Preparing for Retirement? Your Step-by-Step Financial Checklist

When retirement is 5 to 15 years away, your assets are often scattered across multiple 401(k) accounts, IRAs, bank accounts, and debt obligations. Organizing these moving parts into a cohesive retirement planning guide is critical to knowing if you are truly on track. Our Retirement Financial Health Checkup workbook gives you an instant, itemized framework to audit your numbers and take control of your financial timeline today.

Key Takeaways

• Structured Assessment: Reviewing your finances across key categories highlights structural income gaps long before you leave the workforce.
• Itemized Expense Planning: Moving from general savings goals to itemized cash-flow modeling provides clarity on your real monthly living costs.
• Gap Mitigation: Identifying potential shortfalls early lets you leverage catch-up contributions, debt payoff plans, or annuities to establish a predictable income floor.

The 7-Part Retirement Readiness Checklist

Use this structured overview from our workbook to do an immediate baseline check of your retirement preparation.

Check Your Financial Health Today — Download the Workbook

1. Total Up Your Savings and Assets

What counts as a retirement asset

Catalog all liquid balances, high-yield certificates of deposit (CDs), bonds, fixed annuities, equities, real estate equity, and life insurance cash values. Over-concentrating assets in a single stock or sector increases portfolio vulnerability as you near retirement. Spreading assets across distinct options provides stability and protects underlying principal from broader market downturns.

2. Review Your Contributions

Are you using catch-up contributions?

If you are age 50 or older, workplace 401(k) or 403(b) plans, IRAs, and Health Savings Accounts (HSAs) allow additional annual catch-up contributions. Maximizing these contributions accelerates tax-deferred accumulation during your final working years. Read our dedicated catch-up contribution guide to explore current tax rules and funding options.

3. Build a Debt Payoff Plan

Eliminating high-interest debt before your last day of work significantly lowers your required monthly income. Prioritize credit cards and personal loans, then design a mortgage payoff schedule aligned with your retirement date. Entering retirement debt-free protects your liquid assets from ongoing interest drag.

4. Estimate Your Healthcare and Living Costs

Medicare basics

Original Medicare coverage begins at age 65, but it does not cover all prescription, dental, vision, or long-term care expenses.

Budgeting for the costs people forget

Data from the Center for Retirement Research at Boston College shows that median retiree out-of-pocket healthcare expenses were $5,444 per year in 2022 (roughly $453 per month). Beyond medical expenses, build line items for home maintenance, travel, hobbies, and long-term inflation.

5. Shore Up Your Emergency Preparedness

Maintain 3 to 6 months of living expenses in accessible liquid accounts. Audit your insurance coverage—including long-term care and home coverage—and verify estate planning essentials such as your will, trust, power of attorney, healthcare directives, and primary account beneficiaries.

6. Decide Whether You Need Professional Guidance or Part-Time Income

If your cash-flow projection indicates a potential deficit, transitioning into part-time consulting can bridge the gap. There are also other products, including annuities, that can help provide additional asset growth before retirement or income during retirement. Canvas has dedicated, US based agents that can provide information on contract structures and income strategies without sales pressure.

Could a Retirement Strategy Gap Need an Annuity?

If your predictable income sources fall short of your baseline monthly bills, adding a Canvas annuity can help close the gap.

• Future Fund: A Multi-Year Guaranteed Annuity: best for tax-deferred growth and protection from market volatility. It offers 3, 5, or 7-year terms, predictable fixed returns, 10% annual penalty-free withdrawals, and a surrender-charge-free death benefit.
• Forever Fund: A Single Premium Immediate Annuity: converts savings into an immediate monthly "paycheck for life." Features include single or joint coverage, flexible cash or installment refund options, and an optional 3% annual increase to combat inflation.

Get Your Personalized Retirement Financial Health Checkup

Take control of your retirement advice and timeline with simple, clear tools.

Download the Retirement Financial Health Checkup workbook here.

Looking to run your own scenarios? Use our direct online annuity calculator or connect with our non-commissioned U.S.-based licensed representatives. Issued by Puritan Life Insurance Company of America (AM Best rating B++, A+ rated by the Better Business Bureau), Canvas products require no middlemen, charge zero agent commissions or hidden account fees, and can be completed online in minutes—all backed by a 30-Day Money Back Guarantee, no questions asked (see policy for terms and conditions).

Frequently Asked Questions

What should be on a retirement checklist?

A comprehensive retirement checklist covers seven primary areas: total savings and assets, contribution rates, debt payoff timelines, expected income streams, estimated healthcare and living costs, emergency preparedness, and overall portfolio distribution strategies.

How many years before retirement should I start preparing?

While saving begins early in your career, itemizing costs and using a detailed retirement planning guide should begin 5 to 10 years before your target retirement date.

What's the biggest retirement expense people underestimate?

Healthcare costs are frequently underestimated; CRR at Boston College reported a median annual cost of $5,444 in 2022. Ongoing home maintenance and cumulative inflation are also major unbudgeted expenses.

Can an annuity help fill a retirement income gap?

Yes. Fixed annuities offer protection of principal and predictable returns, helping bridge the timeline between your retirement date and Social Security or providing a steady, lifelong monthly income.

Do I need a financial advisor to prepare for retirement?

Not necessarily. Canvas offers direct online self-service educational tools and simple online purchasing so you can execute your plan independently. If you have questions, our non-commissioned licensed representatives are available to provide information without a sales pitch.

Want to learn more? Download the Retirement Financial Health Checkup here.

The Future Fund is a single premium deferred annuity, form number ICC20-PLICA-CANVAS, and applicable state variations. The Forever Fund is a single premium immediate annuity, form number ICC25-PLICA-SPIA, and applicable state variations. The Future Fund permits up to 10% in annual withdrawals without surrender charges. Withdrawals above this amount may incur a surrender charge and are taxed as ordinary income. Withdrawals before age 59½ may also be subject to a 10% federal income tax penalty. The Forever Fund does not have a cash value and cannot be surrendered once issued. Canvas Insurance Agency LLC ("Canvas") is a licensed insurance agency. All annuity policies sold by Canvas are issued by Puritan Life Insurance Company of America ("Puritan Life") (NAIC #71390), domiciled in Arizona and headquartered in Scottsdale. A.M. Best assigns ratings from A++ to S based on a company's financial strength and ability to meet obligations to contract holders. Puritan Life has received a B++ (Good) financial strength rating, the 5th highest of 16 ratings, originally issued 3/1/2018 and reaffirmed 2/20/2026. Products and features may vary by state and are not available in all states, including New York. Canvas is licensed in 45 states and the District of Columbia, with license numbers 3000819852 in Arkansas and 6002060 in California. All quotes are non-binding and do not guarantee insurability. Neither Puritan Life nor Canvas provide legal, tax, or financial advice. Please consult appropriate professionals for advice specific to your situation. The information provided is intended for use by the general public and is not individualized to address any specific investment objective. Annuities are insurance products. Not FDIC/NCUSIF Insured • Not a Bank Deposit • Not Insured by Any Government Agency. Rates and payment options are subject to change. Using qualified funds to purchase an annuity does not provide additional tax deferral. CDs are bank and credit union deposit accounts insured by the FDIC or NCUA and are distinct from annuities in their characteristics and purposes.