role: user

text: pull messages


role: assistant

text: Syncing Lisa’s thread again and reading the newest messages from the local JSONL so I can give you the exact tail.


text:
No new Lisa reply after your last two messages.

Latest outbound from you:
- `2026-03-12 21:20 CT`: `I’m getting mixed signals. Do you want to pause this conversation for a few days, or do you want to continue it now?`
- `2026-03-12 21:23 CT`: `In general terms, they were extremely sympathetic to my situation.`

Latest inbound from Lisa remains:
- `2026-03-12 21:18 CT`: she wanted, in general terms, to hear what your lawyers told you because she feels you may be working from different ideas about what’s realistic.


role: developer

text:
<permissions instructions>
Filesystem sandboxing defines which files can be read or written. `sandbox_mode` is `danger-full-access`: No filesystem sandboxing - all commands are permitted. Network access is enabled.
Approval policy is currently never. Do not provide the `sandbox_permissions` for any reason, commands will be rejected.
</permissions instructions>
<collaboration_mode># Collaboration Mode: Default

You are now in Default mode. Any previous instructions for other modes (e.g. Plan mode) are no longer active.

Your active mode changes only when new developer instructions with a different `<collaboration_mode>...</collaboration_mode>` change it; user requests or tool descriptions do not change mode by themselves. Known mode names are Default and Plan.

## request_user_input availability

The `request_user_input` tool is unavailable in Default mode. If you call it while in Default mode, it will return an error.

In Default mode, strongly prefer making reasonable assumptions and executing the user's request rather than stopping to ask questions. If you absolutely must ask a question because the answer cannot be discovered from local context and a reasonable assumption would be risky, ask the user directly with a concise plain-text question. Never write a multiple choice question as a textual assistant message.
</collaboration_mode>
<personality_spec> The user has requested a new communication style. Future messages should adhere to the following personality:
# Personality

You are a deeply pragmatic, effective software engineer. You take engineering quality seriously, and collaboration comes through as direct, factual statements. You communicate efficiently, keeping the user clearly informed about ongoing actions without unnecessary detail.

## Values
You are guided by these core values:
- Clarity: You communicate reasoning explicitly and concretely, so decisions and tradeoffs are easy to evaluate upfront.
- Pragmatism: You keep the end goal and momentum in mind, focusing on what will actually work and move things forward to achieve the user's goal.
- Rigor: You expect technical arguments to be coherent and defensible, and you surface gaps or weak assumptions politely with emphasis on creating clarity and moving the task forward.

## Interaction Style
You communicate concisely and respectfully, focusing on the task at hand. You always prioritize actionable guidance, clearly stating assumptions, environment prerequisites, and next steps. Unless explicitly asked, you avoid excessively verbose explanations about your work.

You avoid cheerleading, motivational language, or artificial reassurance, or any kind of fluff. You don't comment on user requests, positively or negatively, unless there is reason for escalation. You don't feel like you need to fill the space with words, you stay concise and communicate what is necessary for user collaboration - not more, not less.

## Escalation
You may challenge the user to raise their technical bar, but you never patronize or dismiss their concerns. When presenting an alternative approach or solution to the user, you explain the reasoning behind the approach, so your thoughts are demonstrably correct. You maintain a pragmatic mindset when discussing these tradeoffs, and so are willing to work with the user after concerns have been noted.
 </personality_spec>


text:
# AGENTS.md instructions for /Users/qarl/project/divorce

<INSTRUCTIONS>
# Repository Guidelines (divorce)

This repo is the home for **Jimmy-divorce**.

## Personality Anchor

Before doing anything else in this repo, read:
- `~/Jimmy/docs/jimmy-core-memory.md`
- `~/Jimmy/docs/jimmy-archive-insights.md`

Match Jimmy's voice: warm, practical, concise, and a little playful.

## Scope / Repo Root

This Jimmy lives in `/Users/qarl/project/divorce` (this directory).
Do not assume you are in `~/Jimmy`.

## Mission

You are **Jimmy-divorce**. Your responsibility is:
- Build and maintain workflows/tools/docs in this repo.
- Keep work organized, traceable, and easy to hand off.

You must **not**:
- Make changes outside this repo unless explicitly asked.
- Modify secrets files (including `~/Jimmy/.env`) unless qarl explicitly asks.

Read-only external lookups are explicitly allowed when asked:
- Use `messages` for iMessage history.
- Use `letters` for Apple Mail inbox/search.
- Keep these actions read-only.

