A common question new investors have is: “How do I time the stock market?”

In reality, trying to time the market is one of the biggest mistakes new investors make. Clickbait headlines scream “Recession ahead!” or “Stocks at record highs!” and emotions start pulling you in every direction.

The result? Hesitation, missed opportunities, or buying at the wrong time. Instead of trying to outguess the market, smart investors learn to work with it.

Why Most People Get This Question Wrong

The average investor doesn’t miss because of bad math. They miss because they don’t have a strategy and without one, emotions run the show instead of data.

• Fear of Missing Out (FOMO): Jumping into meme stocks or Tik Tok plays because “everyone else is making money.”
• Waiting for perfection: Holding out for the absolute lowest price, which almost never comes and usually leaves you sitting on the sidelines while others are already building wealth.
• Analysis paralysis: Research is critical, but eventually you have to act. If you keep waiting for the “perfect” entry, you’ll end up sabotaging yourself and never investing at all.

The Best Time to Buy: Long-Term View

If you zoom out, history shows that the best time to buy stocks is whenever you have money to invest.

Why? Because time in the market matters more than timing the market.

Here’s how I recommend approaching it:

• Automate your investing. Set up automatic transfers into your brokerage account every month or pay period. Once the money is there, you’re more likely to put it to work  and you’ll be ready to take advantage of opportunities when they present themself.

But automation alone isn’t enough. You also need a framework, so you know when and how to act once the money hits your account.

My Strategy for Buying Stocks

1. Build a Watchlist.
Pick 5–10 companies (or ETFs) you know, use, and understand. Apple if you’re on an iPhone. Netflix or Disney if you stream movies. Lowe’s if you’re a DIYer. Or a tech ETF like XLK if you want exposure to the entire sector. The point is: invest in what you understand so you can follow it closely.

2. Establish Tiered Entry Points.
Once you’ve researched your watchlist and identified good fits for your portfolio, set clear price levels for when you’ll invest. This removes emotion from the process and answers the original question: “When should I buy?”

Here’s an example using Disney (currently around $117):

• Tier 1 – Entry Price: Where you’re comfortable starting a small position ($100-105).
• Tier 2 – Double Down: A stronger opportunity to add ($88-$92).
• Tier 3 – Go All-In: A very attractive level to significantly increase your stake ($80 or lower).

By setting these tiers in advance, you avoid chasing headlines and let the market come to you.

Pro Tip: Use AI tools like ChatGPT to spot historical patterns, compare valuations, and even set alerts for your tier prices. It helps you stay disciplined and flags risks you might otherwise miss.

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Final Word

Don’t worry about timing the market. Instead use a strategy like the one above and just get in. If you’ve got a crystal ball and can predict the exact bottom at the exact time, congrats you don’t need this article.

For the rest of us it’s not about chasing the lowest price point, It’s about consistency, discipline, and having a plan that keeps emotions out of the driver’s seat. Automate your contributions, build a watchlist you understand, and set clear entry points. That way, you’re never guessing, you’re just executing.

If you found this helpful, join my newsletter for more simple, actionable investing strategies. And don’t miss my free Savvy Investor AI Toolkit — it’s loaded with AI-powered prompts to help you research stocks, build smarter portfolios, and invest with confidence.