Retirement planning has become remarkably sophisticated.

We can model investment returns, inflation, life expectancy, property values, withdrawal rates and dozens of other variables. Put enough numbers into a spreadsheet and the result can look reassuringly precise.

But that’s exactly the problem.

While they all appear equally precise, not every number in your retirement plan can be relied upon equally.

Imagine these three numbers:

$500,000 — the value of investments you own today.

$500,000 — what you calculate those investments could be worth in ten years.

$500,000 — an inheritance you expect to receive.

Put them into a spreadsheet and they look identically reassuring.

They aren’t.

The first is something you know.

The second is something you can reasonably expect, based on assumptions about future returns.

The third may be something you have good reason to believe will happen — but it’s still an assumption about an event outside your control.

The spreadsheet doesn’t know the difference. You need to.

Because good planning doesn’t require us to pretend we know the future.

It requires us to understand what kind of information we’re making decisions with — and how much of our future we’re relying on each kind to support.

The problem isn’t making assumptions

Any plan that stretches years or decades into the future has to contain assumptions.

How long will you work?

What will your investments return?

How much will you continue to save?

What will inflation do to your spending?

What will your property eventually be worth?

If you own a business, what might someone eventually pay for it?

Will your children still need financial support?

You can’t build a retirement plan without making some judgement about the future.

So the answer isn’t to eliminate assumptions.

Nor is it to replace optimistic assumptions with pessimistic ones.

The problem begins when we forget which parts of the plan are assumptions.

“I intend to work until 65” gradually becomes “I will receive another 13 years of salary.”

“My business is worth around $2 million” becomes “I’ll have $2 million when I sell it.”

“My investments have historically produced this kind of return” becomes “my portfolio will be worth this much at 65.”

“My property has appreciated substantially” becomes “my house will provide this much money for retirement.”

Those aren’t necessarily bad assumptions.

Some may prove completely correct.

But notice what has happened.

Something we expect has become something we’re counting on.

And once it becomes a number in a spreadsheet, the distinction becomes remarkably easy to miss.

The mathematics may be flawless. The inputs may not be.

Try putting your retirement plan into three buckets

There’s a simple way to make these differences visible.

Take the things you’re counting on and separate them into three buckets.

Bucket 1: What do I know?

These are things that exist today.

The assets you own. The debts you owe. Your current income. Your current expenditure. The cash and investments you already have.

They can change tomorrow, of course.

But you’re not forecasting their existence today.

Bucket 2: What do I reasonably expect?

These are things that haven’t happened yet, but for which you have a reasonable basis in evidence.

Future savings.

Long-term investment growth.

Continued employment.

Pension or retirement income you’re on track to receive.

Continued income from an established business.

None is guaranteed. But neither are they guesses.

You’re making a reasoned judgement about the future based on information you have today.

Bucket 3: What am I assuming?

These are things that might well happen, but which depend substantially on circumstances you don’t control.

Receiving an inheritance of a particular size.

Selling a business for a particular price.

Your property reaching a particular valuation.

Remaining healthy and employable until a particular age.

Being able to extract a particular level of income from your investments.

Your children becoming financially independent when you expect.

There’s nothing inherently wrong with Bucket 3.

The mistake is treating Bucket 3 like Bucket 1.

Now ask the question that matters

Once you’ve separated the buckets, don’t stop there.

Ask:

Which expectations and assumptions does my future depend on most?

That’s where the exercise becomes useful.

How much of the retirement you envisage is already supported by Bucket 1?

How much still depends on Bucket 2 or Bucket 3 becoming true?

And, most importantly:

What happens if one of the things you’re relying on doesn’t happen?

Suppose you intend to work until 65.

That’s a perfectly reasonable plan.

But if your retirement calculation only works if you receive every one of those remaining years of salary, continued employment isn’t merely an expectation.

It’s a dependency.

Suppose you expect to sell your business when you retire.

Again, perfectly reasonable.

But “my business is worth $2 million” and “I will have $2 million available to fund my retirement” are very different statements.

There must be a buyer.

The valuation must hold.

The timing must work.

The terms must be acceptable.

A valuation is not liquidity.

The same applies to property.

A home worth $2 million doesn’t automatically provide $2 million to fund retirement. You may need to sell, downsize or borrow against it — and you need the property market and your own circumstances to cooperate when you do.

And investment projections inevitably rely on assumptions about future returns.

That’s not a reason to abandon them. It’s a reason to remember what they are.

A projection is not a promise.

Not every assumption deserves the same attention

This leads to an important distinction.

The assumption most likely to be wrong isn’t necessarily the one you should worry about most.

Imagine you expect to receive an inheritance someday, but your retirement plan works perfectly well without it.

The inheritance might be highly uncertain.

But it isn’t particularly important to the plan.

Now imagine you have every reason to expect you’ll remain employed until 65.

That may be considerably more likely.

But if retiring at 60 instead creates a large shortfall, those five years of employment matter enormously.

So the useful question isn’t simply:

“How certain is this?”

It’s also:

“How much am I relying on it?”

An uncertain outcome upon which very little depends may not matter very much.

A seemingly reasonable expectation upon which your entire plan depends deserves much more attention.

The less room you have for an expectation or assumption to be wrong, the more important it becomes to understand that dependency.

What happens if you’re wrong?

This is where I think retirement stress-testing becomes genuinely useful.

Don’t assume everything goes wrong at once.

That’s not planning. That’s simply pessimistic “doomsday” prediction.

Instead, take the important expectations and assumptions one at a time.

What if you stop working at 60 rather than 65?

