There’s a peculiar contradiction in the way we make decisions today.
We have access to more information than any generation in history.
We can compare investment strategies, calculate retirement scenarios, research business opportunities and ask AI to explain almost anything we don’t understand.
Questions that once required a specialist, a library or several days of research can now be answered in seconds.
You would expect all this information to make us more confident about our decisions.
Yet many people seem to be experiencing the opposite.
They know more.
They have more options.
They can see more possibilities.
And somehow, they find it harder to decide what to do.
Perhaps the problem isn’t that we don’t have enough information.
Perhaps we’ve misunderstood what information is supposed to do for us.
The retirement confidence paradox
A recent study by Singapore wealth management platform Endowus illustrates the problem rather well.
Its 2026 Wealth Insights Report surveyed 500 Singaporeans about retirement planning, financial advice and AI.
The findings were striking.
75% considered a secure retirement important. Yet only 28% felt confident that their plans were on track.
In other words, almost three-quarters weren’t confident they were heading toward the retirement they wanted.
And it wasn’t simply because they didn’t know retirement planning was important.
They knew.
Many had already taken steps.
But they remained uncertain about whether those steps would get them where they wanted to go.
The report also examined how many information sources people used when making financial decisions.
Those who felt confident used an average of 2.58 sources.
Those who weren’t confident used 2.43.
That’s hardly the dramatic difference we might expect if access to more information were the principal source of confidence.
The more revealing finding concerned planning. Respondents with a clear plan they were executing were substantially more likely to feel confident about their retirement prospects than those who had taken some steps but weren’t sure whether they were on track.
Now, a survey about confidence doesn’t establish whether someone’s retirement plan will actually succeed.
People can feel confident and be wrong.
They can also feel uncertain despite having made perfectly sensible decisions.
But the findings raise an interesting question.
If information is so readily available, why is it still so difficult to turn what we know into decisions we can act on?
Information and understanding aren’t the same thing
Imagine you’re trying to decide whether you can afford to retire in five years.
You begin researching.
You discover articles about how much money people supposedly need for retirement.
You read about the 4% withdrawal rule.
You compare dividend-paying investments, bonds, annuities and property.
You calculate how inflation might affect your expenses.
Then you ask AI to evaluate your retirement portfolio.
It produces an impressively detailed analysis, complete with projections, assumptions and possible strategies.
You’ve learned an enormous amount.
But can you retire in five years?
You still don’t know.
And the reason isn’t necessarily that you need more information. It’s that the information you’ve collected hasn’t yet been organised into an understanding of your particular situation.
A retirement calculation that assumes you’ll live to 85 may look perfectly reasonable.
But what if you live to 95?
A portfolio projection that assumes a 7% annual return may appear reassuring.
But what happens if the market falls 30% shortly after you retire?
You can gather more information about longevity, historical returns and market volatility.
Yet none of it will tell you precisely how long you’ll live or what markets will do.
The information may help you understand the risks.
It cannot eliminate them.
So you can continue researching indefinitely, hoping the next piece of information will finally make the decision obvious.
Or you can recognise that the problem has changed.
You no longer need to answer every possible question about retirement.
You need to identify which uncertainties matter to your decision, which you can do something about, and which you must learn to manage.
That’s a different kind of work.
More information can create more uncertainty
We tend to assume that uncertainty comes from not knowing enough.
Sometimes it does.
If you’re buying a house and don’t know whether the roof is leaking, a building inspection can reduce uncertainty.
If you’re considering an investment and don’t understand how it generates returns, learning about its business model can help.
Information is extraordinarily useful when it answers a question that matters.
But not every additional piece of information makes a decision easier.
Suppose you’re considering changing careers.
Initially, you see two options: remain in your current job or find another.
Then you begin researching.
You discover consulting, freelancing, starting a business, retraining, investing for income, part-time work and several other possibilities.
AI can help you explore every one of them.
Within an afternoon, you might have ten plausible alternatives, each with its own advantages, disadvantages, risks and requirements.
You now know considerably more than when you started. But you also have more decisions to make. And every new option creates additional questions.
What if consulting is better than employment?
What if starting a business offers greater long-term potential?
What if retraining makes more sense?
What if AI changes the economics of all three?
The problem is no longer a shortage of possibilities.
It’s that you haven’t established how to choose between them.
Information has expanded your choices without giving you a basis for making the choice.
Clarity begins by removing what doesn’t matter
Consider two people evaluating the same investment.
Both have access to identical information.
The first person wants the highest possible return.
The second needs reliable income to meet living expenses over the next ten years.
An investment offering substantial growth potential but unpredictable cash flow might be attractive to the first person and unsuitable for the second.
Neither person necessarily has better information.
They have different purposes.
And those purposes change which information matters.
This is why I believe clarity begins before analysis. You first need to understand what you’re actually trying to achieve. Only then can you determine which information is relevant.
Otherwise, you risk spending enormous amounts of time analysing things that have little bearing on your decision.
It’s rather like planning a journey.
You can study every road, train route and airline schedule in the country.
You can compare prices, travel times and reliability.
But until you’ve decided where you’re going, you cannot determine which route is best.
The information isn’t useless.
You simply haven’t established what you’re using it for.
The same principle applies to careers, businesses, investments and retirement.
Before asking which option is best, ask:
Best for what?
That question can eliminate an extraordinary amount of unnecessary complexity.
Understanding also means knowing what you might be getting wrong
Even when we know what we’re trying to achieve, there’s another obstacle.
Our conclusions depend on the assumptions we make.
And assumptions are particularly dangerous because they often don’t look like assumptions.
They look like facts.
