I don’t know what exactly I thought would happen, but I got back to Sag Harbor the day before yesterday and my car is still filled with boxes of my belongings. I’m still scrounging around my suitcase looking for my granny-panties at a friend’s house, and I still haven’t reminded my ex that his card is attached to my Uber account. I’ve been living with my brother and his family in Canada most of the summer—still out of a suitcase, but in a different environment it felt more like summer “vacation” and less like the bottom of the barrel.

Please, I am not asking for sympathy (and dear God, don’t tell Dave). What I’m sharing instead is what I hadn’t banked on: how long and uncomfortable it feels between doing the thing and waiting for it to produce a new reality.

I’ve forever been a glutton for a makeover. I was ten years old, watching The Young and the Restless with my nana, when Paul’s dowdy girlfriend went into the bathroom, took off her glasses, undid her bun and walked out a new woman. I remember it like it was yesterday. It ignited in me the belief that there was something elusive I could discover that would magically turn me into someone different.

I had a few foster sisters growing up and one gave me a gray purse. She smoked, so I loaded it with Popeye cigarettes, expecting that would do the trick. I had a stack of Young Miss magazines in my closet dried crinkly from being waterlogged during Saturday’s Big Hair installment of the weekend makeover series. I have seen Pretty Woman a hundred times, at least a handful of those after founding a 501(c)(3) supporting sex-trafficked women. I rewound the opening of The Devil Wears Prada, studying the women getting dressed for work as if one of them might reveal a tip or trick that would make me stylish. I’m pretty sure I still have the photograph of Bethenny Frankel posing in a red bathing suit for Us Weekly three weeks after giving birth saved on my phone—my measure for my own bounce back a year later, after having my son.

This is all to say my expectations around time horizons aren’t particularly realistic on a good day, let alone when it comes to a life transformation of this size. So I guess it’s no wonder I’m sitting here asking myself: How the fuck am I still here?

By “here,” I don’t just mean back in Sag Harbor with my belongings in the car. I mean the place where the old life has stopped working and the new one doesn’t exist yet.

This particular “here” began on February 4. I had therapy that morning, so I was a little softer than normal, but nothing out of the ordinary. My brain was whirling, as it pretty much did—and still does—all day every day, running solutions to my financial issues. I was walking through my room to go pee when all of a sudden I felt weird and weak and collapsed onto the side of the bed just in time for this feeling of discomfort to emerge from the depths of my body. Before I could grab my phone, a tequila or a Xanax and abandon myself, I was in it. There was no escaping.

I know how crazy this sounds, but my brain shut down and I finally had access to a feeling I suppose I’d been repressing for decades. It railed out of me as a long, hard, guttural scream, and on the other side was surrender. It wasn’t my brain that finally called it on the façade. It was my body.

I had been in an approximation of “here” at least three different times in my life, and I’d used my survivor skills to claw my way back. Months before this moment, I had created three rules for financial engagement to keep me out of dangerous territory:

• No big pitches I wasn’t absolutely certain I could execute.

• No investments or loans without a clear view of how and when I would pay them back.

• No romantic relationships with even a whisper of “save” to them.

These rules meant there would be no dramatic rescue and no instant makeover. I couldn’t claw my way back into something that looked successful if getting there meant abandoning myself again. Not only would I have to accept the reality I’d been avoiding, I would have to walk a path I couldn’t see, using the one tool I had stopped trusting years ago: my truth.

And here is a truth I never thought I would utter. So many things made this moment of bodily integration possible, all of which I can’t wait to tell you about. But at the most basic level, this change clicked for one specific reason, and it wasn’t my children. It was my age.

It struck me: I don’t have time for this shit anymore. I can’t learn this lesson any more times. It is now or never.

That was February. The discomfort, humiliation and shame I needed to drill through before I could finally press publish on “Broke in the Hamptons” three weeks ago were grueling. And yes, I know that word is relative. But if you have experienced a bottom that looked like leaving a relationship, losing your money, confronting an addiction, walking away from a job or relinquishing an identity—and decided to take a new, uncertain path using skills you don’t know you have, let alone trust—you understand what I mean. After all that hardness, the patience it takes to just let life happen feels like it should come with a prize.

Maybe you also understand the part I wasn’t prepared for: the impatience. When do I get my voilà? I’m walking into an end-of-summer pool party later today and I’m dreading it. I thought I’d have enough time between announcing my defeat in an essay and seeing these women face-to-face to be five pounds thinner, Botoxed and, at the very least, driving a car where an actual person could sit without shit on their lap.