What if your investments grow more slowly than projected?

What if you don’t receive the inheritance?

What if your property is worth less than expected when you need to access its value?

What if your business can’t be sold at the price or time you expect?

Then look at what changes.

If very little changes, good. You have room for that assumption to be wrong.

If the entire plan changes, you’ve discovered something important.

Not that the assumption will be wrong.

That you’re relying too heavily on it being right.

Those are very different conclusions.

The goal isn’t to predict better

Our natural response to uncertainty is often to seek another prediction.

Which investments will perform best?

Where will interest rates be in five years?

What will property prices do?

How long will this bull market last?

What will AI do to my profession?

But another forecast doesn’t remove uncertainty.

And someone else’s confident answer doesn’t turn Bucket 3 into Bucket 1.

Sometimes a much better response is to ask:

What can I do today that gives me more options if my assumptions turn out to be wrong?

That might mean saving more.

Reducing debt.

Diversifying what you own.

Changing how dependent you are on a single asset.

Building more flexibility into when you retire.

Or developing another source of income that isn’t entirely dependent on your current employer or portfolio.

The answer will be different for different people.

The principle is the same.

You may not be able to control what happens. But you can change how dependent your future is on any one thing happening.

Clarity is not certainty

None of this will tell you what markets will do next year.

It won’t tell you what your property will eventually be worth, how long you’ll work, what your business will sell for or whether you’ll receive an inheritance.

That’s not what clarity means.

Clarity is not certainty.

Clarity in this context is seeing what you know, what you reasonably expect and what you’re assuming — and knowing how much you’re relying on each.

Retirement planning will always involve uncertainty.

The goal isn’t to eliminate it.

It’s to make sure the future you’re planning doesn’t depend on too many uncertain things happening exactly as expected.

There is an enormous difference between not knowing what will happen and not knowing what you’re assuming will happen.

The first is unavoidable.

The second is fixable.

Because a robust retirement plan shouldn’t require you to predict the future correctly.

It should give you enough room to be wrong.

For a long time, starting an online business seemed like a young person’s game.

Perhaps you remember the images.

Twenty-somethings working from laptops on beaches. Dropshipping businesses built between university lectures. YouTubers turning followers into fortunes. Founders sleeping under desks and surviving on instant noodles while they chased the next billion-dollar idea.

Even the language seemed designed for people with more energy than experience.

Hustle.

Move fast.

Fail fast.

Work while they sleep.

For someone halfway through a successful career, it was easy to look at all of that and conclude that the online world belonged to somebody else.

I increasingly wonder whether the opposite may now be true.

Not because age suddenly confers some magical entrepreneurial advantage.

But because the internet has changed.

Technology has changed.

And so have we.

At 25, You Have Youth. At 50, You Have Something Better.

There are obvious advantages to starting young.

You generally have more time to recover from mistakes. Your commitments may be lower. You can spend several years trying things that go nowhere and still have most of your working life ahead of you.

What you don’t necessarily have is much to build with.

At 25, I certainly didn’t possess thirty years of professional experience.

I hadn’t sat in rooms where consequential decisions were being made.

I hadn’t seen businesses succeed, fail, recover, restructure, expand or disappear.

I hadn’t spent decades watching people negotiate, lead, invest, hire, fire, persuade, manage risk and make decisions with incomplete information.

I hadn’t accumulated a network of people across industries and countries.

And I hadn’t yet learned the uncomfortable difference between knowing something in theory and understanding it because you’ve watched it go wrong.

Those things take time.

Yet we have a peculiar tendency to treat them as valuable only inside the career in which we acquired them.

A senior executive leaves a company and suddenly decades of accumulated judgment are described as “experience” on a résumé.

A consultant retires and an extraordinary body of knowledge becomes something they “used to do.”

A specialist leaves a profession and begins introducing themselves as a “former” something.

But knowledge doesn’t disappear when the business card changes.

Neither does judgment.

Neither does the ability to solve problems.

Perhaps the more interesting question is what else we could build with them.

The Economics of Starting Something Have Changed

There was a time when building a business usually meant making substantial commitments before you knew whether the idea worked.

You might need premises.

Employees.

Inventory.

Equipment.

Distribution.

Working capital.

Professional fees.

Perhaps a franchise fee or a substantial initial investment.

And after making all those commitments, you would finally discover whether enough customers wanted what you were selling.

That’s a fairly uncomfortable proposition when you’re 50.

At this stage of life, most of us aren’t looking for another opportunity to put a large chunk of our accumulated wealth at risk.

Nor do we necessarily want to spend the next ten years managing warehouses, leases, payroll and staff rosters.

But the internet has changed the order in which some businesses can be built.

You can find an audience before renting an office.

You can test demand before building the finished product.

You can speak to potential customers before hiring employees.

You can sell expertise without opening premises.

You can distribute information at almost zero marginal cost.

You can reach customers in another country without establishing an office there.

And increasingly, technology can handle tasks that once required people, infrastructure and significant fixed cost.

None of that makes building a business easy.

That’s an important distinction.

Lower barriers to entry are not the same as higher probabilities of success.

In fact, when almost anyone can start something, almost anyone can start the wrong thing.

What has changed is something more useful.

It has become possible, in many cases, to learn whether an idea deserves a larger commitment before making that larger commitment.

For someone in their fifties, that may be far more valuable than the promise of getting rich quickly.

AI May Have Shifted the Advantage Even More

There was another reason online business once seemed to belong to the young.

They understood the technology.

If you wanted to build something online, you had to know how to build websites, connect software, create graphics, edit videos, write code, manage email systems, understand search engines and navigate an ever-expanding collection of digital tools.

