When Should I Start Investing? Why Starting Small Beats Waiting to Go Big

The tree you wish you'd planted

You've heard it before:

"The best time to plant a tree was 20 years ago. The second-best time is today."

It's cliché for a reason. But when it comes to investing, this principle holds up.

Here's what most people misunderstand: the goal isn't to time the market. What matters is giving your money time in the market.

And the earlier you start—even with small amounts—the more freedom you create down the road.

Compound interest favors the early starter

Let's compare two fictional investors:

Ava starts investing $250/month from age 20 to 30, then stops.

Ben waits until age 35, then invests $400/month until 65.

At 7% annual returns, Ava only contributed $30,000 total. Ben contributed $180,000.

Yet Ava ends up with more by retirement.

Why? Time. Her money had more years to compound.

The early start is worth more than higher contributions later.

Starting small is better than waiting to go big

Many 20- and 30-somethings think, "I'll start investing when I make more, when I have no debt, when life calms down."

But those windows often don't open for a while. If ever.

Start small. $100/month is better than zero. Set up an automated transfer. Make it invisible.

"Wealth gained hastily will dwindle, but whoever gathers little by little will increase it." — Proverbs 13:11

Investing is a long game. Small, consistent deposits beat big, inconsistent ones every time.

You don't need to be an expert to begin

You don't need to know everything. You just need to start.

Pick a simple, low-cost index fund in a Roth IRA. Or use your 401(k) at work and get the match. That's a win.

Don't let perfectionism be your excuse. It's like waiting to get in shape until you understand every muscle group. Just start walking.

Business owners: this is for you, too

Business owners are often the worst at investing for their future.

You pour everything into the business. That's great—for a season.

But at some point, you need to build wealth outside the business too.

What if your business doesn't sell? What if the market shifts?

A SEP IRA, Solo 401(k), or simple brokerage account can help you build wealth and reduce taxes.

Start with what you can. Don't wait until you "make it."

The market will always feel uncertain

Waiting for a "better time" to invest is like waiting for the perfect weather to go on a hike.

It'll never come.

Every decade has had a reason to stay on the sidelines: dot-com bust, 2008 crash, COVID, inflation, elections.

But if you had stayed invested through it all? Your portfolio would likely have grown a lot.

Start today—however small

The goal isn't to hit a home run. It's to get in the game.

Start with what you can, where you are. Stay consistent.

Over time, it adds up to freedom.

"Gather little by little." It's not just wise—it works.

Want some help thinking this through?

I did too. That's part of why I started my financial planning firm—to walk with folks like you through decisions that feel complicated, but don't have to stay that way.

If you've got questions, reach out. I'm a real person, and I won't pressure you into buying products you don't need. You don't have to navigate this alone.

📩 [Email Me] or 📞 [Schedule a Call]

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