Now come the questions.
When should you tell your employer? When do you contact Social Security? What happens to your health insurance and workplace retirement account? Which forms do you need—and who are you supposed to call?
Take a breath. You do not have to understand every retirement rule today. Start with these seven basic steps, keep a record of each decision and use the linked RetireNerd guides when you are ready for more detail.
Your Retirement 101 starting point
- Choose a working retirement date.
- Decide when to claim Social Security.
- Arrange health coverage.
- Call the right people.
- Decide what to do with workplace retirement accounts.
- Complete the paperwork.
- Confirm the plan before your final workday.
1. Choose a working retirement date
Pick a tentative last day of work. It does not have to be permanent yet, but you need a date before you can organize the decisions around it.
Your retirement date can affect your final paycheck, employer health coverage, pension start date, Social Security timing, Medicare enrollment, retirement-plan contributions and the month you first need money from savings.
Your first call
Contact your employer’s human resources or benefits department before submitting a formal retirement notice. Ask:
- When will my employee health coverage end?
- What happens to unused vacation or paid leave?
- When will my final paycheck arrive?
- Do I have a pension or retiree-health benefit?
- Which retirement forms will I receive?
- Is there a deadline for giving notice?
Go deeper: Build your Retirement Roadmap to see which decisions and deadlines may apply to your age and timeline.
2. Decide when to claim Social Security
Retiring and claiming Social Security are two different decisions. You can stop working before you claim, claim while you continue working or do both at about the same time.
Start by signing in to your my Social Security account. Review your earnings record and benefit estimates. If any earnings are missing, address that before choosing a claiming date.
Social Security allows you to apply up to four months before you want retirement benefits to begin. Before applying, compare your estimated monthly benefit at the ages you are considering and think about spouse and survivor benefits when they apply.
Where to go and who to call
- Apply online at SSA.gov/apply.
- Call Social Security at 1-800-772-1213 if you need help.
- Call before visiting a Social Security office to ask whether you need an appointment.
Go deeper: Read the RetireNerd Social Security Guide before making the claiming decision.
3. Arrange health coverage
Do not leave work until you know the exact date your employer health coverage ends and what will replace it. A verbal assumption is not enough. Ask for the date and your options in writing.
If you will be younger than 65
Possible coverage sources include a spouse’s employer plan, COBRA, retiree coverage or a Health Insurance Marketplace plan. Compare the full premium, deductible, provider network and prescription coverage—not only the monthly price.
Go deeper: See Health Insurance Before Medicare.
If you are 65 or older
Find out whether you need Medicare Part A and Part B when your employment or job-based coverage ends. Medicare says the employment-based Special Enrollment Period can last up to eight months after employment or qualifying job-based coverage ends, whichever happens first. COBRA and retiree coverage do not extend that deadline. If you want Part B to begin when employer coverage ends, Medicare advises enrolling before retirement rather than waiting until the end of the eight-month period.
- Call Medicare at 1-800-MEDICARE (1-800-633-4227).
- For free, independent Medicare counseling, contact your State Health Insurance Assistance Program through SHIP or call 877-839-2675.
Go deeper: Start with the RetireNerd Medicare Guide.
4. Call the right people
You probably do not need to call everyone below. Use this list to identify the people and organizations connected to your retirement.
| Who to contact | What to ask | When |
|---|---|---|
| Employer or HR | Final pay, benefits end date, unused leave and retirement forms | Before giving formal notice |
| Pension administrator | Benefit amount, start date, payment choices and survivor options | Several months before retirement |
| Social Security | Earnings record, estimates and application status | Before claiming; apply up to four months before benefits start |
| Medicare or SHIP | Enrollment dates and coverage choices | Before employer coverage ends |
| Workplace-plan administrator | Fees, distribution choices and rollover procedures | Before moving or withdrawing money |
| Tax professional | Withholding, estimated payments and taxable withdrawals | Before the first large distribution |
| Financial adviser or custodian | Investments, cash reserves and first withdrawals | Before retirement income begins |
| Estate attorney | Will, trust and powers of attorney | Before or soon after retirement |
Keep notes from every important call. Record the date, telephone number, representative’s name, what was decided and any confirmation number.
Use telephone numbers from official statements or websites. Do not give personal or account information to someone who contacts you unexpectedly. See How to Protect Your Retirement Savings From Scams.
5. Decide what to do with workplace retirement accounts
Leaving a job does not automatically mean you must withdraw or move your 401(k), 403(b) or other workplace retirement account.
Depending on the plan and your situation, your basic choices may include:
- Leaving the money in your former employer’s plan
- Rolling it into another employer’s plan, if that plan accepts rollovers
- Rolling it into an IRA
- Taking some or all of the money as a distribution
Do not request a check payable to you until you understand the tax consequences. The IRS says eligible workplace-plan distributions paid to you are generally subject to 20% federal withholding, even when you intend to complete a rollover later. A direct rollover can avoid that mandatory withholding.
Your next call: Ask the plan administrator for its written distribution and rollover instructions. Compare fees, investment choices, services and withdrawal options before deciding.
Go deeper: Read the 401(k) and Retirement Savings Guide.
6. Complete the paperwork
Create one retirement folder. It can be paper or digital, as long as you and a trusted person know where it is.
Documents you may need
- Your written retirement notice
- Employer benefit and health-coverage information
- Pension election and survivor-benefit forms
- Social Security application confirmation
- Medicare enrollment forms and coverage confirmations
- Retirement-account statements and rollover instructions
- Tax-withholding elections
- Direct-deposit information
- Beneficiary confirmations
- Your will, powers of attorney and healthcare documents
Keep copies of every submitted form. A screenshot or confirmation email can be valuable when a start date or election is later questioned.
Go deeper: Use Taxes and Paperwork and the Retirement Checklist and Glossary.
7. Confirm the plan before your final workday
A week or two before leaving, perform one final check.
Final-workday checklist
- My final paycheck and unused-leave treatment are confirmed.
- I know the exact date my employer health coverage ends.
- My next health coverage is arranged.
- My Social Security and pension start dates are confirmed, if applicable.
- I can access every retirement and bank account.
- I know where spending money will come from during the first few months.
- I have considered tax withholding.
- My beneficiaries and contact information are current.
- I saved copies of important forms and confirmations.
If one item is unresolved, that does not automatically mean you cannot retire. It means you have identified the next question to answer.
Run a final check: Use the Retirement Readiness Check.
What about spending, savings, taxes and withdrawals?
Those questions matter, but you do not have to solve them all inside this checklist. RetireNerd has separate guides and tools that walk through each subject:
- Estimate what retirement will cost: Retirement Spending Planner
- See how much spending savings must cover: Spending Gap Calculator
- Check your savings: Retirement Savings Benchmarks
- Plan your first withdrawals and cash reserve: 24-Month Withdrawal Planner
- Understand long-term withdrawals: Retirement Withdrawal Strategies
- Review debt and mortgage choices: Retirement Calculators and Tools
- Test the complete plan: Compass® Retirement Planner & Modeler
- Prepare for the transition after work: The First 90 Days of Retirement
Start with one call
Retirement does not begin with one perfect calculation. It begins with a date, a few important phone calls and a clear list of what comes next.
If you feel overwhelmed, make the first call to your employer’s benefits department. Confirm when your coverage ends and ask for your retirement paperwork. Then move through the remaining steps one at a time.
You have already made the biggest decision. Now you can turn it into a plan.
Educational information: This article provides general retirement-planning information. Deadlines and choices can depend on your age, employer coverage, plan documents and personal circumstances. Confirm important decisions with the applicable agency, plan administrator or qualified professional.