Someone once asked me to describe my career path.
I said: "Picture a plate of spaghetti."
They laughed. I wasn't joking.
I went from the US Army to software research at Sun Laboratories. From building e-commerce platforms in the early 2000s to leading the Android team at one of Europe's biggest banks. From managing 43 engineers at a UK fintech company to keynoting at HR conferences in Iceland and Croatia. I wrote a book. I launched a podcast. I now run a company.
No 10-year plan came close to predicting it.
The Ladder We Were Sold
Every careers advisor, every well-meaning parent, every LinkedIn thought leader tells you the same thing: plan your career. Set goals. Pick a direction. Climb.
The image they sell you is a ladder. Start at the bottom, work your way up, step by step, rung by rung. Neat. Orderly. Safe.
For most people? Complete fiction.
Research cited by Together Platform, drawing on Bureau of Labor Statistics data, puts the average number of jobs held across a career at 12 for baby boomers. Twelve. Not a ladder. A scribble on a napkin.
And yet the ladder myth persists. Schools still teach it. HR departments still plan around it. Managers still frown at people who don't follow a tidy, logical upward progression.
I'm done with the ladder.
My Actual Path
Let me walk you through the spaghetti.
I served in the US Army. After leaving service, I studied Computer Science at the University of North Texas. From there, I worked as a research engineer at Sun Laboratories. It was the organisation responsible for Java and much of the infrastructure modern enterprise software runs on.
Then years of building things. E-commerce platforms. High-availability leaderboards in C. No-code tooling in Tcl/Tk. A VAX/VMS networked database. Founder and partner in several tech ventures. Every project was a masterclass in something school wouldn't have taught me.
Then mobile. I led the Android team at Santander's personal banking app. 2.2 million monthly active users. Cut incident rates by 30 percent. Launched an Android Academy to accelerate new engineer onboarding. Hired 56 engineers over four years.
Then I joined Curve, a UK fintech company, as Senior Engineering Manager. Seven cross-functional teams. Up to 43 people. Manager of managers. Building engineering culture inside a fast-moving startup.
And then I turned again. Now I'm Chief Innovation Officer at Step It Up HR. I keynote at conferences across Europe. I host a podcast. I co-authored Bad Bosses Ruin Lives, a book on what makes leadership work and what makes it catastrophic. I speak to HR professionals, L&D practitioners, and senior leaders about the one thing organisations consistently get wrong: management.
My CV reads like someone who kept changing their mind. I read it as someone who followed the interesting problems wherever they led.
Why the Ladder Fails You
The ladder model rests on a few assumptions.
First, it assumes you know what you want at 22. Second, it assumes your industry stays stable long enough for a multi-year plan to survive contact with reality. Third, it assumes your value to an organisation sits neatly on a single vertical track.
None of those hold.
I had no idea I'd end up in HR technology when I was writing C code at a Sun workstation. The prospect of keynoting in Reykjavik about bad bosses would have seemed like someone else's life to the engineer I was at Santander.
And yet every strand of my career fed the next one.
The military gave me accountability, standards, and the habit of following through under pressure. Research gave me intellectual rigour. Mobile development taught me how to build products people love at enormous scale. Managing large engineering teams showed me how organisations work... and how they fail. All of it travels with me every time I step on a stage.
Sarah Ellis and Helen Tupper coined the term "squiggly career" in their book of the same name. Their argument: the most effective professionals today move laterally, build broad skill sets, and treat careers as sequences of experiments rather than a predetermined climb. They're right.
What You Get From Spaghetti
A ladder takes you up one wall. Spaghetti takes you across the whole room.
Here is what broad, winding experience gives you.
Pattern recognition across domains. When you have worked in defence, research, fintech, and HR technology, you see patterns others miss entirely. Problems in one industry often have solutions sitting in a completely different one. Someone who has spent 20 years in a single vertical develops one lens for seeing the world. Someone who has crossed domains develops several. In a room of specialists, being a generalist is an advantage, not a weakness.
Resilience. If your entire career sits on one rung of one ladder and the rung disappears... because companies downsize, industries shift, or AI changes what the job requires... you face a much harder rebuild. People who have reinvented themselves before know how to do it again. They have already proved to themselves it is possible.
Better stories. Nobody wants to hear about 30 years on the same ladder. A former soldier who ended up keynoting at HR conferences in Iceland? People lean in. They want to know how it happened. Your breadth is a credibility engine, not a liability to apologise for.
Stronger networks. Staying in one lane means your professional contacts narrow over time. Crossing industries means knowing people everywhere. Doors open differently when you have built relationships across a wide range of fields. And when you bring a perspective most people in the room don't have, those relationships open in ways they wouldn't otherwise.
The Part Nobody Mentions
Spaghetti careers are uncomfortable.
Every significant change I made meant starting again lower on the knowledge curve. I was the Android lead who didn't know the banking domain. I was the engineering manager who didn't know HR. Each time, there was a period of feeling out of depth. The imposter feeling is real. The people around you raise their eyebrows. Some say it to your face.
And then you figure it out, faster than you expected, because everything you have done before is still in the room with you. Your prior experience doesn't vanish when you change direction. It recontextualises. It becomes the lens letting you see the new environment more clearly than the people who have never left it.
The discomfort is the price. The breadth is the reward.
Stop Planning, Start Moving
I'm not saying abandon goals. Goals matter. A direction matters.
But a rigid 10-year career plan is mostly a story you tell yourself to feel in control of things you don't control. Markets change. Companies fold. Whole industries get rebuilt from scratch. Your interests evolve. You do too.
Worth having instead: a clear sense of your values and what kind of work gives you energy. A willingness to say yes to things which scare you a little. A habit of learning relentlessly, regardless of where you sit on the org chart.
The best career move I ever made looked, at the time, like chaos. So did the next one. And the one after.
Twelve jobs in a career is the average. Your path is far from straight. Stop apologising for the detours. They are the education.
My career looks like a plate of spaghetti. Every strand is there for a reason.
What does yours look like?