I spent 18 years working in B2B tech in Silicon Valley, from 2000 to 2018.

I loved the work. I was ambitious, competitive and wanted to move up. But becoming a mother changed the way I was treated at work in ways I hadn’t fully expected.

The strange thing was that having children seemed to work in opposite directions for men and women. A man became a father and could look more stable, responsible and established. A woman became a mother and suddenly people started wondering whether she was still serious about her career.

I saw that difference up close.

Despite being married, I was afraid to tell my boss I was pregnant because I didn’t want it to negatively impact my career. So I didn’t say anything until I was five months along.

When I finally told my boss

The company had more than 7,000 employees at the time, and I found out there wasn’t even an official maternity leave policy in place.

When I asked HR why not, they said:

“Well, we haven’t really needed one yet.”

That was 2002.

When I finally told my boss I was pregnant, she gave me a tight-lipped smile and said:

“I thought you wanted me to help fast-track you for management, but looks like your plans have changed. Congratulations.”

The irony was that, at more than seven months pregnant, I pulled an all-nighter at work because a new software build had run into serious technical problems.

I eventually went home, slept for a couple of hours, and came straight back.

Whatever anyone thought about my pregnancy, I definitely wasn’t slacking on the job.

The thing is, I actually liked my boss.

She was a nice person and, for the most part, a good manager. I don’t think she was trying to make my life difficult. Looking back, I think she simply had no idea how to handle a situation like this.

And honestly, I’m not sure the company gave her much help.

This was a company with more than 7,000 employees that didn’t even have an official maternity leave policy. So what kind of training were managers getting on pregnancy, maternity leave, breastfeeding, sick children, or helping someone return to work after having a baby?

Probably not much.

That’s what makes this bigger than one manager. She was trying to manage a situation the company itself didn’t seem prepared for.

Returning to work

After my short, unpaid California maternity leave, I came back to work determined to prove that nothing had changed.

Almost immediately, I was told not to expect any “special favors.”

If my child was sick, I needed to take the entire day off. Working from home next to a sick child was considered “vacation time.”

I was also breastfeeding, which meant I needed to pump during the workday.

I was told I could use a utility closet.

My boss would regularly circle around my cubicle while I was gone. I can only assume she was making sure I hadn’t decided to disappear in there for a luxurious nap.

So I rushed.

Pump. Clean everything up. Get back to my desk.

A lot of days I barely ate lunch because pumping had essentially become my break.

I remember one day heading toward the elevator when my boss stopped me and asked why I was going home so early.

I said, “I’m not going home. I just need to get outside for ten minutes. I haven’t had fresh air or a real lunch break in months.”

There were physical realities too

Coming back to work also meant dealing with things that had nothing to do with how ambitious or committed I was.

I was exhausted because I had been up with the baby all night.

I kept extra clothes at work because sometimes I leaked through my shirt.

Pregnancy and breastfeeding had changed my body dramatically, and I dealt with men staring at my chest even though I was wearing completely normal clothes.

Sometimes simply thinking about my baby could trigger my milk to let down.

A father could sit at his desk and miss his child.

My body could physically remind me that mine needed me.

And then I still had to clean myself up, walk into the next meeting and perform my job exactly as expected.

That’s the part I think a lot of workplace conversations missed. Having a baby didn’t just add something to my calendar. My body had gone through a massive physical change, I was caring for a newborn at night, and then I was expected to walk back into work as though none of that existed.

The same family looked different on a man

My boss’s boss was a friendly man who took an interest in mentoring me.

When he saw me after maternity leave, he joked:

“I’m so glad you came back.”

I think he meant it warmly. He liked working with me and wanted me there.

But just imagine: would he ever have said that to a man who had just had a baby?

His office was filled with photos of his five children and his stay-at-home wife.

He could have five children and keep climbing.

I had one child, and suddenly it felt like management was questioning whether I even wanted a career anymore.

That contrast stayed with me because you saw versions of it everywhere.

Men talked openly about their children. They kept framed photos on their desks. Becoming a father could make a man look more stable, more responsible, even more established. He had a family to support.

Motherhood often triggered a completely different set of assumptions.

Will she need more flexibility?

Will she be distracted?

Will she turn down the promotion?

Will she eventually leave?

And those assumptions affect careers. They influence who gets mentored, who gets trusted, who gets stretched, who gets promoted, and who gets watched more closely.

That was the real double standard. The same life event could strengthen a man’s professional image and weaken a woman’s.

There was a networking cost too

Being a woman also changed how I built relationships at work.

If a male executive wanted to mentor me, or I was working closely with a male client, I had to think about things men working with other men probably never had to consider.

Are we going to end up alone somewhere late at night?

Is the office door closed?

Is this dinner getting too late?

Is he interpreting this relationship differently than I am?

At conferences, it could get even more awkward.

I was hit on. I was propositioned. I was invited into situations that had absolutely nothing to do with business.

Meanwhile, the men could go out drinking together, keep talking shop, and build relationships.

Sometimes I went back to my hotel room instead.

And that has a career cost.

From 9 to 5 to 24/7

The other thing nobody really acknowledged was that my life had essentially doubled.

At work, I was still expected to show up as the same employee I had been nine months earlier. Same energy. Same output. Same availability.

But my day looked nothing like it had before.

I was usually up between 5:00 and 5:30 in the morning to feed the baby. If he went back to sleep, I’d use that little window to exercise in the living room, do my Kegels and try to rebuild a body that had just gone through pregnancy and childbirth.

Then shower. Get dressed for work. Pack my breast pump, bottles and cooling bags. Pack the diaper bag. Make sure the baby had everything he needed for daycare. Get my own food together.

All of that happened before about 7:30 in the morning.

I had used public transportation before having a baby, but suddenly I needed a car because now I was commuting with a baby, a car seat, daycare supplies and pumping equipment.

Funny story: a single male colleague ended up carpooling with me and the baby. We used to laugh about the baby seat permanently installed in his car and what his friends must think. He got half the gas money, I got help with the commute, and we actually had a lot of fun driving together.

Then I’d drop the baby at daycare and go do a full workday.

At the end of that workday, the second one started.

Pick up the baby. Drive home. Take him for a walk. Dinner. Bath. Story. Bedtime.

Then I’d often open the company laptop again and finish whatever I hadn’t managed to get done during the day.

And, yes, I still had a husband in all of this. If we were lucky, there was a little bit of time left for each other before bed.

Then repeat.

There was food to prepare too. Breastfeeding made me ravenously hungry, while at the same time I felt enormous pressure to lose the baby weight. So I was batch cooking, packing lunches and making salads late at night, constantly caught between wanting to eat everything in sight and wanting my old body back.

And the next morning, 5:00 or 5:30, it started again.

What I find strange looking back is how little acknowledgment there was that anything had changed.

At work, you were just supposed to carry on. Be the same person. Keep up. Don’t ask for too much flexibility. Don’t look tired. Don’t let motherhood interfere.

Except you weren’t the same person.

You were somebody’s mother now.