The judgment I’m bracing for is mine. Not theirs.

I’m beginning to wonder whether I don’t recognize the transformation because, for the first time in my life, I don’t have a visual for the woman I’m trying to become—I literally just met her seven months ago. I’m still trying to figure out who I am. For a control freak accustomed to manifestation practices, vision boards and reverse-engineering her way into a specific result, not having a picture in my mind to aspire to is killing me.

I’m assuming the universe and my higher self are busy working on the external makeover, even if it is taking longer than I’d like.

But I’m no longer looking for the thing that’s going to transform me. The transformation was ending my lifelong habit of abandoning myself. That nasty habit was fifty years in the making. The learning, the amends, the restructuring and the creation of something genuinely different are going to take a while. Apparently longer than three weeks. Possibly longer than seven and a half months.

Anyway, that is why I decided to publish this, even knowing it sounds whiny. Some days, living in the in-between, you feel whiny—and hungry and lonely and depressed. That is a fact we so often don’t get to see in other people because we’re introduced to the transformation only once it is ready to be photographed.

That is the dangerous part to leave out. If you don’t acknowledge how long, uncomfortable and decidedly unmagical real change can feel, your impatience becomes the quickest route back to your old tricks. You decide the transformation isn’t working. You reach for the person, performance, substance, scheme or credit card that once made you feel safe and call it a solution.

There is no room for Instagram comps or anxious pushing in this waiting room. There are only days when you trust what you cannot yet see and days when you forgive yourself for drunk-texting, deciding to buy one record for your son but walking out with four, or ordering Goldberg’s on your ex’s Uber account for the last time (I think).

In the red, surrounded by fake cash. Nobody tell 2007.

I didn’t title my essay Broke in the Hamptons, with a photo of my restricted driver’s license, without expecting a response. But holy shit. If you could see my inbox, you’d think I’d announced a terminal diagnosis instead of a cash-flow problem.

The responses ranged from strangers coming at me with the energy of I showed up at your house and shot your dog in front of your kids, to supposed best friends with the energy of Nicole who?

After the hundredth well-meaning “I’m so sorry,” I started cutting and pasting some version of the same response:

Please don’t feel sorry for me. I don’t.

My external life will require a dramatic recalibration, yes. But internally, I have never felt sturdier or more aligned. I can’t tell you exactly what I’m rebuilding because the collapse of my finances followed the collapse of almost everything I believed to be true about success, security, myself and the world around me.

I wouldn’t necessarily suggest you crash and burn like I did. But coming clean about the thing I had spent years convinced would kill me, has finally brought me back to life.

Which made me wonder: I told you I was broke. Why are you panicking?

Eventually, I stopped sorting the responses into kind and unkind and started thinking about what we do when someone else’s life goes sideways.

I know this reflex because I have it too. When Harrison was a newborn, a child in a building near ours in NYC was hurt by a babysitter. My first reaction was, of course, dear God that’s tragic. Butting right up against that feeling was: tell me exactly what happened so I can make sure it doesn’t happen to my son.

And then, after the shock wore off, I’m embarrassed to say, the gossip. Did you hear she didn’t check the references? She missed the signs. A tragedy became a judgment about her as a mother, which is exactly what you do when you want to inoculate yourself against tragedy. If she had done something wrong, I could do it right. Her mistake became my protection.

And what comes after your child’s wellbeing? Your money. The Madoff fallout produced the same three beats in the same order: concern, dissection, then she was just stupid. What did they fail to check? How could they not have known? Careless, greedy, whatever the word is, it has to be a word about who you are and not what happened to you. If you’re in that category, I’m not and this is a thing that only happens to people like you.

Broke, I discovered, is a Rorschach test. People see their own relationship to money splattered across your bank balance.

Take my dad, to whom I sent the essay in advance with a note warning him it was going to be published. He’s a proud man, and the pride runs in a very specific direction, attached to his tough-love parenting being responsible for my “success.” At my first wedding, my best friend Jenn stood up and told everyone how her mother used to take me out for nachos when I brought home good grades. My father waited for the laugh, then rose and turned to the room. “Jenn’s mother promised to feed my daughter,” he said. “I threatened not to.”

