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.

It started with a few whispers.

Substack.

I’d hear the name here and there, usually from writers, and I’ll admit I never paid much attention. My impression was that it was basically like Medium, a place for professional writers to write very writerly things for other writers.

Then I started hearing about it more often.

People I followed on LinkedIn would post something and say they’d written the full article on Substack. Writers I remembered from Medium were suddenly publishing there. Eventually curiosity got the better of me, so I wandered over to see what everyone was talking about.

That’s when I discovered something mildly ridiculous.

I already had a Substack account.

Since 2020.

Apparently Past Krista had arrived at the frontier years earlier, looked around, and quietly gone home without leaving Present Krista any useful instructions.

I no longer had access to the account, and Substack wasn’t able to help me recover it, so I started over. And because apparently I learned nothing from the first incident, I created two accounts this time for security.

Excellent start.

Then I entered the Wild West

I had no idea what I was looking at.

Notes. Publications. Restacks. Chats. Recommendations. Writers recommending writers. Notes that seemed to be doing extraordinarily well for reasons I couldn’t begin to explain.

And then there was my feed.

For reasons known only to the algorithm, Substack seemed convinced I was deeply interested in perimenopause, divorce, men behaving badly, and women with several cats rebuilding their lives.

To be fair, maybe the algorithm knows me better than I’d like to admit.

Professionally, though, I was confused.

I’m a marketer and entrepreneur who writes. I care about business models, money, positioning, work, creators, audiences, professional identity, and why smart people sometimes build businesses they eventually realize they don’t want.

So I figured I needed some help understanding this strange new land.

I joined a cohort run by a couple of genuinely lovely people who knew Substack well. Unfortunately, it also made something clear pretty quickly: I wasn’t really their target audience.

Most of the conversation revolved around becoming a full-time writer, growing through the writer community, recommending one another, commenting on each other’s work, and participating heavily in the Substack ecosystem.

There’s nothing wrong with that. It just wasn’t what I was trying to build.

Some of the growth advice also felt uncomfortably close to the engagement-pod and follow-for-follow behavior I’d spent years avoiding on LinkedIn.

So I finished the experience thinking I’d either have to figure Substack out my own way, or accept that maybe it wasn’t for me.

Naturally, I kept coming back.

Meanwhile, LinkedIn was testing my patience

LinkedIn has been incredibly good to me.

I’ve found clients there, built relationships around the world, grown a large audience, and had opportunities I never would have had otherwise.

I’m not leaving.

But by 2025, reach had dropped dramatically, the platform was changing, and I was becoming much more aware of something I had always known intellectually:

I could spend years building an audience there and still own none of it.

LinkedIn owns the platform. LinkedIn controls distribution. LinkedIn can change the rules whenever it wants.

At one point I was frustrated enough that I seriously considered walking away altogether, but abandoning an audience I had spent years building would have been ridiculous.

So instead, I started paying closer attention to what was happening elsewhere.

And Substack kept giving me reasons to look again.

Paid subscriptions.

Your own publication.

Chats and community features.

A direct relationship with readers.

And then I discovered the feature that really got my attention:

You can download your subscriber list.

You can leave.

That was huge for me.

After years of thinking about professional equity, audience ownership, platform dependence, and how much of our careers we build on land that belongs to someone else, Substack suddenly made more sense.

Maybe this wasn’t Medium 2.0 after all.

Maybe everyone really was loading up their wagons and heading west because somebody had heard there was gold out there.

So eventually, I packed mine too.

So where exactly is the gold?

For me, it starts with ownership.

I’ve spent years building an audience on LinkedIn, and I’m extremely grateful for it. But if LinkedIn disappeared tomorrow, I couldn’t exactly pack up my followers and take them with me.

On Substack, if someone subscribes to my publication, I have their email address. I can export the list. If one day I decide Substack has completely lost its mind, I can pack up the wagon again and leave.

That changes the relationship.

Then there’s the business model.

