'}}
“Will My Money Last?”: Your Month-by-Month Guide to the 5 Years Before Retirement

WealthStrategist.ai helps normal people understand retirement without the jargon. We'll help you know what to do and connect you with retirement specialists who explain things in plain English.


Wondering if your savings will last through retirement? WealthStrategist.ai’s month-by-month guide for the five years before retirement simplifies the planning process, helping you avoid common pitfalls and feel confident about your future.

"I want to retire in the next few years, but I'm worried I'll miss something important."

You're right to think ahead. According to Fidelity's 2024 Retirement Analysis, 71% of recent retirees wish they'd started planning five years earlier[1].

"What should I do first?"

Most people jump straight to "Do I have enough money?" But there's actually a more important question: "How much money will I actually need?"

A 2023 T. Rowe Price study found that most new retirees actually spend 20-40% less than they expected to in retirement[2]. Why? Because they overestimated some costs and completely forgot others.

"The Most Important Number: Your Guaranteed Income Gap"

This is the number that actually matters most, and almost nobody talks about it.

Here's how to find yours:

  • Add up your guaranteed monthly income:
  • Social Security (average $1,907 in 2024)[4]
  • Pension if you have one
  • Any other guaranteed income
  • Add up your must-pay monthly expenses:
  • Housing
  • Utilities
  • Healthcare
  • Food
  • Basic transportation
  • Subtract guaranteed income from must-pay expenses

That difference is your "Guaranteed Income Gap" - the amount you need to fill from your savings each month.

Real Example:

Monthly Must-Pay Expenses:

  • Housing: $1,800
  • Utilities: $300
  • Healthcare: $500
  • Food: $600
  • Basic transportation: $300 Total: $3,500

Monthly Guaranteed Income:

  • Social Security: $2,000
  • Small pension: $500 Total: $2,500

Guaranteed Income Gap = $1,000 per month

This means you need your savings to reliably generate $1,000 every month. According to J.P. Morgan's 2024 retirement analysis[15], retirees who cover at least 80% of their must-pay expenses with guaranteed income are significantly more likely to maintain their lifestyle throughout retirement.

Step 1: Figure Out Your Real Numbers

The Bureau of Labor Statistics shows the average retiree household spends[3]:

  • 35% on housing
  • 16% on healthcare
  • 14% on food
  • 16% on transportation
  • 19% on everything else

"What about healthcare? That's what keeps me up at night."

Here are the real 2024 numbers from Medicare.gov[6]:

  • Part B: $174.70/month (standard premium)
  • Part D: Average $34/month for prescriptions
  • Medigap Plan G: Average $150/month
  • Annual deductible: $240 for Part B

Plus, Fidelity estimates the average couple needs $315,000 saved just for healthcare in retirement[7].

Your Year-By-Year Checklist

5 Years Before Retirement

The IRS lets you contribute extra to retirement accounts after 50[8]:

  • Extra $7,500 in 401(k) - total $30,500
  • Extra $1,000 in IRA - total $8,000
  • Extra $1,000 in HSA if eligible - total $4,850 (single) or $8,750 (family)

4 Years Before

Check Social Security scenarios[9]:

  • Age 62: 30% reduction
  • Age 67: Full amount
  • Age 70: 24% increase

3 Years Before

Build your cash cushion. Vanguard research shows keeping 2 years of expenses in cash reduces risk significantly[10].

2 Years Before

Healthcare planning becomes crucial:

  • Average COBRA cost: $623/month for single coverage[11]
  • Average ACA marketplace plan: $496/month before subsidies[12]

1 Year Before

Medicare enrollment windows[13]:

  • Initial Enrollment: 3 months before turning 65
  • General Enrollment: January 1 - March 31
  • Special Enrollment: 8 months after work coverage ends

"What mistakes should I avoid?"

The big ones we see:

  1. Not calculating your Guaranteed Income Gap
  2. Forgetting about taxes
  3. Underestimating healthcare costs
  4. Taking Social Security too early
  5. Not having a backup plan

"What should I do right now?"

  • This Week: Track these categories (Bureau of Labor Statistics model)[14]:
  • Housing (35% of retirement spending)
  • Transportation (16%)
  • Healthcare (16%)
  • Food (14%)
  • Other (19%)
  • This Month:
  • Calculate your Guaranteed Income Gap
  • Get your Social Security statement at SSA.gov
  • List all retirement accounts
  • Check employer benefits
  • Next Steps: Take our 2-minute quiz to:
  • See where you stand
  • Get a personalized timeline
  • Know what to do next
  • Connect with help if you need it

[TAKE THE QUIZ]

Sources:

[1] Fidelity Investments Retirement Mindset Study, 2024 [2] T. Rowe Price Retirement Spending Study, 2023 [3] Bureau of Labor Statistics Consumer Expenditure Survey, 2024 [4] Social Security Administration Benefits Update, 2024 [5] Bureau of Labor Statistics Employee Benefits Survey, 2024 [6] Medicare.gov Premium Updates, 2024 [7] Fidelity Retiree Health Care Cost Estimate, 2024 [8] IRS.gov Retirement Contribution Limits, 2024 [9] SSA.gov Benefits Calculator, 2024 [10] Vanguard Research "Retirement Income Strategies", 2024 [11] Kaiser Family Foundation Employer Health Benefits Survey, 2024 [12] CMS.gov Healthcare Marketplace Report, 2024 [13] Medicare.gov Enrollment Guidelines, 2024 [14] Bureau of Labor Statistics Retirement Spending Patterns, 2024 [15] J.P. Morgan Guide to Retirement, 2024

About Us: WealthStrategist.ai makes retirement planning understandable for everyone. We don't provide tax or investment advice - instead, we help you understand your options and connect you with retirement specialists who speak your language.