If you’re trying your hand at stock trading for the first time, know that focusing on anything but long-term results will expose you to frequent bouts of agita. Most investors are best served by keeping things simple and investing in a diversified mix of low-cost index funds to achieve — and this is key — long-term outperformance. Because, oof… the short-term ups and downs in the market can be brutal.
Keep good records for the IRS. If you’re not using an account that enjoys tax-favored status — such as a 401(k) or other workplace accounts, or a Roth or traditional IRA — taxes on investment gains and losses can get complicated. The IRS applies different rules and tax rates, and requires the filing of different forms for different types of traders. (Here’s an overview of the IRS rules for stock traders.) Another benefit of keeping good records is that loser investments can be used to offset the taxes paid on income through a neat strategy called tax-loss harvesting.
IMPORTANT – Like paid subscriptions, be careful with classes and courses. Most are easily over $1,000 and are sold with false promises to acquiring valuable knowledge. Their fantastic sales funnels will suck you in, take your money, excite you during the course, then leave you with a strategy that wasn’t even profitable to begin with. See, 10 Things I Wish I Knew About Trading Before I Got Started.
Find a good online stock broker and open an account. Become familiarized with the layout and to take advantage of the free trading tools and research offered to clients only. Some brokers offer virtual trading which is beneficial because you can trade with play money (see #9 below). A great tool for comparing online brokers can be found at StockBrokers.com.
Thinkorswim, on the other hand, is a powerhouse designed for the advanced. This desktop application regularly racks up awards for its superior tools and features, things any other broker would charge a premium for — research reports, real-time data, charts, technical studies. Also included: customizable workspaces, extensive third-party research, a thriving trader chat room, and a fully functional mobile app.
A mentor could be a family member, a friend, a past or current professor, co-worker, or any individual that has a fundamental understanding of the stock market. A good mentor is willing to answer questions, provide help, recommend useful resources, and keep spirits up when the market gets tough. All successful investors of the past and present have had mentors during their early days.
Learning about the greatest investors of years past will provide perspective, inspiration, and appreciation for the game which is the stock market. Greats include Warren Buffett, Jesse Livermore, George Soros, Benjamin Graham, Peter Lynch, John Templeton and Paul Tudor Jones, among others. One of my favorite book series is the Market Wizards by Jack Schwager.

Measure your returns against an appropriate benchmark. This is essential advice for all types of investors — not just active ones. The bottom-line goal for picking stocks is to be ahead of a benchmark index. That could be the Standard & Poor’s 500 index (often used as a proxy for “the market”), the Nasdaq composite index (for those investing primarily in technology stocks) or other smaller indexes that are composed of companies based on size, industry and geography. Measuring results is key, and if a serious investor is unable to outperform the benchmark (something even pro investors struggle to do), then it makes financial sense to invest in a low-cost index mutual fund or ETF — essentially a basket of stocks whose performance closely aligns with that of one of the benchmark indexes.
Robo-advisors like Wealthsimple, Wealthfront, and Betterment use algorithms to determine your investment strategy. You just plug in your time frame and risk tolerance and their computers do the rest. And because they’re targeted for a younger crowd, fees are rock bottom. Wealthsimple and Betterment both have no account minimum, while Wealthfront requires $500. Wealthsimple charges an annual 0.5% advising fee; Wealthfront and Betterment charge just 0.25%.

Warren Buffett is the best example to hit this point home. In 2008, he bet some hedge fund managers $1 million that they wouldn’t be able to make more money in a decade than a cheap, boring index fund. An index fund uses simple investing algorithms to track an index and doesn’t require active human management. Conversely, hedge funds stack management fees on top of trading fees to pay for the time and knowledge actual strategists are putting into your investments.

If you trade stock regularly, you might find yourself accidentally violating the dreaded wash-sale rule. This means you've sold shares of stock and then bought the same or similar shares shortly thereafter. This can cost you huge tax penalties. With a little planning, you can avoid this fate and still enjoy trading stocks aggressively with a little planning. 


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