The career confusion I usually write about involves people in their early twenties trying to figure out which direction to go. But there’s a different kind of confusion that sits with people who are ten or fifteen years into something. They already chose. They’ve been executing that choice for over a decade. The question now is whether to abandon the investment.
This is the person who spent twelve years qualifying for a role that might exist for five more. Who’s watching their industry consolidate, their company restructure for the third time, their colleagues get made redundant in waves. Who makes decent money, holds seniority they earned, and knows that both might evaporate in the next round of cuts.
The question sitting with them: whether the last decade was preparation for obsolescence.
The Ten-Year Trap
Ten years into anything builds three locks simultaneously.
The economic lock is straightforward. A decade of progression means a salary that supports a particular life. Mortgage, school fees, the lifestyle that assumes this income level. Your household budget depends on it. Your partner’s career decisions factor it in. Leaving means accepting a significant pay cut or starting over in a field where you’re competing with people ten years younger who cost half as much.
The psychological lock runs deeper. You’ve been a senior whatever-you-are for years. The title is how you introduce yourself, how your parents describe you, how you think about your place in the world. The identity has fused with the person. Starting over means becoming junior again, and that feels like regression even when it’s rational movement.
Then there’s the skills problem. You’ve spent ten years becoming excellent at navigating a particular regulatory framework, or marketing a channel that’s dying, or accumulating institutional knowledge of systems that won’t outlast you. The expertise might not transfer anywhere else. You won’t know until you try, and trying means leaving.
Each year adds weight to these locks. The salary increases. The identity solidifies. The skills specialise further. You’ve optimised yourself for one context, and now that context is uncertain.
Why This Hits Different
This has happened before. Miners watched pits close. Typists saw word processors arrive. Factory workers watched production move overseas. Entire industries disappeared, often rapidly, leaving people with skills that had no market.
But those were working-class jobs. The middle-class professional path was supposed to be different. University degree, graduate scheme, steady progression, pension at the end. The bargain was: get educated, specialise in something professional, and you’ll have security.
That bargain is breaking for a different class of worker now. The comfortable middle-skilled roles, the ones requiring degrees and years of training, are the ones getting automated or consolidated. People who did everything right by the old rules are discovering their expertise has an expiration date.
The decline happens fast enough that you can’t pivot gradually, but slow enough that you keep thinking you have time. Restructures happen every eighteen months. Colleagues disappear in rounds. The company says it’s about efficiency, about staying competitive, about the future. You watch the org chart shrink and know that your highly paid, highly specific role could be next.
The Recognition Point
Something specific triggers the realisation. Someone five years younger gets made redundant and you understand that seniority makes you expensive to keep. You see your exact role automated at a competitor. You’re in your third restructure in five years and the pattern becomes impossible to ignore. You try explaining what you do and realise you’re describing institutional knowledge of a dying system rather than a transferable skill.
The recognition makes everything worse because now you know you’re trapped and you’re still not leaving.
The questions that follow have no good answers. How severe is the decline? Is this slow erosion over another decade or rapid collapse where half the roles disappear in three years? Industry analysis is always backwards-looking. By the time consensus forms that a sector is dying, it’s already dead.
What transfers? You’ve become excellent at something specific. Maybe it’s risk assessment and it works everywhere. Maybe it’s navigating particular regulations and it works nowhere else. You discover this in job interviews, explaining why someone should hire you for work you’ve never done, competing against people who have.
The financial calculation involves variables you can’t control. How long could you survive without income? What pay cut is survivable? These depend on your partner’s salary, your savings, your mortgage, your tolerance for uncertainty. They have to be assessed without admitting you’re considering blowing up the household finances.
Timing becomes impossible to judge. Leave now and you preserve some career momentum. You’re choosing to go rather than being pushed. But you’re walking away from salary and seniority you might keep for another three years. Wait for redundancy and you get a package, but you’re also older, in a market flooded with other redundancies, and you’ve lost time you could have spent retraining.
The worst question sits underneath everything: what if your skills are too specific and you genuinely can’t transfer? What if the last ten years made you excellent at something nobody else needs? What if you leave, burn through savings trying to pivot, and discover you’re competing for entry-level positions against twenty-five-year-olds who’ll work for half what you need?
None of these have answers because they all depend on information you don’t possess. You can’t know your skills transfer until you’ve transferred them. You can’t know when redundancies hit until they hit. You can’t know if you’ve waited too long until you’ve already waited too long.
Some people can move with incomplete information and accept they might be wrong. Most people can’t. The uncertainty paralyses, so they wait for certainty, and by the time certainty arrives, the decision has been made for them.
by Alex McCann, The Republic of Letters | Read more:
Image: istock/Getty via
[ed. ed. See also: Confessions of a job hugger: Still at my desk, still in denial (ADN):]
"Job huggers — employees clinging to roles long past their expiration date — lurk in cubicles in many workplaces. According to Monster’s 2025 Job Hugging Report, 48% of surveyed employees say they stay in their current role for comfort, security or stability.
For these employees, job hugging is the workplace version of comfort food: familiar, filling and guaranteed to leave you sluggish. They don’t love their jobs but don’t see anything better on the horizon. They stay because the devil they know offers dental coverage, even though the spark that once made them excited about their jobs wheezes for oxygen.
Behind many “grateful to have a job” smiles sits quiet dread. Sunday nights hit like sentencing hearings. Job huggers run mental marathons of justification: Maybe my boss will retire. Maybe next quarter will improve. Maybe leadership will finally hire that extra person they promised back when TikTok was new.