This was probably the biggest reason I started noticing so many writers migrating from Medium.

Medium has its own ecosystem and its own model for paying writers.

Substack makes it incredibly easy to create your own publication and charge readers directly.

No pitching an editor.

No submitting an article and waiting to see whether somebody wants it.

No asking permission to start.

You could wake up tomorrow, decide you’re now the proud publisher of The Weekly Potato, and have subscribers by lunchtime.

I find that kind of incredible.

And you don’t have to become a full-time paid newsletter writer for any of this to be useful.

I already have a business.

What interests me is having a place where my writing, audience, community, products, and business can actually connect.

That’s where Substack became much more interesting to me than simply “a place for writers.”

LinkedIn and Substack are useful for different reasons

I don’t really see one replacing the other.

LinkedIn is still incredibly good for discovery.

Someone who has never heard of me can come across one of my posts because somebody in their network commented on it. A CEO can find an article. A potential client can look at my profile and immediately understand my background.

And I can do the same with them.

That’s something I didn’t fully appreciate until I came to Substack.

On LinkedIn, I usually know who I’m talking to.

I can see that someone is a founder in London, a consultant in New York, or a marketing director in Singapore. I can see their work history, company, posts, and often whether we know some of the same people.

On Substack, sometimes I click a profile and get a first name, a tiny photo of a dog, and approximately zero additional information.

Who are you?

What do you do?

Are you a Nobel Prize-winning economist?

Are you twelve?

Do you even own that dog?

I have questions.

The anonymity also has a downside.

I’ve already come across things I would never expect to casually stumble across in my LinkedIn feed, including racist content, extremist propaganda, and explicit sexual material.

I’m perfectly capable of reading opinions I disagree with.

But there’s disagreement, and then there’s opening your feed over coffee and wondering how you accidentally wandered into a part of the internet you definitely weren’t looking for.

So no, I’m not declaring Substack the promised land.

The wagon has hit a few potholes.

And then there are Notes

I still don’t understand Notes.

I’ve spent years studying content and distribution. I understand LinkedIn pretty well. I can usually look at a post and make an educated guess about why it traveled.

Notes?

No idea.

I’ll see something like:

Sunday.

Apparently 4,000 people needed to hear that.

Meanwhile, I’ll publish something I spent actual time thinking about and Substack appears to show it to seven people and a squirrel.

Clearly I still have some frontier skills to acquire.

Oddly enough, I kind of enjoy that.

I’m new here.

I don’t have the platform figured out.

And after spending years being the person who supposedly understands LinkedIn, there’s something refreshing about being a beginner again.

What I’m actually here to write about

After eight years of entrepreneurship, 12 revenue streams, six pivots, a few spectacular mistakes, some things that worked far better than expected, and several moments when I wondered what on earth I was doing, I have plenty to talk about.

I’m interested in what happens after the shiny announcement.

What happens when the business you built stops fitting the life you want.

Why talented people can make good money and still feel trapped by what they created.

What happens when a title disappears.

How you turn experience into something you actually own.

How you build recognition without becoming an internet personality.

How you create multiple ways to earn without accidentally creating six different jobs for yourself.

And occasionally, why LinkedIn has 99 problems and somehow keeps finding another one.

I care much more about the messy middle than someone standing at the finish line explaining their perfect five-step formula.

Those formulas usually look a lot cleaner in hindsight.

Who I hope finds me here

Smart, experienced people who are questioning the traditional script.

Maybe you already have a business, but something about it no longer fits.

Maybe you have a great career and want to build something that belongs to you alongside it.

Maybe you’ve been laid off, burned out, retired, scaled back, changed industries, moved countries, raised children, started over, or simply reached the point where you’re asking:

Is this really how I want to spend the next ten years?

Those are the conversations I’m interested in.

I’m still building, experimenting, changing my mind, and occasionally driving the wagon into a ditch myself.

But I’m willing to talk about what happens between the success stories.

The pivots.

