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.
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?
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?
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?
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?
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?
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?
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?
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?