Many people I speak to could stop working tomorrow if they chose to. The income from employment stopped being the obstacle some time ago. And yet many keep going.
Sometimes, that's because they love what they do, and there's nothing wrong with that. More often, when we talk it through, something else is holding them in place. They lack clarity and aren't sure what the next stage looks like, or who they'll be once the job title goes.
That hesitation deserves attention. Work gives far more than just an income. It gives your week a shape, puts people around you, makes you feel useful and hands you real problems to solve. Most of us don't notice how much we rely on that until it's gone.
Other people have the opposite problem. Their retirement date arrives because they've had enough. Sometimes it comes suddenly, after a particularly hard year. Sometimes it builds over years of deadlines and long days, until their patience finally runs out. They leave to get away from something, which is a perfectly good reason to go, of course.
I've seen capable, financially secure people leave this way with everything in order on paper. Then they find themselves unsure what to do with a Tuesday morning.
Some stay too long and others leave too fast, but both are wrestling with the same question.
Am I ready for what comes next?
Readiness comes down to whether you've built something to step towards. Everything a career gave you can come from somewhere else, provided you set it up.
Structure can come from any standing commitment you take seriously. A fixed morning with a coach or trainer, a residential programme at a university you've long admired, a weekly lesson towards your pilot's licence, or a protected day each week with the grandchildren all give the diary its shape back.
Connection takes more effort than it did at work, where clients and colleagues filled your diary without you lifting a finger. A club where you see the same faces each week, a regular dinner with former colleagues and clients who've become friends, or a sailing syndicate can fill that gap. So can more unhurried time with family, who'll be glad to see more of you.
Purpose is often the hardest to replace. Many executive leaders draw their sense of worth from being the one others call when it matters. That can carry forward through a non-executive role, chairing a charity or an endowment, advising founders in your field, or taking an active hand in how your family's wealth is governed and given away.
These roles nearly always come through your existing network. That makes them far easier to secure while your title still opens doors than after you've left.
Stimulation matters too. Your work has kept you addressing genuinely hard problems for decades. Serious study can do the same, whether that's a master's in a subject you set aside at 20, learning a language well enough to argue in it, or mastering an instrument, a craft or a sport. It works best when it keeps stretching you and puts you among peers.
None of this falls into place overnight. It takes some trial and error, and the people who settle best tend to start years before their last day.
So, if you've been putting off a date you could have afforded some time ago, it may be worth asking what you'd be stepping towards, and starting to build it now.
The advice provided in our columns does not constitute legal or financial advice and is provided for your information only. Readers should seek appropriate independent legal and financial advice from a regulated professional