I knew the rub wouldn’t be that I shared with the world he once told me I wouldn’t love my grandparents if they didn’t have money. It would be that I had made my own financial failure public and how that reflected on him. He wrote back with a commitment not to offer advice, but saying he would never “open himself up to criticism or pity like this.” What I heard was: neither should I.

The guilty-by-association response was real too. One of the first to reach out was a woman I worked with years ago, far out in my network. I admire her tremendously; she’s made incredibly brave choices in her career and life. I was sure she’d be first in line to spread the word, so I asked her directly if she would repost it.

“I’m so proud of you,” she texted.

She would praise the bravery. She just wouldn’t stand next to it.

At least she answered. A surprising number of people much closer to me said nothing at all when I asked for help spreading the word. A few said the link wouldn’t load and they’d try again later. They didn’t.

None of this fraying of relationships started with the essay. It started the year before, when I could no longer afford to Venmo a couple of hundred bucks. Looking back at those texts from friends now, they were never how are you. They were how are you, and by the way.

We all run a balance in our professional relationships, and most of us have watched a layer of contacts fall away the moment we had nothing to offer. Anyone who has taken time away from work to raise children knows the lightning speed at which professional calls stop coming when the thing you have to leverage becomes advice about nipple cream. That loss of utility I understood. What I hadn’t understood was how quickly the same math gets run on a friendship.

Broke, it turns out, is the bottom of that barrel when it comes to lose my number.

Some people immediately began looking for the error. Had I lived without a budget? Had the Hamptons finally delivered the punishment implied by the title? Spreadsheets, budgeting apps and podcast episodes about compound interest arrived unsolicited and lickety-split. Nobody sends a spreadsheet to comfort you. They send it to check their own math.

And then, of course, there was: what about the kids?

That was the question I couldn’t dismiss as projection because it was the question keeping me up at night too. I spent many months agonizing over it, sharing the situation with their dad long before I published so we could work together to soften the blow—again, another privilege. The impact on fifteen- and twelve-year-old boys, where money norms are already well established in a community like Sag Harbor, is real.

I have lived with these children in a big house with money in the bank and been unable to be present because of the sheer effort required to hold up the facade. But the fallout is real too. Like when a lien was put on my son’s bank account because, at the time, he had more money than I did. I shudder as I write this, thinking: What kind of mother does this? There are the days when I think I’ve got this all fucking wrong.

But I go back to what I wrote in the journal I keep for my boys to read when they are older:

I’m going to do something that will require I expose myself and I’m deeply terrified. I’m writing an essay that will pull the string, unraveling to the place in me that feels most vulnerable. My mind is preoccupied playing out all the ways this has the potential to hurt you. But at the same time my heart is asking me to imagine you, in this position—feeling afraid with your head but led by your heart and, even more than that, alone. I don’t know how this plays out. If you’ll ever read this or need to read this, but I see you in my mind’s eye, making the equivalent of your own leap, and I want you to know that I know, that I see you, that you are not alone.

There are going to be short-term, painful hits for long-term gains, and at this stage all my kids care about is why they are only getting one pair of back-to-school shoes. I am not going to turn that into a tidy lesson about resilience while they are still living it. It is painful. It is also honest. I’m still trying to understand whether honest is enough.

But the overwhelming response hasn’t been judgment or silence. It’s been recognition. People have written back with their own stories and questions.

One woman wrote about trading her looks to get by, and used Margot’s Got Money Troubles as her frame of reference. I brought up the cliffhanger — Margot posting her hoo-ha for clicks and cash — and told her I’d have considered it too, if only my vagina weren’t so old.

Another told me to get out of the winner’s circle and join her in the untouchable section. I’m still working out whether that was an invitation or a dare. I love these exchanges. Real, honest, reflective—and so much more interesting than whether the night nurse insists on being paid in cash, or which camp the kids are going to.

And then yes, there are the legions of I wish I could be so brave, which is bravery right there in the admission, and exactly the first step I took too. Finding proof there are people who have also made mistakes, desperate for relief and hoping for redemption.

Most of them were strangers. And that’s what I find the most interesting. The people closest to me had years invested in the version of me who knew what to do and had the money to do it. Strangers don’t need me to remain her. They could meet the person I had just admitted I was and say: me too.

Money is a real fucker, and not in any of the ways I read about in Rich Dad Poor Dad—or wrote about in my own money book, which had exactly the right title but, if I wrote it today, would contain considerably less advice about lattes.