The bad bets.

The things I spent money on and regretted.

The things I nearly didn’t do that changed everything.

And the lessons you generally acquire only after paying for them in time, money, ego, or all three.

What you’ll get if you stick around

Free subscribers get my essays and observations on marketing, money, work, reinvention, business models, and the creator economy.

Paid subscribers get closer to what’s actually happening behind the scenes: breakdowns, numbers, experiments, decisions, what worked, what didn’t, and what I’m changing next.

After eight years, 12 revenue streams, and six pivots, I’ve accumulated a decent collection of scars.

I might as well make them useful.

So if you just discovered this publication, welcome.

Pull up a chair.

Or climb into the wagon.

Apparently we’re heading west.

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.

If you want to learn how to build FU money so you have more independence, more choices, and more freedom to work and live on your own terms, you’ll probably want to subscribe.

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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.

Warning: Professional Writers, Please Skip This

A quick disclaimer before we begin: if you are a professional writer, studied literature, or care deeply about prose, rhythm, and the finer points of literary craft, there is an excellent chance this article will irritate you.

I am not a professional writer, and I’m not entirely convinced I’m even a particularly good one. I write the way I think, which tends to be through systems, patterns, contradictions, and blunt observations about how people behave.

So you will find no claim to literary excellence here. What follows is simply one businessperson’s field notes after spending a couple of months wandering around Substack, trying to understand what exactly is happening here.

That has been long enough to see some of the good, quite a bit of the bad, and a few things that are genuinely bizarre.

Consider this less of a serious platform analysis and more of a Sunday wildlife documentary.

Welcome to Substack: A Wildlife Documentary

When I first arrived on Substack, the platform felt enormously promising. There were thoughtful writers, long-form ideas, interesting conversations, and far less of the frantic professional performance I had become accustomed to elsewhere online.

Then I spent more time here and began noticing something.

Substack has species.

There are distinct tribes with their own rituals, incentives, language, mating calls, migration patterns, and preferred methods of attracting subscribers. Once you begin seeing them, you cannot unsee them.

This is not a scientific taxonomy, obviously. It is simply what I have observed so far.

1. The Top Writers Clique

You usually notice this group fairly quickly because they seem to know everyone, and everyone seems to know them.

Many built sizable audiences on places such as Medium or X before becoming active on Substack, so they did not necessarily arrive here as anonymous writers starting from scratch. They brought years of writing practice, established relationships, existing readership, and a finely tuned understanding of what people respond to online.

They are often excellent writers, extraordinarily consistent, disciplined about publishing, and much more experienced at this than the average founder or professional who decided six weeks ago that perhaps they should start a newsletter.

They also tend to support one another. They recommend each other, comment on one another’s work, appear in the same conversations, and naturally create a network effect around their writing.

There is nothing sinister about this. In fact, it is how healthy professional networks work everywhere. The important thing is understanding what you are actually comparing yourself against.

If you run a company, advise clients, manage people, sell services, or have another demanding profession and write when you have time, comparing your publishing output with someone whose primary occupation is writing is a wonderful way to manufacture unnecessary feelings of inadequacy.

You are not playing the same game, so stop using the same scoreboard.

2. The “How to Grow on Substack” Crowd

This species appears almost immediately after you join.

Their subjects are subscriber growth, Notes strategies, recommendations, monetization, engagement, conversion, pricing, audience building, and the many mysterious ways one might persuade more people on Substack to follow a publication about growing on Substack.

There is an impressively circular economy operating here.

A surprising amount of Substack content is essentially advice about becoming successful at the platform on which that advice is being sold, shared, or used to attract subscribers.

Some of it is genuinely useful, particularly when you are new and trying to understand how the mechanics work. Much of it, however, begins to sound familiar after a while because the same ideas are packaged and repackaged with slightly different headlines.

The bigger problem for me is relevance.

