I stayed too long in tech, because...healthcare.

I've since left tech and my wife has held down our benefits since. But in the past couple months, it became clear that she needed to leave her non-profit for a career reset and time to rest.

The problem: we needed health insurance.

Between the two of us, we’ve switched benefit ownership for years. But this time, neither of us could stomach another corporate/philanthropy job.

So we found a self-pay plan through the ACA marketplace that covers the bulk of doctor visits, urgent care, x-rays, etc. It’s not the Cadillac of health insurance, but it works.

During the sign-up process, I realized something big.

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The lever we miss

In a W-2 job, your employer holds several levers over you.

Compensation is obvious. Health insurance is the sneaky one. We take it for granted until something goes wrong at work. We realize we can’t just leave, especially with kids and dependents.

I stayed in jobs longer than I should have. Not because I loved the work, but because I needed the insurance. Few people say this out loud.

Self-pay insurance is not perfect. My wife and I have a lot of privilege to be on a “good enough” plan. But the freedom we both felt taking ownership of our own insurance, reduced the stress of staying or needing to find a new misaligned job.

I’m not saying you have to switch to self-pay. Rather, I’m pointing out that supplying your own insurance removes a lever your company can hold over you. Removing that layer can shift the dynamic, big time.

Tenure

I once asked a favorite professor, “Do you have tenure?”

I needed to know how she got away with open criticism of the university.

She smiled and said, “I gave myself tenure.”

Not literally, metaphorically. She built her career so that she didn’t need the university to survive. She had other income streams, which led to her refreshing idgaf attitude. Whereas professors seek tenure to feel financially secure, she did that for herself.

And because she had options, she could maintain her value system even in a dysfunctional ivory tower.

That’s what self-pay insurance is doing for me too.

Even if I went back to tech tomorrow, I’d keep our self-pay plan. The company would still control my salary. But they wouldn’t control that lever.

Eliminating even one lever, changes how you show up. How much you tolerate, how long you wait, and whether you speak up.

It reduces the chronic loop: I need to stay for insurance.

Rationalizing bad management, moral issues — even embarrassment about your company — quiets down.

You say, “I no longer need this place for insurance.”

This is a mindset shift; it’s not about being reckless. You still need income. You still have to pay the mortgage. But health insurance doesn’t have to be part of the golden handcuff equation.

Now that my wife and I supply our own insurance, no one holds that over us anymore. We’re free agents.

The practical part

If you’re curious, we used the ACA marketplace and a health insurance broker to understand our healthcare options. The process took about 5 hours, a to z. It’s not perfect and there are gaps, but our family is no longer trapped by this one variable.

Don’t brush this off.

Look into your options before assuming self-pay insurance is too expensive. You might pay less annually than your company-sponsored plan. Regardless, the cost of staying in your tech job may be higher than the cost of leaving.

Give yourself tenure.

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My client Maya was in tears telling me how her mental health feels secondary to her spouse’s physical health.

She had wanted out of her corporate role for years, but stayed so her husband could continue expensive health treatments after a brutal car accident several years prior.

I’ve been in this boat too, and so has my wife. It’s painful.

Especially if there are issues at work.

Each time you fantasize about leaving your company, the need for healthcare clotheslines you. The fantasy evaporates and you’re back to your horrible meeting.

But Maya couldn’t take it anymore; she was at risk of falling into depression.

So I helped her decide to quit her job using simple math.

First, I asked her to get a quote for private market healthcare.

She called the number and worked with an agent to find the best possible plan for her and her husband, prioritizing the cost of his pain management shots and physical therapy.

She got the quote, telling me “it’s not as bad as I thought it would be.”

Then we made the key move.

We subtracted the unsubsidized monthly cost of her current healthcare from the private healthcare monthly cost.

It was $576. This means she would pay $576 more per month in insurance if she went with that private insurance policy.

Then I said, “Is leaving your job worth an extra $576 per month?”

“Yes, 100%.”

Immediately, she started breathing deeper and made a joke about crying.

Her body started relaxing, because she saw a way out.

This basic math made her path clear.

And it works both ways.

A different client recently calculated a $1258 difference, which she deemed a “hell no.” Again, her path was made clear: she needed to find a new job with benefits before quitting.

But what if you can’t afford to leave but need to?

I recommend setting up a separate savings account for these emergency monthly healthcare costs and double down on putting savings there.

Build that financial exit (as you can).

So here’s what I want you take away from this article:

don’t assume you can’t quit (because of benefits) without first getting a private market quote.

Do you feel any lighter after learning about this simple approach?

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Here’s some instructions on how to get such a quote for yourself.

1. Go to healthcare.gov and click “Browse plans & costs”

2. Enter your zip code, household size, and estimated income to see subsidy eligibility and some available plans.

3. And/or call 1-800-318-2596 to work with a free navigator who can match you to the best plan (I recommend this route over online only, because they’re more knowledgable).

4. Explain your specific needs (ongoing prescriptions, specialist visits, etc.) so they can prioritize them when assessing plans.

5. Get your monthly premium, then subtract what you currently pay via your pay stub.

6. That difference is the benefits’ cost of leaving without another job lined up.

“Cozy.”