For someone who grew up with the internet, much of that came naturally.

For someone who had spent the previous twenty years running businesses, managing teams, practising law, treating patients or advising clients, it could feel like learning another profession before you were allowed to start the one you actually wanted.

That gave younger entrepreneurs a genuine advantage.

AI may be removing much of it.

Today, I can describe what I want a piece of software to do and have AI help me work out how to do it.

I can ask it to explain an unfamiliar technology in language I understand.

It can help build webpages, analyse data, edit images, research markets, draft code, create presentations, automate processes and perform dozens of tasks that once required either specialist knowledge or someone I had to hire.

I’m not suggesting AI does all of those things perfectly.

It doesn’t.

And that’s precisely where the argument becomes interesting.

Because AI is extraordinarily good at making capability more accessible.

What it doesn’t give you automatically is judgment.

It can generate twenty business ideas in seconds.

It can’t tell you, with any certainty, which one deserves the next five years of your life.

It can produce a marketing strategy.

It doesn’t have twenty years of experience watching strategies collide with customers, competitors, budgets, organisational politics and reality.

It can analyse a negotiation.

It hasn’t sat across the table from someone when millions of dollars, people’s careers or the future of a business depended on what happened next.

It can give you answers.

It hasn’t lived with the consequences of being wrong.

Those distinctions matter.

For years, younger people had something many older professionals lacked: fluency with the tools required to build online.

Older professionals had something younger people couldn’t accelerate quite so easily: experience.

AI has changed that equation.

It is rapidly making many of the technical skills that once created a barrier to entry easier to access, easier to learn or, increasingly, unnecessary to perform personally.

But it hasn’t compressed thirty years of judgment into thirty minutes.

A 25-year-old can use AI.

So can a 55-year-old.

But the 55-year-old can bring something else to the conversation: decades of pattern recognition, context, mistakes, relationships, domain knowledge and an instinct for when an answer that looks perfectly sensible on a screen is unlikely to survive contact with the real world.

That’s why I think the age advantage may be shifting.

The young haven’t suddenly become less capable.

One of their structural advantages has simply become less scarce.

Meanwhile, one of ours hasn’t.

Technology can increasingly supply the skills we didn’t spend our careers acquiring.

It is much harder for technology to supply the judgment we did.

And that creates an intriguing possibility.

Perhaps AI isn’t merely another technology older professionals need to catch up with.

Perhaps it’s the technology that finally allows us to capitalise on everything else we’ve spent our careers learning.

At This Stage, the Objective Changes

At 25, you may be trying to build your future.

At 50, you’ve already built quite a lot of it.

That changes what you need from a business.

You may not be looking to build the next multinational company.

You may not want employees.

You may have no interest in raising capital.

You may not want to replace your existing career tomorrow.

And you probably don’t want to spend the next decade proving that you can work even longer hours for yourself than you once did for somebody else.

The objective may be much simpler.

You want something you own.

Something that can produce income independently of your salary.

Something you can build gradually while your existing career still provides financial stability.

Something that might eventually give you greater control over your time.

Something that uses what you’ve spent decades learning rather than asking you to begin again from zero.

And perhaps something you can continue doing long after you’ve decided you no longer want the career that currently occupies most of your week.

That’s a very different entrepreneurial ambition from the one we’re accustomed to celebrating.

It may also be a more sustainable one.

Online Is Not a Business Model

This is where the conversation about “online business” often becomes unhelpful.

There is no such thing as the online business model.

The internet is infrastructure.

Saying you want an online business is a little like someone thirty years ago saying they wanted a business that used a telephone.

The interesting question is what you use the infrastructure to do.

For someone with decades of professional expertise, the obvious answer might be consulting.

The internet makes it possible to find, attract and serve clients far beyond your existing personal network.

But consulting is only one possibility.

Perhaps you teach what you know.

Perhaps you coach people through problems you’ve spent years learning to solve.

Perhaps you turn part of your knowledge into intellectual property that can be delivered without your direct involvement every time.

Perhaps you build a specialist service and use technology to make it more efficient.

Perhaps you build an audience around a subject you understand unusually well.

Perhaps you write.

Perhaps you create products.

Perhaps you recommend other people’s products and earn when someone buys through you.

Perhaps you take an existing offline business and discover that online distribution changes its economics entirely.

Or perhaps your expertise has nothing to do with the business you eventually build.

That’s possible too.

The important point is that “building online” describes the environment, not the destination.

And that distinction matters because it prevents us from making one of the most common mistakes in entrepreneurship:

Falling in love with the vehicle before understanding where we actually want to go.

Your Experience Is an Advantage — But Only If Someone Values It

There’s a danger in the argument I’m making.

After a successful career, it’s very easy to assume that because you’ve accumulated experience, somebody must be willing to pay for it.

Those are not the same thing.

The market doesn’t pay us for having spent thirty years doing something.

It pays when something we know, do, make or provide helps somebody else achieve an outcome they value.

That’s a much less flattering test.

It’s also much more useful.

You may have extraordinary expertise that has little commercial value outside a particular corporate environment.

Or something you regard as completely ordinary may solve an expensive problem for somebody who doesn’t know how to do it.

Years of experience don’t answer that question.

The market does.

And this is another reason I find online business increasingly interesting for experienced people.

Not because the internet guarantees a market.

Because it gives us relatively inexpensive ways to look for one.

You can publish an idea and see whether it resonates.

You can speak to prospective customers.

You can offer a service manually before automating it.