If your primary goal is building a media business or earning money directly from an audience, this information may be enormously valuable. If you are running an operating company, advising organizations, investing, managing a team, or using writing as one part of a larger professional ecosystem, the obsession with platform growth begins to feel disconnected from what you are actually trying to accomplish.

There is nothing wrong with the creator economy. I simply do not want every road to lead back to becoming a creator.

3. The “Hi, I’m New Here” Networkers

You have probably seen these posts.

Someone announces that they are new to Substack, would love to connect with like-minded people, promises to support anyone who supports them, and receives dozens of cheerful responses welcoming them to the neighborhood.

Everyone is pleasant, everyone is supportive, and for approximately twelve minutes it appears that lifelong friendships are about to form.

Then almost nothing happens.

I understand the instinct because arriving on a new platform feels awkward, and most of us have been taught that community growth begins with introducing ourselves and networking. The problem is that reciprocal politeness is not the same thing as a relationship.

Following someone because they followed you rarely creates meaningful intellectual exchange, collaboration, friendship, or business opportunity. It mostly creates two people who now have one more account appearing in their feeds.

I think of it as networking cosplay. It looks like networking, contains many of the same words, and produces a satisfying little burst of activity, but the underlying relationship usually has no reason to continue.

4. The Monetization Mystics

Every platform eventually develops a priesthood of people who have cracked the code, and Substack has no shortage of them.

They will explain what they earn, how quickly they grew, the conversion rate on a particular offer, how they structured paid subscriptions, which funnel produced the best results, and what they would do if they were starting again today.

I actually enjoy studying business models, so I do not object to the subject itself. What interests me more is how self-referential these ecosystems can become.

Many of the people teaching others how to make money on Substack are primarily attracting readers who also want to make money on Substack. The product, audience, distribution mechanism, and subject matter begin collapsing into one another.

Again, there is nothing inherently wrong with this. It is simply a very specific business model being discussed as though it were the universal destination for anyone who writes online.

I am curious to see how long the gold rush lasts.

5. The Personal Essay Cinematic Universe

Then there is the emotional wing of Substack, which may be the biggest adjustment for anyone arriving from a more professionally oriented platform.

You will encounter divorce, reinvention, grief, betrayal, menopause, dating, aging, identity changes, family relationships, career collapses, personal awakenings, and an enormous number of essays explaining who someone was before a major life event and who they became afterward.

Some of these pieces are exceptional. They are beautifully observed, vulnerable without being manipulative, and capable of making you see an ordinary human experience differently.

Others leave me feeling as though I accidentally opened someone’s diary.

That distinction is obviously personal. One reader’s extraordinary vulnerability is another reader’s oversharing, and Substack allows considerably more emotional range than the platforms many professionals came from.

For someone wired toward systems, strategy, business, and analysis, however, it can take some getting used to. If you arrived expecting an intellectual salon and suddenly find yourself knee-deep in menopause, divorce, betrayal, spiritual awakening, and the intimate details of someone’s childhood, welcome to Substack.

It is definitely not LinkedIn.

6. The Quiet Operators

This is the group I find most interesting, and ironically it is often the hardest to discover.

They are founders, investors, analysts, executives, researchers, builders, consultants, and practitioners who have spent enough time doing something to have developed a point of view about it.

Their writing often comes from decisions they have actually made, things they have built, mistakes they have paid for, industries they understand, or patterns they have watched unfold over years.

They may publish irregularly because writing is not their primary job. They tend not to spend much time talking about audience growth, and some seem almost mildly embarrassed by the idea of promoting themselves.

As a result, their work may never generate the engagement numbers that dominate a feed.

That does not make the writing less valuable.

In many cases, the opposite is true. A thoughtful essay written by someone who has spent twenty years wrestling with a problem can be more useful to me than fifty perfectly optimized posts about how to increase newsletter engagement.

The difficulty is finding these people because the characteristics that make them interesting are often the same characteristics that make them relatively invisible.

