MIDLIFE BY DESIGN: CURATING YOUR NEXT CHAPTER

MIDLIFE BY DESIGN: CURATING YOUR NEXT CHAPTER

The Midlife Circle

What If You've Been Measuring Wealth All Wrong?

On a book that just reframed everything, and what it means for women in midlife.

Kiran Singh, Midlife by Design's avatar
Kiran Singh, Midlife by Design
Jul 06, 2026
∙ Paid

I came across Sahil Bloom’s The 5 Types of Wealth the way I come across most things that end up staying with me, not through a carefully curated reading list, but through a quiet collision of timing and recognition.

I wasn’t looking for a business book or another framework. I’ve read enough frameworks, thank you. I’ve filed them, highlighted them, built Notion databases around them that I later deleted. You know how that goes.

But this one landed differently, because it didn’t start with a strategy; it started with a question so simple it almost sounds naïve:

What does it actually mean to be wealthy?

Not financially comfortable. Not successful by someone else’s definition. Not winning by a scoreboard you didn’t design and never consciously chose.

Wealthy. In the fullest, truest, most honest sense of that word.

Here’s what Sahil found when he spent years asking elderly people, individuals collectively representing over a thousand years of lived experience, what they wished they’d understood sooner.

Not one of them mentioned money. Not one. Instead, they talked about love, presence, friendships they’d let go of quietly, evenings they’d spent too tired to be there for the people they adored, mornings they’d rushed through on their way to somewhere that, looking back, mattered so much less than they thought.

One wrote simply: "Never let a good friendship atrophy.”

Another: “Dance at weddings until your feet are sore.”

And the one that hit me hardest: “Regret from inaction is always more painful than regret from action.”

These are not productivity insights; these are dispatches from the future. From women and men who had the advantage and the ache of perspective.

And in all of it, Sahil noticed something that quietly reshaped his entire approach to life.

We have been measuring the wrong thing.

Most of us have been running a race we didn’t consciously enter: work hard, make money, accumulate things. Arrive.

And then, if you’re honest, you arrive at the promotion, the house, the salary, the goal, and feel a brief, almost embarrassed flicker of “Is this it?” before the next goalpost quietly shifts itself another mile down the road.

The treadmill doesn’t stop; it just gets faster, and somewhere in midlife, a lot of us quietly pause and think: “I don’t want to run anymore, not like this.”

I’ve sat with this book long enough now to know which parts have settled into something I can’t unknow.

There is a calculation Sahil describes: a simple piece of maths involving the people you love and the time you have left, that I did in my head one evening and have not entirely recovered from. Not in a bad way, but in the way that clarity, even uncomfortable clarity, tends to rearrange things.

It changed how I spend certain days and weekends, and the phone calls I had been meaning to make but kept deferring to a quieter moment that never quite arrived.

There is also a single-sentence exercise in the book, one that asks you to define, simply and honestly, the type of person you are becoming in this season, and I have written my answer down and placed it somewhere I see it daily. It has become a kind of quiet compass. When a decision comes, a yes or a no, a leap or a stay, I return to it.

And there is a practice he calls the Enough Life. Not more or optimal, but enough. Writing down, specifically and honestly, what the life you actually want looks like on an ordinary day. Most of us have never done this properly. We’ve chased numbers without ever asking what they’re for. We’ve worked toward freedom without ever defining what we’d do with it.

When I wrote mine down, really wrote it, not as an aspiration but as a description, I found that the life I actually want is not as far away as I’d assumed.

That is what this book does, I think. It doesn’t give you a morning routine; it makes you reorder something.

What I keep coming back to is this: Sahil argues that the things you switch off entirely don’t just pause, they atrophy.

The relationship you don’t tend to in your forties won’t be there in your fifties. The body you don’t maintain now will carry the debt later. The purpose you keep deferring never gets to bloom.

For women who have spent decades being told, implicitly, persistently, to choose between self and others, ambition and ease, presence and progress, that is quietly revolutionary. You don’t have to choose; you simply have to tend. Thoughtfully, seasonally, honestly.

Midlife, I think, is exactly the right moment to learn the difference.

The Practice

This week, sit with one question, and actually write the answer down.

If I spent the next twelve months genuinely investing in all five areas of my life, not perfectly, not dramatically, but honestly, what would my life look like at the end of them?

Let yourself want it. Let the answer be specific. Then notice what it tells you about where you need to begin.


If this has landed somewhere real, if you recognised yourself in the treadmill, in the deferred friendships, in the vague unease of measuring the wrong things for too long, the deeper work is waiting for you inside The Midlife Circle.

Below, we go through all five types of wealth properly: what they are, how they connect, and, more importantly, how your life actually looks against each one right now. The audit is honest, the questions are real, and the exercises are the ones I have done myself.

Because knowing you’ve been measuring the wrong things is the beginning. Deciding what to measure instead is where the change actually starts.


Member Content: Join The Midlife Circle to Continue Reading

The full Midlife Circle version of this piece goes deeper into what it actually feels like to apply this framework to your real, imperfect, beautiful midlife, not as a self-improvement project, but as an act of genuine self-respect.

Inside, we explore:

  • A guided Midlife Wealth Audit across all five areas, honest questions, no performance required

  • The remaining time calculation, and how to sit with what it reveals without panic

  • How to map your relationships and finally be honest about where your energy is really going

  • The Life Razor exercise, writing the single sentence that can guide this entire season of your life

  • The Enough Life practice, defining what you’re actually working toward, in your own words

No overwhelm, no overhaul, just a quieter, more honest relationship with how you’re living, and what you want the next chapter to feel like.

User's avatar

Continue reading this post for free, courtesy of Kiran Singh, Midlife by Design.

Or purchase a paid subscription.
© 2026 Kiran Singh · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture