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The Next Dollar · Free Resource

The Next Dollar Checklist

A practical worksheet of the categories worth working through before sending more money toward investing. No email required, nothing to sign up for — read it here or print it.

Work through each item for your own situation. None of this is a personal recommendation — see the disclaimer below.

01

Cash Reserves

A cushion of accessible cash for the unplanned, before money is tied up elsewhere.

  • How many months of essential expenses do I have in cash I could access quickly?
  • Is that cash earning anything, or sitting in an account that pays close to nothing?
  • How stable is my income, and how would that change how much cushion feels right?
02

Employer Retirement Match

Many employer retirement plans match a portion of what an employee contributes.

  • Does my employer offer a retirement plan match, and what's required to get the full amount?
  • Am I currently contributing enough to capture that full match?
  • Is there a vesting schedule that affects when that money is really mine?
03

High-Interest Debt

Debt above roughly 7–8% is a known, ongoing cost working against any return earned elsewhere.

  • What interest rate am I actually paying on each balance I carry?
  • How does that rate compare with what I'd reasonably expect from investing instead?
  • Would paying it down faster free up cash flow I'd value even beyond the math?
04

HSA (Health Savings Account)

For those who qualify, an HSA carries a tax treatment that other accounts don't fully replicate.

  • Am I enrolled in a health plan that qualifies me to contribute to an HSA?
  • Have I contributed enough to cover expected medical costs — or am I leaving room to invest it longer-term?
  • Am I keeping receipts if I'm paying medical costs out of pocket now to reimburse later?
05

IRA (Traditional or Roth)

An individual retirement account outside of a workplace plan, with its own yearly limit.

  • Have I contributed to an IRA this year?
  • Do I understand the difference between Traditional and Roth tax treatment for my situation?
  • Does my income affect my eligibility or the deductibility of a contribution?
06

Workplace Retirement Accounts Beyond the Match

Contributing beyond the matched amount, up to plan and IRS limits.

  • How much of my available contribution limit am I currently using?
  • Does my plan offer after-tax or “mega backdoor Roth” contributions beyond the standard limit?
  • How does contributing more here compare with other accounts I haven't funded yet?
07

Taxable Investing

A regular investment account with no contribution limit and no special tax treatment.

  • Have I worked through the accounts above, or is there a reason to prioritize this one first?
  • Am I comfortable with the tax treatment of gains and dividends in a taxable account?
  • Does the lack of withdrawal restrictions here matter for how I plan to use this money?
08

Near-Term Goals & Major Expenses

Money needed within the next few years generally carries different considerations than long-term savings.

  • Do I have a major expense planned in the next 1–3 years?
  • Is that money currently invested, or held somewhere more stable given the shorter timeline?
  • Would a market downturn at the wrong time change my plans for that goal?
Educational Disclaimer: This checklist is for educational and informational purposes only and does not constitute individualized financial, investment, legal, or tax advice. It does not recommend a universal order of operations, specific accounts, funds, or brokers — use it to identify what to research further, and verify current rules and eligibility with a qualified professional or plan documents before acting.