Your body had changed. Your sleep had changed. Your mornings had changed. Your evenings had disappeared. Your relationship had changed. There was another human being whose survival literally depended on you.

And there wasn’t much space to talk about any of it.

The other working mothers were mostly doing exactly what I was doing: trying to get through the day.

And I often found it difficult to relate to stay-at-home mothers because our days looked so completely different.

Maybe the stay-at-home moms had more opportunity to support one another.

The working moms were just too damn tired.

Mostly, we shuffled along and figured it out ourselves.

The women who stay play by the rules

I watched talented women make very different choices once marriage and children entered the picture.

Some got married and left the workforce as soon as they could. Others stayed, but many became incredibly tough.

Some of the hardest managers I ever worked for were women. At the time, I often experienced that as coldness.

Now I think it was something different.

It was survival.

Because the women who stay learn very quickly what the workplace rewards.

Don’t show too much emotion. Don’t ask for too much flexibility. Don’t look overwhelmed. Don’t let family interfere. And never give anyone a reason to question whether you’re committed.

Femininity can be useful strategically. Charm helps. Looking attractive can help. A little warmth can go a long way politically.

In the workplaces I knew, the traits rewarded at the top were still largely the ones traditionally coded as masculine: toughness, control, detachment, decisiveness, the ability to make difficult calls without appearing affected by them.

Look feminine.

Act like one of the boys.

That’s the game.

And if that’s how you learned to survive and move up, of course you’re more likely to expect the women coming behind you to play by the same rules.

We were all women, but we weren’t necessarily having the same experience.

I don’t remember much sisterly solidarity in those environments. Everyone was dealing with her own version of the problem.

Working mothers were exhausted. Women without children were busy proving themselves. Women who had already made it into management had often done so by adapting to a workplace that wasn’t particularly interested in making room for caregiving.

So women make different choices.

Some leave. Some reduce their hours. Some change careers. Some decide they’d rather work for themselves.

And the women who stay?

They learn the rules. And they play by them.

Eventually, I left too

By the time I was pregnant with my second child, I sat down and did the math.

And the math just didn’t math.

Daycare for two kids. The commute. My salary. The constant logistics required just to get everyone where they needed to be every day.

And I knew it was only going to get more complicated. School schedules. Activities. Doctor appointments. Sick days. Holidays. Pickups. Somebody had to manage all of that.

Then I looked at what moving up in my career would require.

More responsibility meant more hours. More hours meant less time with my kids.

And I remember thinking: then why the hell did I have them?

But I didn’t want to stop working.

I didn’t become a stay-at-home mom.

I left corporate. I didn’t leave my career.

I joined a B2B agency working with tech companies in Silicon Valley. I was still doing serious work, still earning money and still building my career. I was just looking for a way to do it that gave me more control over my life.

That eventually led me further into entrepreneurship.

I could work from home when I needed to. I could research, make sales calls, do cold outreach and build something from my computer. I could arrange childcare when I needed to pitch a client or attend a networking event instead of handing over most of my week by default.

Eventually I had an office and employees, but I still controlled my time. I could pick up my kids, go to school events, volunteer in the middle of the day, and rearrange things when one of them needed me.

It wasn’t perfect. Running a business while raising children came with an entirely different set of headaches.

But it worked.

And more importantly, it gave me control.

I didn’t call it an FU Money Plan then

I didn’t have a name for any of this at the time.

I just knew I needed more control.

I still wanted to earn money. I still wanted a career. I still wanted to be ambitious. But I didn’t want one employer or one rigid way of working to decide how much of my children’s lives I was allowed to be part of.

Looking back, that was probably my first FU Money decision.

FU Money, at least the way I think about it now, isn’t about becoming rich enough to never work again. It’s about having enough income, skills and options that you can look at a situation that no longer works for you and say, I need another way.

That’s what I did.

I left corporate, but I didn’t leave my career. I kept working in B2B tech, eventually built my own company, and created a way of working that gave me considerably more control over my time.

Thank God it worked.

I also know entrepreneurship isn’t an answer for everyone. Women shouldn’t have to start businesses just to make motherhood and meaningful work coexist.

But that experience is a big part of why I care about FU Money today.

I know what it feels like when the math stops working and you realize you need more options.

This is part of why women leave

I’m not telling this story because I’m bitter. I had a good career, worked with some wonderful people and had opportunities I’m genuinely grateful for.

I’m telling it because I think we still underestimate what happens when women eventually sit down and calculate whether the whole setup makes sense.

That’s what I did when I was pregnant with my second child.

Two kids in daycare. The commute. My salary. The logistics. And if I wanted to keep climbing, I would need to work even more hours and spend even less time with my children.

At some point, the math just stopped working.

I didn’t stop caring about my career. I left corporate and kept working in B2B tech. Eventually, I built my own company and created a way of working that gave me more control over my time.

Looking back, that was probably the beginning of what I now call FU Money Plan.

I didn’t need enough money to never work again. I needed skills, income and options so that when one way of working stopped making sense, I could choose another.

A lot of women eventually make some version of that calculation. Money matters, but so do childcare, time, flexibility, career upside and how much of your children’s lives you’re willing to miss to keep moving up.

So before we ask why women leave, I think we should ask a better question:

What made staying stop making sense?

Maybe the least we can do is stop treating motherhood as evidence that a woman is less serious about her career.

I don’t care where you live in the world. There’s one idea that seems to transcend cultures, languages, and distance: what a good life is supposed to look like.

The details vary, of course, but the checklist is remarkably familiar:

✓ Get a good education.
✓ Build a successful career.
✓ Make good money.
✓ Find a partner.
✓ Buy a nice home.
✓ Have a family.
✓ Travel and enjoy life.
✓ Be happy.

That last one is almost treated like an automatic consequence of checking all the others.

By the time I was 30, I had checked almost every box.

I was married with three children, helping build an eight-figure creative agency, working as CMO and co-owner, and getting to work with clients I once would have considered dream clients. We had a beautiful home in San Francisco. We traveled. We lived comfortably. I had reached the point where I didn’t have to think about whether I could afford the groceries in my cart.

And I don’t want to rewrite history and pretend I was secretly miserable through all of it. I wasn’t. For a long time, life really was good. I felt lucky.

That’s partly what made what happened next so confusing.

I had checked the boxes. So why did I increasingly feel like I couldn’t breathe?

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The Finish Line Moves

What I didn’t understand at 30 was that there really isn’t a finish line.

I thought we had worked hard, built the business, bought the house, created the family and reached this comfortable place where we could finally relax and enjoy it. But something strange happens when you achieve things you once thought would be extraordinary. After a while, they stop feeling extraordinary. They just become your normal life.

The beautiful house becomes the house you live in. The nice car becomes your car. The expensive vacation becomes where you go on vacation. You stop thinking, Wow, I can’t believe I get to do this, and without even realizing it, you start looking around at what comes next.

And there is always a next level.