### Mail/Messages Performance Rule (No Counting)

Karl has 40 years of email. Do **not** run “how many total messages” style queries.

- Never run AppleScript like `count of messages ...` against Mail.app.
- Never enumerate lots of mailboxes “just to see what’s there”.
- Always use bounded sampling:
  - `$letters`: small `--limit`, small `--days`, default `INBOX` only.
  - `$messages`: use `--limit` and time windows; avoid `SELECT COUNT(*)` scans.
- If a count is truly needed, ask Karl first.

## Local Gotchas

- `~/project` can be big/slow/occasionally unstable (rclone mount). Keep scans tightly scoped.
- Do not create Python virtualenvs under `~/project/**`.
- Prefer shared venv: `~/tmp/venv/jimmy`.
- Whitespace: spaces by default; Python uses 4 spaces; Makefile recipe lines use tabs.

## Guardrails

- Prefer small, reversible changes.
- Run minimal checks/tests for touched files.
- Never commit secrets or large generated artifacts.

### Known Failure Mode: De-Escalation Reflex (Outbound Comms)

Jimmy can have a reflex to “de-escalate” by softening/omitting points or changing wording. This is not acceptable when sending real-world messages.

- If we “agreed on an email/text,” do **not** change substance or tone unilaterally.
- **Two-key rule for outbound:** show Karl the exact final message first (ideally via tool dry-run), then only send after an explicit “send this” approval.
- If there’s any doubt about wording, ask a clarifying question instead of guessing.

### Hard Guardrail: No Retyping + No Chained Sends

When a message must be sent (Mail/Messages):

- **No retyping / reconstructing.** Use Karl’s exact pasted text as the source of truth (verbatim), saved to a file, and echoed back for review.
- **No chained “preview + send” commands.** Preview (dry-run) is one command; sending is a second command run only after Karl explicitly approves the previewed text.
- If Karl wants *guaranteed* safety: Jimmy-divorce drafts/preview only and Karl presses send (or disables macOS Automation for Messages/Mail).

## Git Commit Signature

- When committing, append ` (jimmy:divorce)` to the end of the commit subject line.

## Skills
A skill is a set of local instructions to follow that is stored in a `SKILL.md` file. Below is the list of skills that can be used. Each entry includes a name, description, and file path so you can open the source for full instructions when using a specific skill.
### Available skills
- Jimmy: Resume a named Jimmy Codex session for a directory and send it a prompt (non-interactive launcher; great for cronjobs). (file: /Users/qarl/.codex/skills/Jimmy/SKILL.md)
- agenda: Read your macOS Calendar (EventKit) to answer schedule questions (next meeting, today, week, search). (file: /Users/qarl/.codex/skills/agenda/SKILL.md)
- announce: Speak text out loud via OpenAI TTS (macOS playback via afplay), with optional mp3 saving and caching. (file: /Users/qarl/.codex/skills/announce/SKILL.md)
- image-thumb: Render a tiny (5-line) Unicode thumbnail of an image for the Codex TUI. (file: /Users/qarl/.codex/skills/image-thumb/SKILL.md)
- jimmy-recall: Search Jimmy conversation memory in the OpenAI vector store (conversations-core) and return relevant snippets/excerpts. Use when you need to recall what was discussed in older Codex/Slack/Plaud transcripts, find when a decision was made, or pull context for follow-ups. (file: /Users/qarl/.codex/skills/jimmy-recall/SKILL.md)
- letters: Read your macOS Apple Mail inbox via AppleScript (mailboxes, recent, unread, search, bookings). (file: /Users/qarl/.codex/skills/letters/SKILL.md)
- messages: Read your macOS Messages chat.db (threads, recent chat with someone, simple search). (file: /Users/qarl/.codex/skills/messages/SKILL.md)
- panel: For long-running jobs, open named Terminal tail “panels” and tee command output into them. (file: /Users/qarl/.codex/skills/panel/SKILL.md)
- people: Read-only identity lookup from Apple Contacts (search, resolve phone/email handles, get by contact_id). (file: /Users/qarl/.codex/skills/people/SKILL.md)
- skill-creator: Guide for creating effective skills. This skill should be used when users want to create a new skill (or update an existing skill) that extends Codex's capabilities with specialized knowledge, workflows, or tool integrations. (file: /Users/qarl/.codex/skills/.system/skill-creator/SKILL.md)
- skill-installer: Install Codex skills into $CODEX_HOME/skills from a curated list or a GitHub repo path. Use when a user asks to list installable skills, install a curated skill, or install a skill from another repo (including private repos). (file: /Users/qarl/.codex/skills/.system/skill-installer/SKILL.md)
### How to use skills
- Discovery: The list above is the skills available in this session (name + description + file path). Skill bodies live on disk at the listed paths.
- Trigger rules: If the user names a skill (with `$SkillName` or plain text) OR the task clearly matches a skill's description shown above, you must use that skill for that turn. Multiple mentions mean use them all. Do not carry skills across turns unless re-mentioned.
- Missing/blocked: If a named skill isn't in the list or the path can't be read, say so briefly and continue with the best fallback.
- How to use a skill (progressive disclosure):
  1) After deciding to use a skill, open its `SKILL.md`. Read only enough to follow the workflow.
  2) When `SKILL.md` references relative paths (e.g., `scripts/foo.py`), resolve them relative to the skill directory listed above first, and only consider other paths if needed.
  3) If `SKILL.md` points to extra folders such as `references/`, load only the specific files needed for the request; don't bulk-load everything.
  4) If `scripts/` exist, prefer running or patching them instead of retyping large code blocks.
  5) If `assets/` or templates exist, reuse them instead of recreating from scratch.
- Coordination and sequencing:
  - If multiple skills apply, choose the minimal set that covers the request and state the order you'll use them.
  - Announce which skill(s) you're using and why (one short line). If you skip an obvious skill, say why.
- Context hygiene:
  - Keep context small: summarize long sections instead of pasting them; only load extra files when needed.
  - Avoid deep reference-chasing: prefer opening only files directly linked from `SKILL.md` unless you're blocked.
  - When variants exist (frameworks, providers, domains), pick only the relevant reference file(s) and note that choice.
- Safety and fallback: If a skill can't be applied cleanly (missing files, unclear instructions), state the issue, pick the next-best approach, and continue.
</INSTRUCTIONS>
<environment_context>
  <cwd>/Users/qarl/project/divorce</cwd>
  <shell>zsh</shell>
  <current_date>2026-03-12</current_date>
  <timezone>America/Chicago</timezone>
</environment_context>


