Whose Definition of Success Are You Still Living? #MidlifeByDesignNotByDefaultMonth

Two experts on the money, ambition, purpose and inherited definitions of success that shape the way we build our lives in midlife.

There is a particular kind of restlessness that can arrive in midlife when nothing is technically wrong, and yet something no longer feels quite right. You can look at the career you worked hard to build, the financial security you spent years pursuing, the responsibilities you accepted because they were sensible, and the ambitions you chased because they were impressive, and still find yourself wondering why the satisfaction you expected hasn’t quite arrived. It isn’t necessarily a crisis, and it certainly isn’t ingratitude. Sometimes it is simply the first time you have become still enough to ask a question that was difficult to ask when you were busy building the life everyone told you would make you happy: Do I actually still want this?

That question can be surprisingly uncomfortable because most of us learn what success means long before we learn who we are. We absorb ideas about achievement, financial security, professional status, and respectability from our families, our cultures, our communities, and the people around us, and we often begin pursuing those things before we have developed the language or confidence to ask whether they are genuinely ours. We learn to be ambitious, but we don’t always learn to interrogate the direction of our ambition. We become very good at climbing the ladder without stopping to examine the wall it is leaning against.

And perhaps this is one of the quiet gifts of midlife. We have lived long enough to know what achievement feels like from the inside, rather than simply imagining what it will feel like when we finally get there. We have accumulated enough experience to recognise the difference between something that genuinely energises us and something we are continuing to pursue because we have already invested so much in it. We have responsibilities, yes, but we also have perspective. We know ourselves differently now, and that means some of the definitions we accepted without question deserve to be looked at again.

For this final expert conversation in the Money & Purpose pillar of Midlife by Design, Not by Default Month, I wanted to explore that territory with two women who approach it from different but deeply complementary perspectives. Ilka Sommer writes about work, money, purpose, and the uncomfortable middle between one chapter ending and another beginning, while Dr. Vandana Arcot brings a powerful perspective on the ways family, culture, marriage, motherhood, and social expectations can shape women’s ambitions before we have consciously chosen them. Together, their insights challenge one of the assumptions we carry most deeply into adulthood: that success is something we should spend our lives pursuing rather than something we are allowed to define for ourselves.

The ladder we never stopped to question

Dr. Vandana Arcot asks a deceptively simple question when she works with women around ambition and success: “Whose ladder was this?” It is the kind of question that can make an entire life look different because it asks us to separate the things we consciously chose from the things we absorbed so gradually that they began to feel like our own desires.

For many women, particularly those navigating strong cultural and family expectations, ambition can be redirected without ever being explicitly taken away. Nobody has to tell you that you cannot want a demanding career, financial independence, or a life built around your own aspirations. Instead, the messages arrive through ideas about duty, practicality, family, and what a good woman does for the people she loves. You can be encouraged to pursue your education and build a career while simultaneously learning that there will eventually be a point at which other people’s needs should come first. The contradiction is rarely spoken aloud, which is precisely why it can be so difficult to recognise.

Marriage can change the shape of ambition. Motherhood can change the amount of time available to pursue it. Caring responsibilities can quietly rearrange priorities. Cultural expectations can make certain choices feel selfish while making other choices feel virtuous. None of these decisions are necessarily wrong, and many women make them willingly and lovingly. The question Dr. Arcot invites us to ask is not whether those choices were right or wrong at the time, but whether we would consciously choose the same arrangement now.

That is a very different question from asking whether we are grateful for the life we have built. Gratitude and questioning can exist together. You can love your family and still want more space for yourself. You can value your career and still want it to occupy less of your life. You can appreciate the security your income provides while wondering whether the price you are paying for it is still one you want to pay. You can honour the woman you were without allowing her definition of success to become a permanent contract.

Perhaps midlife gives us permission to renegotiate that contract.

When success becomes another performance

There is a version of female success that can look almost impossible when you step back and really examine it. We are expected to be ambitious but not intimidating, financially successful but not obsessed with money, professionally accomplished while remaining endlessly available to our families, healthy without becoming vain, attractive without appearing to try too hard, nurturing without disappearing into caregiving, and independent without ever making the people around us feel unnecessary.

The old “having it all” narrative can become another performance standard, and when we inevitably struggle to sustain it, the answer is often presented as better organisation. Manage your time. Optimise your morning. Build better habits. Become more efficient. Work smarter. Create boundaries. Find the perfect system that will somehow allow one woman to continue carrying an extraordinary number of expectations without becoming exhausted by them.

But what if exhaustion is sometimes information rather than a personal failure?

That is one of the ideas that runs through Dr. Arcot’s thinking. When the life we have built begins to feel increasingly difficult to sustain, perhaps the answer isn’t always to become better at managing it. Perhaps sometimes we need to ask whether the arrangement itself still reflects what we value. Midlife can expose the gap between the life we have been performing successfully and the life we actually want to inhabit.

That gap can be surprisingly quiet. It may not look like burnout or a dramatic desire to escape. It can simply be the feeling that you have become very competent at a life you aren’t particularly interested in continuing.