You can run a workshop before building a course.

You can test an offer before creating an entire business around it.

You can discover that nobody cares.

That’s not failure.

That’s information.

And information acquired cheaply is enormously valuable.

The Greatest Advantage May Be That You Don’t Need It to Work Yet

There is another advantage many established professionals possess that younger entrepreneurs would envy.

A salary.

That may sound strange in an article about building something outside your career.

But financial stability changes how you build.

If the new business has to pay your mortgage next month, every decision becomes urgent.

You need customers now.

Revenue now.

Growth now.

And urgency has a nasty habit of turning bad evidence into good news.

When your existing income is still paying the bills, you have a luxury:

You can afford to be patient with the truth.

You can test something and admit that it didn’t work.

You can reject an opportunity that doesn’t fit.

You can spend time understanding a market before committing to it.

You can build around your life rather than immediately restructuring your life around the business.

And you can allow evidence, rather than desperation, to determine what you do next.

There is an irony here.

Many people wait until they leave their career to think seriously about what comes afterwards.

That may be precisely when the pressure to make the next thing work becomes greatest.

Perhaps the better time to experiment is while you still don’t need the experiment to succeed.

You Don’t Have Time to Waste. That’s an Advantage Too.

One argument against starting something in your fifties is obvious.

You have less time.

That’s true.

But I’m not sure the conclusion follows.

Having less time doesn’t necessarily mean you shouldn’t build.

It means you should be much more careful about how you build.

When you’re 25, spending three years pursuing the wrong idea is painful.

At 50, those same three years feel rather more expensive.

But that can impose a useful discipline.

Don’t spend two years building something before showing it to a customer.

Don’t invest heavily because someone tells you an industry is booming.

Don’t assume enthusiasm is evidence.

Don’t mistake learning for progress.

Don’t spend months choosing logos, websites, software and business cards for a proposition nobody has agreed to buy.

And don’t make a large irreversible decision when a small reversible experiment could tell you what you need to know.

Experience should make us better at this.

After decades in business, most of us already understand ideas like due diligence, staged investment, risk management, proof of concept and pilot programmes.

We use them at work without thinking.

Then, strangely, when considering something for ourselves, we’re tempted to abandon all of them and ask:

What’s the best online business to start?

Perhaps we should apply the same standards to our own ideas that we’ve spent decades applying to everybody else’s.

There Is No Prize for Starting From Scratch

There’s another misconception I think holds experienced people back.

We imagine entrepreneurship means reinventing ourselves.

It doesn’t have to.

The internet is full of stories about dramatic pivots: the accountant who became a travel influencer, the lawyer who opened a bakery, the executive who abandoned everything to live in Bali.

Those stories are interesting precisely because they’re unusual.

There is no prize for throwing away everything you’ve learned.

The more interesting opportunity may be to ask what becomes possible when you combine what you already know with capabilities that weren’t readily available when your career began.

Your expertise plus global distribution.

Your reputation plus an audience you own.

Your judgment plus inexpensive technology.

Your experience plus AI-enabled capabilities that once required an entire team.

Your relationships plus a scalable way of serving people.

Your intellectual property plus digital delivery.

Your ability to solve a valuable problem plus access to people who have that problem.

That isn’t starting again.

It’s starting from somewhere.

And after thirty years, “somewhere” can be a remarkably valuable place.

The Hard Part Is No Longer Starting

The barriers to starting have fallen so dramatically that starting itself has become almost trivial.

You can register a domain this afternoon.

Build a website tonight.

Ask AI to write the copy.

Create a product tomorrow.

Open social-media accounts.

Buy software.

Run advertisements.

Call yourself a founder.

None of that means you have a business.

The difficult questions remain stubbornly human.

What should I build?

Who is it for?

What problem am I solving?

Why would they choose me?

Do I actually want to spend the next ten years doing this?

How much time do I want it to consume?

Do I want to monetise my expertise or do something entirely different?

Do I want another profession, or an asset?

Do I want maximum growth, or enough income with maximum freedom?

What am I prepared to invest?

And perhaps most importantly:

What am I actually trying to make possible in my life?

Those questions don’t become easier because technology does.

If anything, technology makes them more important.

When the cost of starting falls, the number of things you could do explodes.

The constraint shifts from access to judgment.

And judgment may be precisely where age has the advantage.

Perhaps We’ve Had the Age Question Backwards

We’re accustomed to asking whether someone in their fifties is too old to start something new.

Perhaps that’s the wrong question.

The better question might be:

What can you build now that you couldn’t have built at 25?

Not because the technology didn’t exist.

Because you didn’t exist yet.

Not this version of you.

You didn’t have the experience.

The failures.

The successes.

The relationships.

The pattern recognition.

The understanding of what you’re good at — and, equally importantly, what you never want to do again.

You didn’t have the financial base you’ve spent decades building.

You didn’t have thirty years of evidence about yourself.

And perhaps you didn’t yet understand that the objective isn’t necessarily to build the biggest thing you can.

It’s to build something that serves the life you actually want.

The internet has made it cheaper and easier than at almost any previous point in history to test what that something might be.

AI may have shifted the equation further still.

The technical fluency that once gave younger entrepreneurs such an obvious head start is becoming increasingly accessible to everyone.

The judgment that comes from decades of experience is not.

That doesn’t mean you should quit your job.

It doesn’t mean you should risk your savings.

And it certainly doesn’t mean every 50-year-old should start an online business.

It means something much less dramatic.

You may be better equipped to build one than you think.

And perhaps the smartest way to use the stability, expertise and judgment you’ve spent decades accumulating isn’t to wait until your career ends before deciding what comes next.