Our money issues are wound tight and hard to see objectively. Money can look like safety when it is actually control. It can look like generosity when it is actually a receipt. It can look like love, competence, good motherhood, a successful marriage, a successful life. And when someone removes it from the room, even temporarily, everybody starts checking what else might go with it.

I know the privilege contained in calling any part of this an opportunity. Actual poverty is not an experiment in self-discovery. It is hunger, danger, impossible choices and doors that don’t reopen because you learned something meaningful. I have people who love me, places to land and a professional history I can still try to turn into a future. I don’t confuse that with having nothing.

But somewhere in there, not entirely on purpose, I took a chance most people wouldn't volunteer for: to find out who I am without the thing I spent most of my life using as proof. I thought money was protecting me from needing people. From being judged. From being ordinary. From finding out whether I was loved or merely useful. Mostly, it was protecting me from having to meet the woman underneath everything I could pay for, produce or prove.

And don’t think for a second I’ve “arrived.” The defensiveness and embarrassment are still sitting right here beside me. I still want to explain the math, prove that I’m not irresponsible and show you the heroic plan that will make this whole thing look intentional in retrospect. I still have days when the bank balance wins.

But I’m here. Sturdier than I thought. Happier, somehow. More alive. And increasingly unwilling to rebuild another life that requires me to disappear in order to afford it. And my hope is this ignites a spark that this may be possible for you too.

Jenn—my best woman in the wedding story and my best woman in life—I hid it from her too. In the months since, she gave me the only response that had nothing to do with what I had lost.

“I’m so happy to have my best friend back.”

By God, me too.

So please don’t feel sorry for me.

I don’t.

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Disappointed, overpromised, didn’t deliver, disappeared. And while there is a list of reasons a mile long that took many years of therapy to unpack, the people on that list don’t give a shit about my inner child.

Even when I wrote the About section of this Substack and asked Claude to do a copy edit, he came back with: Are you sure you want to say that you’re building new relationships because you burned bridges? Do you want to lighten that up? And of course I do, but I won’t.

Each day this week, I’ve gotten gradually braver as I open my laptop. But the feeling I have upon waking and getting there is like what I used to feel every time I opened the mailbox—or answered the door to the imaginary officer who had come to arrest me for not opening the stack of letters from the IRS. I shamefully told my therapist about this fear one day when the doorbell rang as we sat across from each other on Zoom and she clocked the abject terror on my face.

I was clearly aware then, as I am in the retelling now, that this was a problem—and that it was getting bigger with each delivery. She gently suggested I go get one of the letters and open it with her on the screen. But first, she asked: What are you afraid of?

How do you describe a dread so deep it feels like you'll die upon the reveal of what's on the other side? It was an envelope.

She sat with me as I closed my eyes and pushed my thumb into the space above the seal.

Of course it wasn’t good news, but I didn’t die either.

I’m working on a project in which the main character named Kitty, is a crisis manager. While doing my research, I memory-banked an important technique: getting ahead of the news. They call it stealing thunder. At first blush, I was incredulous. So you voluntarily reveal the thing you’ve worked your entire life to hide? That’s fucking crazy. But it stuck in my mind as I decided to publish the fact that I’m broke and laid myself out in the most undefended way I could imagine.

It’s been about a year now since I finally allowed myself to see the full magnitude of my mistakes and move past the debilitating heft of self-condemnation, with a dusting of compassion. But understanding why we did something is not the same as taking responsibility for what we did. Compassion can explain behavior. It cannot erase its consequences, even though I was kinda hoping it could. I spent a lot of time over this past year negotiating with myself: Can’t we just move? We’re midlife—are you sure we can’t just fade away? Or wait until we’re armed with the protection of money and success? I’m pretty sure I could have hidden it and even rebounded without anyone noticing. But running and hiding from the consequences of your life is no different from living with a stack of threatening letters in your bedside drawer: haunting.

Maybe you have your own unopened envelope.

Maybe it’s an actual piece of mail. Or the friend you betrayed. The marriage you damaged. The money you owe. The promise you didn’t keep. The career you stepped away from so long ago that, forget someone thinking poorly of you, they’ve forgotten you altogether—and you have to rebuild from scratch because you no longer have a reputation at all.

Stealing thunder is about controlling the narrative and, ideally, what people think of you. But at this stage of the game, if you want the internal fortitude and power to face the consequences and make amends for your behavior, it’s infinitely less about how other people feel about you than how you feel about yourself.