There is always someone with a bigger house, more money, a more impressive career, better connections, more interesting vacations, or access to a room you haven’t been invited into yet. As our success grew, our social circles changed too, and so did my idea of what was normal. Things I once would have considered extravagant barely registered anymore because everyone around me was doing some version of the same thing.

That changed me, and not entirely in ways I’m proud of.

I became more judgmental. I noticed where people lived, what they drove, where their kids went to school, what they wore, where they traveled and what they had accomplished lately. I spent more time around people who noticed those things too. I hate admitting that because I don’t particularly like that version of myself, but she existed.

I had spent so many years trying to become successful that somewhere along the way, success itself had become another form of keeping score.

And the problem with a scoreboard is that there is always someone ahead of you.

A Tuesday Morning

I found something else I wrote years ago describing an ordinary Tuesday morning in our house. Reading it now, I can almost feel my shoulders tense.

It starts at 7:00 a.m., with all three kids already awake and the house in chaos. One child is arguing with me about what to wear. Another is crying after a fight with a sibling. Someone is yelling for me from another room. Breakfast is half-eaten, school things are missing, and I am moving from one small emergency to another while watching the clock because we are going to be late.

Eventually I manage to herd everyone toward the garage. Of course, things have been forgotten, so somebody has to run back inside. Then the front door gets left open. I’m already sitting in the car with the engine running, calling for everyone to hurry up.

We finally pull away. I remind them to buckle their seat belts. There are maybe two minutes of silence before my youngest asks where his lunchbox is.

I look at the clock.

7:50 a.m.

And my workday hasn’t even started yet.

Not every morning looked exactly like that, but enough of them did. Other days I was squeezing in a 6:30 yoga class before getting everyone ready, or trying to fit in time with my trainer after school drop-off. Then I would shower, do my hair and makeup, walk to the office and switch almost instantly from Mom managing morning chaos to CMO managing clients, employees, projects and deadlines.

Afternoons became another logistics exercise. For a while I handled much of the pickup and after-school shuffle myself. Later we used aftercare and eventually hired a nanny, largely because driving three children around while running a company had become ridiculous. We had help cleaning the house too, which sounds as though it should have made life easy, but it never really felt that way.

Years later, when I tried to describe what consumed my days, I wrote the list down in this order:

Driving.

Work.

Kids.

House.

Husband.

Errands.

Working Out.

I put driving first because I genuinely felt like I lived in the car.

Looking back, this is what seems so crazy to me. We had money. We had help. We had built the kind of life that was supposed to make things easier, yet somehow maintaining that life had become a full-time job of its own.

Maintaining the Good Life

Then there was everything required to maintain the life itself.

I spent a lot of money on my appearance. My hair-color appointments could run around $400. I had manicures, eyelash extensions, facials that cost hundreds of dollars, expensive skincare and makeup, and a wardrobe that always seemed to need something new. I worked out constantly, sometimes twice in one morning, and had a personal trainer several days a week.

Reading that now, I realize how excessive it sounds. At the time, it didn’t feel particularly excessive.

That’s an important distinction.

When the people around you live similarly, your definition of normal quietly changes. I had friends who spent far more than I did on clothes, beauty, travel and everything else. In my own social circle, I actually thought of myself as relatively restrained.

The same thing happened with travel. There always seemed to be another trip on the calendar or being discussed. Hawaii. Mexico. Vegas. Somewhere overseas. A weekend away. A nice restaurant. Something to look forward to.

And then there was the world around our children’s private school, where status seemed to seep into everything. Which neighborhood you lived in. What you drove. Where you traveled. What your children were doing. Which activities they had gotten into. Which schools came next.

I don’t want to make everyone from that period of my life sound awful. They weren’t. Some were wonderful people, and many were probably caught in exactly the same cycle I was.

But I do know that I became more judgmental during those years.

I cared more about appearances. I noticed things about people that the younger version of me probably wouldn’t have cared about at all. I spent more time around people who noticed those things too, and after a while it became difficult to tell which desires were actually mine and which ones I had simply absorbed from the environment around me.

Years later, I wrote that I had spent much of my life trying to be the good student, good wife, good mother, good friend and competent businesswoman. As long as I played the role well, I got to keep my part in the play.

By then, the role had just become more expensive.

The strange thing is that none of this felt like a trap while I was doing it. It mostly felt like success.

Until it didn’t.

I Don’t Recognize Us Anymore

Somewhere along the way, my husband and I grew apart.

Not overnight. There was no single fight or dramatic moment I can point to.

It happened slowly, while we were busy building the life we thought we wanted.

One day I remember thinking:

I don’t recognize us anymore.

And I didn’t mean that in a good way.

I had started to dislike our lifestyle. The constant upgrading. The pressure. The schedules. The expectations. The feeling that every decision had already been made for us by the life we had created.

But it wasn’t just the lifestyle.

I felt like we had stopped knowing each other.

Sometimes we would sit across from each other at dinner, just the two of us, and have nothing to talk about beyond the kids and work.

That scared me and made me fall into a deep depression.

We had built this incredible life together, but somewhere inside it, we had lost the part where we were simply two people who enjoyed and choosing to be together.

So I was the first one to suggest getting away.

Not forever. Just for one school year.

Part of me hoped that if we could remove ourselves from the noise for a while, we might find each other again. Close some of the distance that had grown between us.

I wanted us to step outside our normal life long enough to take a break from the madness.

I thought it would be good for us as a couple, and good for the kids too. I wanted them to experience a different way of living, go to school somewhere new, and maybe even learn another language.

So I started researching Brazil, Australia, and even parts of Europe where we had family, primarily looking at places with international school partnerships that would allow the kids to spend one school year abroad without creating problems with their transcripts.

I even looked into house-swap programs.

The destination almost didn’t matter.

I just wanted us to leave for a while.

To live somewhere else. Slow things down. Put some distance between us and the machinery of our everyday life.

To me, it sounded like freedom.

To my husband, it wasn’t realistic.

He was running the company and had a full team of people in the office depending on him, along with clients, employees, and commitments he couldn’t simply walk away from.

And because his company was the main thing paying for our lifestyle, he won.

I think that was the first time I really understood that we were wearing golden handcuffs.

We had built a life that looked like freedom because we could afford so much.

But we couldn’t leave it.

The house, the cars, the schools, the employees, the clients, the bills, the lifestyle. Maintaining all of it required us to keep doing exactly what we were doing.

We had more money than I had ever imagined having.

And somehow, fewer choices than I expected.

From the outside, there was nothing to escape.

We weren’t broke. We weren’t failing. Nothing had obviously collapsed.

We had the house, the careers, the children, the vacations, the cars, the schools.

Our life looked too good to walk away from.

But inside that life, I was becoming increasingly desperate for something to change.

So I tried to ignore it and lose myself in our routine.

It wasn’t that hard.

There was always something that needed to be done. Work. Kids. School. Activities. Dinner. Errands. Weekends. Vacations. Another Monday morning.

We still had a happy life in many ways.

We just weren’t really united anymore.

And it was surprisingly easy to go on autopilot and just keep living the life we had built while ignoring the divide between us.