It’s to start testing the possibilities while you still have the luxury of choosing carefully.

There is something irresistible about having a number.

$1 million.

$1.5 million.

$2 million.

Whatever the number happens to be, once someone gives it to us, we can immediately start doing the maths.

How much have I accumulated?

How many years do I have left?

What return do I need?

How much more should I be saving each month?

And, perhaps most importantly:

Am I on track?

For people in their 40s and 50s, that last calculation can be particularly uncomfortable.

Because the closer retirement gets, the less theoretical the number becomes.

But I think there is a problem with the entire exercise.

Not necessarily with the maths.

With the question.

The Question Sounds More Objective Than It Really Is

Ask someone how much money you need to retire and you will usually get an answer based on a series of assumptions.

How much will you spend?

How long will you live?

What will inflation be?

What returns will your investments generate?

What will healthcare cost?

What happens to interest rates?

How much of your portfolio can you safely withdraw each year?

Change any of those assumptions and your retirement number changes with it.

Sometimes considerably.

Which means the number that feels reassuringly precise is actually the output of a collection of estimates about a future nobody can know.

That doesn’t make retirement modelling useless.

Far from it.

It simply means we shouldn’t mistake a useful model for certainty.

And there is another assumption buried even deeper inside most retirement calculations.

One we rarely question at all.

We Assume Retirement Means Income Stops

Think about the conventional retirement model.

For perhaps 30 or 40 years, you work.

Your knowledge, experience and ability to solve problems produce an income.

You use some of that income to live.

And you use another portion to accumulate assets: shares, funds, property, pensions, retirement accounts and so on.

Then retirement arrives.

At that point, the model assumes something important happens.

Your earned income largely stops.

The assets you accumulated over the preceding decades must now support you instead.

Seen that way, the obsession with the retirement number makes perfect sense.

If the tap is about to be turned off, you’d better have a very large tank.

The question becomes:

How large does the tank need to be?

But what if the tap doesn’t have to be turned off completely?

Stock of Wealth Versus Flow of Income

There are two related but very different things involved here.

The first is a stock of wealth.

The value of the assets you own at a particular point in time.

The second is a flow of income.

Money continuing to come in over time.

Traditional retirement planning quite reasonably spends a great deal of time thinking about the first, because the stock of wealth must eventually produce the second.

But that distinction creates an interesting question.

Suppose you wanted $100,000 a year to support your desired lifestyle.

There is an enormous difference between needing your accumulated portfolio to produce all $100,000…

…and needing it to produce $60,000 because another asset or activity reliably produces the remaining $40,000.

I’m deliberately not suggesting those numbers as a retirement plan.

The point is conceptual.

The amount of capital you need depends partly on how much income that capital has to replace.

Yet we tend to begin at the other end.

We ask for the number first.

Your Retirement Number Is Really an Income-Replacement Number

This is what I think gets missed.

For most of our working lives, we already possess an extraordinarily productive asset.

Our ability to earn.

If you’re an experienced executive, professional or business leader, that asset may have taken decades to build.

Education.

Judgment.

Relationships.

Reputation.

Industry knowledge.

The ability to communicate, negotiate, lead, sell, analyse or solve difficult problems.

Together, those things produce cash flow.

Then our conventional retirement model assumes that, on a particular date, we’ll largely stop monetising that capability.

So we spend the preceding decades accumulating a second collection of assets large enough to replace the income generated by the first.

That’s perfectly rational if that’s the retirement you want.

But it isn’t the only possible model.

What If You Didn’t Have to Replace All of Your Income With Investments?

This does not mean working full-time until you’re 85.

For me, that would rather defeat the purpose.

Nor does it mean abandoning conventional retirement assets. I own investments myself and consider them an important part of my financial future.

The more interesting possibility sits between those two extremes.

What if, before leaving your career, you deliberately developed another income-producing asset?

Something you owned.

Something that wasn’t dependent upon remaining employed in your current role.

Something that could potentially continue producing income with considerably more control over when, where and how much you worked.

Suddenly, retirement planning becomes a different problem.

You are no longer asking only:

How much money must I accumulate before I can stop earning?

You can also ask:

How much of my future lifestyle needs to be funded from accumulated capital at all?

That is a very different question.

This Changes the Meaning of “Enough”

Imagine two people with identical lifestyles and identical investment portfolios.

One reaches retirement with no income beyond what the portfolio produces.

The other has spent the preceding years developing an asset that produces an additional stream of income.

They may have exactly the same net worth.

But financially, they are not in the same position.

The second person has another lever available.

They may be able to withdraw less from their portfolio.

They may be less dependent on what markets happen to do in the first few years of retirement.

They may be able to delay drawing down certain assets.

Or they may simply have more choice over what retirement looks like.

None of those outcomes is guaranteed.

But that’s precisely the point.

Instead of trying to predict one future perfectly, you’ve created another option.

The Goal Isn’t to Replace One Big Number With Another

There is a trap here.

We could simply swap:

“How much do I need to retire?”

for:

“How much passive income do I need?”

And we’re back where we started.

Another magic number.

Another prediction.

Another attempt to make an uncertain future certain.

I don’t think that’s the answer.

A better retirement plan may involve thinking in terms of multiple assets performing different jobs.

Some provide liquidity.

Some provide growth.

Some provide income.

Some provide resilience.

And perhaps one of those assets is something you build yourself.

Not because it is guaranteed to work.

No asset is.

But because a financial future that depends on several sources of value may give you more options than one built around a single target number.

