Learn index investing to a self-managed portfolio in two months
Two months of evening reading and one Saturday afternoon at a brokerage — about 25 hours total — gets a beginner from "I should probably start investing" to a three-fund portfolio they understand and won't panic-sell. The math is trivial. The discipline is the whole game.
2 months · ~25 hours · three-fund portfolio with automatic monthly contributions
1.The Little Book of Common Sense Investing — Jack Bogle
Read this before anything else. Bogle invented the index fund and ran Vanguard for thirty-five years; this short book is his pitch in 250 pages. The argument is simple: nobody beats the market consistently, costs compound brutally, so own the whole market through one cheap fund and stop touching it. Read it once, then keep it on the shelf for the next time a stock tip seems exciting.
~$18 hardcover
The Little Book of Common Sense Investing →2.The Bogleheads' Guide to Investing
The practical companion to Bogle's philosophy. Larimore, Lindauer and LeBoeuf walk through asset allocation, account types, tax-efficient placement, and how to actually structure a portfolio across 401(k), IRA and taxable accounts. Where Bogle gives you the religion, this book gives you the spreadsheet. Read chapters one through eleven; skim the rest as reference.
~$22 paperback
Bogleheads' Guide to Investing →3.bogleheads.org wiki — open the account, buy the funds
Open a Roth IRA and a taxable brokerage at Vanguard, Fidelity, or Schwab — they're functionally interchangeable and all charge zero commissions. Use the wiki's "Three-fund portfolio" page to pick the actual tickers (a US total-market, an international, a bond fund) at whichever brokerage you chose. Set automatic monthly contributions. Then leave it alone — that's the entire skill.
Free; expense ratios ~0.03–0.10% on the funds themselves
Three-fund portfolio wiki →If this doesn't fit you
If you genuinely will not remember to rebalance once a year, replace step three with a single target-date retirement fund matched roughly to the year you turn 65. It's a hair more expensive (around 0.08% vs 0.04%) and slightly less tax-efficient in a taxable account, but it auto-rebalances forever and removes the only manual decision the three-fund approach requires. For 95% of investors this is fine.
Why this path
Index investing is the rare field where the right answer has been known for fifty years and nobody disputes it among the people actually managing money. Bogle's book is the conviction; the Bogleheads book and wiki are the implementation. Skip stock-picking, options, crypto allocations, and anyone selling courses on "active strategies" — the data is unambiguous and the cost of being wrong is decades of compounding. The only way to fail this path is to keep tinkering.