Have you ever properly imagined yourself at 80?
Not where you live, whether you’ve paid off the mortgage or how much is sitting in your pension. Not the soft-focus version of you in a linen shirt, drinking tea in a beautiful garden and looking remarkably good for your age. I mean you. The woman herself.
What is she like?
Does she still get excited about things? Is she curious? Does she trust herself? Can she laugh at the mistakes that once kept her awake at night? Has she stopped comparing herself with women she never really wanted to be in the first place? Does she still have strong opinions, change her mind, try things she isn’t very good at and occasionally make decisions that surprise the people who thought they had her figured out?
And does she like the woman she became?
It’s a different question from asking what you want to have achieved by 80. We are good at thinking in those terms. The career. The business. Financial security. The house. The places we want to see. The things we still want to accomplish. All of that matters, but achievement tells you what you have accumulated. It doesn’t necessarily tell you very much about the woman who accumulated it.
So perhaps there is another way to look at the life you’re creating.
Imagine yourself at 80 and look backwards.
She already knows how this turns out
The woman at 80 knows things you don’t know yet.
She knows what happened with your career. She knows whether you built the business, took the promotion, stayed another ten years or eventually walked away. She knows whether you made the money you’re working so hard for and whether it bought what you hoped it would. She knows which relationships lasted, which ones changed, who surprised you and who you eventually had to let go.
She also knows what happened to the decisions that frighten you today.
Think about one of them.
Perhaps you’re doing work you’re exceptionally good at, but you’ve known for some time that you don’t want to spend the rest of your working life doing it. Maybe there is something else you keep thinking about, but it would mean giving up certainty, status or income. Perhaps you want to build something of your own. Maybe you want to grow what you’ve already built and you’re frightened by the size of your ambition. Or perhaps what you actually want is less, and admitting that feels strangely harder than wanting more.
From where you are standing now, you have years of evidence telling you what makes sense. Experience accumulated. Salary earned. Reputation built. People depending on you. Commitments made. There may be very good reasons to stay exactly where you are.
But your 80-year-old self is holding a different set of accounts.
She knows what staying cost you too.
That doesn’t mean she would tell you to leave. Maybe staying will turn out to be one of the best decisions you ever made. Looking at your life from the other end isn’t a clever way of giving yourself permission to do something reckless.
It does something much more useful.
It doesn’t tell you to be braver. It asks you to be more truthful.
Are you staying because you genuinely want to stay, or because leaving frightens you? Are you saying yes because you want the opportunity, or because being wanted still feels a little too much like being valuable? Are you working this hard because the work matters deeply to you, or because you’ve become so good at carrying responsibility that nobody, including you, has thought to ask whether you still want to carry quite so much of it?
Only you know.
But I suspect the woman at 80 will.
Some of the safest decisions have very good disguises
Fear and guilt rarely walk into the room and announce themselves when intelligent women make important decisions. They’re much cleverer than that.
They sound like responsibility. Loyalty. Timing. Prudence. Being realistic. They remind you how much you’ve already invested, how many people depend on you and how foolish it would be to disturb something that is working perfectly well. Sometimes they’re right. Responsibility is real, money matters and other people don’t disappear simply because we’ve decided to become more intentional about our lives.
But there is a difference between considering other people and repeatedly abandoning yourself.
There is a difference between choosing security because it genuinely matters to you and choosing it because fear has made every alternative look irresponsible. There is a difference between loving people and needing to be needed by them. There is even a difference between being kind and saying yes because you can’t tolerate somebody being disappointed in you.
Those distinctions matter in business too. You can build a successful career because you’re excellent at the game and eventually discover you never particularly wanted the prize. You can create a business around what the market rewards and accidentally build yourself another job you don’t want. You can keep chasing more money while quietly trading away the independence you thought money was supposed to buy.
Money matters. A lot. Especially for women. It creates options, security and the ability to make decisions that don’t depend entirely on somebody else’s permission.
But independence is bigger than money.
It’s being able to decide who you are when nobody is applauding.
It’s knowing what you want when comparison isn’t doing the choosing for you.
And perhaps it’s being able to disappoint someone without automatically concluding that you’ve done something wrong.
The relationship you’re taking all the way to 80
This morning I heard a sentence that stopped me.
It came from Diane von Furstenberg, who turns 80 in a few months:
Sit with that for a moment.
