I’m married to a critical government employee.

Or at least I thought he was critical, but who the hell knows anymore? 🤷🤞

This isn’t a political statement—

It’s a comment on the fact that no job is actually “stable”, no matter what lies we tell ourselves to keep feelings of impending doom under control.

So if you’re clinging to a miserable job because of the “stability”...

This newsletter will make you very uncomfortable. 😬

Stability is a salty seductress

Last week, I was on a podcast about empowering corporate employees to leave their jobs and start businesses.

The host asked me about my career "cycle" — a pattern I've repeated more times than I ever should have:

And for the first time, I was forced to articulate why I kept falling for this trap.

I thought back to my real estate development consulting practice…

I was f*cking crushing it:

• Fantastic blue-chip clients

• Freedom to choose my projects

• Commanding premium rates

• Making a real impact on NYC’s cityscape

Then one of my clients dangled a fancy job in front of me. 

Even though my business was going gangbusters, I hastily wrapped up my other client commitments (some of whom had been with me since day one), closed my company, and stepped into my new "stable" role.

I was convinced I was making the mature, responsible choice.

But here's the truth that has taken me years to realize…

I was mistaking “stability” for “routine”.

“Stability” is secure. “Routine” is simply comfortable.

When you run your own business, there’s no established routine. No one is holding you accountable, or setting any structure. You wake up to a blank canvas every morning, and immediately need to:

👉 Decide what deserves your attention

👉 Be the visionary AND the task master

👉 Make lonely decisions that could make or break your business

👉 Set deadlines without a manager breathing down your neck

👉 Motivate yourself when there’s no performance review coming up

This shit is exhausting in a way that's impossible to explain to anyone who hasn't lived it.

And it’s why I found myself cycling between entrepreneurship and employment like a drunk hamster.

But as hard as entrepreneurship is…

I am a truly shitty employee

I’m impatient. I have zero tolerance for corporate politics. And I piss people off.

I’m usually decent enough at my job, but I don’t know how to set boundaries and not treat it like my own business.

🤦 I’ll go months without a day off to get a project across the line.

🤦 I’ll model out 20 projection scenarios when they only asked for two because the idea of missing something important is more painful than texting “Big Dick Nick” to a group of grandmas.

🤦 I even once took on personal debt while working for a $65 BILLION DOLLAR company because they were terrible about paying vendors on time, so I just started swiping my own credit cards.

Hey, shit needed to get done. 🤷

But here’s the problem—

I expect everyone else to behave the same way I do. 

I also expect my employer to compensate me appropriately for all the extra work I put in.

And that NEVER happens.

Why would it?

I’m the one who made those choices. It’s my fault.

Then I start to resent everyone around me, because I feel like they’re all lazy assholes who don’t place any value on the fact that I’ve been absolutely killing myself for the sake of this damn company.

When really, they’re just normal corporate employees who show up to their normal corporate jobs and do precisely what they get paid to do — no more.

Which is A LOT healthier than my stupid approach.

So of course I get frustrated, quit, then dive back into entrepreneurship until the siren song of "stability" lures me back to another job.

Except...

Jobs. Aren’t. Stable.

A job can disappear in an instant. 

(Just ask anyone who worked at Twitter pre-Elon.)

What brings actual stability isn't a job — it's having enough money in the bank to weather life's storms.

My dad calls this “f*ck you money”, but most of us would call it liquid savings.

Whether you lose your job, or have a bad quarter in your business, if you don't have cash to cover at least 6 months of living expenses, you're not stable.

Period.

The “routine” of a job just masks the fact that it’s NOT really stable.

It makes you feel stable without providing any real security. You report for duty, are given goals to work toward, follow a structure, and cash a paycheck every two weeks.

This is obviously a huge generalization — some jobs are more chaotic than others — but all jobs have some level of routine. 

And humans love routine. We’re pattern-seeking creatures, and operate so much better when we adopt routines.

But labeling a great routine as great stability is a huge mistake.

Look, if you’re one of those employees who is happy in your job, great at setting boundaries, and loves your routine, I’m thrilled for you! Sincerely.

But carefully consider whether or not you’re actually stable.

And if you’re miserable in your job, but you’re clinging to it because you need to be “stable”, just ask yourself one question:

“What would happen if they fired me tomorrow?”

Is routine possible in entrepreneurship?

It’s f*cking hard to do it by yourself.

But it’s easier with friends.

The last time I quit a job, I vowed never to fall for the myth of “stability” again. But for that to happen, I knew I had to create a system to keep myself accountable.

So I pulled together a small group of the most badass entrepreneurs I know, and we started a mastermind.

Now I get structure, accountability, and the bluntest feedback imaginable (thanks Gabe… I think) from peers who truly understand this shit.

Because that's what we're really craving when we yearn for a "stable job" — not the false promise of security, but the comfort of routine.

The trick is learning to build that routine yourself, instead of outsourcing it to an employer who thinks a “great culture” means trauma-bonding over LaCroix. 🤦

Cheers! 🍻

-Kristin :-)

P.S. — Are you trapped in the stability myth? Hit reply and tell me about it.