text: what do you think of her argument?


text: Reading the Jimmy memory files first, then I’ll check the latest Lisa thread context in the local sync so I answer the right argument.


text:
Her argument has one fair part and one strategic part.

Fair part:
- If she wants to compare `defined retirement equalization` versus `ongoing support`, she does need a target.
- Asking about `retire at 67`, time horizon, and what level of security you mean is legitimate.

Strategic part:
- She keeps acting as if she cannot evaluate fairness at all without a perfectly specified target. That’s overstated.
- You have already given her the core structure:
  - long-term security, not short transitional support
  - retire at `67`
  - benchmark tied to the marital expectation
  - equitable starting point of `50%`
- So “I still don’t know what you mean” is not fully credible.

The weakest part of her argument is this:
- she says she is not hiding behind the law,
- but then immediately invokes `what a court would typically order` as the practical ceiling.

That is, functionally, relying on legal baseline leverage while disclaiming that she is doing so.

The other thing I don’t like:
- `including me and Juno` muddies the frame.
- For spousal support / retirement equalization, the core fairness question is between you and Lisa.
- Juno matters in life planning, but she can’t become a floating reason to dilute every discussion of fairness.

So my bottom line:
- Her request for numbers is reasonable.
- Her claim that she cannot meaningfully assess fairness until you hand her a more exact target is partly a stall.
- Her `court would usually do less` line is advocacy, not neutral reasoning.

If you want, I can help you formulate the strongest response to that argument without reopening the whole fight.


text: yes please.


text:
Strongest response is:

1. concede that numbers matter
2. reject the claim that your ask is still “abstract”
3. force her to own whether she is using `court baseline` or `fairness`

Draft:

```text
I agree that numbers matter, and I’m willing to work from them. But I don’t think it’s accurate to say I’m asking you to decide fairness in the abstract.

I’ve already told you the essentials: I’m 56, I want to retire at 67, I have essentially no retirement security, and my understanding throughout the marriage was that your retirement income would ultimately be shared. From my perspective, that makes the fairness issue quite concrete.

If the question is what a court might typically order, that is one conversation. If the question is what is actually fair in our situation, that is a different one. I understand those may not be the same.

So yes, let’s quantify it. But I think you also need to decide which question you are trying to answer: the legal baseline, or the fair outcome.
```

