Planning for retirement can feel overwhelming, but breaking it into manageable steps helps you stay on course. At Spitfire Financial here in Billings, we’ve helped many Montanans map out this journey. Use this local-focused “retirement checklist” as a guide to see whether you’re headed in the right direction, and where you may want to adjust.
Pro tip for Billings-area readers: Incorporate Montana‐specific tax rules, cost of living projections, and healthcare options into your planning. Local context matters.
Define your retirement vision and timeframe
Start with the “why.” How do you want to spend your retirement years? Some common scenarios:
- Staying in Billings or elsewhere in Montana
- Downsizing, relocating, or becoming snowbirds
- Part-time work, volunteerism, or starting a passion business
Travel, hobbies, or family commitmentsThen decide on a target retirement date (or window). Use this to build backward: what must you have in place 10 years out, 5 years out, and 1 year out?
Assess income sources & estimate income needs
You’ll want to account for every potential source of retirement income and compare that to your projected expenses.
Sources to consider:
- Social Security benefits
- Employer pensions or retirement plans (401(k), 403(b), Montana state retirement systems)
- IRAs: Traditional and Roth
- Taxable investment accounts, real estate income
- Part-time work or consulting
- Other sources (annuities, royalties, etc.)
Estimate your expenses:
Create a budget for life in retirement and include housing, utilities, insurance, travel, health care, leisure. Note that your spending pattern may shift (more travel or health costs, less commuting).
Plug your income estimates and expenses into a model. If projected income falls short, you should (a) adjust your retirement age, (b) increase savings now, or (c) temper expenses later.
Review and optimize retirement accounts
A thorough review of your retirement accounts can reveal opportunities to tighten your trajectory:
- Check your current balances, performance, and fees
- Consider consolidating multiple accounts for easier oversight
- Adjust your portfolio allocation as retirement nears (shift gradually toward more conservative holdings)
- Make “catch-up” contributions if you’re age 50 or older
- Confirm if you have employer matches or other benefits you’re not fully using
Vanguard’s guidance on a retirement planning checklist emphasizes that gradual rebalancing and periodic evaluation are critical moves.
Determine timing of Social Security and withdrawal strategy
Social Security timing:
You may begin taking Social Security as early as age 62, but doing so usually results in reduced benefits. Waiting until your full retirement age (or beyond, up to age 70) boosts benefits. Weigh this decision carefully, especially if you’re married or have health considerations.
Withdrawal sequencing:
You’ll need a strategy for drawing down your accounts. For example:
- Which bucket to tap first (taxable, tax-deferred, Roth)
- When Mandatory Required Minimum Distributions (RMDs) kick in
- How to structure withdrawals so your savings last
Address healthcare, insurance, and risk planning
Healthcare is often one of the largest uncertainties in retirement. Key steps:
- Understand Medicare eligibility and coverage options (Parts A, B, D)
- Select supplemental or Medigap plans if needed
- If retiring before age 65, plan interim coverage (COBRA, spouse plan, ACA marketplace)
- Evaluate long-term care insurance (or self-funding)
- Review life insurance, disability, and liability coverage
Also consider legacy planning: wills, powers of attorney, health care proxy, estate tax planning, and beneficiary designations on your retirement accounts.
Eliminate or reduce debt and large upcoming obligations
Entering retirement with heavy debt can eat into your fixed income. Key moves:
- Pay off high-interest debt (credit cards, personal loans)
- Decide whether to eliminate mortgage (if any) or downsize your home
- Defer or pay off car loans, major home repairs, or major purchases before retirement
- Prepay or plan for property taxes, especially in Montana where property taxes can vary
U.S. Bank recommends getting “major expenses off the books” in the last few years prior to retiring.
3–5 years before retirement: tighten the plan, test scenarios
In the last 3 to 5 years, the focus shifts from accumulation to preservation and stress testing. Tasks include:
- Running “worst-case” scenarios (market downturns, inflation, health changes)
- Revalidating your withdrawal assumptions
- Adjusting portfolio to reduce volatility
- Gathering official Social Security statements and pension estimates
- Confirming insurance coverage and Medicare readiness
- Planning for legacy, gifting, or charitable bequests
- Coordinating with tax and legal professionals
The U.S. Department of Labor’s “Retirement Toolkit” provides timeline tools and guidance to help you manage these stages.
Final 12 months: check all boxes & communicate your plan
Your final year of work is when execution matters most. Here’s a condensed “to do” list:
- Lock in your retirement date and submit necessary paperwork
- Apply for Social Security (if you plan to begin it)
- Ensure all beneficiary and estate documents are current
- Host family conversations to clarify expectations
- Coordinate with your tax preparer to estimate retirement tax liabilities
- Confirm that health coverage (Medicare or otherwise) starts on time
- Make final adjustments to your investment allocation
- Practice “living on retirement income” to detect cash flow issues
How to tell if you're on track (red flags and check signals)
Here are a few signals and red flags:
On-track signs:
- Your projected income exceeds your projected expenses
- You’re steadily reducing high-cost debt
- Your savings rate is high enough to bridge any gap
- You have multiple income sources (not just withdrawals)
- You revisit and stress-test your plan regularly
Red flags:
- Large income shortfall in your model
- Heavy debt or overleveraged assets
- Overly aggressive portfolio too close to retirement
- No contingency for health or longevity risk
- Lack of updated legal or estate documents
If any of these red flags apply, consider adjusting by delaying retirement, increasing contributions, trimming expenses, or seeking guidance.
Leverage local insight and periodic checkups
Because local conditions affect your plan, use Billings-area knowledge:
- Monitor Montana tax law changes (e.g. state income tax, property tax rules)
- Follow local housing markets and cost-of-living trends in your specific county
- Stay informed on healthcare facilities and provider networks in our region
- Meet annually (or semiannually) with a local financial planner who understands Montana’s rules and trends
Your plan isn’t “set it and forget it.” Regular checkups, especially when major life changes occur, are essential.
Final Thought: start early, act consistently
No matter your current age or proximity to retirement, using a structured checklist gives you clarity and momentum. Even small changes in the early years often compound meaningfully over time. Pair disciplined planning with professional guidance, and you’ll be far more confident that you’re headed toward a retirement that fits your vision.
If you're in or near Billings and want to run through a tailored version of this checklist together, yield scenarios with local assumptions, or simply run your numbers, Spitfire Financial is ready to walk with you. Let’s help make sure your retirement roadmap matches your goals and that you remain firmly on track.