The Truth About Starting over in Midlife
the 7 essential stages of a reckoning and reinvention
Between 8:00 am and 11:00 am on Thursday, November 30, 2017, I blew up my career and launched my midlife reckoning.
It was to be my first day at a new job. A role I spent months negotiating and had convinced myself was perfect.
At 7:45 am, I put my two children on their school bus, then, instead of starting work, I returned to my apartment, phoned my new boss, and quit.
There were three phone calls in all.
During the first, in shock and disbelief, my boss kindly cajoled me to reconsider.
In the second, he called me names: despicable, irresponsible.
Finally, furious, he threatened to sue me. “You’ve just ruined your career,” he hissed. “I’ll make sure no one in New York ever hires you again.”
By 11:00 am, I was sweaty and nauseous, mortified at what I had done.
***
At 43, I was a disappointing failure who could not answer the question: “Who do you want to be when you grow up?”
On paper, I had it all: a good education, glowing references, valuable skills. I had spent over a decade at Goldman Sachs, a hallowed name in global finance. I then pivoted to working for charities. I excelled at getting hired.
I carefully adhered to the rules for good girls like me: seek approval, be grateful, put everyone else first, and always over-deliver.
My most treasured goal was to find a job that felt like a calling and gave me a sense of purpose. I wanted to contribute meaningfully to the world. I wanted my husband to be proud of me and to set a good example for my children.
But I seemed intent on destruction, and with a history of serious mental illness in my family, I worried I was going mad.
***
That Thursday morning, as I paced around my apartment in my pajamas, disheveled and distraught, my reputation in tatters, I desperately bargained with whatever force in the universe might provide me with a simple, easy way to find peace.
I had created a situation I couldn’t explain away. I could no longer do what I had always done: pretend there was nothing wrong and that I was content with my perfectly good-on-paper life.
The uncertainty and shame felt unbearable. I now understand this was for a reason.
***
The reckoning I forced upon myself was not a catastrophe. It was the essential beginning of a path toward the vivid, satisfying life I dreamed of.
Here’s what I wish I’d known then about the work I had to do, what it felt like, and the lessons I learned along the way.
Whether you’re vaguely aware of a growing sense of unease as you approach midlife, or are in the midst of your own reckoning, I hope to provide you with comfort, a guide, and reassurance that the upheaval is worth it.
Life on the other side is every bit as wonderful as you dare hope.
Stage 1: The long, uncomfortable hum.
Before the crisis, there’s often a persistent hum in the background of life: a sense that, despite all evidence to the contrary, something important is wrong or missing.
In my twenties, while working at Goldman Sachs, a very senior executive expressed his concern that finance wasn’t right for me. “You’re exceptionally talented and valued here,” he said, “but I don’t see you having a deep interest in the work we actually do.”
My face burned as he continued, “I’m fascinated and obsessed with finding value in companies and markets. My clients are my closest friends. This is my life’s work, and it feels natural and easy to give it everything I have. I don’t think you feel that way. It’s hard to stick with an intense career like this without a passion for it.”
I told myself it was outrageous that a man who barely knew me would dare comment on my motivations. It made no sense: I had just been given a promotion.
But his words haunted me for the next twenty years, because I knew he was right.
I became an expert at silencing the hum, performing the roles I was raised to value: wife, mother, dedicated volunteer at my children’s school, then a new, worthy career, working for nonprofits.
When I felt dissatisfied, I did what I had been trained to do: chastised myself for selfishness and ingratitude. Wanting something I couldn’t neatly label was, clearly, a character flaw.
The hum is not exclusively a career phenomenon.
It vibrates in marriages that function well on the outside while something unnamed is curdling inside. In the body, which begins producing symptoms — insomnia, anxiety, a vague physical malaise — that doctors struggle to explain. In the growing awareness that your life was assembled according to other people’s specifications.
Stage 2: The reckoning.
The night before my “premature resignation,” as I subsequently dubbed it, I fell asleep to a familiar internal debate: one voice dreading my first day of work, while another insisted I had no choice but to show up with a smile.
