This year has been rough on the work end of things. In the last several months:

• My wonderful skip manager retired into the sunset.
• A mass company-wide layoff occurred alongside a heavy push to use AI.
• I was re-orged to a different team that has absolutely no idea what I actually do.
• And, perhaps as the final straw, my brand-new manager was just poached by one of the frontier AI companies.

It has been a wild ride, to say the least.

TBH, I really do want to quit — at least I think I do. But I have a scarcity mindset that has held me back from doing so. I’ve never left a job without something lined up first.

And I’m terrified to start now. I’ve been working non-stop since I was 17.

Anyways, instead of just flip flopping, I was hoping that writing my thoughts out and sending them out to the world would help me build some sort of framework I can hopefully commit to. So here’s my painfully transparent current situation:

• Burned out and exhausted 26-year-old
• Net worth is north of $700k individually (but honestly, this money feels like Monopoly money — and it’s somewhat volatile given ~30% is tied up in a single company’s stock)
• I have a supportive husband who can cover all our bills when push comes to shove
• But his net worth is significantly less than mine — and I’d really like that to be more equal someday

Here’s the ridiculous part about that scarcity mindset though: I actually sat down and ran the math. I have years of runway before I’d be in any real financial trouble — between liquid accounts and yes, even the volatile stock. It’s not a perfect safety net. But it’s a lot more than six weeks.

Fear is a terrible accountant.

So here’s what my brain has been churning through. I’ve basically identified six high-level options, and they’re all just variations of “how long can I hold on for more money.” Very healthy, I know.

Option 1: Quit end of next month

• The case for it: six weeks. That’s all I’d have to survive. And I’d snag one more RSU vest on the way out the door.
• The case against it: I have absolutely no idea what I’d do next. Like, none.

Option 2: Quit end of year

• The case for it: another RSU vest plus an ESPP vest. And okay, there’s something psychologically appealing about closing out a chapter at year end. But I also recently realized there’s an actual strategic reason to quit specifically at EOY rather than, say, January: if my W-2 income drops to zero in 2027, I could finally sell off that terrifying concentrated stock position at a way lower capital gains rate — potentially 0% or 15% federal instead of getting crushed at ordinary income rates. Which means quitting in December isn’t just “holding on for one more vest.” It’s also a tax move. I did not expect to become someone who thinks about this stuff but here we are.
• The case against it: I have to make it to December. Current status: unclear.

Option 3: Quit end of February 2027

• The case for it: one more RSU vest, and I’d hit 40 Social Security credits — which is the threshold you need to actually qualify for benefits someday. A surprisingly boring thing to care about at 26, and yet.
• The case against it: I don’t know if I can hold on.

Option 4: Quit end of May 2027

• The case for it: another RSU vest. More money, I guess??
• The case against it: I really don’t know if I can hold on.

Option 5: Quit end of August 2027

• The case for it: I’d complete my full RSU vest schedule.
• The case against it: I genuinely do not know if I can hold on.

Option 6: Quit by EOY 2027

• The case for it: $1M isn’t just a round number. At a 4% withdrawal rate, that’s roughly $40k a year from investments indefinitely — which, combined with my other half’s income, actually covers our life. That’s the number where I don’t feel like I have to work if I don’t want to. Genuinely.
• The case against it: I genuinely do not know if I can hold on.

You’ll notice a pattern. The pros are basically always “more money.” The cons are basically always some version of my slow psychological unraveling.

Which is when it hit me: this isn’t actually a framework. It’s just a scoreboard.

So let me try to build a real one.

The tripwire

There are two things that would make me quit regardless of where I am in the vest schedule. If my breathing is consistently hurting for a month. Or if the migraines get to a point where I genuinely can’t cope anymore.

No amount of money is worth that. Those are my non-negotiables, and I think I needed to say them out loud.

The active piece

In the meantime, I’m committing to applying to at least one relevant job per week through the end of the year. Not because I have a plan — I really don’t — but because white-knuckling it and waiting to see how long I can survive isn’t a framework either. At least this way I’m building an exit ramp while I figure the rest out.

What the options actually mean now

The six options don’t go away. But they’re less “which one do I pick right now” and more a range of possibilities. Where I land depends on how the above two things go. If the tripwire never gets hit and something good comes through the job search, great. If it does, the vest schedule stops mattering.

That reframe helps. A little.

There are probably other things I should be thinking about here — what I actually want to do next, what it even means that I’m terrified to stop working when objectively I probably don’t have to. I can’t quite see all of it yet.

And I think that’s okay. That’s kind of the whole point of this blog.

So. I don’t know which option I’ll land on. The money math is real — staying longer means a bigger nest egg, and $1M is an actual finish line, not just a round number. But it’s a scoreboard, not a framework.

The framework is: I know when I’m out. I know what I’m doing in the meantime. And I’m trying to trust that’s enough for now.

That’s something.