The Hardest Part About Golden Handcuffs

I’m going to stop my story here.

What happened next is a much bigger story, and I’ve written about pieces of it elsewhere. I also want to be respectful of my family’s privacy. This isn’t about calling out my ex-husband or assigning blame. Neither of us was perfect, and we both contributed to the distance that eventually grew between us.

This article isn’t really about what happened after I left. It’s about why leaving something that looks so good can be so incredibly difficult.

For me, the hardest part about the golden handcuffs was the guilt.

There wasn’t one terrible thing I could point to. There was no domestic violence, alcoholism, drug addiction, cheating, or toxic boss making my life unbearable.

Sometimes, as awful as it sounds, I almost wished there had been one obvious reason. Not because I wanted something terrible to happen, but because then I would have had an explanation people understood.

Someone could ask, “Why would you leave all of that?” and I could give them one clean answer. They would nod. They would understand. Maybe they would even feel sorry for me.

But “I’m no longer happy with my life” doesn’t get the same response.

Especially when the life you’re unhappy with is a life many other people would love to have.

It made me question whether I was being selfish or entitled. Maybe I should have been more grateful for what I had. Maybe the problem wasn’t my life at all. Maybe it was me.

Believe me, I spent a long time thinking about that, both before I left and throughout the year that followed. If I’m being honest, I carried some of that guilt for much longer.

That’s part of what makes golden handcuffs so difficult. They don’t necessarily keep you inside something terrible. They can keep you inside something good enough that leaving feels irrational.

As I got closer to 40, though, another thought became harder to ignore: How much time do I actually have?

I don’t mean that in some morbid way. I simply became much more aware that life wasn’t infinite.

There were things I still wanted to experience while I was young enough, healthy enough, and free enough to do them. My children were getting older. I was getting older. Opportunities wouldn’t necessarily remain open forever.

I started wondering how many more years I was willing to spend hoping that someday I would feel differently about a life I already knew wasn’t right for me.

Of course I worried about the consequences. I knew leaving would hurt people. I knew there would be financial consequences, and I knew I could be making an enormous mistake.

But I also believed I would find a way to make things right afterward.

My situation was particular and, in many ways, extreme. You don’t have to leave a company, a marriage, a house, and almost everything familiar to understand what I’m talking about.

Golden handcuffs can look much more ordinary.

They can be a salary you’re terrified to lose, a mortgage that requires you to keep earning at a certain level, stock options you’re waiting to vest, private school tuition, a prestigious title you’ve worked years to earn, or a business you built that now owns most of your time.

Sometimes it’s simply a lifestyle you can afford but can no longer imagine stepping down from.

Or a life everyone around you keeps telling you that you should be grateful to have.

Sometimes the hardest life to leave isn’t a bad one.

It’s a good life that no longer feels like yours.

The Way Out

I wish I could tell you that this ended like an action movie, where I grabbed a parachute, jumped out the window, and sailed off toward some wonderful new life.

Obviously, that wasn’t what happened.

I had three children. Ending a marriage and dismantling the life we had built together was incredibly painful, and it isn’t something I celebrate or feel proud of. I’m certainly not advocating divorce. For me, it was the last possible option, after reaching the point where I no longer believed there was another way forward.

What I can tell you is that somewhere in everything that followed, I found a new purpose.

At the time, I wouldn’t have known how to describe it that way. If you had asked me what I was looking for, I probably would have said independence. I wanted the ability to support myself, make my own decisions, and build a life that wasn’t dependent on someone else’s company, salary, or choices.

If you’ve read some of my other articles, you already know I didn’t figure out how to do that immediately. Not even close. I tried a lot of things before I eventually understood what I was really trying to build.

And the conclusion I came to changed my life enough that it still shapes the work I do today.

Next week, I’m going to tell you what that was and why I think far more people need to start thinking about it long before they ever find themselves trapped by golden handcuffs.

But I’ll give you the spoiler now.

It comes down to two words:

FU money.

Not billionaire money. Not private-jet money. Not even millionaire money.

FU money is having enough financial independence and enough ways to support yourself that you can make an important life decision because it’s right for you, rather than because you’re terrified of what will happen if you say no.

If golden handcuffs are what can keep you in a life you no longer want, FU money is what gives you choices.

That’s where we’re going next.

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Thank you for reading.

As you can imagine, this is an incredibly personal story, and I know some of you may be judging me right now. I have to live with that. Trust me, I’ve judged myself enough over the years too.

I’m not sharing this story for attention. I’m sharing it because I want you to understand why building FU money matters so much to me.

My story is unique, but so is yours. Over the past eight years, I’ve met people from all walks of life with completely different circumstances, different struggles, and different reasons for wanting more control over their lives.

But so many of those stories eventually came back to the same thing:

Having enough independence to make your own choices.

That’s what FU money is really about.

Thanks for following along.

-Krista

In early 2020, I left California with three bags, my toddler, and a one-way ticket to France.

I wasn’t moving to France. At least, that wasn’t the plan.

After several very difficult years, I was exhausted and financially stressed. My marriage was over, I had sold my shares in the agency I had helped build, and my attempt to return to a traditional career had gone nowhere.

My dad invited me to visit him in France, so I packed what I could carry, took my little girl, and left.

I figured we’d stay for about a month.

A few days after we arrived, France went into lockdown.

Suddenly I was in a wooden cabin in the French Alps with a toddler, very little money, unreliable heat, and three older children back in the United States whom I had no idea when I would see again.

Then my dad got COVID and died very quickly.

When I look back at the photos from that time now, it’s strange. There are mountains, little villages, green fields, my daughter smiling.

You could easily think I had gone off to Europe to start some wonderful new life.

That is not how it felt.

I wasn’t thinking about reinvention or building my dream life. I was trying to make enough money, take care of my kids, and figure out what the hell I was going to do next.

I’ve written before about becoming unemployable at 38 and losing the professional identity I had spent years building.

But that’s the career version of the story.

I’ve never really written about what those years felt like.

The photos probably tell that story better than I can.

So I’m going to show you.

The Life I Was Leaving

There was a time when my life looked pretty damn good from the outside.

Before I turned 30, I had helped build a successful eight-figure agency, operating as its CMO and working with brands like Apple, HP, and Google. We owned a million-dollar home in San Francisco, I was married, and I had three beautiful children.

I had worked incredibly hard for that life. And for a long time, I thought it was the life I was supposed to want.

But I was deeply unhappy.

My marriage had become increasingly rocky, and it wasn’t only my marriage. I still loved my work, but after years of pushing so hard, I was exhausted and getting dangerously close to burnout.

I remember looking at myself in the mirror one day and thinking:

I can’t do this anymore.

That decision changed almost everything.

I sold my shares in the agency. My husband and I divorced. We sold the house and liquidated most of what we owned. Then came the lawyers and legal fees, which ate through years of financial security faster than I ever imagined possible.

Still, the biggest surprise came afterward.

I assumed I would simply get another senior marketing job.

