Guide to Investing: Navigating Financial Challenges

If your goal is anywhere from three to 10 years away, you might take more of a hybrid strategy. If you want to buy a home in five years but can be a little flexible on timing, you might invest one half in a savings account and the remainder in a fund balanced between stocks and bonds.

“A good rule of thumb is to expect that in any given year you could lose half of whatever money you have in the stock market,” Mr. Becker said. “Of course, you would also expect to recover that over time, but over shorter time periods that may be harder to do.”

If you want to buy a home in five years from now or longer and know you’ll need at least $60,000, he said you might put half of your monthly savings into a savings account or a certificate of deposit, while the other half goes into a taxable brokerage account that holds something like Vanguard’s LifeStrategy Moderate Growth Fund, which is 60 percent stocks and 40 percent bonds. That means you’d have about 30 percent of your money in stocks — in other words, 15 percent of your savings could vaporize in a down market. For absolutely certainty your money will be there by a certain date, use a high-yield savings account.

Where should I go to get started?

Outside of a solid employer-sponsored retirement plan, the best place to get started is at one of the brokerages where you can gain access to index funds with ease — Fidelity, Schwab and Vanguard all provide solid options for entry-level investors, for example, depending on your personal preferences.

You might also consider a so-called roboadviser, which will ask you a series of questions before formulating an automated investment plan for a specific goal. Several of them also offer help from human advisers for an extra fee.

The Robo Report, which tracks and analyzes roboadvisers, ranked Betterment as its top pick for entry-level investors.

“Their platform is intuitive and simple, has a $0 minimum balance and has a high-interest savings account for cash reserves,” said Ken Schapiro, president at Backend Benchmarking, which publishes The Robo Report. “They have strong online features, and a client can easily graduate from their digital-only service to their service with live advisers as their needs grow.”