Investing & Retirement · Topic hub

Investing and retirement,
in the right order.

UPDATED·APPLIES TOUnited States
For anyone investing or planning retirement.

Every investing and retirement guide on the site, grouped by the question it answers, with the calculators that check the numbers for your situation.

Short answer

Most people start with a starter cash buffer and any employer match, then clear high-interest debt and finish an emergency fund, then fund tax-advantaged accounts with low-cost, diversified funds. After that, retirement planning is mostly your savings rate, costs, taxes and a withdrawal plan you can stick to. The order of operations walks through each step.

On this page
  1. Start with these
  2. Every Investing & Retirement guide, by topic
  3. Calculators for this topic

Start with these

How to start investing, which accounts to use first, and how to turn savings into retirement income.

Investing basicsInvesting for BeginnersWhat a stock is, what a bond is, what an ETF is, and why index funds beat almost everything else.Retirement and tax-advantaged accountsAccountsDeep dives on Solo 401(k), SEP-IRA, HSA as a stealth retirement account, 529 for college, and 457(b).Funds and portfoliosThree-Fund PortfolioThree low-cost index funds cover roughly the entire investable world.Planning and living in retirementThe 4% RuleWhat the Trinity Study actually said. Why Pfau and Kitces argue 3.3% is safer today.

Every Investing & Retirement guide, by topic

Investing basics

  • Asset AllocationOverviewWhat asset allocation is and why it drives ~90% of long-term return variance.
  • Compound InterestExplainerThe rule of 72, the 22-vs-32 comparison, why time horizon is the dominant variable.
  • Fidelity vs Vanguard vs SchwabComparisonThe three dominant low-cost brokerages compared. Where each wins, where each falls short, when consolidation matters, and how to choose for your…
  • Index FundsOverviewOwn the entire market at minimal cost. The Bogleheads three-fund approach: total US, total international, and total bonds.
  • Investing for BeginnersOverviewWhat a stock is, what a bond is, what an ETF is, and why index funds beat almost everything else.
  • Passive InvestingOverviewSPIVA evidence, Bessembinder on individual stock returns, the Bogleheads philosophy.
  • Your First InvestmentGuideNot the theory. The actual steps. Open an account, pick a fund, set up automatic contributions.
  • Lump Sum vs DCAComparisonResearch shows lump sum investing outperforms dollar cost averaging roughly two thirds of the time.
  • Portfolio TheoryHubAsset allocation, sequence-of-returns risk, the real 4% rule, and rebalancing.
  • Understanding RiskExplainerEight types of financial risk, three responses (avoid, retain, transfer), and capacity vs tolerance.

Funds and portfolios

  • Choosing FundsGuideUS stocks, international stocks, bonds. Specific tickers at Vanguard, Fidelity, Schwab.
  • Target Date FundsOverviewA target date fund automatically shifts your investment mix from aggressive to conservative as you approach retirement.
  • Three-Fund PortfolioOverviewThree low-cost index funds cover roughly the entire investable world.
  • Bond BasicsOverviewBonds, duration, the 2022 lesson, why bonds in a portfolio, fund options by use case.
  • RebalancingExplainerCalendar vs threshold rebalancing. Tax-efficient rebalancing across account types.
  • SCHD vs VYMComparisonQuality-screen dividend growth vs broad above-average yield.
  • VTI vs VOO vs FSKAXComparisonSide-by-side comparison of VTI, FSKAX, SWTSX, SPY, VOO, FXAIX, and VT.
  • DRIP ExplainedExplainerA DRIP automatically reinvests dividend payments into additional shares of the same stock or fund.
  • VOO vs SPY vs IVVComparisonThree of the largest ETFs in the world track the same index.