Instead, I spent the next two years applying for more than 200 positions, hiring three career coaches, rewriting my résumé, working my network, and doing pretty much everything people tell you to do.

Nothing worked.

I’ve written much more about that chapter in Unemployable at 38, so if you’re curious about what happened professionally, you can read that story here.

For this story, you only need to know where those two years left me.

By 40, I was divorced, jobless, in debt, without a home of my own, raising four children, and still owed back taxes I could no longer pay.

Yep.

I was basically totally f*cked.

I Had to Make Money Fast

I had to figure out how to make enough money to support myself and my kids, without a job, in the middle of a global lockdown.

And I had to do it fast.

I wasn’t sitting in the French Alps mapping out my future as an entrepreneur or thinking about personal branding and multiple revenue streams.

I needed money for groceries.

What I did have was more than 20 years of marketing experience, a laptop, and an internet connection.

So I started with what I knew.

I took on consulting work and helped people with positioning, branding, websites, newsletters, advertising, podcasts, LinkedIn, and pretty much anything else someone was willing to pay me for.

Some things worked. Some absolutely did not.

At the time, fractional work wasn’t nearly as common as it is now, so sometimes I was also explaining why a company might hire someone like me without putting me on payroll full-time.

But people started paying me.

After two years of applying for jobs and trying to convince companies I was worth hiring, that felt significant.

Sometimes it was only a small project. It didn’t matter. A few hundred dollars could mean groceries, gas, or getting a bill paid.

My three older kids were staying in San Francisco with their dad, but my toddler was with me. There is nothing quite like having a small child depending on you to make “I need to figure this out” feel very real.

And slowly, something started clicking.

Companies might not have wanted to give me a job, but people were willing to pay me directly for what I knew.

The internet became my lifeline. It gave me a way to work and connect with people from a place where I otherwise had very few options.

I’m still incredibly grateful that we live in a time when you can start something with almost no money. Back then, I was using free LinkedIn, free Zoom, one free Calendly link, WhatsApp and Slack. That was basically my tech stack.

We massively overcomplicate what we think we need to get started. Most of my first clients came from putting myself out there and having conversations with people.

Eventually, though, I ran into another problem.

I had plenty of experience.

Almost nobody knew who I was.

Nobody Knew Who I Was

For most of my career, I had never really needed people to know my name.

I had a company, a title, clients, and a team. There was always some context around who I was and why someone should listen to me.

Now there wasn’t.

I had more than 20 years of experience, but very little visibility of my own. If I was going to make money without relying on another company to hire me, that had to change.

I experimented a little with Facebook and YouTube, but LinkedIn became my main platform.

And LinkedIn back then was actually really fun.

People were genuinely open to meeting each other. I was having conversations all day long and getting on calls with new people almost every day. People introduced each other, collaborated, shared ideas, and actually got to know one another.

So while I was sitting at a tiny desk in the French Alps, I was doing a ridiculous amount of networking.

I wrote a lot too, mostly about things I knew from experience and usually through stories. I didn’t have some sophisticated content strategy. I wrote about things I cared about and tried to make them useful.

One of my earliest breakthroughs came from something I barely planned.

I spontaneously decided to run a free five-day challenge.

There was no elaborate launch. I announced it, invited people to join, and nearly 1,000 people signed up.

I wasn’t selling myself as a LinkedIn coach, and most of them weren’t trying to become LinkedIn experts. They had businesses they were trying to grow, and nobody knew they existed.

After the challenge, people started asking if they could work with me. Some wanted coaching. Others wanted help with their businesses. Pretty quickly, those conversations started turning into customers.

LinkedIn was also rolling out new features like live streaming and newsletters, so I tried those too.

Honestly, I tried almost everything.

Some things went nowhere. Some worked far better than I expected.

But from that little desk in France, I was slowly building something I hadn’t really had before:

A network that knew me, not just the company I worked for.

Then I Started Selling Things

Once I was talking to people all day and working with clients one-on-one, I started getting a much clearer idea of what people actually needed.

And I started selling things. A lot of things.

I would hear the same problem come up several times and think, okay, why am I explaining this individually to five different people? I could just create something around it and teach everyone at once.

So I started doing a lot of live masterclasses.

If several people were struggling with positioning, I might build a masterclass around positioning, announce it on LinkedIn, and see what happened.

I created workshops, challenges, coaching offers, and all kinds of experiments based on what people were already asking me about.

I wasn’t doing months of market research or building elaborate funnels. I was close enough to the people I was trying to help that they were basically telling me what they needed.

So I listened, built something, put a price on it, and tried to sell it.

Some things sold really well. Some didn’t.

But I learned far more from actually selling things than I ever would have from endlessly planning what I might sell someday.

And eventually, I learned something else:

Just because people will pay you for something doesn’t necessarily mean it’s something you should build your business around.I wasn’t doing months of market research or building elaborate funnels. I was close enough to the people I was trying to help that they were basically telling me what they were struggling with.

So I listened, built something, put a price on it and tried to sell it.

Some things sold really well. Some didn’t.

And then I would try again.

I Started Diversifying My Income

Around this time, I started thinking more seriously about having multiple ways to make money.

After everything that had happened, relying on one employer, one client, or even one offer made me nervous. I wanted options.

By then, I was earning from coaching, live masterclasses, cohorts, paid challenges, and marketing services. For a while, I got really good at building quiz funnels for clients, and I also took on some social media management.

Then I got my first brand deal.

It was with a huge Fortune 500 company, and they paid me what felt like a ridiculous amount of money at the time.

I remember thinking, wait, companies will actually pay me for this too?

Then came affiliate income.

If I genuinely liked something and was already recommending it, I started using trackable links. I didn’t expect much from it, but people bought things.

That worked surprisingly well too.

Every time I figured out another way to make money, I felt a little more confident.

And honestly, a little less scared.

If one client disappeared, I had other clients. If coaching slowed down, maybe a masterclass sold. A brand deal, affiliate income, or service project could cover the gap.

Little by little, my entire financial life stopped feeling dependent on someone else giving me a job.

I started thinking:

Okay. I think I’m actually going to make it.

What This Actually Looked Like

I should add some context here, because I don’t want to make any of this sound easier than it was.

I absolutely had an unfair advantage: more than 20 years in marketing.

But for most of my career, I had been managing the work, not doing every single piece myself. If I needed copy, graphics, video editing, or a website built, I had talented people around me.

Now there was just me.

And admittedly, I kind of sucked at some of it.

It’s very different directing the work versus sitting there trying to figure out why the graphic looks terrible, the video won’t export, or the landing page isn’t selling.

It was humbling. It also gave me a much greater appreciation for how hard good marketing actually is.

I was also building my own business while actively serving clients. I still had coaching calls, workshops, projects, and deadlines. I wasn’t sitting around marketing myself all day.

And then there was real life.

I was alone with my toddler. No childcare. No partner at home to split the load. Meals, bedtime, laundry, groceries, household stuff, and a house that seemed to have something broken at all times were mine too.

So no, I wasn’t peacefully sitting in the French Alps building my dream business from my laptop.

