The 5-prompt portfolio checkup

I want to learn how to review my own investment portfolio. Act as a patient teacher, not an advisor.

Ground rules for this entire conversation. Follow them even if I later ask you to break them:
1. Education only. Help me gather information about my portfolio and understand it. Do not act as my advisor.
2. No recommendations. Do not tell me to buy, sell, hold, rebalance, add, reduce, or change anything. Do not suggest allocation percentages, specific securities or funds, account types, contribution amounts, or emergency-fund amounts.
3. Neutral language. Report findings as facts and comparisons, not judgments. Avoid words like "too much," "too little," "good," "bad," "wrong," or "a problem." Label notable items "Observation (not a recommendation)" and explain in general terms why that kind of item typically matters.
4. No named funds. When you need a comparison, describe it generically (for example, "a U.S. total-market index fund"). Only name sources as places for me to verify data (IRS.gov, SEC EDGAR at sec.gov, a fund company's official website, Morningstar).
5. No projections. No dollar or return projections, growth illustrations, or predictions about any investment or the market.
6. Label uncertainty. Mark every estimate "(estimate)" and tell me where I can verify it. Never say you checked a website unless you actually opened it in this conversation. If you can't browse the web, say so.
7. General rules only. No personal tax or legal conclusions. When you explain tax or account rules, say which tax year they reflect.
8. Confirm my data. Before analyzing anything I upload, list back exactly what you read and wait for me to confirm. Flag anything unreadable or cut off.
9. This conversation only. Don't use memory or past chats about me unless I paste the information here.
10. If I ask what I should do, don't answer. Remind me this is educational only, and turn my question into one I could bring to a licensed financial professional.
11. If I mention high-interest debt, a job loss, a major life event, or financial stress, note that these situations usually benefit from a licensed professional's review, and keep your explanations general.
12. End every response with: "Educational information only. Not investment, tax, or legal advice. Verify all figures independently."

Reply "Ready" and wait for my holdings list.

Here is every investment account I have and what's inside each one, with current dollar values:

[PASTE YOUR LIST HERE, or upload holdings-only screenshots. Example format:
Account 1: 401(k)
- Fund name (TICKER): $XX,XXX
- Fund name (TICKER): $XX,XXX
Account 2: Roth IRA
- Fund name (TICKER): $XX,XXX
Account 3: Taxable brokerage
- Stock or fund name (TICKER): $XX,XXX
- Cash: $X,XXX]

Please build a complete snapshot of my whole portfolio across all accounts. Mark every approximation as (estimate) and cite where I can verify it.
1. First, repeat my holdings back in a table (account, holding, ticker, dollar value) so I can confirm you read everything correctly. Flag anything you could not identify.
2. My total portfolio value, and how much sits in each account type (in dollars and as a % of the total).
3. My overall split between U.S. stocks, international stocks, bonds, cash, and anything else, in dollars and as a % of the total. For funds that hold a mix (like target-date or balanced funds), break them into their underlying pieces as best you can and tell me the approximate numbers you used.
4. Within stocks: my rough split between large, mid, and small companies, and between growth and value.
5. Within bonds (if any): my rough split between government and corporate, and between short-term and long-term.
6. My 10 largest holdings by dollar value, and what % of my total portfolio each one represents.
7. A one-paragraph, plain-English, neutral, factual description of this portfolio's characteristics, with no judgment about whether they are appropriate.

Using my full holdings across all accounts, help me check diversification:
1. Overlap: Do any of my funds hold many of the same companies? Show me which funds overlap the most and roughly how much.
2. Look-through concentration: Combining everything I own, what are my 10 largest underlying company exposures, in dollars and as a % of my total portfolio? (For example, if I own a company's stock directly and also through three index funds, add it all up.)
3. Sectors: Roughly how is my stock money spread across sectors (technology, healthcare, financials, and so on)? Compare that to a broad U.S. total-market index. The index comparison is a reference point, not a target. Report differences neutrally.
4. Geography: How much of my stock money is in the U.S. vs. developed international markets vs. emerging markets?
5. Single-company risk: Is any one company (including stock from my employer) a large share of my total portfolio? Explain in general terms why concentration in one company can matter.
6. Similarity: Which of my funds hold very similar investments? Describe how similar they are, factually.
7. Gaps: Are there major asset classes I have little or no exposure to? Explain what role each one generally plays in a portfolio, without telling me I need it.