Someone might assume that because they’ve earned a high salary throughout their career, they’ll always be able to find another well-paying job.
Someone else might assume that because an investment has performed well for the past decade, it will continue performing well.
A third person might assume that because they’ve never run a business, they wouldn’t be capable of building one.
These beliefs can shape decisions long before anyone thinks to question them.
You can conduct extensive research and still arrive at a poor conclusion if the research is built around the wrong assumption.
In fact, the additional information may make you more confident in that conclusion.
Because the problem isn’t always what you don’t know.
Sometimes it’s what you think you know.
This is where judgment becomes important.
Judgment involves recognising which assumptions deserve scrutiny, which risks are significant and which details are unlikely to change the outcome.
It’s the ability to distinguish between a question that genuinely needs answering and one that’s merely interesting.
And that ability isn’t necessarily improved by collecting more information.
It improves when you learn to examine how you’re interpreting the information you already have.
A good decision doesn’t require a certain outcome
There’s another reason people can remain uncertain despite extensive research.
They may be asking information to provide something it cannot.
A guarantee.
Think about an important decision you’ve made in your life.
Perhaps accepting a job.
Buying a property.
Getting married.
Making an investment.
Leaving a career.
At the time, you couldn’t possibly have known everything that would happen afterward.
You made the decision using the information available, your understanding of the situation, and your judgment about the risks and opportunities.
Some decisions worked out well.
Others probably didn’t.
But an unfavourable outcome doesn’t automatically mean the original decision was poor.
You might make a sensible investment that loses money because of an unforeseen event.
Or a reckless investment that makes money because you happened to get lucky.
If we judge decisions entirely by their outcomes, we risk learning the wrong lessons from both.
A better question is whether the decision was reasonable given what you knew, what you could reasonably have discovered, and the alternatives available at the time.
Did you understand what you were trying to achieve?
Did you identify the important assumptions?
Did you consider what could go wrong?
Could you afford the consequences if things didn’t work out?
Were there ways to test the idea or limit your exposure before making a larger commitment?
Those questions won’t guarantee success.
But they can help you make decisions without needing to predict the future.
Clarity is not certainty about what will happen. It’s understanding enough to make a decision despite not knowing what will happen.
The danger of waiting until you know enough
Of course, there’s a reasonable objection to all this.
Surely it’s better to research carefully than to make an uninformed decision?
Absolutely.
The problem isn’t research.
It’s failing to recognise when additional research is no longer improving the quality of the decision.
Imagine someone who has been thinking about starting a small business for three years.
They’ve read books, watched videos, attended webinars and researched dozens of business models.
They understand the terminology.
They can explain the advantages and disadvantages of different approaches.
But they’ve never spoken to a potential customer.
They’ve never tested whether anyone would pay for what they want to offer.
They’ve never taken the smallest practical step toward finding out whether their idea works.
At some point, another course or another book is unlikely to resolve their uncertainty.
Because the missing information can only be obtained through action.
They don’t need another explanation of how businesses work.
They need evidence about whether their particular idea has a market.
The same applies to many other decisions.
You can research a career change for months, but a conversation with someone already doing the work may reveal more than another hundred articles.
You can study investment strategies indefinitely, but until you’ve established your actual income requirements and risk tolerance, you may still be unable to choose.
Sometimes understanding comes from analysis.
Sometimes it comes from experience.
And often, it requires both.
The question to ask before gathering more information
The next time you find yourself researching an important decision, try asking yourself something.
What would I need to learn that could actually change my decision?
It’s a deceptively useful question.
Suppose you’re considering an investment.
If learning that it could lose half its value would change your mind, then understanding its downside risk is important.
If learning that its fees are slightly higher than a competing product wouldn’t affect your choice, then spending another week comparing minor fee differences may not be worthwhile.
Suppose you’re thinking about building another source of income.
If your biggest concern is whether anyone would pay for your proposed solution, then researching website designs and business names probably isn’t the next useful step.
Finding out whether customers actually want the solution is.
The point isn’t to stop learning.
It’s to make learning serve a decision.
That requires three things.
First, knowing what you’re trying to achieve.
Second, understanding which information and assumptions actually affect your choice.
Third, identifying what you can do to reduce the remaining uncertainty to a level you can reasonably accept.
You may still decide to wait.
You may decide not to proceed.
Or you may discover that a small, reversible experiment is a better next step than a large, irreversible commitment.
All three can be perfectly sensible decisions.
The important thing is that you’re making them deliberately, rather than remaining trapped in an endless search for reassurance.
Perhaps we need a different measure of progress
For years, we’ve treated access to information as though it were almost synonymous with progress.
More books.
More courses.
More research.
More sophisticated tools.
And now, AI systems capable of producing answers to questions we might never previously have thought to ask.
These developments are genuinely valuable.
But the Endowus findings remind us that knowing something is important and having the information to pursue it aren’t the same as making progress toward it.
You can be well-informed about retirement and still have no workable retirement plan.
You can understand entrepreneurship and still have no evidence that your business idea will succeed.
You can know everything about the risks of changing careers and still be unable to decide whether to make the move.
Perhaps the more useful measure isn’t how much information we’ve accumulated.
It’s whether that information has improved our understanding sufficiently to make a better decision.
And whether we’ve acted on that decision.
Because information is only one ingredient.
Purpose tells us what we’re trying to achieve.
Understanding helps us interpret what we know.
Judgment helps us decide what matters.
And action allows us to discover what information alone cannot tell us.
The objective was never to know everything.
It was to know enough of the right things to make better decisions.
And perhaps the next time you feel stuck, the answer isn’t to learn something new.
It’s to look differently at what you already know.