I just kept figuring out what I could do with the time, money, energy, and skills I had.

I Wanted Something I Owned

Eventually, I wanted something more permanent than a collection of offers.

I wanted my own platform.

So I created From Zero 2 Six Academy, an online entrepreneurship academy for people building service businesses.

Over time, I built six courses, The Solopreneur MBA mastermind, and the Profitable Solopreneur community, along with live coaching, workshops, and cohorts.

I ran it for three and a half years, working closely with people trying to turn their skills and experience into businesses that could actually support them.

It gave me a front-row seat to what happens when business advice meets real life.

And eventually, I started noticing something that made me question the whole premise of what I had built.

Why I’m Not Giving You the Numbers

You may have noticed that I haven’t told you how much money I was making during any of this.

That’s intentional.

Income numbers are everywhere online, especially in the coaching world. $20K months. Seven figures. Screenshots of Stripe accounts.

Personally, I find a lot of it tacky.

The minute you give people a number, they start measuring themselves against it. Why did she make that much and I didn’t? Am I behind? Am I doing something wrong?

Suddenly the number becomes the story.

I do think you need to know your number. How much do you actually need? What would make you feel financially secure? What kind of life are you trying to pay for?

Those answers will be different for everyone.

There is one money moment I will tell you about.

The first time I realized I had made more on my own than I ever thought I could, I cried.

After spending years wondering whether anyone would even hire me again, I had figured out how to support myself without waiting for someone else to give me a job or decide what I was worth.

That felt pretty amazing.

The Happy Ending That Wasn’t

This is probably where a normal reinvention story would end.

I had survived the divorce, career collapse, lockdown, and starting over. I had built an audience, created multiple ways to make money, and built an academy of my own.

Great. She figured it out.

Except I hadn’t.

The longer I ran From Zero 2 Six Academy, the more obvious it became that I had made a pretty big assumption when I built it.

On the surface, everyone was an entrepreneur trying to build a business. Beyond that, they had wildly different skills, goals, available time, families, ambitions, and ideas about what success even looked like.

And I had created something that essentially said:

Here’s the blueprint. Follow these steps.

At the time, I thought that was a strength. I wanted people to know exactly what to do.

Eventually, I realized I was trying to give very different people the same roadmap.

I knew the model no longer felt right, but I didn’t yet know how to fix it.

So I shut the academy down.

Yes, I walked away from revenue.

I still think it was the right decision.

I didn’t know what I would build next. I just knew I couldn’t keep teaching one version of success to people who clearly wanted very different lives.

Back to What I Knew Best

After closing the academy, I went back to what I knew best: being a CMO.

I had already spent years doing this work, so I was very much in my comfort zone. The problem was that getting hired in San Francisco had already proved nearly impossible. Now I was living remotely in France, so the chances of landing a traditional CMO job felt even worse.

So instead of trying to get hired again, I started offering my experience as a Fractional CMO.

Honestly, it felt natural.

I knew how to walk into a business, figure out what wasn’t working, and help fix it. After several years of trying all kinds of new things, I was back doing work I had already spent decades learning how to do.

And I have to admit, getting the CMO title back felt good too.

If you’ve read my story about becoming unemployable at 38, you know how much of my identity had once been tied to my career. Becoming a Fractional CMO gave me some of that confidence back.

For about two years, it worked really well.

Then, sometime during year three, I started getting restless.

I realized I was once again spending most of my time and energy building other people’s businesses.

And I couldn’t stop thinking:

What am I building for myself?

Of Course I Built Something New

If you’ve read this far, it probably won’t surprise you to learn that I started building something new.

Of course I did.

Even while I was working as a Fractional CMO, I kept thinking about From Zero 2 Six Academy and what I had gotten wrong.

I still cared deeply about solopreneurs and independents, and I wanted another shot at building something for them.

But this time, I didn’t want to hand everyone the same six steps and assume they were all heading to the same place.

That’s how Creator Paybook came about.

Instead of starting with a blueprint, I’m starting with the person. What do you actually want? What are you good at? How much do you need to earn? How much of your life do you want work to consume?

Then we build from there.

And no, I can’t promise Creator Paybook is the last thing I’ll ever build.

You’ve just read this article. You know me better than that by now.

My bigger vision is to keep building services and media under Unignorable Brands that help more people create successful independent businesses, careers, and lives.

Years ago, I left California with three bags, a toddler, and absolutely no plan.

At the time, I thought my biggest problem was that I didn’t know what came next.

It took years of businesses, offers, pivots, clients, courses, successes, mistakes, and starting over to understand that nobody could hand me the answer anyway.

I had to decide what I wanted to build.

And apparently, I’m still deciding.

Which, at this point, feels pretty normal.

So the next time a coach shows you a beautifully neat path from one offer to millions of dollars, think of me.

Real businesses rarely move in a straight line. There are experiments, bad ideas, things that work until they don’t, things you outgrow, and plenty of pivots.

You just don’t usually see all of that in the success story.

A lot of entrepreneurship stories begin with a happy announcement.

Then comes some version of:

“I wasn’t going to put my dreams on hold anymore.”

Usually accompanied by a very confident caption about finally choosing yourself.

Mine looked very different.

I’ve taken the entrepreneurship route twice in my life. The first time, I helped build an agency. Years later, I built a business on my own.

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Both decisions were personal, but the second came from a very different place. I wasn’t chasing freedom or trying to escape corporate life. I was trying to figure out how to support myself after almost everything I had relied on, professionally and personally, had changed.

A difficult divorce had dragged on for nearly three years. I had lost my professional identity and income. I was raising four children while navigating life after divorce, and I spent two years trying to find my way back into a traditional career.

I applied to more than 200 jobs and hired three career coaches.

Nothing was really changing.

By then, my savings were disappearing and debt was replacing them.

I didn’t need another inspirational quote about following my dreams.

I needed a way to take charge of my own future, put food on the table, and stop waiting for some recruiter to decide whether I was worth calling back.

That’s when entrepreneurship stopped feeling like an option.

It became the way forward.

Then COVID Hit

I left for France just days before lockdown restricted travel and the whole world shut down.

I thought I was going for a month—to regain strength and clarity about my career.

Life had other plans.

My dad became one of the early COVID victims, going from healthy to gone in a very short time. It was devastating.

Suddenly, I was in the mountains with a toddler, isolated in an old wood cabin with poor heating, constant problems, barely any money, and days without seeing another adult.

Every day, I worried about getting sick myself, not knowing who would take care of my daughter if I did.

It was one of the hardest periods of my life.

Not exactly the glamorous beginning to an entrepreneurial journey.

All I Really Needed Was Internet

The house had one thing that turned out to matter more than almost anything else: internet.

And apparently, I didn’t need much more than that to start building.

I posted content every day. I networked constantly, went live, hosted Zoom events, and made a point of talking to new people every week.

I also experimented like crazy.

Over the next few years, I tested around a dozen different revenue streams and pivoted six times. Some ideas worked. Plenty didn’t. Every attempt taught me a little more about what people valued, what they would pay for, and what kind of business I actually wanted to run.