Because whatever happens between now and 80, there is one woman who is coming with you.
You.
And perhaps that changes what self-belief means.
We often talk about self-belief as though it’s confidence that things will work out. Believe in yourself. Take the leap. Trust your gut. Lovely when printed on a mug, but not especially useful when you’re making a decision with real consequences.
What if self-belief isn’t knowing you’ll make the right decision?
What if it’s knowing you won’t abandon yourself when you make the wrong one?
Because you will make some wrong ones.
You’ll trust someone you shouldn’t. Stay too long. Leave too early. Spend money badly. Miss an opportunity. Build something that doesn’t work. Say something you wish you hadn’t. Perhaps you’ll spend three years pursuing something and eventually realise you don’t want it anymore.
At 80, do you want to be a woman who avoided all of that?
Or a woman who learned that getting something wrong didn’t make her wrong?
There is enormous freedom in that distinction. Your mistakes can become information rather than identity. You can learn without turning every wrong decision into another reason not to trust yourself. You can change your mind without treating the previous version of you with contempt for not knowing then what you know now.
Imagine carrying that relationship with yourself into 80.
What will have compounded because you were here?
Then there is the question of legacy.
It’s a word that can sound unnecessarily grand, particularly when you’re sitting at the kitchen table on a Tuesday with emails waiting and laundry that has shown absolutely no respect for your desire to contemplate the meaning of life.
But legacy doesn’t have to mean having your name on a building.
Look at the people around you.
Who has become more confident because you believed in her? Who became more independent because you loved them enough not to make yourself indispensable? Whose career changed because you opened a door? What knowledge did you pass on rather than protect as proof of your own importance? Who remembers that you were kind at a moment when there was absolutely nothing in it for you?
And what have you built?
Maybe it is a company. Maybe it’s wealth that gives your family choices you never had. Perhaps it’s work that matters, a book, a body of knowledge, a community, a home people love returning to or children who know they can stand on their own feet.
Kindness and ambition aren’t opposites.
Neither are independence and love.
Perhaps legacy is simply what has compounded because you were here.
We understand compounding when it comes to money. We talk about it considerably less when it comes to courage, generosity, knowledge, self-belief and kindness. Yet those things move from person to person too. Something you say to someone at 46 may influence a decision she makes at 52, which changes something for somebody you’ve never even met.
You may never know.
That doesn’t make it less real.
You don’t need to design her
So what kind of 80-year-old woman are you becoming?
I hope you don’t have a complete answer.
Imagine having another 20 or 30 years ahead of you and already knowing exactly who you’ll be at the end of them. How incredibly dull. 😂
I hope she surprises you.
I hope she has changed her mind about things you currently consider settled. I hope there are people around her you haven’t met yet. I hope she’s made mistakes you can’t currently imagine and recovered from them. I hope she has tried things you once thought weren’t for you and let go of a few things you were once certain defined you.
Maybe she’ll still be working. Maybe she’ll have built the business. Maybe she’ll be writing her third book, travelling somewhere you’ve never considered visiting or learning something she’s spectacularly bad at.
Perhaps she’ll be quieter than you are now.
Perhaps she’ll be louder.
The point isn’t to design her today.
It’s to notice that you’re already creating the life she’ll eventually look back on.
So every now and then, perhaps it’s worth borrowing her chair and looking at your life from there.
Look at the work you’re doing. The money you’re making. The things you’re postponing. The people you love. The things you’re tolerating. The ambitions you’re hiding. The mistakes you’re still punishing yourself for. The kindness you’re putting into the world.
Then ask yourself whether they are taking you towards a woman you would actually like to meet.
Diane von Furstenberg turns 80 in three months. Listening to her this morning, what struck me wasn’t simply what she has achieved. It was the woman speaking about the life she had lived. The self-belief. The independence. The mistakes she was willing to own without allowing them to define her. The value she places on kindness. And the relationship she has built with herself through all of it.
It made me wonder what I’ll sound like when I’m 80.
I don’t need her answers to be mine.
But I would quite like to reach that age still unmistakably myself, only with another 25 years of living added.
And hopefully enough self-belief to have made a few questionable decisions along the way.
Otherwise, where’s the fun in making it to 80? 😂
Know a woman you’d like to be sitting beside at 80?
Send this to her.