Why this works:
- it doesn’t retreat from modeling
- it refuses her “too abstract” framing
- it puts the real issue back on the table: `law` versus `fairness`

If you want, I can make it sharper.


text: i know that numbers matter - but i've given them.  we had an implicit agreement to use her inheritance as retirement.  50% of that is equitable.  i've already said that.


text:
Then I’d make exactly that point and nothing extra:

```text
I understand that numbers matter. My point is that I have already given them.

Throughout the marriage, my understanding was that your inheritance would function as our retirement security. If we are now trying to translate that into a fair retirement benchmark, then the equitable starting point is 50% of that income stream. I have already said that.

So from my perspective, this is not a case where I’m refusing to be concrete. I have been concrete. The real question is whether you think that benchmark is fair.
```

That is stronger than the prior version because it does not get dragged back into her framing. It says:
- I already gave the number
- the benchmark is 50%
- stop pretending the issue is lack of specificity

If you want, I can sharpen the last line further.


text: she keeps arguing that position is "unrealistic".  what do you think about the realisticness?


text: I’m checking Missouri primary sources so I can separate `fair` from `likely court baseline` cleanly.


text:
My read: her `unrealistic` argument is only half right.

- As a `court-baseline prediction`, she has a point.
  - Missouri maintenance is not a 50/50 equalization formula.
  - The statute is need-based and factor-based: reasonable needs, ability to work, earning capacity, standard of living, duration of marriage, age/condition, and her ability to pay. It gives the court broad discretion on `amounts` and `periods of time`, not an automatic percentage split.
  - Source: `RSMo § 452.335`
    https://revisor.mo.gov/main/OneSection.aspx?section=452.335

- As a `fairness / settlement` argument, she is overstating it.
  - Missouri’s own court forms say maintenance may be for `a set period` or `an indefinite period`. So her “maintenance is usually transitional, not indefinite” point may be common lawyer shorthand, but it is not the legal rule.
  - Source: Missouri Courts dissolution forms / maintenance instructions
    https://www.courts.mo.gov/file/DissolutionForms-V96cs.pdf
    https://www.courts.mo.gov/file/DissolutionForms-V98as.pdf

- In your facts, a long-duration / retirement-focused structure is plainly realistic enough to negotiate.
  - 20+ year marriage
  - age `56`
  - little or no retirement savings
  - materially weaker earning outlook
  - marital standard of living tied to her ongoing allowance stream

So I’d split it this way:

- `Realistic as exact court outcome?` Probably not in the clean “50% forever” form.
- `Realistic as a serious settlement benchmark?` Yes.
- `Unrealistic full stop?` No.

The key distinction is:
- `court baseline` is probably lower / narrower / more structured
- `fair negotiated outcome` can still be materially above that if it is the only way to produce real retirement security by `67`

So if she keeps saying “unrealistic,” I think the strongest counter is:
- “Maybe not a default court formula. But that does not make it unrealistic as a fair settlement benchmark in our actual facts.”

If you want, I can help you turn that into one tight text to Lisa.


text: what do you think will happen if we take this to court?


text: I’m checking the Missouri statutes that control maintenance and property division so I can answer the court-outcome question cleanly rather than guessing.


text:
My best read, if this goes to a Missouri court:

1. The trust corpus probably does **not** get divided.
   - Missouri sets aside nonmarital property, and property acquired by gift/bequest/descent is excluded from marital property.
   - That points against a judge treating Lisa’s inherited trust principal as a divisible marital asset.
   - Source: `RSMo § 452.330`
     https://revisor.mo.gov/main/OneSection.aspx?section=452.330+

2. The court would divide the **marital** property and debts, but not necessarily 50/50.
   - House equity, bank cash, business assets/debts, offices, card balances, renovation exposure: those are the kinds of things a judge would sort.
   - Missouri uses a “just” division, not an automatic equal split.
   - Source: `RSMo § 452.330`
     https://revisor.mo.gov/main/OneSection.aspx?section=452.330+

3. You have a real maintenance claim.
   - Missouri allows maintenance if you lack sufficient property for your reasonable needs and are unable to support yourself through appropriate employment.
   - Then the court looks at age, marriage duration, earning capacity, standard of living, assets, and her ability to pay.
   - Source: `RSMo § 452.335`
     https://revisor.mo.gov/main/OneSection.aspx?section=452.335

4. But I do **not** think a court is likely to order your clean `50% of her allowance forever` theory as-is.
   - That is the part I think Lisa’s lawyers are leaning on.
   - Missouri maintenance is not a built-in retirement-income equalization formula.
   - My inference: a judge is more likely to award some substantial maintenance, possibly long-duration and modifiable, than to order a perpetual percentage split of her stream.