But I woke with a strange sense of inevitability: I knew I was going to resign. There was only one voice, and it was clear: This job is a mistake. You will call your boss and quit, no matter the consequences.
I couldn’t have articulated what I was really doing, but an exhausted, fed-up part of me wasn’t just quitting a job. I was scorching the earth to reset my lifelong pattern of saying yes when I wanted to say no.
Later, it would occur to me that the timing was not accidental. My children were almost teenagers, and I didn’t want them to become like me: perpetually unfulfilled, floundering, wasting their talents and lives.
The reckoning can arrive in a myriad of ways: a betrayal, a diagnosis, a death, or the empty nest. A milestone birthday that’s a reminder of life’s brevity. A decision to move, resign, or divorce after years of inner vacillation and bargaining.
The architecture of your life is suddenly exposed, and you are standing in the middle of it, blinking, terrified at the prospect of starting again.
Stage 3: The void.
My joblessness felt like a death: along with my career, I lost a large part of my identity. The part I was convinced made me appear competent, acceptable, and appealing to others.
A casual inquiry from a well-meaning friend about “what I’d been up to lately” induced guilt. I dreaded being asked what had happened to the job I’d been so excited to start. I held my breath each time I checked my email, terrified I’d receive a message announcing I was being sued for my despicable behavior.
If I could have gotten another job to patch the void, I would have — but that impulse, I now understand, doesn’t help.
As Brene Brown writes, “If there’s one thing that we’ve mastered by midlife, it’s how to take the edge off of feeling pain and discomfort. We are so good at numbing—eating, drinking, spending, planning, playing online, perfecting, staying really, really busy. Unfortunately, what makes midlife different from the other stages that we’ve managed to survive is that the symptoms don’t improve over time. Choosing to numb the midlife unraveling is choosing to numb for the rest of your life.”
Stage 4: Getting help and getting honest.
Worried I was losing my mind, I found a therapist to fix me. I wanted a quick, painless, permanent solution.
During my first therapy session, I told her what I needed: “I’m ready to give up on this hope I have for a calling or some kind of purpose. Maybe what I need is to learn to be happy with the life that I have, to stop searching for something that is just a fantasy.”
My therapist held my gaze and said, calmly, “No. If you feel there’s something you’re meant to do and you haven’t found it yet, I’m sure it’s real. We will find it, but it will take work.”
I felt something hopeful unfurl.
The work with my therapist consisted of forensically questioning every decision and experience that led to my reckoning: which choices had I made myself, and which felt pre-ordained, socially acceptable, and made because I felt I should?
I was stubbornly attached to several ideas I held sacred:
I believed that finding the right job would solve my problem.
I believed I needed someone else’s permission to prioritize what I wanted most for myself.
I believed I had already adequately processed my childhood trauma.
I believed I was selfish for wanting meaning in my life beyond what I already possessed as a wife, mother, and good citizen.
Many women live by rules like these, shaped by what it means to be a good girl in our homes, culture, and religions. They keep us compliant, helpful, and completely disconnected from our own desires.
The hardest work was the most potent: a scrupulously honest accounting of my childhood, including physical abuse I had never disclosed to anyone, not even my husband. I learned that the way to dispatch hurt, anger, and shame was to name and experience those emotions: that the only way out of any painful feeling is through.
Gail Sheehy spent decades interviewing women about how they navigated the second half of life. Her conclusion, in New Passages, was unambiguous: the women who thrived were the ones willing to do this kind of work.
“You are moving away,” she wrote. “Away from institutional claims and other people’s agenda. Away from external valuations and accreditations, in search of an inner validation. You are moving out of roles and into the self.”
The women who resisted that movement — who kept trying to solve an inner problem with an outer fix — were the ones who stayed stuck.
Stage 5: Becoming a beginner, again.
My therapy sessions were intense. The energy required to process decades of buried secrets and emotions was overwhelming. I was suddenly grateful for the open space on my calendar.
I learned to pay attention to the signals coming from my body—signals I’d dismissed for years, like the sense my neck was choked by invisible hands when I sat at my desk, working.
Gradually, I began giving myself permission to do what I wanted in my free time, rather than feeling I should fill it with something for my kids, family, or community.
