JUNE 25, 2026

When self-improvement stops working

I was recently walking around my local Barnes & Noble with no particular book to find. After exploring the kids section with my 6 year old daughter, I drifted into the self-help section.

Ever since I can remember, I’ve always been drawn to nonfiction more than fiction; biographies from an early age and as I got older, the self-improvement titles. For some reason, other people’s advice on improving myself has always intrigued me (even in areas I had no idea were important :)

This time as I was browsing the shelves, a new question surfaced in my mind related to self-improvement, yet one that the books weren’t exactly answering.

The tapes my mother listened to

When I was around my daughter’s age in the early 80’s, I remember my late mother listening to cassette tapes on assertiveness training in her car.

She was an 5' tall Indian woman who had arrived to the US only 10 years prior and was now a computer programmer working with a leading defense contractor, presenting to the Navy and other predominantly male (and much taller, imposing) military officers. While raising two American-born children as an immigrant woman, she wasn’t listening to those tapes just to get better at her job. She was trying to figure out who she needed to become, to feel like she belonged in a culture that saw her as an outsider on virtually all accounts.

Like many immigrant families who arrived in the 70s, my parents met the challenge of fitting in, through education and self-improvement. My mother in particular was culturally curious, progressive and willing to experiment beyond her comfort zone. Self-improvement connected us, even when it also brought the inevitable undercurrent of criticism and never feeling “successful” enough.

Every year, thousands of self-improvement books are published because it connects millions of readers just like me and my mother. There are countless books on habits, productivity, leadership, confidence, communication, purpose. And they all wrestle with a common question: how do I become better?

But standing in that bookstore, reflecting on all of it, a different question came to me:

What happens when becoming better is no longer the challenge?

The hidden assumption behind self-improvement

Most self-improvement assumes continuity: the future “better” version of you is largely the same person you already are, just more disciplined, more confident, more productive. In this way, improvement is additive. So, habit stacking, morning routines, optimization systems and the like, work really well when the challenge is daily, incremental performance.

For instance, do you want to be a better writer? Write consistently. Do you want to be healthier? Move more and eat better.

For many seasons of life, these solutions hold. But at other times, life introduces a different kind of challenge.

When the game changes

Sometimes it’s not enough to simply do more and get better.

Consider a leader who spent years building a reputation as the go-to expert in a particular domain.

Now they’ve been elevated into a role that demands something entirely different, like driving results at scale.

More answers won’t help them here and in fact, having all the answers will likely undermine their empowerment of others.

Their new team needs inspiration and vision, not expertise. So this leader actually needs to have more questions than answers and to move slower than their instincts suggest. Simply improving at the old game by being more prepared as the expert is a recipe for derailment, not success.

Or consider the parent who spent years thriving by anticipating every need of their young child. Then the season shifts and that child moves toward independence. Suddenly the relationship requires something the parent hasn’t practiced. Being better at the previous version of the relationship isn’t the answer.

In both cases, the game has changed. And the identity that built the old success can quietly become the barrier to the next chapter.

When familiar goals lose their pull

Transitions like the above, rarely announce themselves clearly. Sure, a promotion at work or a child becoming a teen represents a visible new stage, but from the perspective of evolving your identity, it’s hard to know where one chapter ends and the next begins.

The things that do tend to show up are signs. Something starts to feel different.

A goal that once energized you now requires more effort to sustain.

Or an ambition you carried for years just doesn’t pull like it used to. And the future that used to feel fully mapped out now becomes harder to envision.

Two years ago, I moved my family from Dallas back to the NJ/PA area where I was raised. It wasn’t because I didn’t like where we were, and it wasn’t because I was dying to go somewhere else.

But I couldn’t deny a restlessness that came about in our life. I was running a virtual business that could be based anywhere so couldn’t shake the feeling I was committing to Texas when I didn’t have to. And we were now parents of a 4 year old girl, which as the political and cultural landscape was shifting in Texas, made it clearer that I didn’t want to raise her there.

But there was no clear map of when to leave, and where to go. Just a feeling that the current chapter had completed something, and that staying would mean pretending otherwise.

For me, that was my most recent threshold, and it illuminated a feeling I never paid attention to before: the actual space between the chapters in our lives.

The space between stories

The anthropologist Victor Turner used the word “liminal” to describe these in-between periods: the spaces between identities and between one story and the next. They are painfully ambiguous times but also ripe with “pure potential.”

What strikes me is how little attention we give them. We celebrate beginnings like the new job, the new baby, the new house. But we rush through endings like the lost role, the grief of a loved one passing. When it comes to the in-between space, we often treat it as a problem to solve, so we can escape its grip as quickly as possible.

Self-improvement, I think, serves that anxious need perfectly. They give us another framework, another system or another set of habits and satisfy that need to feel like we’re moving.

But some of the most important growth happens in that liminal space, precisely because we’re not moving fast.

I think it’s where the old story loses its grip. And it’s where we become curious before we become certain. I noticed for myself, it’s where if I’m able to sit with the discomfort, I can better sense who I need to become, not just how to get better at who I was.

Evolving requires releasing

My mother wasn’t just building assertiveness skills when she listened to those tapes.

I think she was letting go of an older identity. It was the one that had served her in India, in her family of origin, in the life she’d known before being married and having kids. Through the tapes and other books she read, she was making room for something new. Indeed she was improving on certain skills. But underneath that was something more fundamental: a willingness to become a different version of herself.

This is the distinction I keep thinking about. Improvement adds and evolution rearranges, reinvents. The first asks, what skills do I develop? The other asks, what identity do I need to update?

Without question, there are times when a new habit or system is exactly what’s needed. But there are other seasons when you’re being invited to loosen your grip on a version of yourself that has carried you faithfully for years. And it’s not because that identity was wrong, but because the work it was doing is now complete.

A different question

As I’ve moved into my 50s, I’ve come to appreciate this idea that some seasons ask us to become better; and others ask us to become different. I think the challenge is recognizing which season you’re in. In the first kind of season, you ask yourself, “How do I get better at this?” But in the second, a more honest question might be, “Who am I becoming now?”

The second question won’t produce immediate answers. But gradually, through attention and experience and a willingness to embrace the uncertainty, a new identity begins to emerge. It’s not forced or optimized for success. It’s something you notice, and it’s yours to carry forward.

Thresholds feel uncomfortable because they offer movement before clarity, and rarely come with a map. But as the old story loosens its grip, I think the new one waits patiently for us to notice it.

For your reflection this week

Where in your life are you trying to improve, when the deeper invitation may be to evolve?

Until next week, wishing you all my best,

Nihar