Content ended up being one of the biggest catalysts.

It helped me become visible again after years of feeling professionally invisible. My LinkedIn audience eventually grew to more than 77,000 followers, my newsletter to more than 37,000 subscribers, and I was named a LinkedIn Top Voice three years in a row.

None of that happened quickly or according to some clever master plan.

I was figuring it out by doing it.

My Link to the Outside World

In total lockdown and deep isolation, the internet became my lifeline.

It was how I stayed in regular contact with my three older children, who were isolated back in the United States. But it also became the way I started rebuilding my career.

I had decades of marketing experience and had already been a CMO, so I understood fairly quickly what I could sell. Fractional CMO work wasn’t really a thing yet, but consulting certainly was.

So I started there.

I began posting content aimed at business owners who needed help becoming more visible, and then I said yes to almost anything I knew how to do.

Positioning. Rebranding. Websites. Podcast strategy. Newsletters. Advertising. LinkedIn strategy. If it fell under marketing and I knew how to help, I probably did it.

At the same time, I began coaching people who were much earlier in their entrepreneurial journey and needed help figuring out how to market themselves.

There wasn’t some beautifully designed business model behind any of this.

My attitude was much simpler:

Figure out what people need. Help them. Learn. Adapt. Keep going.

Looking back, that may have been the best business plan I could have had.

The Solopreneur Bottleneck

Eventually, I ran into a problem almost every solopreneur recognizes: there was only one of me.

As the business grew, so did everything I had to manage. Clients, courses, coaching, content, email, community, administration. I brought on a VA and started building better systems around myself, including a CRM, project management tools, Kit for email, and Kajabi for the academy.

The business became much more organized.

But organization didn’t solve the bigger problem.

I had built six courses, two masterminds, a paid community, and a coaching business around teaching people how to market and grow their businesses. And somewhere along the way, my people-pleasing tendencies had turned that into an enormous amount of teaching.

I kept adding more because I wanted people to have everything they needed.

The problem was that many of the people I was helping were still early in their businesses. They didn’t have the time or capacity to execute everything themselves, and they often didn’t have the budget to hire people to do it for them.

More information wasn’t the answer.

And I was burning myself out trying to provide it.

Eventually, I had to admit that the business model wasn’t working for me anymore.

So I shut down the academy.

A Different Business Model

After shutting down the academy, I went in a very different direction.

By 2023, fractional executive work was becoming much more common, and Fractional CMO was a natural fit for my background. Instead of trying to help dozens of people at once, I could work deeply with a small number of established businesses that had the resources to actually execute on the strategy.

I capped myself at five clients a year.

For a while, it was exactly what I needed.

The business became simpler. I could charge well, work with fewer people, and spend my time solving higher-level problems instead of constantly creating courses, running a community, and trying to support people at completely different stages of business.

But I never really forgot about the people I had been trying to help through the academy.

There was still a problem I hadn’t solved.

How do you help someone earlier in their entrepreneurial journey build something that actually fits their skills, circumstances, income needs, and the life they want to live?

I knew by then that simply handing someone more courses, worksheets, and strategies wasn’t the answer.

I just didn’t know what the answer was yet.

To Be Continued

My entrepreneurial journey isn’t over.

If the last six years have taught me anything, it’s that I probably shouldn’t expect it to be.

I’ve watched successful creators shut down courses, close communities, and walk away from businesses they spent years building. I used to find that surprising. Now I don’t.

We change. Our lives change. What we need from our work changes too.

There are seasons when we want to grow, seasons when we want more time, and seasons when something that once fit no longer does.

I no longer see every pivot as a failure to focus.

I’m actually grateful I tried so many things. That’s how I learned what I liked, what people valued, what exhausted me, and what I never wanted to do again.

Six years ago, I thought I needed to figure out what I was going to do with the rest of my career.

Now I’d rather build work that fits the life I have today and give myself permission to change it when I change.

Maybe six years from now, I’ll be doing something completely different.

I’m okay with that.

I’m enjoying the journey.

I hope you’ll follow along.

At 38, the idea that I might be unemployable felt surreal.

Thirty-eight is supposed to be a pretty good age professionally. In fact, when this happened to me in 2018, women between 35 and 54 were in the highest-earning age groups in the U.S.

That makes sense. By then, you’ve had enough time to build real experience, make mistakes, develop judgment, lead people, manage difficult situations, and actually know what you’re doing. I had always assumed experience worked a little like compound interest: the more of it you accumulated, the more valuable you became.

At 38, I thought I should be entering some of the strongest earning years of my career. Instead, I was struggling to get hired.

Before everything fell apart

A few years earlier, I thought I had done everything right.

By my early 30s, I had what I considered the good life. I was married, raising kids who went to private school, living in a nice house in a city I loved, and financially comfortable enough that travel or the occasional splurge didn’t require a major calculation. We weren’t living some billionaire Silicon Valley fantasy, but we were comfortable.

Professionally, I was doing work I was proud of. I was CMO and co-owner of a thriving agency that had grown into an eight-figure business. I had a title, a company, clients, colleagues, and a professional identity that felt established.

I had been working since I was 20, including through three pregnancies, and work had always been fulfilling to me. I had built a career, a business, a family, and financial stability. I remember looking at my life sometime in my 30s and thinking, more or less, I did it.

That didn’t mean I was finished or that I wasn’t ambitious. I was always thinking about what came next. But I believed the foundation underneath my life was solid.

That’s important because I wasn’t bored with my career or looking for an excuse to blow up my life in pursuit of some romantic idea of freedom. The life I had carefully built simply stopped being the life I could count on.

Then Everything Changed

At 38, that foundation disappeared.

I got divorced, sold my shares in the agency, and liquidated assets. Within a relatively short period, the household, career, and financial structure I had spent years building had fundamentally changed.

This wasn’t some deliberate midlife reinvention. I wasn’t bored with my career or chasing a romantic idea of freedom. I was trying to figure out how to rebuild a life that, not long before, I thought was secure.

I wasn’t asking myself an exciting question like, What do I want to do next? I was trying to answer a much more practical one: How am I going to support the life and family I already have?

Given everything going on, full-time employment seemed like the obvious answer. What I didn’t know yet was that the career security I thought I had accumulated didn’t work quite the way I assumed it would.

So I Did the Responsible Thing

San Francisco is an expensive place to start over, especially while going through a divorce and trying to create two separate households for your kids. For much of that period, I was staying in Airbnbs while trying to secure a long-term rental, and the costs kept piling up: housing, school, food, activities, transportation, and enormous legal fees.

Moving somewhere significantly cheaper wasn’t really an option because we shared custody and I needed to stay close to my ex and the kids’ schools. For context, San Francisco was already the second-most expensive rental market in the country in 2018, with the average apartment renting for about $3,600 a month. I wasn’t exactly looking for a one-bedroom, either. I needed enough space for my kids.