There’s Another Advantage to Starting Before You Need It

This is particularly important if you’re still several years from retirement.

An income-producing asset doesn’t have to work immediately.

In fact, I would much rather discover that something doesn’t work while I still have a salary than after I’ve handed in my resignation.

That changes the way I think about building one.

I don’t need to bet my future on an idea.

I can test it.

I can look for evidence.

If the evidence is encouraging, I can invest more time and money.

If it isn’t, I can adjust or walk away.

That is a very different proposition from waiting until retirement and then discovering that you urgently need another source of income.

Time before retirement isn’t merely time to accumulate more money.

It is also time to test and build things while the consequences of being wrong are still relatively small.

Perhaps We Need a Better Retirement Question

None of this makes the traditional retirement number irrelevant.

You should know what you own.

You should understand your spending.

You should model different futures.

And you should understand how much income your investments might reasonably support.

But I wouldn’t stop there.

Because “How much do I need?” quietly assumes that the solution to retirement is accumulating a sufficiently large stock of wealth and then drawing from it for the rest of your life.

Perhaps it will be.

But perhaps there is a more useful question:

What combination of assets and income-producing capability could support the life I want?

That question doesn’t give you a neat seven-figure answer.

It gives you something I think is more valuable.

Options.

And when the future is uncertain, having more options may matter considerably more than having the perfect number.

There was a time when one of the biggest obstacles to making a good decision was simply getting enough information.

You needed access to information and the expertise to locate and make sense of it.

Sometimes you even needed what we used to call an “expert” – someone who had spent years mastering a certain skill.

That constraint is disappearing remarkably quickly.

Today, you can give AI details of your income, assets, expenditure, age, retirement goals and risk tolerance and ask it to help you think through your financial future.

Within seconds, it can produce projections, compare strategies, identify considerations you may have missed and construct something that looks remarkably like a financial plan.

And this isn’t some distant hypothetical.

Vanguard now describes AI as capable of analysing enormous datasets, optimising portfolios and updating financial plans in real time. The analytical work that once consumed enormous amounts of professional time is becoming increasingly automated.

That sounds like extraordinarily good news.

And in many ways, it is.

But it also exposes something we’ve misunderstood about difficult decisions for a very long time.

We Thought We Had an Information Problem

Think about how we usually respond when we’re uncertain about an important decision.

We research.

We read another article.

We watch another video.

We ask another expert.

We compare another option.

The assumption underneath all of this is perfectly reasonable:-

If I can just get enough information, the right answer will eventually become obvious.

For most of human history, that wasn’t an entirely bad assumption.

Information was scarce.

Expertise was expensive.

Analysis took time.

AI has changed all three.

Which creates an interesting test.

If lack of information were the primary reason intelligent people struggled to make good decisions, AI should be rapidly eliminating the problem.

Instead, many of us now have something quite different.

More answers than we know what to do with.

AI Has Made Answers Cheap

Ask AI whether you should put more money into equities.

You’ll get a perfectly plausible analysis.

Ask whether property should form part of your retirement strategy.

Another plausible analysis.

Ask about bonds, private markets, annuities, dividend investing, entrepreneurship or maintaining some form of earned income beyond traditional retirement.

Again, you can receive a sophisticated answer in seconds.

Then change one assumption.

Or ask the question differently.

Or introduce another objective.

Suddenly, another course of action may look equally reasonable.

This isn’t necessarily a failure of AI.

It’s the nature of the decision.

Because many important decisions don’t have a single objectively correct answer waiting to be discovered.

They involve trade-offs.

Risk.

Incomplete information.

Competing objectives.

And a future nobody can know with certainty.

AI can help us analyse those things.

It cannot make the uncertainty disappear.

More Information Doesn’t Necessarily Create More Certainty

This is where something counterintuitive happens.

Once we have access to almost unlimited analysis, we don’t necessarily make decisions more easily.

Sometimes decisions (in particular decisive ones) become much more difficult.

Every answer creates another question.

Every strategy has a counterargument.

Every opportunity has a risk.

And every confident prediction can be matched by someone—or increasingly, something—capable of constructing an equally convincing argument for the opposite conclusion.

So we keep looking.

Not because we lack information anymore.

Because we’re hoping the next piece of information will give us something information cannot provide…

certainty.

That’s a very different problem.

The Bottleneck Has Moved

For decades, knowledge was enormously valuable because acquiring it was difficult.

AI is rapidly changing the economics of knowledge.

That doesn’t make knowledge worthless. Far from it.

But it does change where the constraint lies.

When information becomes abundant, the scarce resource becomes the ability to decide what matters.

To distinguish evidence from prediction.

To recognise which assumptions should apply.

To understand the downside if you’re wrong.

To weigh competing objectives.

And eventually, to make a decision without pretending that things are no longer uncertain.

In other words:

While AI has made information cheaper. It has made good judgement more valuable.

Vanguard makes a related distinction in its work on AI and financial advice.

It argues that data gathering, portfolio construction and financial-planning simulations are increasingly susceptible to automation, while interpretation, behavioural guidance and understanding what actually matters to someone remain much more dependent on human judgement.

In my view, the implications go well beyond financial advice.

The Same Problem Appears Everywhere

Consider almost any important decision.

Should I leave my job?

Should we buy this business?

Should I invest in this opportunity?

Should I retire now or work another five years?

Should I start something of my own?

Should we enter this market?

AI can make you dramatically better informed before making any of those decisions.

That’s valuable.

But eventually you encounter the same boundary.

The available evidence ends.

The future begins.

And someone still has to decide.