Substack Feels Like Several Platforms Living on Top of Each Other

Once I started thinking about Substack this way, my frustration with the platform made more sense.

There is a creator-economy layer focused on audience growth and monetization. There is a deeply personal layer built around essays, identity, relationships, and lived experience. Then there is a quieter professional and intellectual layer populated by people using newsletters to document expertise, develop ideas, or communicate with a relatively specific audience.

Obviously these categories overlap, and some of the best publications move comfortably between them. Still, the incentives and cultures are different enough that two people can both say they “use Substack” while having almost nothing in common.

The mistake I made initially was assuming the platform itself would somehow sort this out for me.

It did not.

Why the Feed Can Become Exhausting

Like every social platform, Substack has incentives, and people eventually learn what receives attention.

Replies create conversation. Recommendations accelerate discovery. Reciprocity helps people build networks. Emotion prompts reactions. Stories are easier to connect with than abstract arguments.

None of those things are inherently bad, but they do shape what becomes visible.

Depth, experience, rigor, technical knowledge, and long-term thinking do not always generate immediate responses. A detailed analysis of an industry problem may be extraordinarily useful to 300 people and almost invisible to everyone else, while a highly relatable observation about the emotional experience of being a writer can travel much further.

That does not mean the system is malicious. It means visibility and value are not the same measurement.

Once I accepted that, I stopped expecting the feed to do all of my intellectual filtering for me.

How I’m Fixing My Feed

The biggest improvement came from becoming much more selective.

Ruthless unfollowing

If someone’s publication is primarily about growing on Substack, monetizing Substack, or building an audience on Substack, I now ask whether I genuinely need more of that information.

Usually I don’t.

So I unfollow, unsubscribe, or filter without feeling guilty about it. There are too many intelligent people publishing online to spend scarce attention consuming subjects that no longer interest you.

A feed is a mental diet, and allowing an algorithm to choose the entire menu seems like a terrible idea.

Manual discovery

I also stopped relying heavily on the Recommended section and began using a much older method of finding interesting people.

I find one person whose thinking I respect, look at what they read and recommend, follow a few trails, and repeat the process.

This is slower than algorithmic discovery but produces much better results because human judgment travels through networks. Interesting people tend to know other interesting people.

Inbox over feed

For publications I genuinely value, I prefer email.

The feed encourages browsing, reacting, and moving on. Email creates a clearer decision: either I care enough about this person’s work to open it or I don’t.

That tiny bit of friction is useful.

Reframing what Substack is for

The biggest shift, though, has been changing what I expect the platform to do for me.

I am not treating Substack as a lottery ticket or another audience-growth competition. I see it as a place to develop ideas, create a searchable archive of my thinking, distribute longer-form work, meet interesting people, and build intellectual and professional equity over time.

That is a very different objective from trying to become a Substack celebrity.

It is also much more sustainable for me.

The Part Worth Sticking Around For

My feed is already better than it was when I arrived because I have stopped assuming the most visible people are necessarily the people I will find most interesting.

There are extraordinary writers here. There are fascinating operators, unusual thinkers, highly experienced practitioners, and people with knowledge I would probably never encounter through my normal professional network.

They simply require a little digging.

You may have to pass through the monetization advice, growth hacks, reciprocal networking, personal drama, and endless explanations of how to succeed on Substack before finding the quieter corners of the platform.

That is fine.

Every ecosystem has noise.

The useful skill is learning how to distinguish signal from popularity and then building your own map accordingly.

I am still figuring Substack out, and I suspect my opinion of it will change several more times before I understand what I am doing here.

For now, though, I intend to keep wandering through the wildlife.

If you found yourself nodding at any of this, there is a decent chance we will get along.

I write primarily for founders, operators, consultants, and leaders who are building things in the real world and are interested in how businesses, careers, brands, and ideas actually develop over time.

You will probably not find many growth hacks here, and I have no intention of becoming a professional Substack expert.

There are already plenty of those.

Subscribe if this sounds like your corner of the internet.