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#20
#20

Trading Options

InvestmentHard

Income Range

$500 - $20,000/month

Startup Cost

$2,000 - $25,000

Difficulty

Hard

First Dollar

Immediate (but losses equally immediate)

All 25 Side Hustles

Why It Ranks #20

Consistent income from existing capital when done correctly, but high barrier to entry and significant risk for the inexperienced. A side hustle for investors, not beginners.

The Full Breakdown

Options trading is the side hustle that can either accelerate your wealth or destroy it. I include it on this list because, when done correctly, selling options (not buying lottery tickets) creates consistent income from capital you already have. Covered calls and cash-secured puts are strategies that generate 1-3% monthly returns with defined risk.

The key distinction is between gambling and strategy. Buying out-of-the-money weekly calls on meme stocks is gambling. Selling covered calls on stocks you already own at prices you would be happy to sell at is a legitimate income strategy. Selling cash-secured puts on stocks you want to buy at prices below the current market is getting paid to place limit orders. These are not exotic strategies — they are the bread and butter of institutional investing.

That said, this ranks low on the list because the capital requirements are high, the learning curve is steep, and the psychological challenges are real. You need at least $10,000-25,000 in a brokerage account to make options income meaningful, and you need the discipline to stick to your strategy when positions move against you. If you do not have both the capital and the temperament, skip this and focus on the side hustles higher on this list.

Requirements

  • Options-approved brokerage account (Schwab, IBKR, TD Ameritrade)
  • Minimum $10,000-25,000 in investment capital
  • Deep understanding of options Greeks (delta, theta, gamma, vega)
  • Emotional discipline to manage positions through volatility
  • Understanding of risk management and position sizing

Tools Needed

1Interactive Brokers or Schwab (thinkorswim)
2Options profit calculator
3OptionStrat or OptiStrat for visualization
4Market data feed (Yahoo Finance, TradingView)
5Trading journal for tracking performance
6Books: Options as a Strategic Investment, The Options Playbook

Key Stats

Trading Options

Options Volume (US)

12B+ contracts/year

Covered Call Return

1% - 3%/month

Put Selling Win Rate

~80% for ATM puts

Capital Required

$10K - $25K minimum

Fun Facts

  • 1Approximately 77% of options expire worthless — which is why sellers (not buyers) have the statistical edge.
  • 2The CBOE S&P 500 BuyWrite Index has outperformed the S&P 500 on a risk-adjusted basis over 30+ years.
  • 3Warren Buffett uses options strategies extensively — Berkshire has sold billions in put options over the decades.

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