Last week, the fear of what was in the envelope finally became less powerful than my desire to get out of my cage. And the actual cage I’m so desperate to escape is not the debt. Not the mistake. Not even the person who may be furious with me. It’s the hiding.

Because in hiding, you start arranging your life around whatever you’re trying not to face. You don’t answer the door. You don’t open the mail. You stop calling people. You make yourself smaller so fewer people will look closely. You stop taking risks because visibility makes confrontation more likely.

And for all of those reading this who were on the receiving end of my misbehavior, I realize that while this Substack may let me out of a cage, it doesn’t make you whole. You can expect a call. I know. Pick up anyway.

As of today, no one has confronted me about Broke in the Hamptons. But someone will. There will be a comment, a call, an email or a name appearing on my screen.

I’ve opened the mail, ready to hear from the people I’ve disappointed, overpromised to or disappeared on. I don’t know what facing my mistakes will cost me. But I know the one thing they won’t:

My life.

I pressed publish with the two people whose opinion I care most about in this world on the screen in front of me (not pictured because they would kill me).

Because in hiding, I’m not living in reality — and by not living in reality, I’m not present. That’s the price I can’t afford.

I love work (mostly). It’s where I feel most inspired. It’s how I orient.

But the way career gets written about—productivity hacks, leadership frameworks, the power pause—has never quite done it for me. It’s not reflective of the conversations I’m having with women in real life or in my WhatsApp group chats.

Mine are littered with photos of Reformation pencil skirts from five years ago and questions like, Can I still get away with this? Causes we’re rallying behind — gun control, perimenopause, what’s actually in our food. The Zoom setting that makes it look like you’re wearing lipstick. Whisper networks to figure out whether an investor is actually a good guy. Debates about the ethics of monetizing a life experience when someone else remembers it differently. Requests for a thumbs-up or thumbs-down on whether hooking up with an old client six weeks after a divorce is a good idea. Book clubs that begin with Belle Burden and somehow end in confessions that our net worth is humiliating for someone who’s done what we’ve done.

These are career conversations.

They’re also life conversations.

And for the first time, they’re the same conversation.

I’ve taken my life down to the studs. And I’m writing from inside it.

A fresh break-up. New professional relationships because I’ve burned bridges. Co-parenting with a man who has another family. A business rebuilt from scratch. Cutting my hair shorter for the first time in over ten years. Learning to accept help in ways I never imagined possible.

And harder than any of that—telling the truth about all of it for the first time. Ever.

Career, integrated with life. Written without the pretension, gloss, or bullshit that’s kept us from the kernels of truth that actually move the needle.

I’m Nicole Williams. I’ve spent twenty-five years helping women build careers—as LinkedIn’s first Career Expert and Consumer Spokesperson, a TODAY Show contributor, bestselling author, and advisor to Fortune 500 companies.

Today I’m fifty-five, broke, single, living in the Hamptons, rebuilding everything. And I’ve never been happier.

I get it. This isn’t a conversation for everyone. Some people will think I’m self-indulgent. Some will think I’m privileged.

I understand why.

Others will think career should stay in its lane. Still others will wonder why we’d talk about ambition, money, motherhood, identity, divorce, fashion, freedom, and legacy in the same breath as work.

That’s exactly the point. I don’t think they’re separate conversations. I think life becomes infinitely more interesting when viewed through the lens of career.

nlw

WHY SUBSCRIBE?

As a public speaker they teach you: even when you lose your train of thought, never stop cold.

I did this once, early in my career. Unable to find my way back, with more than thirty minutes still on the clock, I asked the audience for questions. The mic went around the room until a young woman I couldn’t make out in the darkness asked:

“Why do you do this?”

My first instinct: because it’s my passion, because I get to travel, because I get paid.

But instead of answering from my head, I spoke from my heart.

“Because I feel alone. And I don’t want you to feel alone. I’m hoping you see yourself in me.”

That’s still the answer. It’s why I’m here, doing this, in public.

I’m going to expose my life through the lens of career — and prove, in real time, that the line between your personal life and your professional one was never real. Pretending it was is what’s made everything so fucking hard.

Why subscribe? Because I don’t want to feel alone. And if you’re afraid to tell the truth about your life — the complexity, the nuance, the parts that don’t add up — I don’t want you to feel alone either.

