The Pre-Retirement Paper Chase: What to Keep, What to Toss, and How Long to Hold On 

If you’re like most Alaskans approaching retirement, you’ve probably accumulated years (maybe decades!) of financial paperwork. Pay stubs stuffed in drawers, old tax returns in storage boxes, insurance policies you’re not sure are still active, and statements from accounts you might have forgotten about. As you prepare for retirement, getting your financial house in order isn’t just about peace of mind; it’s essential for making informed decisions about your future.

Let’s talk about what documents you really need to keep, how long to hang onto them, and how to organize everything so you’re ready for this next chapter.

Why Document Organization Matters More as You Approach Retirement

When you’re preparing to retire, you’ll need documentation to:

  • Verify your years of service and calculate your PERS, TRS, FERS, or CSRS pension benefits
  • Make informed decisions about Social Security timing
  • Coordinate Medicare enrollment and supplemental insurance
  • Review your TSP or Deferred Comp distributions
  • Plan for required minimum distributions (RMDs)
  • Ensure your estate planning documents are current
  • Substantiate your tax filing if audited

Missing paperwork can delay benefit applications, lead to incorrect calculations, or create unnecessary stress when you should be celebrating your retirement.

The Essential Documents to Keep (and for How Long)

Keep Permanently (or Until No Longer Relevant)

Retirement account statements

  • All statements for PERS, TRS, FERS, CSRS pensions
  • Annual statements from TSP, Deferred Comp, IRAs, and 401(k)s
  • Documents showing non-deductible IRA contributions (crucial for tax purposes)

Social Security records

  • Your annual Social Security statements
  • Records of your earnings history
  • Application confirmations and benefit election documents

Estate planning documents

  • Wills, trusts, and power of attorney documents
  • Beneficiary designation forms for all accounts
  • Life insurance policies (keep until no longer in force)

Property records

  • Home purchase documents, including original cost basis
  • Records of significant home improvements (affects capital gains calculations)
  • Mortgage payoff documentation

Investment purchase records

  • Records showing when you purchased investments and at what price (essential for calculating capital gains)

Keep for 7 Years

Tax returns and supporting documents

  • Federal and Alaska state tax returns
  • W-2s, 1099s, and other income statements
  • Receipts for deductible expenses
  • Documentation of charitable contributions

Why 7 years? The IRS typically has 3 years to audit, but it’s 6 years if you underreported income by 25% or more. Seven years provides a comfortable buffer.

Medical bills and EOBs

  • Keep for 7 years, especially if you’re deducting medical expenses or using HSA/FSA funds

Keep for 1 Year (Then Shred)

Monthly statements

  • Bank statements (after reconciling with annual summary)
  • Credit card statements (after verifying on annual statement)
  • Investment account statements (keep the year-end statement)

However, statements used to support tax returns should be kept for three to seven years to satisfy potential IRS inquiries.

Pay stubs

  • Keep until you receive your W-2 and verify the information matches

Safe to Shred

ATM and deposit receipts

  • Once verified on your monthly statement

Credit card offers and expired warranties

  • Shred immediately to prevent identity theft

Special Considerations for Alaska State, Federal, and Union Employees

If you’re in one of SBS’s specialty areas, pay extra attention to:

State of Alaska employees (PERS/TRS)

  • All correspondence from the Alaska Division of Retirement and Benefits
  • Records showing your years of credited service
  • Health insurance election documents
  • Documentation of any service purchases or military service credits

Federal employees (FERS/CSRS)

  • SF-50 forms (Notice of Personnel Action) showing your entire career
  • TSP contribution and loan records
  • Federal Employees Health Benefits (FEHB) elections
  • Records of any unused sick leave (this can add to your pension calculation)

Union members

  • Union pension statements and benefit summaries
  • Collective bargaining agreements that affect your benefits
  • Records of any breaks in service or work-related injuries

Creating a Retirement Document Filing System

A simple system can save you hours of frustration:

  • Create main categories: Tax Returns, Retirement Accounts, Insurance, Estate Planning, Property, Medical, Banking
  • Use sub-folders or labeled envelopes within each category by year or account type
  • Go digital where possible: Scan important documents and store them securely in the cloud or on an encrypted external drive. But keep original estate planning documents, property deeds, and marriage/birth certificates in physical form.

Set up a “Retirement Planning Binder” with:

  • Recent statements from all retirement accounts
  • Social Security earnings history
  • Pension benefit estimates
  • Current beneficiary designations
  • List of all accounts with contact information
  • Important advisor and attorney contacts

Share access: Make sure your spouse or a trusted family member knows where everything is located.

How SBS Can Help You Get Organized

As you prepare for retirement, document organization is just one piece of the puzzle, but it’s an important one. When you work with us, we’ll help you:

  • Identify any missing documentation you’ll need for benefit applications
  • Review your statements to ensure your retirement accounts are properly positioned
  • Coordinate the timing of pension elections, Social Security, and Medicare
  • Ensure your beneficiary designations align with your estate plan
  • Create a comprehensive retirement income strategy

Getting your documents in order now means fewer headaches later. It’s one of the most practical steps you can take as you move toward retirement.

Ready to Get Started?

If you’re feeling overwhelmed by the paperwork or aren’t sure what you have versus what you need, we’re here to help. Schedule a complimentary discovery appointment with our team, and we’ll walk you through what documentation matters most for your specific situation.

Call us at 907.374.0487 or visit our office at 907 University Avenue in Fairbanks to get started. Let’s make sure you have everything organized and ready for the retirement you’ve worked so hard to achieve.

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