5 Money Moves People Regret Not Making in Their 20s (and How to Fix Them Now)

July 28th, 2025

5 min read

5 Financial Decisions People Wish They’d Made in Their 20s — and How to Address Them Today

Many people look back on their 20s with financial regret, but it’s never too late to get back on track. Here are five smart money moves to make now, plus a better way to handle shortfalls without turning to payday loans.

5 Financial Decisions People Wish They’d Made in Their 20s — and How to Address Them Today

If you're reading this in your 30s or later, chances are you've had moments where you've wished you'd managed money a little better in your 20s. It's easy to reflect on the past and think, "If only I'd known…"—but here's the great news: it's never too late to change course. The financial knowledge you lacked a decade ago can still affect your future in some really profound ways.

Here are five crucial money moves that most people regret not doing in their 20s—and realistic, achievable steps to take today.

1. Invest Earlier – Even A Little

What they regret

Waiting on investment because they didn't think they had enough to make it worth it—or they were scared of the stock market or retirement nomenclature.

Why it mattered

Even small weekly payments can compound to astounding levels over decades. Delaying until age 30 or 40 means having to work much harder later, just to get back on track.

How to correct it now

Start with low-expense index funds or retirement accounts that automatically invest. Most sites now allow you to begin with just $50 a month. Set up automatic contributions—no delay. If you can't save much at the start, create micro-investing: round up your transactions or direct spare change into index funds. Slowly but surely, this cultivates habit and wealth.

2. Create Credit with Purpose, Not Fear

What many later regret

Steering clear of any use of credit for fear, believing credit cards always result in debt.

Why it mattered

Good credit opens doors—better loan terms, easier housing approval, and more financial freedom. Without it, many pay more in the end or struggle to get basic services.

How to fix it now

Select one low-limit, low- or no-fee credit card and charge it for a regular known expense—such as a subscription or utility—and pay it in full each month. This establishes credit without risk or interest. Check your credit score periodically. When rebuilding, use a secured card or credit-builder loan.

3. Negotiate Salary (or Request Raises)

What many regret

Just taking entry-level wages or forgoing a first raise—assuming, "That's just how it is."

Why it mattered

Your initial salary can set your earnings path for decades. Even a 5% higher wage amplifies with raises, bonuses, and savings that grow over time.

How to fix it now

Research competitive rates for your position and location. Practice negotiating salaries—or raise requests—in advance. If you're freelancing or doing gig work, bump up your rates slightly or bid a bit higher on client work. When you change jobs, negotiate the offer. It doesn't have to be aggressive—call it fighting for your worth.

4. Save for Emergency Funds Early

What many regret

Skipping saving when you first start out, thinking emergency savings were for "when I have more money."

Why it mattered

Things come up—the car breaks down, medical bills arrive, paycheques are late. Without a cushion, individuals get into high-interest debt or self-destructive patterns before age 30.

How to fix it now

Don't wait to save thousands. Target $500 or a week's expenditure as a starting fund. Automate a weekly or bi-weekly small transfer—$10 or 2% of your net income—into a side account. Consider it non-negotiable fixed savings. Once a baseline is established, incrementally raise it.

5. Master Cash Flow Timing

What many regret

Overlooking paycheque timing differences—such as rent owing before payday—or missing bill payments due to timing lapses.

Why it was important

They result in late charges, stress, credit penalties, and the temptation to take on short-term borrowing at high expense.

How to repair now

Monitor your cash flow: note your paydays and significant expenses on a weekly summary instead of a monthly budget. If your income timing continues to rub you the wrong way, explore tools with early access to your pay—this assists with bridging those short spaces without leaping into high-interest debt. For instance, a wage advance app can provide get your pay early features, allowing you flexibility when weeks don't fit.

Cash Advance vs Payday Loan: A Wiser Solution to Financial Shortfalls

Reflecting on lost financial possibilities tends to introduce an added sense of haste when dealing with money today. Whether it's saving, keeping up with debt, or just paying the monthly bills, too many find themselves resorting to quick-cash solutions when the stakes are high. But all solutions are not created equal.

This is where the difference between a cash advance vs payday loan matters. Payday loans are easy to get, but they often come with steep fees, tight repayment windows, and a cycle that’s hard to break. On the other hand, wage advances through a pay advance app offer a more flexible, lower-risk way to get through shortfalls without spiralling into debt. Instead of borrowing from a lender, you’re simply accessing the money you’ve already earned.

Sites like Wagetap let you get your pay ahead of time, offering you advance access to your pay when surprise expenses strike—no credit check and no lengthy paperwork.

Because sometimes, repairing yesterday's errors begins with making smarter choices today

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