This is for you if:

• You can’t find yourself in the stories told about professional women or mothers. You’re somewhere in between and increasingly sure the separation was bullshit to begin with.

• You built the life you thought you wanted, and now you’re not sure you want it and whether it’s too late to start again. You’re looking for women beginning at forty, not thirty.

• You’re exhausted from sizing up other women by what they have — the nanny, the husband, the family money, the help — and using it to decide whether your own struggle counts.

• You want to tell the truth about ambition, money, motherhood, marriage, identity, failure, sex, and starting again while you’re still living it — not after you’ve solved it and packaged it into a tidy lesson.

• You’re tired of living two lives: the professional one where motherhood is an inconvenience, and the personal one where ambition makes you selfish. You want one life, where all of you is allowed to exist.

• You want influence without becoming an influencer — without curating a life that looks nothing like the one you’re living.

COME WITH ME

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“You’re wearing that?”

This is what my fifteen-year-old son yells out to me as I dart from the car back into the house, for the third time, loading the trunk for a trip to the beach while he shoots hoops. I’ve been silently resisting the urge to yell can you give me a fucking hand over here, but this is the first time I’ve seen him in over two weeks — our longest separation ever — and I’m not ready to risk being unlikable.

He, apparently, is.

“What,” I stop, looking down at myself, “this is great.” The defensiveness in my voice exactly proportional to how threatened I feel by his question-slash-statement.

Without missing a hoop, he yells behind him, “you look like you’re wearing a bathrobe.”

This same child, who used to track his long-lashed gaze up and down and ask why I looked so pretty on my way out to dinner, has become interested in fashion, and girls, and his own appearance. And he’s turned that dreaded corner. It’s not just his opinion anymore. He’s seeing me through everyone else’s eyes — and worrying about how their verdict on me lands on him.

As glorious as his approval once felt, his disdain feels worse.

I consider myself through his eyes for a moment. I’d already been questioning the outfit — a caftan I bought ten years ago, when I could still squint and kind of picture myself half a foot taller and ten pounds thinner, like the model online who made it look less “housewife” and more woman-who-owns-a-villa-in-Marrakesh.

But I don’t let myself squint anymore.

I think for an entire three seconds about giving him a talking-to about not judging a woman — or a man, for that matter — on appearance, and then I stomp into the house and rifle through the suitcases on the floor, oscillating between two questions: am I changing for him? Or am I changing for me?

I’ve been playing this game of looking-the-part for years. When I first moved to New York and was building my business, I’d change in the back of a cab between meetings at Saks and my new publisher, who’d come from a Christian imprint at Hachette. She’d poo-pooed my working title, Date Your Way to the Corner Office — a facetious, but not, title for a book that took dating advice and applied it to career. I fucking loved that title. You can imagine my surprise when they went with Girl on Top.

I’ve spoken publicly for just as many years, and I believe you have to be comfortable to have confidence, to exude your own power — but that it doesn’t happen in a vacuum. My vacuum, for the last ten years, has been a world where wearing clothes that say I’ve-just-come-from-a-workout (whether true or not), twelve hours a day, is a-okay.

Which makes me think of the time a pantyhose-required relic of a law firm hired me to give a talk about making an impression through appearance. It was held in a conference room full of men and women, but it was meant to land on one woman in particular: a fresh tattoo still wrapped in Saran under her sleeve, her tongue newly pierced. I asked about her goal to make partner, and suggested this might not be the right fit.

The rules I was enforcing then, and trying to make sense of now, still exist. Pretending they don’t is a choice — a naïve one, because it doesn’t make the consequences disappear. I remember her, and others, saying I don’t give a shit what other people want me to wear. And that’s fair. But like I told her: that works at an edgier, non-profit firm, where you’re making significantly less than what you say you’re after. We can say we don’t care — and as long as that’s aligned with the outcomes you actually want, you’re golden.

My issue isn’t that I don’t know what I want. I want all of it. It’s that each thing costs something different — and I can’t afford all of it at once. So I’m ranking, on the daily.

• Do I want to be comfortable and feel like myself? Of course.

• Do I want Harrison not to be embarrassed to be my son? I’m not going to pretend I’m bigger than that.

• Do I want the man across the restaurant to look twice? I’m not going to say I’d rather be single than brush my hair.

• Do I want the new client to take me seriously? Obviously.