I actually tried moving about 15 kilometers south for a while to reduce my housing costs. It made perfect sense on paper, but the extra commuting was hard on the kids, who were already dealing with enough change from the divorce. Eventually, I moved back close to their dad. I didn’t want my financial problems to become another disruption they had to absorb.

During mediation, I remember going through our monthly expenses for the kids. The mediator studied the numbers, went quiet for a moment, and finally said, “You guys spend way too much money on your kids.”

She wasn’t wrong. I just hadn’t yet accepted how much our financial reality had changed.

When we were together, I thought we earned more than enough to support the life we had built. I didn’t pay that much attention to what everything cost because we could afford it. Divorce changed that calculation very quickly. Now there were two households instead of one, huge legal expenses, new housing costs, and no predictable income coming in on my side.

I could literally watch the money leaving my account. More than anything, I was worried about making sure my kids had what they needed without destroying my own financial future in the process.

The truth is, full-time employment wasn’t what I really wanted. If my circumstances had been different, I probably would have gone straight back into entrepreneurship. I had loved the independence of owning the agency, and deep down I knew I wanted to build something of my own again.

But I also knew exactly how long it could take for a new business to produce reliable income. I had already lived through the early agency years when we barely made anything and had to work incredibly hard to get it off the ground. With kids to support, high expenses, and a shrinking financial runway, I didn’t feel like I had the luxury of doing that again.

So I made a deal with myself. I would get a full-time job for maybe five years, pay for my kids’ school, rebuild my finances, and get back on my feet. In the meantime, I could start something small on the side and gradually build my way back into entrepreneurship.

For this season of my life, I thought I needed to do the responsible thing rather than the thing I actually wanted. And with my experience, I assumed finding a good full-time job would be the easy part.

I Hired Three Career Coaches

Once I decided to pursue full-time employment, I took the job search seriously. Over the next two years, I hired three different career coaches: one to help with my résumé and overall search strategy, a former recruiter who specialized in LinkedIn and applications, and another former recruiter who coached me specifically on interviewing.

My finances were already under enormous pressure while I was paying for all of this, but I saw it as an investment in my future. If professional help could shorten the search and get me into a solid full-time role, it felt worth it.

I rewrote my résumé, got new professional headshots, overhauled my LinkedIn profile, and started posting regularly. At the time, I had no intention of becoming a creator or building an audience. LinkedIn was simply part of my strategy to get hired.

The search itself quickly became a second job. By then I had a full-time contract role, so most of my job hunting happened after hours. I would put the kids to bed, sit down at my computer, and spend the evening researching companies, tailoring applications, writing cover letters, following up with recruiters, preparing for interviews, and tracking everything in a spreadsheet.

I was also active on LinkedIn every day, commenting, posting, reaching out to people inside companies, and setting up informational conversations. I joined one of the largest tech job-seeker communities in the Bay Area and started attending events. I met people for coffee, spoke with recruiters, worked with my coaches, and went to networking events whenever I could.

Over two years, I submitted more than 200 applications. I gave the search everything I had.

One thing nobody really tells you about seriously looking for work is how much unpaid labor it requires before anyone pays you a dollar. In my case, I was fitting that labor around a contract job and a family.

Community Matters When You’re Job Hunting

A long job search can become incredibly isolating. You spend hours behind a computer applying, following up, getting ghosted, and trying not to turn every rejection into a judgment about your worth.

I made a point of getting out of the house and around other people. Through the Bay Area tech community, I became involved with LinkedIn Local, a grassroots movement where people organized free in-person meetups with people they had connected with on LinkedIn. I eventually started helping host the San Francisco events every couple of months.

I also started volunteering what I knew. Through career organizations, I gave free talks to people trying to break into product marketing. As I learned more about LinkedIn and started growing my own following, people began asking how I was doing it, so I started teaching that too.

None of this got me hired, but it gave me community and a way to keep contributing at a time when rejection was constantly testing my confidence. Helping other people reminded me that I still had something valuable to offer.

I Was Working, But Still Falling Behind

Early in the search, a placement agency found me a contract role that was genuinely interesting. It had a lot of responsibility and moving parts, and the work itself was a great fit for my product marketing background. I enjoyed the actual work, but morale was low and the environment was bleak. It reminded me how much I had valued the autonomy of owning a business.

My life outside work was exhausting too. I had a newborn at home and was still pumping milk while working. I had temporarily moved outside San Francisco to find a rental large enough for the family at a lower cost, which meant commuting back into the city while also trying to be present for my older kids during my custody time.

Most days felt like one long handoff from one responsibility to another: work, the commute, the kids, the baby, and then the job search after everyone was asleep. I was still pumping milk during that period, which tells you roughly how glamorous this particular chapter of my career was.

The contract brought in income, but it still wasn’t enough to cover my housing costs, legal bills, family expenses, and everything else that had changed after the divorce. My savings kept shrinking, and eventually I crossed the line from spending down savings to accumulating debt.

One of the hardest things for me to accept was that I wasn’t going to recreate the same life I had before the divorce, only in a separate household. Looking back, I was still trying to preserve some version of it. I furnished the kids’ rooms nicely and even took vacations we couldn’t really afford. Those weren’t smart financial decisions, but at the time I was struggling to accept just how much my circumstances had changed.

I Failed

After two years, I had to admit that the plan hadn’t worked.

There had been plenty of rejection and even more silence. Some applications disappeared without a response. I was told I was overqualified for certain roles. Other jobs paid far less than I needed to support my household, or required commutes that simply didn’t work with my life.

There was one opportunity I genuinely thought was going to work. The company flew me out for interviews, and my conversations with the person who would have been my manager and two future colleagues went extremely well.

Then I met my potential manager’s manager, and I could immediately feel something change. Maybe she already preferred another candidate. Maybe I simply wasn’t what she had in mind. I’ll never know, but I didn’t get the job.

That rejection hit hard because by then I had done almost everything I knew how to do. I had invested in professional help, applied to more than 200 jobs, networked constantly, learned LinkedIn, practiced interviewing, worked contract jobs, and kept trying to convince myself that the right opportunity was just around the corner.

Meanwhile, my finances were getting worse. The contract was taking up most of my time but still wasn’t paying my bills. Every month, more money was going out than coming in, and I was now actively going into debt.

The hardest part was feeling as though I was failing everywhere at once. I felt guilty that I wasn’t spending enough time with my newborn. I felt guilty about the long drives back and forth for my older kids. I felt guilty that after the divorce I couldn’t give them the same life and experiences I had been able to give them before.

By then, my life no longer felt like a temporary rough patch. I was working constantly, worrying constantly, and still falling further behind. The contract wasn’t covering my expenses, the job search wasn’t producing a job, and I had crossed the line from spending down savings to accumulating debt.

After two years of trying to make the responsible plan work, I finally had to admit that it wasn’t working.

I didn’t know exactly what I was going to do instead. I only knew I could no longer afford to keep doing more of the same.

Next week, I’ll tell you what happened when I stopped trying to rebuild the life I’d had and started figuring out what came next. So if this topic interests you, follow along.