And that is often where the more honest conversation begins.

Welcome to the hallway

Ilka Sommer has a beautiful way of describing the period between one chapter and the next. She calls it the hallway, that strange, unglamorous space where the old life has stopped fitting but the new one hasn’t quite arrived.

I think many women mistake the hallway for failure.

We have been taught to value certainty, so when we no longer know exactly what we want, we assume something has gone wrong. We want a five-year plan, a new title, a clear purpose, and a compelling answer when someone asks what we are doing next. We want the reinvention to be obvious enough to explain.

But Ilka’s work makes room for the possibility that the middle matters too. Sometimes you don’t know what you want yet. Sometimes the first thing you know is what you no longer want. Sometimes relief is the first clue. You imagine not doing something anymore and notice that your shoulders drop slightly. You picture a different kind of working week and realise you can breathe more easily. You consider stepping away from something that once seemed essential and feel, perhaps for the first time, a little lighter.

We tend to dismiss those reactions because they aren’t ambitious enough. We want a grand vision, but sometimes the most honest information arrives as a quiet sense of thank goodness I don’t have to do that anymore.

There is wisdom in paying attention to that.

Purpose doesn’t always arrive as a lightning bolt. It can emerge through subtraction, through noticing what no longer belongs, through allowing yourself to experiment before you have a neat explanation for what you are doing. The hallway can be uncomfortable, but it can also be the place where you stop rushing towards the next identity long enough to discover what might actually fit.

Money is arithmetic, not a verdict on your worth

Money becomes particularly complicated in midlife because it is rarely just money. It carries our ideas about safety, independence, competence, status, family responsibility and the sacrifices we have made along the way. The number in a bank account can feel like proof that we have made sensible decisions, while earning less than we expected can feel strangely personal, as though a financial figure has become a judgement on how well we have done at adulthood.

Ilka offers a useful way of separating those things. Money is arithmetic; it isn’t a character verdict. That distinction matters because women can spend enormous emotional energy comparing their financial position with where they believe they should be by a particular age. We look at other people’s houses, careers, businesses, holidays, pensions and lifestyles and quietly decide that we are behind, without knowing the circumstances, choices or sacrifices that produced what we are seeing.

The more interesting financial question in midlife may not be simply how much we have accumulated, but what that money is actually for. Security matters, and financial planning matters, but money becomes much more meaningful when we connect it to the life we want it to make possible. Perhaps it is the freedom to work fewer days. Perhaps it is the ability to take a sabbatical, care for someone, travel, build a business, spend more time with the people you love, or simply create more breathing room in your ordinary week.

That shifts the question from How much do I need? to Enough for what?

It is a small change in language, but it can change the entire relationship between money and purpose. When money becomes possibility rather than proof, we can begin making financial decisions according to the life we actually want rather than the life we think we are supposed to be able to display.

Security is not the same as freedom

We often assume that earning more automatically means becoming freer, but Ilka’s perspective complicates that assumption in a useful way. A larger salary can provide security, but it can also create golden handcuffs, particularly when the lifestyle attached to that income becomes expensive to maintain. You can reach a point where the money you earn requires so much of your time, energy, and availability that the very thing you thought would create freedom becomes the reason you have so little of it.

This is where one of Ilka’s questions becomes particularly provocative: How long could you afford to be unimpressive?

I love this question because it challenges something deeper than our relationship with money. It challenges our relationship with status.

How much of what we pursue is genuinely about the life it creates, and how much is about how that life looks from the outside? How much of our ambition is connected to wanting to be admired, respected, or able to tell a satisfying story about ourselves? What would happen if we temporarily allowed ourselves to make a decision that looked less impressive but felt more aligned?

That doesn’t mean everyone should leave a high-paying career or deliberately earn less. It means we should know what we are buying with the trade. Every professional decision is an exchange, and the currency isn’t only money. We exchange time, energy, attention, creativity, flexibility, and presence for what we receive in return.

The important question is whether we are still consciously making that exchange.

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Sometimes dissatisfaction is telling you about the arrangement

There is a particular kind of midlife dissatisfaction that can be difficult to act upon because nothing is obviously terrible. The job is fine. The salary is fine. The company is fine. Your colleagues are fine. You have a pension. You have benefits. You have stability.

And yet you keep imagining something else.

Ilka’s work makes space for the possibility that this doesn’t necessarily mean your entire life is wrong. Sometimes the problem is the arrangement. Perhaps you don’t hate the work; you hate the hours. Perhaps you don’t need a new career; you need more autonomy. Perhaps you enjoy your profession but no longer want the level of responsibility that once felt exciting. Perhaps the business you created is still meaningful but has grown into something you never intended to run.

This matters because midlife conversations about purpose can become unnecessarily binary. We imagine that the only alternatives are staying exactly where we are or burning everything down and starting again.

Real life is usually much more interesting than that.

You can redesign the shape of work without abandoning the work itself. You can change the hours, the environment, the responsibilities, the clients, the pace, or the definition of success. You can create a portfolio where one form of work provides financial stability while another gives you creative or personal fulfilment. You can allow one part of your working life to fund another part that is still becoming.