Spoiler: They won’t.
The truth: Job huggers don’t cling to jobs; they cling to security, identity and even social connection. Letting go of a problem job before an employee finds a new landing spot feels like jumping from a plane without a functioning parachute."
The question sitting with them: whether the last decade was preparation for obsolescence.
The Ten-Year Trap
Ten years into anything builds three locks simultaneously.
The economic lock is straightforward. A decade of progression means a salary that supports a particular life. Mortgage, school fees, the lifestyle that assumes this income level. Your household budget depends on it. Your partner’s career decisions factor it in. Leaving means accepting a significant pay cut or starting over in a field where you’re competing with people ten years younger who cost half as much.
The psychological lock runs deeper. You’ve been a senior whatever-you-are for years. The title is how you introduce yourself, how your parents describe you, how you think about your place in the world. The identity has fused with the person. Starting over means becoming junior again, and that feels like regression even when it’s rational movement.
Then there’s the skills problem. You’ve spent ten years becoming excellent at navigating a particular regulatory framework, or marketing a channel that’s dying, or accumulating institutional knowledge of systems that won’t outlast you. The expertise might not transfer anywhere else. You won’t know until you try, and trying means leaving.
Each year adds weight to these locks. The salary increases. The identity solidifies. The skills specialise further. You’ve optimised yourself for one context, and now that context is uncertain.
Why This Hits Different
This has happened before. Miners watched pits close. Typists saw word processors arrive. Factory workers watched production move overseas. Entire industries disappeared, often rapidly, leaving people with skills that had no market.
But those were working-class jobs. The middle-class professional path was supposed to be different. University degree, graduate scheme, steady progression, pension at the end. The bargain was: get educated, specialise in something professional, and you’ll have security.
That bargain is breaking for a different class of worker now. The comfortable middle-skilled roles, the ones requiring degrees and years of training, are the ones getting automated or consolidated. People who did everything right by the old rules are discovering their expertise has an expiration date.
The decline happens fast enough that you can’t pivot gradually, but slow enough that you keep thinking you have time. Restructures happen every eighteen months. Colleagues disappear in rounds. The company says it’s about efficiency, about staying competitive, about the future. You watch the org chart shrink and know that your highly paid, highly specific role could be next.
The Recognition Point
Something specific triggers the realisation. Someone five years younger gets made redundant and you understand that seniority makes you expensive to keep. You see your exact role automated at a competitor. You’re in your third restructure in five years and the pattern becomes impossible to ignore. You try explaining what you do and realise you’re describing institutional knowledge of a dying system rather than a transferable skill.
The recognition makes everything worse because now you know you’re trapped and you’re still not leaving.
The questions that follow have no good answers. How severe is the decline? Is this slow erosion over another decade or rapid collapse where half the roles disappear in three years? Industry analysis is always backwards-looking. By the time consensus forms that a sector is dying, it’s already dead.
What transfers? You’ve become excellent at something specific. Maybe it’s risk assessment and it works everywhere. Maybe it’s navigating particular regulations and it works nowhere else. You discover this in job interviews, explaining why someone should hire you for work you’ve never done, competing against people who have.
The financial calculation involves variables you can’t control. How long could you survive without income? What pay cut is survivable? These depend on your partner’s salary, your savings, your mortgage, your tolerance for uncertainty. They have to be assessed without admitting you’re considering blowing up the household finances.
Timing becomes impossible to judge. Leave now and you preserve some career momentum. You’re choosing to go rather than being pushed. But you’re walking away from salary and seniority you might keep for another three years. Wait for redundancy and you get a package, but you’re also older, in a market flooded with other redundancies, and you’ve lost time you could have spent retraining.
The worst question sits underneath everything: what if your skills are too specific and you genuinely can’t transfer? What if the last ten years made you excellent at something nobody else needs? What if you leave, burn through savings trying to pivot, and discover you’re competing for entry-level positions against twenty-five-year-olds who’ll work for half what you need?
None of these have answers because they all depend on information you don’t possess. You can’t know your skills transfer until you’ve transferred them. You can’t know when redundancies hit until they hit. You can’t know if you’ve waited too long until you’ve already waited too long.
Some people can move with incomplete information and accept they might be wrong. Most people can’t. The uncertainty paralyses, so they wait for certainty, and by the time certainty arrives, the decision has been made for them.
by Alex McCann, The Republic of Letters | Read more:
Image: istock/Getty via
[ed. ed. See also: Confessions of a job hugger: Still at my desk, still in denial (ADN):]
"Job huggers — employees clinging to roles long past their expiration date — lurk in cubicles in many workplaces. According to Monster’s 2025 Job Hugging Report, 48% of surveyed employees say they stay in their current role for comfort, security or stability.
For these employees, job hugging is the workplace version of comfort food: familiar, filling and guaranteed to leave you sluggish. They don’t love their jobs but don’t see anything better on the horizon. They stay because the devil they know offers dental coverage, even though the spark that once made them excited about their jobs wheezes for oxygen.
Behind many “grateful to have a job” smiles sits quiet dread. Sunday nights hit like sentencing hearings. Job huggers run mental marathons of justification: Maybe my boss will retire. Maybe next quarter will improve. Maybe leadership will finally hire that extra person they promised back when TikTok was new.
Spoiler: They won’t.
The truth: Job huggers don’t cling to jobs; they cling to security, identity and even social connection. Letting go of a problem job before an employee finds a new landing spot feels like jumping from a plane without a functioning parachute."
