Retirement planning is the kind of project that sits in a dozen different places at once. The 401(k) login. The Roth conversion you read about and meant to think through. The health-insurance crosswalk between your employer plan and Medicare. The conversation with your spouse last spring about whether you actually want to move. The advisor's email with the asset-allocation chart you opened once.
None of it is technically hard. It just doesn't live anywhere together, so every conversation about it starts from cold. Then a tax-year deadline approaches, or your advisor asks a follow-up, or your partner brings it up at dinner — and you're rebuilding the picture from scratch.
A vault that holds the financial side, the healthcare side, the housing side, and the lifestyle questions in one place, with the agent doing the searching when something comes up, takes most of the friction out. Below is the shape we'd suggest, with a few examples of how it actually plays out.
One parent page per pillar, then nest from there
In Docapybara, Retirement gets a top-level page, and underneath it sit one child per pillar: Finances, Healthcare, Housing, Lifestyle, Estate, and Conversations. Pages nest indefinitely — OneNote-style — so each pillar can grow as deep as the topic actually goes without forcing structure up front.
The agent treats the whole tree as one searchable surface. So when you ask "what's the latest thinking on whether we move closer to the kids?", it pulls from Conversations and Housing together, not from one folder at a time. If you've already got a setup for the broader version of "capture the messy life decisions in one place," see A Bucket List That Actually Gets Done — same shape, lighter stakes.
Finances — accounts, contributions, and the moves you've considered
The Finances page is where most retirement planning lives, but the trick is keeping it usable instead of a dumping ground for statements.
An inline database via the :::database::: directive handles the account list well: account name, type (401k, Roth IRA, Traditional IRA, taxable, HSA, etc.), provider, current balance, contribution rate, and notes. The agent can update it. "Move the bond allocation in the rollover IRA from 30 to 40 percent — Vanguard, today's date." Row updates with a date stamp.
For the bigger questions — Roth conversion ladders, when to claim Social Security, sequence-of-returns risk, how much in the safe bucket — keep a running notes page per question. Roth conversions gets its own child page with the math you've worked through, the tax-bracket constraints, what your CPA said in March, and the link to the IRS tables. Next time it comes up, the agent can pull a summary instead of you re-Googling the same charts.
Statements drop on the page as PDFs. Docapybara converts uploads to markdown via docstrange, so the agent can actually read the contents. "What was the year-end balance on the rollover IRA last December, and what did the contribution-summary section say?" Comes back with the number and the source.
Healthcare — Medicare, supplemental, and the costs you can't predict
Healthcare is the part most people underestimate. The Healthcare page holds the timeline (when you're eligible for Medicare, when you'll enroll in each part, when supplemental coverage kicks in), the comparison of Medigap vs. Medicare Advantage as you've worked through it, the prescription list, and the long-term-care question.
For the Medicare comparison specifically, an inline database with plan name, type, monthly premium, deductible, network notes, and prescription coverage makes it easier to actually compare apples to apples. The agent can pull the comparison: "Show me the supplemental plans I've shortlisted with their premiums and what's not covered."
For long-term-care planning — whether to buy insurance, self-insure, or rely on home equity — keep the conversations and reasoning on a page. The agent can summarize the latest position when it comes up. If you're also coordinating care for aging parents, the Caregiver Notes: Medications, Appointments, and the Care Plan in One Place shape carries over directly — same vault, same structure.
Housing — stay, downsize, or move
Housing is one of the bigger decisions and the one most prone to drift. The Housing page holds the actual options on the table: stay in place with aging-in-place modifications, downsize locally, move to a different state, move closer to family, sell and rent.
For each option, a child page with the financial picture (cost, equity freed, tax implications), the lifestyle picture (climate, community, distance to people who matter), and the practical picture (what changes about your day) builds up over time. The agent can summarize: "What were the three options I had narrowed down for the move, and what did I write about the trade-offs?"
If you're actively touring places, the Apartment Hunting and House Buying: A Calmer Way to Keep Track shape works for that phase too — drop visit notes, photos, and the per-place pros-and-cons inline.
Lifestyle — what you actually want the days to look like
The financial and healthcare pages get most of the attention, but the lifestyle page often does the most quiet work. Retirement isn't a decade of vacation; it's roughly thirty years of needing somewhere to put your time.
Keep a page for Lifestyle with the things you've talked about wanting: travel destinations, hobbies you'd pick back up, volunteer work that interests you, classes you've thought about taking, the small business or consulting practice you've half-considered. The audio recording feature is helpful here — when you're walking and a thought comes up, tap record and the transcript lands on the page with speaker labels if there's more than one voice.
The agent can summarize the running picture: "Looking at the last six months of lifestyle notes, what are the three or four things I keep coming back to?" Surfacing the patterns is hard to do by reading through scattered notes; easy to do when the agent reads them for you. (For broader career-and-life-shape questions, Career Transitions and Job Searches, With a Vault Behind You handles a related kind of thinking.)
Conversations — what you and your partner actually said
If you're planning with a spouse or partner, Conversations might be the most important page. Most retirement planning falls apart at the disagreement points — when to claim Social Security, whether to move, how much risk to keep in the portfolio, whether you both want to keep working part-time.
After each conversation, drop a quick note. Date, what you talked about, where you each landed, what's still open. Voice works well — thirty seconds of "we agreed on X, still disagreeing on Y, parking it until after we look at the numbers next month" takes less effort than typing.
The agent can summarize the state of any open question: "What's the current state of the Social Security claiming conversation — what have we agreed on, what's still open?" Comes back with the chronology and the open items. This is the kind of thing that prevents the "I thought we said…" moment six months later.
Estate — wills, beneficiaries, and the documents your people will need
The Estate page sits next to Finances but has a different job. It holds the will, the powers of attorney, the healthcare directives, the beneficiary designations on each account, and the list of where everything is. Drop the PDFs — they become searchable.
Most importantly, it holds the what your people will need page. Account locations, who to call, where the keys are, what subscriptions to cancel, instructions for any pets. Hopefully nobody needs to read it for a long time. When they do, it'll be there. The fuller version of this — including the conversations with your attorney and the rationale behind each decision — is in Estate Planning and Will Preparation: A Calm Place to Keep It All.
A starter shape for week one
If you're moving from "scattered across email, browser tabs, and a folder of PDFs" to a vault, this is what we'd suggest starting with:
- Retirement — top-level parent
- Finances — page + inline database of accounts
- Healthcare — page + plan comparison database
- Housing — page with one child per option
- Lifestyle — running notes, voice-friendly
- Conversations — dated entries after every planning chat
- Estate — documents and the what your people need page
That's seven pages. Nothing fancy. The vault grows the way your thinking grows, and the agent handles the searching so you don't have to remember where you put anything. For more on how the same shape extends to running a small business or side consulting practice in retirement, How to Use AI Notes for Side Hustle Management covers that.
Retirement planning isn't really one project. It's a slow conversation with your future self that you have to keep returning to over decades. The vault makes returning to it easier.
Try Docapybara free — start with the Finances page and the Conversations page, and the next time the topic comes up, you'll already have somewhere to put it. Pricing details are at /pricing/.