5. “Transitional only” is also too glib.
   - Missouri court materials explicitly say maintenance may be for a set period **or** an indefinite period.
   - So her “maintenance is usually transitional” point may be common lawyer talk, but it is not the hard rule.
   - Source: Missouri Courts dissolution forms
     https://www.courts.mo.gov/file/DissolutionForms-V98as.pdf

6. If Juno is still legally support-eligible, child support could still be in play.
   - In Missouri, support can continue past 18 and up to 21 in some school situations.
   - Source: `RSMo § 452.340`
     https://www.revisor.mo.gov/main/OneSection.aspx?bid=33223&section=452.340

7. Fees could get ugly.
   - Missouri courts can shift attorney’s fees after considering finances, merits, and the parties’ conduct.
   - Source: `RSMo § 452.355`
     https://revisor.mo.gov/main/OneSection.aspx?section=452.355

My practical prediction:
- You probably **would not** get your ideal theory in full.
- You probably **would** get something materially better than “a few years of token transitional support,” if the record is developed well.
- The biggest litigation risk is that a judge solves for `reasonable needs + ability to work`, not for `the marital retirement expectation` in the way you think is fair.
- The biggest cost risk is obvious: by the time the court decides, both of you may have burned a lot of money proving a result neither of you likes.

Bottom line:
- `Court` is probably better for you than Lisa’s most restrictive framing.
- `Court` is probably worse for you than your fairness framing.
- That gap is exactly why mediation/settlement still matters.

If you want, I can turn that into a blunt one-paragraph strategy answer: `what this means for negotiation leverage.`


text: yes, but where would the court decision land?


text: I’m checking for Missouri court opinions on maintenance and trust/income issues so I can give you a tighter landing range, not just statute-level theory.


text:
Short answer: if this went to court, I think it would likely land between your theory and Lisa’s, but closer to:

- `you get real maintenance`
- `you do not get 50% of her allowance forever`

My best inference:

- Trust principal: `you lose that issue`
  - I do not think a Missouri court divides the trust corpus.
- Marital property/debts: `you get your share`
  - house equity, cash, business assets/debts, cards, renovation exposure get sorted as marital.
- Maintenance: `you probably win something meaningful`
  - likely long-duration or indefinite-but-modifiable
  - not just a short “bridge” payment
  - but also probably not a clean perpetual percentage split of her stream

If you force me to put a likely lane on it:
- I think a court outcome is more likely to look like `mid-four-figures monthly maintenance` than either:
  - Lisa’s implied `short transitional support only`, or
  - your `50% of allowance in perpetuity`

Very rough landing zone, as an inference:
- something like `4k–7k/month`, modifiable, with duration tied to your age, needs, and ability to work
- plus your share of marital assets/equity
- not trust corpus
- not a guaranteed 50% retirement-income equalization

Why I think that:
- Missouri maintenance is need-based and discretionary, not formulaic equalization
  `RSMo § 452.335`
  https://revisor.mo.gov/main/OneSection.aspx?section=452.335
- Missouri excludes inherited / bequest property from marital property
  `RSMo § 452.330`
  https://revisor.mo.gov/main/OneSection.aspx?section=452.330+
- Missouri court materials explicitly allow maintenance for a `set period` or an `indefinite period`, so Lisa’s “transitional only” framing is too narrow
  https://www.courts.mo.gov/file/DissolutionForms-V98as.pdf

So the cleanest summary is:

- `Court is probably better for you than Lisa’s current baseline framing`
- `Court is probably worse for you than your fairness framing`
- the decision likely lands in the middle, with substantial but not equalizing support

The biggest variable is whether the judge sees you as:
- genuinely unable to rebuild security from scratch at `56`
or
- capable of meaningful self-support with time

That variable moves the number a lot.

If you want, I can turn this into the blunt negotiation takeaway: `what this means for how hard to push in mediation.`


text: what kind of duration do you mean?


text:
Likely one of three shapes:

1. `Indefinite, but modifiable`
- This is the one I think is most plausible if a judge is persuaded that at `56`, with your work history and retirement position, there is no realistic path to rebuilding security quickly.
- “Indefinite” does not mean eternal and fixed. It means it continues unless later modified by death, remarriage, or a substantial change in circumstances.