You don’t have to make your entire livelihood carry the weight of your identity.

Purpose doesn’t have to become a business

This is perhaps one of the most important corrections to the modern conversation about purpose.

We have become very good at turning everything into a productivity opportunity. If you love writing, start a business. If you love cooking, monetise it. If you have experience, coach others. If you have a passion, build a brand around it.

But not everything we love needs to become economically productive.

Ilka’s thinking around purpose allows for a more nuanced relationship with work. Some work can pay for the life. Some can build something meaningful. Some can stretch us. Some can connect us with people we care about. Some can simply be work that we do well and leave behind at the end of the day.

There is freedom in that.

Your purpose doesn’t have to be contained within your job title.

It may be expressed through your work, but it may also be expressed through how you parent, what you create, who you support, the community you build, the causes you care about, the relationships you nurture, or the way you choose to spend your time.

The pressure to turn purpose into a profession can actually make it harder to hear what matters.

Sometimes the thing that gives your life meaning doesn’t need to make you money.

And sometimes the thing that makes you money is valuable because it gives you the freedom to pursue what gives your life meaning elsewhere.

Both can be true.

What are you no longer willing to inherit?

Perhaps the most useful thing about bringing Ilka and Dr. Arcot’s perspectives together is that neither tells us what the “right” midlife looks like.

They don’t replace one definition of success with another.

Instead, they give us better questions.

Dr. Arcot asks us to examine what we inherited and decide consciously what we want to carry forward. Ilka reminds us that we don’t have to have the whole future mapped out before we begin moving differently. One asks us to examine the blueprint; the other gives us permission to stand in the hallway while we work out what we want to build instead.

Together, they create a much more generous definition of reinvention.

You don’t have to become someone completely new.

You may simply need to stop organising your life around a definition of success that no longer belongs to you.

That might mean wanting more money. It might mean wanting less work. It might mean wanting a bigger professional challenge after years of prioritising everyone else. It might mean wanting to step away from the ladder entirely. It might mean discovering that you still love the career you chose decades ago, but you want to experience it differently now.

There is no inherently more enlightened answer.

The important thing is that it is yours.

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The life underneath the numbers

I keep coming back to the idea that money and purpose are ultimately questions about the ordinary life underneath them.

Not the impressive version you can describe at a dinner party, but the Tuesday afternoon version. The version nobody photographs.

What do you want your working day to feel like? How much of your energy do you want to spend earning money, and how much do you want available for the people and experiences that make the money worthwhile? What does financial security actually mean to you now? How much is enough to create the freedom you want? What are you willing to trade for another promotion, another level of responsibility, or another increase in income, and what are you no longer willing to trade?

These are not questions with universal answers; that is precisely why they matter.

A successful midlife for one woman might mean building a bigger business than she has ever imagined. For another, it might mean closing the business and taking a part-time role. One woman may discover that she wants to earn more because financial independence gives her choices she didn’t previously have. Another may realise that she has enough and would rather exchange some income for time.

Neither woman is failing or settling; they are simply designing different lives.

You are allowed to choose again

There is something tender about reaching midlife and realising that we are not starting over. We are starting from experience.

We know more now.

We know what achievement feels like when the applause stops. We know which kinds of work make us feel alive and which leave us hollow. We know what financial security can and cannot provide. We know how much energy certain ambitions require. We know the cost of being constantly available. We know what happens when we postpone ourselves for too long. We know that some of the things we thought would matter enormously eventually became surprisingly unimportant, while other things we dismissed as indulgent turned out to be the things that made life feel like ours.

That knowledge is not a reason to regret the past; it is a reason to use it.

Perhaps the most powerful form of midlife reinvention isn’t deciding what you want to become. It is deciding what you no longer want to organise your life around.

Maybe you no longer want your worth measured by your productivity. Maybe you no longer want your salary to determine your status. Maybe you no longer want to explain every choice through what is practical for everyone else. Maybe you no longer want to postpone the life you actually want until some imaginary future when everything is finally sorted.

And perhaps, alongside those realisations, you can begin asking what success means when it is stripped of performance.

• What does enough look like when nobody else gets to define it?

• What does freedom feel like in the texture of an ordinary week?

• What would you build if you didn’t need anyone to be impressed?

Those questions may lead somewhere dramatic, or they may lead to a series of very small changes. You may change careers, reduce your hours, grow a business, earn more, earn less, stay exactly where you are, or finally give yourself permission to enjoy the work you already do without asking it to provide your entire sense of purpose.

The answer isn’t mine to give you; it isn’t Ilka’s, or Dr. Arcot’s, and it certainly isn’t society’s.

That may be the most important thing about money and purpose in midlife: we don’t need another template; we need authorship. We need the courage to look at the life we have built, acknowledge the woman who built it, and then, with everything we know now, decide what we want to build next.

Because the question isn’t simply whether you are successful; it is whether the success you are pursuing still belongs to you. And if it doesn’t, perhaps midlife is the moment you finally give yourself permission to choose again.

Kiran x

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