Intelligence and Judgement Are Not the Same Thing

We tend to associate good decisions with intelligence.

Understandably so.

But intelligence gives us an unusual problem.

The better we are at analysis, the better we can become at constructing arguments for multiple possibilities.

We can see more variables.

More risks.

More scenarios.

More second-order consequences.

AI magnifies that capability enormously.

Give it one course of action and ask for the strongest argument against it.

Then ask it to rebut that argument.

Then ask for three alternative strategies.

Then ask what you’ve overlooked.

You could continue almost indefinitely.

At some point, more analysis stops reducing uncertainty.

It merely describes the uncertainty in greater detail.

That’s when judgement begins.

Good Decisions Have Never Required Certainty

This distinction matters enormously in finance because financial decisions often involve consequences that won’t become clear for years.

A good outcome doesn’t necessarily prove that the decision was good.

A bad outcome doesn’t necessarily prove that it was bad.

You can make a sensible decision based on the information available today and still experience an unfavourable result.

You can also make a reckless decision and get lucky.

That’s why I think one of the most useful disciplines is to judge a decision based on what was knowable at the time you made it, rather than rewriting the quality of the decision after you discover the outcome.

AI can increase what the span of what is knowable.

That is a tremendous advantage.

But it cannot turn the unknowable future into the knowable.

And we shouldn’t ask it to.

The Skill We May Need Most in the AI Age

Much of the discussion about artificial intelligence focuses on which human skills AI will replace.

I suspect an equally interesting question is which skills become more valuable because AI exists.

Judgement may be one of them.

Not intuition masquerading as judgement.

Not confidence.

Not prediction.

The disciplined ability to gather the available evidence, understand the assumptions, assess the downside, recognise what remains unknowable and still make a considered decision.

Because the strange consequence of having nearly unlimited access to answers is that answers themselves become less valuable.

The ability to know what to do with them becomes more valuable.

AI can give us more information than any generation in history has possessed.

It can help us model possibilities our grandparents couldn’t have calculated in a lifetime.

It can challenge our assumptions and expose things we’ve overlooked.

We should use it.

But perhaps the greatest mistake we could make is assuming that better answers eliminate the need to become better decision-makers.

They don’t.

They make it more important.

Because AI may eventually make information almost unlimited.

Our ability to act intelligently when certainty is unavailable will remain scarce.

For most of our working lives, Generation X was given a fairly simple set of instructions about retirement.

Work hard.

Build a career.

Save part of what you earn.

Invest it.

Let compound returns do their work.

And, eventually, accumulate enough that you can stop working.

It wasn’t bad advice.

But as more of us enter our fifties and retirement stops being something that happens to other people, there’s an uncomfortable question worth asking:

What if saving enough isn’t the only problem we need to solve?

For much of the last century, retirement planning rested on what was often called the “three-legged stool.”

One leg was your pension. One was government retirement benefits. The third was your own savings.

Together, they were supposed to provide the income you needed after your salary stopped.

But for many Gen Xers, one of those legs has largely disappeared.

Defined-benefit pensions have become increasingly rare, replaced by retirement arrangements that put much more responsibility on us to accumulate and invest our own money.

So we’ve responded in the most obvious way.

We’ve tried to make the savings leg bigger.

Save more.

Invest more.

Make additional contributions.

Spend less now so we’ll have more later.

Again, none of this is bad advice.

Time Changes the Mathematics

But there’s a problem that becomes increasingly difficult to ignore as you get older.

Time changes the mathematics.

If you discover at 30 that you’re a long way behind where you’d like to be at retirement, you have decades to do something about it.

Even relatively modest additional savings have years to compound.

Discover the same gap at 50 and the available solutions begin to narrow.

You can save considerably more.

You can try to earn higher investment returns, usually by accepting greater risk.

You can reduce the lifestyle you’re planning for.

You can postpone retirement.

Or you can reconsider one of the assumptions sitting quietly underneath the entire calculation.

That the day you retire from your career is also the day your ability to produce income falls to zero.

The Assumption Hidden in Our Retirement Plans

I’ve come to think this is one of the strangest assumptions in conventional retirement planning.

For thirty or forty years, our greatest financial asset has been our ability to produce income.

We apply our knowledge, experience, relationships and judgment to something valuable, and someone pays us for doing so.

We use part of that income to accumulate assets — shares, funds, property, retirement accounts — so that one day, when the salary stops, those assets can produce the income we need instead.

And that’s where an odd assumption creeps into the conventional retirement model.

We assume that when the salary stops, our ability to produce income stops with it.

At some predetermined age, the model effectively assigns our future income-producing capacity a value of zero and expects the assets we’ve accumulated to take over the entire job.

There were good reasons for thinking this way when retirement commonly meant leaving a physically demanding job after forty years of work.

I’m less convinced it makes sense for a modern executive in their fifties.

What Happens to 30 Years of Experience?

Someone at that stage of life could plausibly have another thirty years of productive life ahead of them.

More importantly, they possess something their 25-year-old self didn’t.

Decades of experience.

Accumulated knowledge.

Professional judgment.

Relationships.

Credibility.

Skills that may have taken half a lifetime to acquire.

Yet when we calculate whether we’re “ready” for retirement, we routinely assign almost no economic value to any of it.

We ask:

How large is your portfolio?

Perhaps we should also be asking:

What is your capacity to continue creating income?

Working in Retirement Isn’t the Same as Having to Work

That doesn’t mean working until you die.

Quite the opposite.

There is an enormous difference between working in retirement and having to work in retirement.

The first can be a choice.

The second is an obligation.