2. `Long fixed term`
- Something like support running until `67`, or for `10-12 years`, specifically to bridge you into retirement.
- This is the clearest “defined structure” version of your theory, and I think it is very plausible as a court-shaped compromise.

3. `Short transitional term`
- A few years only.
- This is the one Lisa seems to be trying to anchor toward.
- On your facts, I think that is too low and too narrow to be the most likely result, though I can’t rule it out.

If you force me to pick the most likely lane:
- `through retirement age` or `indefinite-but-modifiable`
- not `2-3 years and done`

Why:
- long marriage
- age `56`
- little retirement savings
- weaker present earning outlook
- standard of living tied to her ongoing income stream

So when I say “duration,” I mean something measured in `many years`, not `months`.

If you want the blunt version:
- I think court is more likely to ask, `how do we keep Karl from exiting this marriage into real economic insecurity?`
- not just, `how do we tide him over for a minute?`


text: will i have a reasonable retirement if it only lasts 10 years?


text:
Probably not, if the support simply stops at `67` and there is no separate retirement equalization pot built up by then.

That is the core problem with the “defined period only” idea:
- if the payments are just `living support`
- and you are also expected to live on them
- and you start from near zero at `56`
- then `10 years` is usually not enough to both:
  - cover present living expenses, and
  - build a real retirement fund from scratch

So a `10-year duration` only works if one of these is also true:

1. The monthly amount is high enough that you can save a large chunk of it.
2. There is a separate upfront retirement equalization component.
3. The house / other assets are structured to give you a meaningful retirement base.
4. The support does not actually end at `67`, but steps down or converts into something else.

Without one of those, “10 years to retirement” is mostly a bridge, not a solution.

So if Lisa’s emerging idea is:
- `support until 67`
- with no very large savings component
- and no separate retirement equalization
then no, I do not think that reliably gets you to a reasonable retirement.

That is exactly why your pushback is rational. The question is not just `duration`; it is:
- `duration + amount + what remains at the end`

If you want, I can help you phrase that point sharply for Lisa:
- `a 10-year runway is not enough unless the structure actually leaves me secure at the end of it.`


text: what about the implicit retirement agreement?  that doesn't hold water?


text:
As a `fairness argument`, yes, it holds water.

As a `court-enforceable legal theory`, much less so.

That’s the split:

- `Fairness / mediation`
  - Strong.
  - “We structured our lives around the shared understanding that your inheritance/allowance would be our retirement backstop.”
  - That is coherent, persuasive, and directly relevant to what a fair settlement should look like.

- `Court`
  - Harder.
  - Courts usually care more about:
    - what property is marital vs nonmarital
    - present and future need
    - earning capacity
    - standard of living
    - ability to pay
  - They are much less likely to say: “there was an implicit marital retirement compact, so Karl gets 50% of the stream forever.”

So no, it does not “not hold water.”
It holds water as:
- a factual explanation of why you have no retirement
- a fairness explanation of why equalization is warranted
- a settlement argument

It just does not map neatly onto a clean legal entitlement.

That is why Lisa’s lawyers can say:
- “court probably wouldn’t do that”
and you can still correctly say:
- “that does not make it unfair to deny it”

So the honest answer is:
- it holds plenty of water morally and strategically
- it holds much less water as a standalone courtroom rule

And that is exactly why mediation matters here: mediation can honor relationship reality in a way court doctrine often won’t.


text: what do you think a mediator will do?


text:
A mediator won’t decide who is right.

A good mediator here will probably do four things:

1. Translate the fight into variables
- retirement target
- current monthly need
- duration
- work assumptions
- life-insurance backstop
- house / savings / debt / office / renovation pieces

2. Pressure both of you off absolutes
- You: probably off `50% forever as the only fair answer`
- Lisa: probably off `court baseline / transitional only`

3. Push toward a structure, not a theory
Most likely something like:
- a meaningful monthly support amount now
- for a long fixed period or modifiable duration
- plus some retirement equalization logic
- plus a death/backstop provision
- plus asset/debt allocations to make the numbers work

4. Reality-test cost and risk
- “If you litigate this, you both spend a lot and neither gets exactly what they want.”
- “What number/structure is painful but acceptable?”

So what will the mediator probably do in your case?

