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AI and your money
The other half of a plan for your job is a plan for the money underneath it. This is that half.
What this cannot do. It cannot tell you what to do with your money. It recommends no product, no account, no allocation and no strategy, and it has no opinion on whether you should sell, borrow or move anything. Those answers depend on your whole situation, and anyone who gives them to you without knowing it is guessing.
What it does instead. Twelve things to find out about your own arrangements, and decide in advance, while you still have a paycheck and a calm head. Most of them are facts you can look up in an afternoon and have never had a reason to.
Why the timing matters more than the tactics. The costly part of losing a job is rarely the decision itself. It is the deadlines that start running the day you leave, which nobody mentions while you are still employed.
Several items below are United States arrangements. If you work elsewhere the questions still apply and the names do not, so find your own equivalents.
First / Find out what you have
What you actually have, in numbers
Not an estimate, not a feeling. Four figures, three of which are written down somewhere you have access to right now.
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How many months you could cover if the income stopped tomorrow. Take the money you could actually reach without penalty or paperwork, divide it by what one month costs when you are being careful rather than what an average month costs now.
— months
We are not going to tell you what that number should be. There is no correct answer, only your answer, and the point of writing it down is that every decision further down this page gets easier once you know it.
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Most people first read it on the day it is handed to them, which is the day they have the least leverage and the least attention. Read it now, when it costs you nothing.
Where it lives: the employee handbook, an intranet HR page, or your offer letter and any subsequent amendment. What to look for: whether it is a formula or entirely at the company's discretion, what it is calculated on, whether it requires signing a release, and whether anything changes in a reduction in force as opposed to an individual termination.
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Two separate questions that people merge. Whether you are owed notice or pay in place of it, and whether accrued time off is paid out when you leave.
The handbook is not the last word on the second one. In the United States whether unused vacation must be paid out is set by state law, and some states require it regardless of what a policy says. Find the rule for your state, then read the policy, and note where they disagree.
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If you hold options, this is the item on the page most likely to cost you real money, and the one almost nobody checks until it is running.
Find three things in your grant documents and plan document: how long after leaving you have to exercise vested options, commonly ninety days but set by your plan and sometimes much shorter; what exercising would cost you in cash; and whether exercising triggers a tax bill in the same year even though you cannot sell anything. For restricted stock units, find out what happens to units that have vested but not yet settled, and to the next vesting date relative to your last day.
Finding these out is not a decision. It is the information without which the decision gets made for you by a calendar.
Second / Find out what is on a clock
The deadlines that start the day you leave
This is the part the rest of the conversation leaves out. None of it is advice and all of it expires.
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In the United States, continuing your employer plan under COBRA is an election you have to make inside a limited window after coverage ends, and the window is measured in days rather than months.
Two things worth knowing before you are in it: the coverage is generally retroactive to the day you lost it, so a gap can be closed later within the window, and you pay the full premium rather than the share you are used to seeing. Find the current federal window length and your own plan's monthly cost now, so the number is not a surprise. A plan bought on the public marketplace is the other option, and losing job coverage opens a special enrollment period with its own deadline.
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Eligibility, the amount, how long it runs and how soon you can file are all set by your state, and they differ more than people expect.
Two practical notes. Benefits are generally not backdated to the day you lost the job, so filing promptly matters more than filing perfectly. And a severance payment can affect timing or eligibility in some states, which is worth knowing before you agree to how a payment is structured.
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If you have borrowed from a 401(k) or similar plan, separating from the employer often changes the repayment terms, and the balance can become due on a short schedule rather than continuing as payroll deductions.
The rules are set by your plan document and the consequences of not repaying are tax consequences, so this is a question for your plan administrator and, if the sum is meaningful, someone qualified to talk about the tax side. Find out whether it applies to you at all before you need to care.
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Money you have already set aside for a purpose, which stops being yours on a schedule tied to your employment.
Check the rules for each: a health flexible spending account is usually forfeited for expenses incurred after you leave, a dependent care account has its own rules, and a commuter benefit balance often simply stops. A health savings account is different and stays yours. Find which of these you have and what each one's cutoff actually is.
Third / Decide while you are calm
The decisions worth making in advance
Not because a plan survives contact, but because deciding under pressure reliably produces worse decisions than deciding early and revising.
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Write the list while nothing is urgent. People cutting under pressure tend to cut whatever is easiest to cancel that week rather than whatever costs the most, and they often protect small comforts while leaving a large recurring commitment untouched for months.
Put it in order and keep it somewhere you will find it. The value is that on the day you need it, the thinking is already done.
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The other half of the same list, and the more useful half. Name in advance the things you are not willing to reach for, so that the question is settled before the month it would be tempting.
We are not going to tell you what belongs on that list. It is genuinely yours, and it depends on things about your life this page knows nothing about.
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If anyone else depends on this income or shares decisions about it, they need the same picture you have, and the worst version of this conversation is the one that happens late because you were protecting somebody from it.
You are not asking them to solve anything. You are telling them your number, what you have found out, and what you decided in items nine and ten.
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The companion to the trigger in the ninety-day plan, which is about your job. This one is about your runway, and it is the number at which you change what you are doing rather than waiting to see.
Decide it now, in writing, with a date on it. Reviewing your own number against a line you set while calm is a different act from looking at your balance and feeling something about it.
Your trigger, in months rather than in feelings
Finish this sentence and keep it: if my runway drops below ___ months, I will ___. The blank on the right is the part people leave out, and it is the part that matters. Examples of a second half that is specific enough to act on:
- I start applying rather than looking, at a rate I write down now.
- I execute the cut list in item nine, all of it, in one sitting rather than gradually.
- I tell the two people in my network who would actually hire me, instead of waiting until I can do it from a position of strength.
- I book the appointment with somebody qualified, because the decisions from here need a professional and not a web page.
Five things not to do
- Do not sign a severance agreement on the day you receive it. There is usually a period to consider it and sometimes a right to revoke afterwards, both of which exist because the drafters expected you to use them.
- Do not let the exercise window on your options run out because you never looked it up. Whether to exercise is a real decision with real risk. Missing the deadline is not a decision at all.
- Do not take advice about your money from anyone who has not seen your numbers. That includes this page, which is why it stops at what to find out.
- Do not tell yourself you will work out the runway later. Item one takes four minutes and every other item is easier once it is done.
- Do not confuse doing this with expecting the worst. The reason to find these things out while nothing is happening is that it is the only time you can do it cheaply and without an audience.
Where this page stops, and who to ask instead
Nothing here is financial, tax or legal advice, and none of it is tailored to you. Goal Boss is a practice for the human side of an AI rollout. We are not licensed to advise anyone on their money and this page does not try to.
The items that genuinely need a professional, once you know your own numbers: what to do about vested options and the tax that can come with exercising them, anything involving a retirement account, and reviewing a severance agreement before you sign it. A one-hour conversation with someone qualified, held while you still have income, is a different thing from a search at midnight after a decision has landed.
Nothing you type or tick here is stored, sent or retained. The number is worked out in your own browser and the page keeps no record of it.
The other half of this pair is AI and your job: the next 90 days. If you have not mapped which parts of your work are exposed yet, start there.