That’s how my new client described her ideal Saturday, two years from now.

There’s a dopey golden retriever. Waking up naturally. A heated blanket. Cooking food from her garden.

She’s been in tech for eleven years. She hasn’t felt cozy on a Saturday — without the work stuff running in the background — in a long time.

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I help women leave tech by doing something very simple: imagining their life as if they weren’t in tech anymore.

Just: what does your Saturday look like when you’re free?

We have to start there, because tech is good at making you forget you wanted something more than tech itself. It replaces your desires with KPIs. It replaces your instincts with performance reviews. It replaces the version of you that had a self with a version that has a job title.

And then it offers you more money to stay, and you do, and another quarter passes.

But imagine not having to play that game anymore.

No more looking for direction from a maniac CEO’s social media. No more lying to yourself that one more quarter should be fine. No more ignoring the part of you that’s been quietly begging you to walk toward something better — and more fun. No more pressure to look hot-but-not-too-hot, all while being handed dead-end projects dressed up as opportunities. No more hearing “This might not be the right environment for you” when you were simply trying to name a real risk.

Here’s the truth: overruling your body’s exit cues doesn’t build your future. It builds theirs. The billionaires and their yes-men get richer. And when the time comes, they lay you off by referencing your total comp. You’re a row on a spreadsheet.

So yeah. We need to talk about your ideal Saturday. It’s the first step to rebuilding a vision.

At first, it’s hard to answer. The imagination-for-fun muscle is atrophied. But my clients start thawing within minutes.

“I walk to the farmers market because I ran out of honey.” I love the specifics.

And every time I guide a client through this exercise, the same thing rises to the top: softness.

These women are exhausted by the hard exterior and interior they’ve had to maintain to survive in tech. When all they actually want is golden retriever cuddles and a garden with too many zucchinis.

So their ideal Saturday becomes our baseline. The north star we starting toward together.

Then I help them turn the table: use the hardness to get the softness. Relentless pursuit, ruthless prioritization, and running through brick walls. All of it, in service of the garden.

So now: your turn.

Below are some prompts from my Ideal Saturday exercise. Grab something warm to drink. Find a quiet corner.

There’s one rule: in this vision, you no longer work in tech.

Don’t worry about how you pay your bills yet. Just walk through your perfect Saturday two years from now: here.

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For a couple years now, AI has been the wild wild west.

But the sheriff has arrived, and that sheriff is litigation.

I’ll show you how to cash in on this new era, so you can find a more stable role while you plot your exit — including a worksheet to help you figure out your best path.

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Every new technology has a honeymoon period. Capital flows and competition intensifies. But the rules aren’t yet fleshed out.

AI has been in this phase the past couple years, but the honeymoon is wrapping up. Litigation, reliably, is the next phase.

By design, litigation lags new technology, because enough harm must occur to incite lawsuits, which then play out in court for upwards of a decade until legal precedent is set. All of that takes time.

Right now we’re in between these phases: honeymoon and litigation. The wild wild west is about to get some law and order. The sheriff is here now.

And therein lies career opportunity for MBA women who want to leave tech, but need a safer role while they plan their exit.

More stable roles can be found at this intersection, while building tech exit plans. Doing so will likely reduce layoff anxiety, so you can get some breathing room to plan.

So how do you do put this in motion? Spoiler: I have a worksheet for you :-)

It includes these steps:

1. Diagnose how AI is used or sold at your company, which will inform —>

2. The lane you can pursue as you become “litigation-adjacent” leading to —>

3. Your positioning statement.

So check out this free worksheet here.

Do you feel more optimistic given these new career options?

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I’ve been working with a UX designer at a major tech company.

She came to me wondering why she felt so damn awful.

She passionately listed off reasons why her company is not okay.

Especially since her CEO is mentioned in the Epstein files.

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Her income now feels “dirty” and “filthy.”

She started crying.

Hard.

“It sounds like you’re ethically misaligned.”

“Exactly,” she said, “I don’t want to do this anymore.”

I knew we had to convert these emotions into data.

So I made her a tool to get data on that misalignment.

This morning, I shared it with her and clear-eyed, she said, “Okay I’m done.”

Seeing that her tech company misaligned with her ethics 66% of the time was the straw that broke the camel’s back.

We’ve spent weeks trying to understand how she could make it work at her company.

But with this data, she broke through the paralysis.

We scheduled her “what’s next?” session then and there.

We’re going to get her out of there.

Because that misalignment is too taxing for her to stay.

So, today, I’m sharing this tool with you too.

This quiz will show you if your company aligns with your ethics — or at least enough to feel good or to stay.

Click this link to access the quiz. Make a copy for yourself in the “File” menu and have at it.

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This will help decide if you want to stick with the golden handcuffs you know or find something better.

Rooting for you,

Rachel

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Should you be worried about layoffs? Take the test.

You keep refreshing Blind. You even look at it before bed. Because you’re just trying to know: will I get laid off and what will happen to me?

When I was in tech, I easily spent a thousand hours worrying whether I would be affected. My layoff rate was 7:1. Survived seven. Impacted by 1.

