I don’t read many business books cover to cover, but this one stuck with me. How Will You Measure Your Life? by Clayton M. Christensen, with James Allworth and Karen Dillon, takes theories built to explain why companies succeed or fail and turns them on the reader’s own life instead. Christensen was a Harvard Business School professor best known for the theory of disruptive innovation, and towards the end of his career he started asking his students a harder question than any case study: how do you actually want your life to turn out, and are your daily choices pointing you there?
Motivation, not just reward
The book leans on a piece of workplace research from Frederick Herzberg, which splits what matters at work into two separate lists. Hygiene factors are things like pay, status and working conditions — get them wrong and people are miserable, but getting them right doesn’t make anyone love their job, it just stops them hating it. Motivation factors are different: responsibility, challenge, recognition for doing something meaningful, the sense that you’re growing. Christensen’s point is that a lot of us chase the hygiene factors — the bigger salary, the better title — because they’re easy to measure, and we assume satisfaction will follow. It often doesn’t. I think most business owners I meet already sense this. They didn’t build a business for the title on the door. But it’s worth being reminded, every so often, that more money is not the same thing as more meaning.
I’ve sat with more than one client chasing the next milestone — the bigger turnover figure, the flashier premises — who found the phone still doesn’t feel any different when it rings. Herzberg’s insight isn’t that pay doesn’t matter; getting it wrong causes real unhappiness. It’s that pay has a ceiling on how good it can make you feel, while doing meaningful work well doesn’t seem to. Worth remembering next time a client tells me they’re planning to work another five years “just to be safe” financially, when the numbers already say they don’t need to.
The strategy you’re actually living
The second idea is one I found genuinely useful outside of business too. Companies have a deliberate strategy — the plan on paper — and an emergent strategy, which is whatever actually happens once real customers, real costs and real competitors get involved. The emergent version often wins, quietly, because it’s built from thousands of small daily decisions rather than one big statement of intent. Christensen’s challenge is to look at where you actually spend your time, your money and your attention, because that — not the plan you’d tell a stranger at a dinner party — is your real strategy. It’s an uncomfortable exercise. Most of us would rather describe our priorities than audit them.
Deliberate versus emergent, at the kitchen table
It’s worth pausing on what deliberate-versus-emergent looks like inside an ordinary family, rather than a boardroom. Picture a couple who fully intend, on paper, to leave their estate equally between two children — that’s the deliberate strategy, and it’s exactly what they’d tell you over dinner. But one child works in the family business and the other doesn’t, and over twenty years, every spare pound gets reinvested “for now”, every guarantee gets signed by the child already involved, and the conversation about what “equally” actually means gets put off another year. None of those choices was meant to change the plan; each looked small and sensible. Taken together, though, they quietly write a different plan than the one the parents believe they still have — an emergent one, built from daily choices rather than the intention stated at the dinner table. They haven’t lied to themselves; they’ve simply never checked whether the deliberate plan and the emergent one still match. That check is, in effect, what a proper Will review is for.
Careers pay back quickly. Families pay back slowly.
This is the chapter that will land hardest for anyone over forty-five with a business and a family. Christensen’s argument is straightforward: when you invest time in your career, the return often arrives within days — a deal closes, a client says thank you, a project ships. When you invest time in your family, the return can take twenty years to show up. So under pressure, in the moment, we quietly reallocate hours away from the slow-paying investment towards the fast-paying one, telling ourselves we’ll rebalance later. The trouble, he argues, is that the bill for underinvesting in a family doesn’t arrive gradually — it arrives all at once, usually at exactly the point when it’s too late to do much about it. I don’t think this is a call to abandon work. It’s a call to notice the pattern before the invoice lands.
The marginal cost mistake
One of the sharper ideas in the book is what Christensen calls the marginal cost mistake, borrowed from how companies justify one-off exceptions to their own rules. The logic goes: “just this once won’t hurt”, and on any single occasion it probably doesn’t. The problem is that life doesn’t offer you a clean, isolated “just this once” — it offers you a pattern of moments that each look like an exception. Christensen’s conclusion, which I think is the most quotable idea in the whole book, is that it is easier to hold to your principles 100% of the time than 98% of the time. Once you’ve decided a line is a line, you never have to relitigate it under pressure. Decide the boundary once, in a calm moment, rather than every time temptation shows up.
I see a quieter version of this with Wills. Someone tells me they’ll get round to updating theirs once the house sale completes, or once a grandchild is born. Each delay, on its own, looks harmless. But life doesn’t offer a single, isolated delay any more than a single isolated exception; it offers a long sequence of moments that each look like the harmless one. The people who keep an up-to-date Will are usually the ones who decided, once, that it gets reviewed every few years regardless of how busy life is.
Hiring your family, designing your purpose
The final section asks you to treat your own sense of purpose the way you’d design anything you actually cared about getting right — deliberately, with thought given to what you want it to achieve, rather than letting it assemble itself by accident. He extends the same logic to family life: decide, on purpose, what kind of family culture you want, what kind of person you want to be to the people who matter most, rather than discovering the answer by default in twenty years’ time.
A few honest caveats
I’d be doing you a disservice if I only told you what I liked. This is a business professor’s book, and it reads like one — the analogies to corporate strategy and resource allocation are clever, but some readers will find them a bit cold for a book about family and purpose. Life doesn’t always behave like a company. The anecdotes, too, are drawn largely from a fairly narrow slice of high-achieving Harvard MBA graduates, which isn’t quite the same as the range of people I sit across the table from every week. And it doesn’t pretend to be a practical manual — there’s no worksheet at the back, no step-by-step plan. It’s a book of questions, not answers.
Who this book actually suits
I’d recommend it, caveats above included, to anyone running a business or a household who hasn’t stopped in a while to ask whether their week actually matches their stated priorities. It’s particularly good for people in their forties and fifties who feel busy and outwardly successful, and slightly uneasy about it, without quite knowing why. If you already have a clear, written sense of what you’re building, and review it regularly, you probably won’t get much new from it. And if you’re after a practical, step-by-step guide to getting your affairs in order, this isn’t that book; it changes how you think before it changes anything you do. For that, a conversation with someone like us beats another chapter.
What this has to do with your estate plan
Here’s why I keep coming back to it. An estate plan is, in Christensen’s terms, a deliberate strategy for your family — written down, chosen, while there’s still time to choose it. Without one, your family gets an emergent strategy instead: whatever the intestacy rules happen to produce, filled in with whatever hurt feelings, assumptions and disagreements surface once you’re not there to explain what you actually meant. A Will, a Lasting Power of Attorney, a clear plan for who looks after what — these aren’t paperwork for its own sake. They’re the deliberate version of a decision that will otherwise be made for you, by default, at the worst possible time. That’s the whole idea behind Legacy Insights, and behind the work we do.
If any of this has got you thinking about whether your own arrangements are as deliberate as you’d like them to be, book a Discovery Call with us at https://www.thelegacywillscompany.co.uk/discovery-call/ and we’ll talk it through, no pressure, just a conversation.