I want back in the game. Only now I don’t want to take the Jitney into the city to schmooze the room, or head to Murf’s to fish for men. So I walk around town instead — where I could run into a new man, a client, a friend, or God forbid a friend of Harrison’s, at any moment. One outfit has to do every job at once.

Here’s what nobody accounts for: there’s no office anymore. Work used to be a place — a commute, a dress code, a building that told you what to put on. I dressed for it in the back of a cab. I taught women to dress for the jobs they said they wanted. The clothes had a destination.

Now the destination is gone, and the work is everywhere. No lobby, no elevator, no nine-to-five — but no off, either. The client is at the farm stand. The next man is behind me in line for coffee. Which means even this — a beach cover-up on a Saturday — is a work outfit. I just don’t get a dress code to tell me so.

If it’s not the sweats. And it’s sure as hell not the heels. There’s supposed to be something in between — a way to look like I tried without looking like I’m trying too hard. Like myself, on a good day, for a life that no longer has a lobby. Nobody makes that outfit. Nobody tells you how to find it. You just know, the second you’ve missed it — in either direction.

Every one of these goals has a different price — paid in comfort, in effort, in how much of myself I’m willing to perform. No single outfit covers them all. So every morning, I decide what I’m willing to lose.

Not for good. I haven’t landed anywhere for good. Like so many of my peers — women who’ve earned enough respect to wear what they want, but are hedging toward the age that’s meant to define what we’re not — I’m as confused as the next girl.

But for today: the kid shooting hoops in the driveway outranked the woman in the caftan. I emerged from the house in the same black, slim-fitting cover-up I always wear.

Am I throwing the caftan away? Not a chance. What would I wear at my villa in Marrakesh?

What’s your version of the caftan — the thing you still want to wear, do, say, or become, but keep seeing through everyone else’s eyes? What’s stopping you?

I have -$375 in my Chase account. My NY State driver’s license is restricted because I have a ton of tax debt. I live in the Hamptons where I am renting my rental for the summer, because I can’t afford it. I’m contemplating applying for a job at the local bookstore because when I told my therapist with disdain, “I can’t make $17/hour,” she said, “Oh yeah, because how much are you making now?”

This would give you legitimate pause as I ask you to follow along — but there’s more.

I’m here because I have drained every single dollar I’ve made over the last 26 years living in New York City, working as a Career Expert, having written a bestseller called Earn What You’re Worth.

I’ve never considered myself an addict. But I have been watching myself orchestrate my own financial demise for the last several years — spending, giving, paying, donating, tipping, investing — burning through money with the fervor I once watched a man dressed in a suit, hiding in his parked car, down a bottle of vodka wondering: is this what addiction feels like? Desperately wanting the spiral to stop, but even more so, needing it not to.

I’m not mentally ill (at least not according to any one of my three therapists), and the last thing you’d call me is irresponsible (not if you look at my LinkedIn page, anyways) — but until I hit the very bottom, I didn’t realize why I had to go broke. Not part of the way. Not struggling to make ends meet. I had to be at the Sagaponack General Store being asked to hand back the paper bag containing two Valentine’s Day chocolate hearts for my sons because my card was declined broke.

From the time I can remember, to the day after the wedding he refused to contribute to, my dad would say to me, “You only love your grandparents because they give you money.”

My grandparents were the loves of my life. My true source of safety and encouragement. My brother and I grew up sleeping over at their house on weekends. My gramps chasing us around with shaving cream slathered on his face, reaching out to kiss us because we called him Bert (his name was Ernie). My nana bending on her arthritic knees on the hard floor beside a cushion to guide me into a backbend. One of the best days of my life? For no dramatic reason — just the one where I came home from working my job in the factory, starving, to find my nana making me a turkey and cheese sandwich on a croissant. That she knew what I needed, my favorite, and she went to the trouble to make it special.

So yes, I loved my grandparents. And yes, they spent the money they made working overtime in the security guard shed and hand-sewing car seats at the Chrysler factory to buy me a Barbie and even a bike — and I loved those things too.

My dad’s accusation created a tangle. A lifetime questioning my own purity of heart. Was the love I had for my nana only because she spent her money on me? And if so, is that how love works? Is that how I get people to love me?

I spent years reenacting this — making choices to create the feeling of internal safety that had no place in business. I confused the two so completely that every business relationship felt personal and every personal relationship felt transactional. Money in, love in. Money out, love out. I couldn’t untangle them.

