From pressure to peace
2027 Path Calendar
Five calm moves a month, twelve months in a row
Path to Sound Retirement
pathtosoundretirement.com
Do each month's moves in the month they belong, and the year stops feeling like pressure. The free calculators and Learning stay free; use them to turn worry into a plan you can follow.
months with hard deadlines
January (has hard deadlines)
Begin- Q4 estimated tax payment for 2026: Jan 15 (if you pay estimates)
- Missed Medicare sign-up? General Enrollment opens Jan 1
- Review beneficiaries on every account and policy
- Write down what "enough" looks like for 2027
- Run the free Retirement Calculator (Monte Carlo tests many market paths) with honest inputs
February
Gather- Save year-end statements for every account in one folder
- Check each tax form that arrives against your own records
- Read your success rate: how often the plan lasted in the test
- Emergency fund check: could it cover a surprise this month?
- List every subscription and recurring bill; cancel what no longer serves you
March (has hard deadlines)
Prepare- Medicare General Enrollment closes Mar 31
- Finish gathering tax paperwork well before Apr 15
- If eligible, decide on a 2026 IRA or HSA contribution (due Apr 15)
- Retiring before Medicare? Map your health coverage
- Confirm your RMD (required yearly withdrawal) starting age; it depends on your birth year (IRS.gov, your advisor)
April (has hard deadlines)
File- Reaching your RMD age in 2026? Your first required withdrawal is due Apr 1
- Federal filing deadline: Apr 15; an extension does not extend payment
- Q1 estimated tax payment for 2027: Apr 15 (if you pay estimates)
- Last day for 2026 IRA and HSA contributions: Apr 15
- File, then save a copy of your return with your records
May
Verify- Sign in to my Social Security and review each year of earnings
- Compare real spending with the spending you entered in the calculators
- Check your investment mix against your plan; rebalance only if it drifted
- Pick one Learning article on a worry and read it this month
- Find the yearly fee on each fund you own
June (has hard deadlines)
Midyear- Q2 estimated tax payment: Jun 15 (if you pay estimates)
- Pressure-to-peace check-in: what feels heavy, and what is one step?
- Project this year's income and taxes while you can still adjust
- Update calculator inputs with your real balances
- Plan one real rest this summer; the plan exists to serve your life
July
Steady- Change one lever at a time: spending, return, or timing
- Check your credit reports, free every week at AnnualCreditReport.com
- Walk someone you trust through your plan and invite questions
- Run a hard case: weak markets early. Write what you would do
- Celebrate one thing your money did for you this year
August
Guard- Set spending guardrails: preset rules for when to trim or raise spending
- Write your rules in plain words while markets are calm
- Size your cash buffer: money set aside so a bad market never forces a sale
- Ask when employer open enrollment starts; many hold it in the fall
- Draft your open enrollment questions before the window opens
September (has hard deadlines)
Align- Q3 estimated tax payment: Sep 15 (if you pay estimates)
- Open enrollment at work: read the options early and note the deadline
- On Medicare? Review your current plan before Open Enrollment (Oct 15)
- Book time for your annual retirement plan review
- Deciding when to claim Social Security? Work through the checklist
October (has hard deadlines)
Choose- Medicare Open Enrollment opens Oct 15; changes start Jan 1
- Extended filing deadline: Oct 15 (if you filed for an extension)
- Make your employer open enrollment choices, then confirm they went through
- Start your RMD plan: which accounts, how much, and when
- Rerun the calculator with fall balances and compare to January
November
Simplify- Giving from an IRA? A QCD (qualified charitable distribution) pays the charity directly
- Ask each custodian how long year-end transfers take
- Confirm your RMD amount for each account
- Tell your family where your documents and logins live
- Close or merge one account you no longer need
December (has hard deadlines)
Finish- Medicare Open Enrollment closes Dec 7; make your choice
- RMD deadline: Dec 31; a first-year RMD may wait until next spring
- QCD must be completed by Dec 31
- Hold your annual retirement plan review and save the notes
- Close the year with one more pressure-to-peace check-in
Education, not advice. Dates shift with weekends and holidays - confirm anything that affects your money with the IRS, SSA, Medicare, or a qualified professional.
Optional coaching is there if you want to learn the path with someone. Never required.