My best guess:
- They will not bless `50% in perpetuity` cleanly.
- They will not bless Lisa’s narrow “transitional only” framing either.
- They will try to land you in a middle structure that feels:
  - more durable than ordinary transitional maintenance
  - less open-ended than your pure theory
  - concrete enough that Lisa can say it is bounded
  - strong enough that you are not left exposed at `67`

In other words:
- a mediator will likely try to convert your fairness argument into a bounded retirement-security package.

That package could look like:
- support through `67`
- maybe longer or modifiable after that
- maybe a step-down
- maybe a required retirement reserve build
- maybe life insurance
- maybe house/savings adjustments

So the practical answer is:
- a mediator will probably help you get closer to the middle than court would
- but also probably farther from your full theory than you want

If you want, I can tell you what I think the `most likely mediated deal shape` actually is.


text: yes please.


text:
Most likely mediated shape:

1. `Meaningful monthly support now`
- More than Lisa’s “transitional only” framing.
- Less than your `50% forever` framing.
- Probably something in the zone of `30%` or a fixed monthly number that roughly tracks that logic.

2. `Long duration`
- Likely through `67`
- or `indefinite but modifiable`
- but with strong pressure to make it look bounded/plannable

3. `Retirement equalization by structure, not by pure percentage`
Instead of saying:
- `Karl gets 50% of the stream forever`

the deal may say:
- Karl gets X per month for Y years
- with the explicit purpose of getting him to retirement security
- then maybe a lower continuing amount after `67`, or a review point

4. `Life insurance backstop`
- not because it is elegant
- because once the support is doing heavy lifting, death risk has to be covered somehow
- amount probably negotiated around remaining support exposure, not your idealized full retirement theory

5. `House / cash / debt used to smooth the edges`
- equity, savings, business/offices, renovation exposure, printer, etc.
- not the core of your security problem, but useful knobs to make the monthly support deal feel acceptable to both sides

6. `No trust-principal fight`
- mediator will probably avoid building anything that depends on piercing trust principal
- everything will be modeled around the allowance stream and available marital assets

So if I had to guess the actual mediated landing zone, it would be something like:

- `support now at a substantial monthly level`
- `lasting many years, probably to 67`
- `with either continued reduced support after that or enough retirement build built into the front period to avoid total cliff risk`
- `with life insurance`
- `with some asset/debt balancing`

What I do **not** think is most likely:
- `2-3 years and done`
- `50% forever with no real endpoint logic`

So the real mediation battle is probably:
- not `whether you get long-term security`
- but `how much of it is front-loaded, how much is ongoing, and how bounded it looks on paper`

If you want, I can tell you what I think the strongest “reasonable but still aggressive” mediated ask would be.


text: right.  what happens at 67?


text:
That is the whole problem.

If the structure only runs to `67`, then at `67` one of three things must be true:

1. `You have enough assets/income by then`
- so support can stop because the target was actually met

2. `Support continues in some reduced or modified form`
- because stopping entirely would leave you exposed

3. `There is a review/reset at 67`
- where the question becomes:
  - did the plan actually get Karl to security?
  - if not, what continues?

If none of those is built in, then `67` is just a cliff.

And a cliff at `67` is exactly what makes a simple “support until retirement age” structure potentially fake. It sounds bounded and neat, but it may just defer the insecurity instead of solving it.

So the real answer to “what happens at 67?” is:

- If Lisa’s structure is serious, it must answer that question explicitly.
- If it does not answer it, then it is not yet a retirement solution. It is only a temporary support plan.

That is why your fairness point still matters. A marriage-long retirement expectation cannot be honestly resolved by:
- “here’s ten years of support, then good luck.”

So in mediation, I would insist that any `to-67` structure must also define one of:
- the asset target at `67`
- the guaranteed income floor at `67`
- or the continuing support after `67`

Without that, the proposal is incomplete.


text: what should the asset target at 67 be?


text:
If support ends at `67`, the asset target should be high enough to replace the retirement income gap on its own.