Retirement and tax-advantaged accounts

  • 401(k) Rollover OptionsGuideLeave it, roll it, or cash it out. One of these destroys a significant portion of your retirement savings.
  • AccountsHubDeep dives on Solo 401(k), SEP-IRA, HSA as a stealth retirement account, 529 for college, and 457(b).
  • HSA BasicsOverviewThe only triple-tax-advantaged account in the US tax code. 2026 limits: $4,400 self-only, $8,750 family.
  • Open a Roth IRAGuideClick-by-click Roth IRA setup at Fidelity. Open, fund, buy FZROX, automate, done.
  • Roth vs TraditionalComparisonThe single biggest legal advantage in U.S. personal finance.
  • Solo 401(k)OverviewContribute as both employee AND employer, up to $72K in 2026.
  • Tax-Advantaged AccountsComparisonRoth IRA, 401(k), Solo 401(k), SEP-IRA, HSA, 529, 457(b) in one comparison table with 2026 contribution limits, tax treatment.
  • 2026 Contribution LimitsData2026 IRS limits: 401(k) $24,500, IRA $7,500, HSA $4,400/$8,750.
  • 457(b) PlansOverviewNo 10% early withdrawal penalty. Can stack with 403(b) or 401(k) for dual-eligible employees.
  • 529 vs Roth IRAComparisonThe honest comparison: 529 vs Roth IRA for college.
  • FSA vs HSAComparisonAn HSA is a stealth retirement account; an FSA is use-it-or-lose-it.
  • Kids & Money AccountsOverviewUTMA/UGMA custodial accounts, Roth IRAs for working teens, 529 vs custodial, and how to teach kids the financial concepts most schools never cover.
  • Pick 401(k) FundsGuideYour 401(k) has 20 fund options. You have no idea what they mean.
  • Roth 5-Year RulesExplainerThe Roth IRA has two distinct 5-year rules: one for earnings (tied to first contribution) and one per conversion.
  • SEP-IRAOverviewSimpler than Solo 401(k) with no Form 5500 ever. 25% of net self-employment income up to the annual cap.
  • TSP (Federal 401k)OverviewThe Thrift Savings Plan has the lowest expense ratios anywhere.
  • 401(k) LoansExplainerA 401(k) loan looks cheap because you pay interest to yourself, but the real cost is the growth you miss and the trap if you lose your job.
  • Choosing an HSA ProviderComparisonWhat to check before opening or moving an HSA for investing: custodian, fees, fund menu, cash thresholds, transfer rules, and where to compare…

Planning and living in retirement

  • FIREOverviewThe math, the Roth conversion ladder, healthcare coverage before 65, the 4% rule over 50 years, and how Bitcoin changes the FIRE timeline.
  • SS Claiming StrategyOverviewClaiming at 62 vs 67 vs 70 can mean $200,000+ difference in lifetime benefits.
  • The 4% RuleOverviewWhat the Trinity Study actually said. Why Pfau and Kitces argue 3.3% is safer today.
  • 2026 SS COLA & Wage BaseData2026 SS COLA 2.8%, wage base $184,500, earnings test thresholds, max benefit $4,152/month at FRA.
  • 72(t) SEPP RulesOverview72(t) SEPP lets you withdraw from an IRA before 59.5 without the 10% penalty.
  • Dividend Income FloorGuideThe core exit strategy: Bitcoin appreciation converted into a SCHD dividend income floor.
  • Healthcare Before MedicareOverviewMedicare starts at 65. If you retire at 45 or 50, you have 15-20 years of healthcare costs to cover privately.
  • IRMAAExplainerIRMAA adds about $81 to $487 per month to Medicare Part B premiums above income thresholds.
  • Required Minimum DistributionsOverviewRMDs force taxable withdrawals from pre-tax retirement accounts, and missing one is penalized.
  • Retirement CalculatorCalculatorInteractive FIRE calculator plus a Bitcoin retirement calculator.
  • Rule of 55GuideThe Rule of 55 lets you access your current 401(k) without the 10% penalty if you separate at 55+.
  • Sequence of Returns RiskAdvancedTwo retirees with identical average returns can have completely different outcomes based on the order.
  • Social Security SolvencyExplainerCBO projects the retirement fund depletes around 2032 with a 23% automatic cut absent action.