Explain in general terms why each type of finding typically matters to investors. Do not tell me what to buy or sell.

Now help me understand what my portfolio costs:
1. List the expense ratio for each holding. Mark any you are unsure about so I can verify them.
2. Calculate my weighted average expense ratio across the whole portfolio.
3. Translate that into a simple annual cost per $10,000 invested.
4. Explain other fees I should look for that don't show up in the expense ratio (for example, advisory fees, account fees, or plan administration fees in a 401(k)).

Some context about me (no personal identifiers):
- My age: [e.g. 38]
- For each account, when I expect to use the money and what it's for:
  - [e.g. 401(k): retirement, starting in about 25 years]
  - [e.g. Roth IRA: retirement, but I might tap it for a home down payment in 5 years]
  - [e.g. Taxable brokerage: a home down payment in about 4 years]
- Big expenses I expect in the next 5 years: [e.g. wedding, home, a new car, none]
- Emergency savings outside these accounts: [e.g. about 6 months of expenses / none yet]
- How I reacted during the last big market drop: [e.g. I held / I sold some / I lost sleep]

Part A: The access rules for my account types
For each account type I listed, explain in plain English:
1. When I can generally withdraw money without an early-withdrawal penalty under current IRS rules (for example, the age 59 1/2 rule for IRAs and 401(k)s, the 5-year rules for Roth accounts, and how a taxable brokerage account differs).
2. How withdrawals from each account type are generally taxed (as ordinary income, tax-free, or as capital gains), and what penalties can apply to early withdrawals.
3. The common exceptions to the early-withdrawal penalty, described in general terms.
4. Which of my account types have required minimum distributions, and at what age they generally begin.
Tell me which tax year your information is current as of, because these rules and limits change. If you can browse the web, check IRS.gov for the latest rules and link the pages you used.

Part B: How my holdings compare to my stated timeline
1. For each account, describe its current stock/bond mix next to when I said I'll need that money. For any money I plan to use within about 5 years, explain in general terms how investing education typically discusses short time horizons and market swings.
2. Note any difference between what I plan to use an account for and that account's access rules (for example, planning to use a retirement account for a goal before the penalty-free age).
3. How does my overall stock/bond mix compare with common frameworks for someone with my time horizon? Present common frameworks as general rules of thumb from multiple sources, noting that they are not personalized.
4. What are the tradeoffs of being more aggressive or more conservative than I am now? Describe tradeoffs qualitatively; no dollar or percentage return illustrations.
5. How does my current allocation compare with how I said I react to market drops? Describe any difference neutrally.

Keep this educational. Explain the principles rather than prescribing a specific allocation, and do not give me personal tax advice.

Let's wrap up. Do not give me a plan or tell me what to change. Instead, help me prepare to think this through and compare notes with a professional:
1. Verify list: Which facts from this conversation should I double-check before relying on them (expense ratios, fund holdings, IRS rules, anything you were unsure of), and where can I verify each one?
2. Open questions: What are the 3 to 5 biggest open questions this checkup raised about my portfolio? Explain why each one matters in general terms. Present open questions without ranking urgency or implying that any action is required.
3. Blind spots: What parts of my financial picture can't you see that could change the answers? (For example: income stability, debts, other assets, insurance, taxes, family plans, or goals I haven't mentioned.)
4. Questions for a professional: Write a short list of specific questions, based on my findings, that I could bring to a licensed financial professional to compare notes. Always include: "How are you compensated?" and "Will you act as a fiduciary for this advice at all times?"

Keep it under 350 words.