So I built a tool to help with this very issue: the tech layoff probability score. I made this after watching some clients get blindsided by layoffs. The signs were there. They just didn’t know which ones mattered most.

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What this calculator tells you

We’re pattern matching, not fortune telling.

I’ve compiled 12 factors that typically come before layoffs at tech companies. I assigned weights to these factors to adjust for the degree of risk. Some things that seem scary like stock price drops or executive departures are less predictive than you may think, while other things that seem minor (like your projects getting deprioritized or a hiring freeze) are red flags.

Where will your score fall?

0-20%: you’re probably fine. Keep track of your work results and start networking when able, but don’t lose sleep.

21-40%: it may be time to update the resume and start taking informational calls. It may not be urgent, but reserve some time each month for this.

41-60%: if you’re not actively job searching, you may be gambling. Start now while you have time to be selective. And build up your emergency savings to at least 3 months.

61-80%: treat this like you have 90 days. Full search mode. Talk to recruiters. Activate every relevant contact. Increase emergency savings to at least 6 months.

81-100%: assume it’s coming. You may want to disengage from work to focus on your search. Or take PTO. Reduce spending and add any remaining cash to your savings.

What to do with your score

If you scored 40% or higher and you’re thinking “well, maybe I’m the exception” - you’re not. That’s the golden handcuffs talking.

Here’s what that voice costs you:

• 3-6 months of unemployment because you waited

• Accepting a lateral move instead of a step up because you’re desperate

• Burning through savings while you figure out what’s next

• Missing the window when your network could have helped you land somewhere better

The women I work with who navigate layoffs well have one thing in common: they trusted the data over wishful thinking.

So, here is the link to the tech layoff probability calculator.

If you scored 40% or higher, book a Results Review with me. We’ll dig into your score and identify 1-3 concrete action items you can start implementing that day. Whether that’s accelerating your search, building a severance negotiation strategy, or doing some personal branding exercises.

This is the calculator I wish I’d had before my Tesla layoff in 2018. It would have saved me six months of anxiety and a fire sale job search.

Don’t wait for the “quick call” meeting notice to land on your calendar.

Rooting for you,

Rachel

P.S. please share this with an MBA woman in tech who’s been feeling like something’s off at work lately. The calculator takes 2 minutes and might be the wake-up call she’s been avoiding.

If you feel trapped by the golden handcuffs, I’ll help you cost that out.

Because for every high achiever, there comes a time when compensation stops feeling like enough.

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You followed the path: an MBA, a fancy title, a six-figure salary with promising equity, stellar benefits.

But you’re also exhausted. Offline. You’ve stopped learning. You have to remain disengaged just to get through the day.

You want something different and better. And you may be willing to take a hit on compensation to do something else. But you need your current comp. Maybe a spouse and/or kids depend on your benefits. Leaving may mean pausing what you’re working toward financially. The thought of walking away feels impossible. Just too difficult. Too much stress.

There’s those golden handcuffs.

But fortunately, I have an exercise to help you cost the price of staying. So rather than relying on vibes, let’s get data.

This exercise was made for my clients: MBA women in tech who feel trapped by their own success. It takes 10 minutes and shows you exactly how much staying costs you.

Here’s How It Works:

Make your own copy of the free Golden Handcuffs Calculator here

Step 1: calculate your 5-year compensation

Enter your current annual salary, bonus, and equity value. Estimates are perfectly okay. The sheet will calculate your total annual compensation and multiply it by five to represent your 5-year compensation.

This is what you’re actually getting paid to stay.

Step 2: price your misery

Now here’s where it gets interesting…

Write down the minimum dollar amount your company would need to pay you — as a lump sum — to endure everything that staying would cost you for five more years.

Be specific and think about:

• Your physical or mental health

• Time with your partner or family

• Your creativity and sense of purpose

• The career pivot you keep putting off

• Your ability to take risks

Step 3: assess your misery tax

The sheet automatically calculates the gap between your “cost of staying” and your actual 5-year earnings.

If your “cost of staying” is higher than what you’re actually earning, then you’re likely underpaid for your own misery.

That gap is your misery tax: what staying is costing you.

What This Exercise Reveals

Most of my clients discover that their stay price is 2-3x higher than their actual compensation. One Head of Product told me she’d need $3 million to stay five more years. Her actual five-year earnings? $1.8 million.

After she saw that discrepancy, we started building her exit strategy.

This exercise doesn’t tell you whether to stay or go. Rather it quantifies what your gut may already know: you’re trading too much of your life for not-enough compensation.

Want to talk about what to do with your results? That’s exactly what I help my clients figure out. Comment below or DM me on LinkedIn and let’s talk about what comes next for you.

You don’t have to stay stuck just because you’re well-compensated.

Golden handcuffs are still handcuffs.

Later,
Rachel

What’s actually keeping you in tech?

The salary? The prestige?

Next Tuesday, I’m launching “How to Leave Tech” a weekly newsletter with a spreadsheet and/or frameworks to help you figure your way out and toward what’s next.

The first issue will be “The Golden Handcuffs Calculator”

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