fine. Pick a direction. Take the next reasonable step. But hold the plan loosely. The most interesting people I know all share one trait... they say yes to weird opportunities when those opportunities show up, even when the opportunities do not fit the plan.
The friend who left law to open a bakery. The engineer who became a midwife. The accountant who started a podcast and now interviews founders for a living. The Army medic who became a tattoo artist. None of them planned it. All of them are happier.
What To Do Instead
If the ladder is a lie, here is what works.
Pick a direction, not a destination. Direction is "I want to learn how teams work" or "I want to build things people use." Destination is "Senior VP of Engineering at Acme Corp by 2030." Direction survives surprises. Destination does not.
Follow the heat. Notice what energizes you. Notice what drains you. Do more of the first and less of the second. This sounds simple because it is. It is also the advice almost nobody follows, because energy is not on a spreadsheet.
Take the weird job once. At least once in your working life, take the job everyone tells you not to take, because it does not fit the plan. You will learn something no straight-line career teaches... about yourself, about what you are willing to risk, about how the world works.
Stop apologizing for your detours. Every "wasted" year teaches you something. The years I spent doing things off-plan have made me a better leader than any of my on-plan years did. They gave me texture, perspective, and stories worth telling.
Be the Person Who Took the Messy Path
When I look at the people I admire... the leaders, the writers, the makers, the friends I would trust with anything... none of them got there in a straight line. All of them have a plate of spaghetti behind them.
The straight-liners are not bad people. They are often impressive on paper. But the messy-pathers are the ones who handle whatever the world throws at them, because they have already handled chaos. They have done it. They know they will do it again.
If you are 25 and reading this, do not panic when your plan falls apart. It is not supposed to hold.
If you are 45 and reading this, do not assume the chapter you are in is the last one. It is not.
And if you are 65 and reading this, do not assume the show is over. It is not.
Throw out the ladder. Pick up a fork.
The spaghetti is delicious.
What is the messiest, best decision you have ever made about your work? Sit with it for a minute. The answer is the one to listen to next time.