A Financial Checklist by Decade

A Financial Checklist by Decade 

By Drake Richey

Money planning isn’t about mastering every decade. It’s about seeing clearly where you are as a finite human being and responding wisely when you can’t see the future.

This isn’t a performance review. Rather, it’s an attempt to see where you are and gain insight into where your kids or parents might be.

In Your Teens: Awareness

This decade isn’t about wealth. It’s about understanding.

• Do you understand the rhythm of earning, saving, and spending?
• Have you seen how small choices compound over time?
• Are you developing an honest understanding of what it means to have very little, and to have a lot?
• Do you know who to ask when money feels confusing?
• What financial mistakes have you made (or are you about to make!)?

Reflection: What money stories are you absorbing, and which ones might not be yours to keep?

In Your 20s: Orientation

Urgency is common. Clarity is better.

• Do you know where your money goes each month?
• Are you building an emergency cushion?
• Do you understand basic tax and account structures, e.g. Roth vs. traditional, 401(k) vs. IRA? (Yes, you are allowed to Google this. Everyone does.)
• Are you contributing to retirement, even modestly?
• Are you setting adult goals beyond retirement, such as living independently, paying off debt, buying a small place, funding travel, marriage, or starting something of your own?
• Are you practicing generosity with both time and money?
• Are you aware of your risk tolerance and the insecurities that may be quietly shaping decisions?

Reflection: Are your financial choices coming from confidence, comparison, fear or clarity?

In Your 30s: Responsibility

Commitments expand. Flexibility often shrinks.

• Do you have a clear system for cash flow?
• As obligations grow, have you adjusted savings accordingly?
• Do you have appropriate insurance (life, disability, liability) to protect those who depend on you? Boring? Yes. Optional? No.
• If income stopped for six months, what would happen?
• Are major commitments aligned with your values or just momentum?
• If income is tied to equity or a business, do you understand the risk?

Reflection: Where have responsibilities increased faster than resilience?

In Your 40s: Ownership

You are no longer becoming an adult. You are one. Congratulations! No ceremony was provided.

• Do income, taxes, investments, and spending work together coherently?
• Are you thinking proactively about college funding without undermining your own future?
• Are your estate documents and beneficiaries current?
• Is your insurance appropriate for today’s obligations?
• Are you keeping financial products because they still fit, or because they’re familiar?
• If you own (or may start) a business, is your personal life protected from volatility?

Life may not look exactly as projected. This is a decade to adjust honestly, not nostalgically.

Reflection: Are you refining your financial life or reacting to its complexity?

In Your 50s: Endurance

Like miles 13–20 in a marathon, steadiness matters more than speed. This is why people either hydrate or run off the course.

• Do you know when work could become optional?
• As retirement approaches, are you honest about whether this is a season to rebuild, recalibrate, or reinforce savings?
• Are you and your spouse aligned about money and the next chapter?
• As your children become adults, are you teaching them how money works and not just supporting them financially?
• Are you protecting your focus, making intentional changes rather than drifting?

Reflection: Are you running your own race at a sustainable pace?

In Your 60s: Conversion

Savings turn into income. Work turns into time.

• Do you know (not just assume) that you have enough? “I think so” is not a strategy.
• Is your income plan understandable to you (and to someone else)?
• Are you working because you want to, or because you need to?
• If markets fall, do you know what changes and what doesn’t?
• If you gift to children or grandchildren, is it aligned with your values?
• Is your financial life becoming simpler?

Confidence in this decade comes from clarity.

Reflection: Are you using your resources in ways that reflect your values while you’re here to see the impact?

In Your 70s and Beyond: Stewardship

Complexity should begin to decline. Communication should increase.

• Is your financial life simpler than it once was?
• Does someone you trust know where everything is and how it works?
• Do your children know who your trusted financial, legal, and tax partners are?
• Is there continuity if those partners retire or step away?
• Are you actively living out your estate plan through conversations or thoughtful gifting?
• To quote David York: Do your children know what to expect, what not to expect, and what is expected of them?
• Are they prepared to manage what they may inherit? If not, have you created structures to help?

Estate planning becomes relational in this decade. Surprises are fun at birthdays, not estate readings. The goal is not only preserving assets, but preparing people.

Reflection: Have you made your financial life understandable and manageable for the people who may one day step in?

At any age, the central question remains: Is your financial life aligned with this season of your life? If you feel behind, welcome to being human. If you feel ahead, keep up the good work.