Tax strategy

  • Tax StrategyHubAsset location, Roth conversion ladder, tax-loss harvesting (including Bitcoin’s no-wash-sale advantage), Social Security optimization.
  • Asset LocationExplainerTax-inefficient assets (bonds, REITs) go in Roth or Traditional.
  • Backdoor Roth at FidelityGuideSix steps. Fifteen minutes. Contribute non-deductible to Traditional IRA, convert to Roth, file Form 8606.
  • Backdoor Roth How-ToGuideIf your income exceeds the Roth IRA limit, you can still contribute via the backdoor Roth.
  • High-Income Tax StrategyHubAbove the Roth IRA income limit, the standard playbook changes.
  • Mega Backdoor RothAdvancedIf your 401(k) allows after-tax contributions and in-plan Roth conversions.
  • NIIT and AMTAdvancedNet Investment Income Tax thresholds are not indexed for inflation, so more households trigger it every year.
  • Qualified DividendsExplainerQualified dividends are taxed at the lower long-term capital gains rate.
  • Roth Conversion LadderGuideIf you retire before 59.5, your 401(k) and IRA are locked behind a 10% penalty.
  • Roth Conversion TimingGuideRoth conversions pay off most in low-income years: early retirement, a gap year, or a layoff.
  • Roth ConversionsOverviewConvert Traditional to Roth in low-income years. Roth conversion ladder for early retirement.
  • State DomicileAdvancedMoving from California to Texas saves 13.3% on capital gains.
  • Tax-Gain HarvestingGuideIn a year when your income is low enough, you can realize capital gains at 0% federal tax.
  • Tax-Loss HarvestingGuideHow to harvest investment losses to offset gains. The wash-sale rule for stocks.
  • Withdrawal SequencingGuideWhich accounts to withdraw from first (and why conventional wisdom is often wrong).
  • NUA StrategyExplainerIf you have company stock in your 401(k) with significant appreciation.
  • QCDs from an IRAExplainerAfter 70.5 you can send up to $108,000 of IRA money straight to charity, tax-free, and count it toward your RMD.

Estate planning and legacy

  • Estate PlanningHubThe non-Bitcoin estate planning pieces: wills vs trusts, beneficiary designations that override your will, power of attorney.
  • Beneficiary DesignationsGuideThe contract that overrides your will. How to check and fix beneficiaries on every account.
  • Living Will & DirectiveGuideAn advance directive says who speaks for you if you cannot. The two documents every adult needs, why they are free, and why HIPAA makes them urgent.
  • Power of AttorneyGuideA financial POA lets someone manage your money if you can't.
  • Special-Needs PlanningGuideThe wrong account can cost a disabled person their benefits.
  • Stepped-Up BasisExplainerHeirs inherit at current market value, not your cost basis. Hold Bitcoin until death, borrow against it for cash, pass at death free of capital…
  • Will vs TrustComparisonBasic will, revocable living trust, pour-over will. When each applies, what each costs, and how Bitcoin fits into a trust structure.

Advanced topics and financial products

  • Annuities GuideOverviewSPIAs are useful longevity insurance. Variable annuities and equity-indexed annuities are usually oversold.
  • Equity CompensationGuideISOs, NSOs, RSUs, the 83(b) election, AMT, and what to do when your company IPOs.
  • ESPPOverviewA qualified ESPP with a 15% discount and a lookback is often the best benefit you have.
  • Find a Fee-Only FiduciaryGuideFee-only fiduciary, fee-based, and commission-based advisors are not the same.
  • AI & Financial AdviceExplainerAn AI chatbot is not a fiduciary, it has no duty of care, it hallucinates on niche questions, and it cannot pick stocks.
  • Concentrated StockOverviewWhen one stock is most of your net worth, the tax bill and the risk fight each other.
  • Covered-Call ETFsExplainerCovered-call ETFs like QYLD, JEPI and JEPQ pay 10-13% yields but trail the index by years.
  • Private Credit & EquityExplainerPrivate credit and private equity sell equity-like returns with bond-like volatility.
  • Product Marketing TacticsExplainerThe five behavioral tactics Wall Street uses to sell financial products: transference, framing, salience, shrouding, and complexity, plus the real…
  • Thematic ETFsExplainerThematic ETFs for AI, clean energy, and blockchain tend to launch after the hype peaks and lag ~30% risk-adjusted over 5 years.
  • Whole Life vs Term vs IULComparisonTerm life plus index investing almost always beats whole life and IUL.

Calculators for this topic

33 free calculators run in your browser; nothing you type is sent anywhere. Browse them by topic: Investing · Retirement · Taxes.

What percentage do I need to contribute to get my full 401(k) match?401(k) Match OptimizerHow much will my savings grow with monthly contributions and compounding?Compound Interest VisualizerWhat will I actually owe in federal and state taxes this year?Full Tax EstimatorAm I on track to retire based on my age and savings?Retirement On Track CheckShould I use a Roth or Traditional account, and does adding bitcoin change the answer?Roth vs Traditional CalculatorShould I claim Social Security at 62, 67, or 70?Social Security Break-EvenHow much federal tax do I actually owe across each 2026 bracket?Tax Bracket Visualizer (2026)How much can I withdraw from my IRA before 59 1/2 without the 10% penalty?72(t) SEPP Calculator

Last updated . UPDATED Educational content, not financial advice. Disclosures · How pages are reviewed

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