And I suspect this distinction matters particularly to people who have spent decades building successful careers.

Most of the executives I know don’t dream of reaching a particular birthday and becoming permanently unproductive.

They still want to build things. Solve problems. Help people. Learn. Teach. Contribute.

What they’re tired of isn’t necessarily work.

It’s everything that came attached to the particular form of work they’ve been doing.

The meetings.

The commute.

The politics.

The targets.

The hierarchy.

The calendar that somehow belongs to everybody except them.

Perhaps, then, the objective of retirement planning shouldn’t necessarily be to accumulate a magical sum of money that means we never have to earn another dollar.

Perhaps the objective is to reach the point where earning money becomes optional — and happens on our terms.

It sounds like a small distinction.

Financially, it can be enormous.

A Small Amount of Income Can Change the Equation

Suppose you believe you’ll need $100,000 a year to live the life you want after leaving your career.

If you assume you’ll never earn another dollar, your investments have to provide the entire $100,000.

But suppose you can create $20,000 or $30,000 a year doing something you enjoy, on a schedule you control.

The amount your investments have to provide changes.

If you can create $50,000, it changes again.

And if you enjoy what you’re doing and choose to continue doing it, the boundary between “working” and “retirement” begins to look rather arbitrary anyway.

Suddenly the question isn’t simply:

How large a pile of money can I accumulate before I stop working?

It’s:

How many different ways can I create the life I want after I leave my career?

That’s a very different question.

It’s a question about optionality.

And perhaps that’s what the traditional retirement model is missing.

Perhaps We Need a Fourth Leg

If the old retirement model had three legs — pension, government benefits and personal savings — perhaps the modern version needs a fourth.

An income-producing asset you control.

That doesn’t necessarily mean another job.

It could be consulting.

Intellectual property.

A small business.

A digital business.

Royalties.

A portfolio of income-producing assets.

Or something else entirely.

Don’t Start With the Vehicle

I’m deliberately not prescribing the vehicle, because I think that’s where another mistake begins.

The moment someone decides they need another source of income, the obvious question is:

What should I do?

And the internet has no shortage of answers.

Property.

Consulting.

E-commerce.

Affiliate marketing.

Courses.

Trading.

Franchises.

Whatever technology happens to be transforming the world at the time.

There will always be another opportunity.

And there will always be someone completely convinced that this one is the answer.

At 50, a Bad Decision Costs More Than Money

But if you’re in your fifties, choosing the wrong one can be considerably more expensive than it was when you were 25.

Not simply because you can lose money.

You can make more money.

The scarcer resource is time.

Evidence Before Commitment

That’s why I don’t think the answer to discovering a retirement gap is to panic and start a “side hustle.”

I’d begin somewhere else entirely.

I’d begin with evidence.

Is there a genuine problem I can solve?

Are there identifiable people who want that problem solved?

Will any of them actually pay to solve it?

Can I test that proposition without risking a significant amount of capital?

Can I gather evidence that it works before committing years of my life to it?

Those aren’t particularly exciting questions.

But they’re considerably more useful than asking which business opportunity happens to be popular right now.

Because the objective isn’t to find the next big thing.

It’s to create another option.

Maybe We’ve Been Using the Wrong Scoreboard

For decades, we’ve been shown a retirement scoreboard with essentially one number on it.

How much have you accumulated?

If the number is large enough, you’re doing well.

If it isn’t, you’ve fallen behind.

And if you reach your fifties without the retirement portfolio you thought you would have, it’s very easy to look backwards.

I should have started earlier.

I should have saved more.

I shouldn’t have bought that house.

I should have made different investments.

Perhaps some of those things are true.

Thinking about them now is also largely useless.

You cannot go back and change what you saved twenty years ago.

You can’t know what markets will return over the next twenty.

You can’t know what inflation will be.

You can’t know what interest rates will be.

You can’t know precisely what governments will do with taxes, pensions or retirement benefits.

And you certainly can’t know whether the investment everybody is excited about today will still look clever a decade from now.

Those things sit on the other side of an uncomfortable boundary between what we can control and what we can’t.

You Can’t Change the Past. You Can Still Build the Future.

But you can still decide what you build from here.

You can build skills.

You can build relationships.

You can build assets.

You can build the capacity to produce income independently of an employer.

And, crucially, you can test those things while you still have an income, rather than discovering whether they work only after you desperately need them to.

Maybe Retirement Requires Two Kinds of Assets

Perhaps that’s the part of the retirement conversation Generation X has been missing.

We spent decades being told to prepare for the day when our salaries stopped by building a sufficiently large pile of money.

Maybe we should have been preparing in two ways.

Build assets that can produce income.

And preserve the ability to produce income ourselves.

The objective isn’t to work forever.

It isn’t even necessarily to earn more.

It’s to arrive at the next stage of life with as many choices as possible.

To be able to work because the work is interesting, rather than because the mortgage payment is due.

To be able to walk away from something that no longer suits you without wondering whether doing so will destroy your financial future.

To be able to use thirty years of accumulated experience rather than treating it as an asset that mysteriously expires on your retirement date.

And, perhaps most importantly, to retain some control over a future in which so much else cannot be predicted.

A Better Question to Ask About Retirement

So I’m no longer convinced that the most important retirement question for someone in their forties or fifties is:

“Have I saved enough?”

It’s an important question.

But I’d put another one beside it.

“What can I build now that gives me more choices later?”

Because ultimately, the retirement I want isn’t one in which I never work again.

It’s one in which whether I work, what I work on, who I work with, and when I work are decisions I still get to make.