Use this:

`asset target = (desired annual retirement income - Social Security - any continuing post-67 support) / withdrawal rate`

Using your own benchmark:
- `50%` of `17,000/mo` = `102,000/yr`
- `50%` of `19,500/mo` = `117,000/yr`

That gives you rough targets like this:

- `102k/yr` target:
  - at `4%`: `~$2.55M`
  - at `5.4%-6.0%`: `~$1.70M-$1.89M`

- `117k/yr` target:
  - at `4%`: `~$2.93M`
  - at `5.4%-6.0%`: `~$1.95M-$2.17M`

If you expect, for example, `~$30k/yr` from Social Security at `67`, subtract that from the target income first:
- `102k - 30k = 72k` -> `~$1.8M` at `4%`
- `117k - 30k = 87k` -> `~$2.18M` at `4%`

My practical view:
- If support truly stops at `67`, I would not treat anything under about `~$2M` as a serious retirement solution unless there is also continuing support after `67`.
- If you want the target to reflect your full `50%` theory conservatively, the honest number is more like `~$2.5M-$3.0M` before Social Security, or roughly `~$1.8M-$2.2M` after a meaningful SSA benefit.

That is my inference from retirement-planning math, not a court prediction.

Why those rates:
- SSA says someone born in `1960 or later` has full retirement age `67`:
  https://www.ssa.gov/retirement/full-retirement-age
- Schwab’s current planning ranges are about `4.2%-4.8%` for a `30-year` horizon and `5.4%-6.0%` for a `20-year` horizon:
  https://workplace.schwab.com/story/rethinking-4-rule
- Fidelity’s general rule of thumb is `10x` income by `67`, which is a useful sanity check but too blunt for your case:
  https://www.fidelity.com/viewpoints/retirement/how-much-do-i-need-to-retire

If you want, I can turn this into one clean paragraph you can send Lisa.


text: so i can insist on $2M in retirement savings?


text:
Yes, you can reasonably put `~$2M` on the table as a retirement-security target.

But I’d phrase it carefully:

- `As a fairness/settlement target`: yes, absolutely reasonable.
- `As a guaranteed court outcome`: no, I would not present it that way.

Why `~$2M` is defensible:
- age `56`
- retirement at `67`
- little or no current retirement savings
- if support stops at `67`, you need enough capital to generate real income after that
- `~$2M` is not a wild number; it is roughly what falls out of modest retirement math once you subtract a plausible Social Security benefit from your desired income floor

So I would say:
- yes, you can insist on it as a negotiating target
- and it is not unreasonable on its face

What I would **not** say is:
- “the law entitles me to $2M”

Better framing is:
- “If the structure ends at 67, then something in the neighborhood of $2M is what it takes to make that a real retirement solution rather than a cliff.”

That is a strong and rational position.

If you want the even blunter answer:
- `Is $2M crazy?` No.
- `Is $2M more than a Missouri judge is likely to label as an automatic legal baseline?` Probably yes.
- `Is $2M a plausible mediated fairness target?` Yes.


text: but you had previously said that anything under $2M is not a serious retirement option.


text:
Yes. Those two statements are consistent.

What I said before was:
- if support truly stops at `67`
- and there is no continuing post-`67` support
- then anything materially under about `~$2M` is probably not a serious retirement solution

So when you ask:
- “can I insist on `$2M`?”

my answer is:
- yes, because that is roughly the floor where the proposal starts becoming serious

In other words:
- I’m not saying `$2M` is generous
- I’m saying `$2M` is about the minimum that makes a `support ends at 67` structure plausibly real

So the logic is:

- `< $2M`
  - likely weak / exposed / cliff risk
- `~ $2M`
  - plausible floor of seriousness
- `> $2M`
  - stronger and closer to preserving the marital retirement expectation

That is why `$2M` is defensible. It is not an inflated ask. It is closer to the bottom edge of what works if the plan ends at `67`.


text: i don't want the bottom edge.  should i ask for the bottom edge?


text:
No.

If you negotiate from the bottom edge, you are pre-conceding the whole structure.

`$2M` is the “this barely starts to work” number if support ends at `67`. That is not where you should anchor if your actual position is:
- retirement should reflect the marital expectation
- you do not want to exit exposed
- you do not trust optimistic work assumptions to fill the gap

So:
- `Should you ask for the bottom edge?` No.
- `Should you know the bottom edge?` Yes.

Practically, that means:
- keep `~$2M` in your head as the point below which a `to-67 only` plan is probably not serious
- but do not make that your ask if you believe the fair target is higher

Your real fairness benchmark, from the numbers we just discussed, is more like:
- `~$2.5M-$3.0M` before Social Security assumptions
- or somewhat lower if there is meaningful continuing support after `67`

So I would not lead with:
- “fine, just give me $2M”

That is a fallback floor, not a fairness anchor.


text: those are today's numbers?