It felt wildly transgressive to put myself first in this way, and I needed repeated assurances from my therapist that being kind to myself, honest about what I wanted, and honoring my need for rest, was not a crime.
Eventually, glimmers of my calling began to emerge: joyful childhood memories and snippets of fantasies I’d quickly dismissed because they did not match my internalized ideas of the “right” life.
For some women, this stage produces a startling professional revelation. For others, it’s quieter: the realization that they want a different kind of marriage, or to move to the country. The form varies wildly. The feeling is universal: tentative, slightly illicit, like wanting something you’re not sure you’re allowed to have…
I wanted to be a writer. A career with no boss, no hierarchy, and no prestige. The exact opposite of what I’d been conditioned to strive for.
Feeling stronger and surer of my desires, I began to test the idea in public.
Results were mixed.
When I told an acquaintance I was writing a screenplay, he was thrilled and immediately offered to connect me with a friend who had just made a short film.
But chatting with a friend at a bar, I was met with the same judgment I was expert at leveling at myself.
After confiding in her that I was writing each day, my friend let out an involuntary laugh, like a burp. “Ha! Really?” she asked, raising her eyebrows, “I’ve met a lot of creative people in my time, and I can tell you, you’re not one of them.” Still chuckling, she took a sip of wine.
To my surprise, her opinion did not destroy or derail me. I was beginning to live on my own terms, no matter what other people thought of my choices.
Stage 6: Trying and failing.
Two years after starting therapy, I began writing a book. I had spent the previous six months dabbling as a writer, inching my way toward doing the thing my inner self truly yearned to do.
A year later, I completed the book. The writing process was challenging but satisfying. I woke early each morning, thrilled to experience a flow state once I began work.
Over the next year, my book was rejected by more than 50 agents and publishers. Determined to write in public anyway, I launched a newsletter.
Then, six years after my midlife reckoning, I set aside writing to lead a complex project that was important to my community. I was honored to be asked and had valuable and relevant experience. The idea of doing something familiar that I’d been praised for in my previous career was seductive.
Within a week, I knew it was a mistake. The old familiar feeling of being trapped in something not right returned. I honored my commitment but learned a valuable lesson: if I wanted to live according to my calling, I would need to guard against this kind of “relapse.”
In Finding Your Own North Star, Martha Beck calls this phase of reinvention “The Hero’s Saga.” She dispels the popular and seductive myth that doing work you were meant to do should feel effortless, and her mantra for this period is bracingly honest: “This is much worse than I expected, and that’s okay.”
The pull backward toward the familiar is a reliable feature of this stage, whatever your reckoning looks like — because the old life, however wrong for you, at least had the comfort of being known.
I learned that staying connected to my purpose required active maintenance. I now rely on meditation, journaling, and confidence-boosting mantras like “it’s never too late,” “no one is watching me as closely as I think,” “everyone loves a reinvention story,” and “if you don’t try, you’re guaranteed to fail.”
Stage 7: A sense of pride emerges. Life looks and feels completely different.
Two years after starting my newsletter, one of my posts was picked up by a well-known blogger, and suddenly, my work felt real. Since then, my audience has grown into the tens of thousands. Recently, I had an encouraging conversation with a literary agent about writing another book.
These are welcome markers. But the greatest reward is simpler and harder to measure: I feel at ease with who I am and my place in the world.
My life — and work — finally match what that Goldman boss described back when I was in my twenties. While building a writing career in midlife isn’t easy, I am compelled to pour everything I have into it.
I give myself permission to want what I want — and the grace to believe I deserve it.
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I started reading this and then had to stop and restart because I was getting emotional! I've been going through this "reckoning" for the last several years, and all of the emotions you brought up felt so reminiscent of the same feelings I had when quitting my "dream job" at an industry leading company. Thank you for sharing how you continue to push your way through to find your true purpose - it's inspiring and gives me hope that I'm on the right track!
I am absolutely floored by the part of you that woke up that morning and just said NO. I'm often struck by how our psyches know what we need and direct us towards that, even when our rational minds do everything they can to fight in another direction. I LOVE this space you've made--cannot imagine Substack without you.