And it was only here, at the very bottom, that I finally realized the question I’d been asking for what feels like a lifetime — “who can I get to give me money” — had gotten twisted. It was just the translation. The real question, the one underneath everything, was always: “who can I get to give me love?”

While I didn’t intellectually understand it at the time, I was driving my life to the bottom for a very specific reason: to learn that yes, there is an exchange inherent in the giving and receiving of money, but that trade is not love.

Money was my armor, my way of controlling perception and with that, people and with that, my sense of safety. It was only in living without it — without the external measure, the control, the assurance it provided — that I had to face the real question: is there anything or anyone beneath the armor worth respecting, worth saving, worth loving? And unlike the way I’ve lived in the past, I had to look in the mirror, face my own heartbreak, own my own culpability, and form my own determination.

It was during this time that something happened that challenged everything I thought I knew about money and love. For the thirteen years I’ve lived in the Hamptons, one woman has cleaned my house. In that time, we’ve raised our children alongside each other, traded gifts at Christmas, supported each other through the things that don’t make it onto a calendar. I’ve always called her my savior — not because she cleans, but because she’s seen the evolution of the mess. The literal kind, the collection notices on the counter, and the other kind, finding me crying in my bed in the middle of the afternoon as she puts my underwear away.

When I finally told her I couldn’t afford her anymore, I braced for the thing I believed always happens when the money stops.

She said, “Okay. I’ll see you next Wednesday.”

Jenny had been earning an honest living for years. Clean money, the exchange clear, not tangled up with anything else. And because she’d never confused the two the way I had, she had the capacity to offer me both: the savings to carry me, and the heart to want to. Her money was just money. Which left her free to love.

Me? I’d been working on a resurrection of my career for almost ten years. Refusing to show my hand, denying reality, calling it strategy. Winding up to take one big swing that would make it all vanish.

Thinking: this will make for such a good story to tell Huberman when I have my very own fuck-you money. I will start to create and publish content and strategies and frameworks when I can prove it worked.

But apparently, that’s not the way this is going to go.

I’ve been the expert — on the TODAY Show, as LinkedIn’s consumer spokesperson, in the boardrooms of Fortune 100s, on a stage at Carnegie Hall. I know what it takes to look like you have your shit together on the outside while being tragically misaligned on the inside. I have been the queen of pretending. And the cost of that pretending — financial, emotional, structural — is the dumpster fire I’m currently crawling out from.

So I’m doing the scariest thing I can do in this moment, which is the opposite of what got me here. I’m publishing this now — broke, mid-build, no ta-da.

My first publisher at Penguin Putnam said, “Don’t ever let your reader see you doubt or be scared or, God forbid, catch you contradicting your advice. You become the expert by telling people you are the expert.”

I’m going in the entirely different direction this go-round. I’m not asking you to trust me because of my accolades and successes. I want you to trust me because of my failures and my faults.

We are entering a world of work so fundamentally different that we are all going to be learning in real time. There is no such thing as an all-knowing, legacy or algorithmically-manufactured expert. Yes, I know a shit-ton about career and that is going to help — but the old playbook is gone.

There is no telling. There is only doing—and then sharing. The real value, mine and anyone’s, isn’t in the product. It’s in the process.

That’s what I’m going to do — rebuild my life outside of the confines of perfection, showing you by way of fumbling and scrambling, getting rejected and learning why — the external blocks but also the internal hurdles we need to get past to live our best lives. I’m going to share the truth — hard-won lessons from the trenches, in real time, without my tail between my legs. And the recommendations: the books, the resources, the things that are actually helping me claw my way back.

This is not the Substack I planned to create when I had my shit together.

This is the Substack I needed to create because I don’t.

I’ve lived my whole life using career as my lens — where I live, what I wear, how I parent, approach romance, make friends and now: how I earn, save and donate money. And that’s where we’re going to focus. All aspects of life, but through the lens of career.

My career has been my guide. For better and, lately, for harder—but more honest—reasons, it’s taught me everything I know. It’s been not just how I’ve earned a living, but how I’ve earned a life.

I say this with absolute certainty: I am going to earn my way, not back, but forward. How much? $1, $10, $100 — I used to write down a number. Now I leave a question mark. The goal isn’t going to be an external projection of worth but an internal measure of integrity.

How am I going to do it?

I can’t wait to find out.

Come find out with me.

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