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OxenFree Financial

Money Order Outline

My MOO: Retire

Whether you are approaching retirement or currently in retirement, use the following planning actions to build a simple, durable plan that supports your goals and values.

Financial and Income Planning

  • Calculate spending capacity

    estimate how much you can spend each year without running out.

  • Retirement budget

    fixed expenses, discretionary spending, travel, health care, gifts, and more.

  • Withdrawal strategy

    decide which accounts to draw from first: taxable, tax deferred, and Roth.

  • Social Security timing

    optimize for longevity, income needs, and spousal benefits.

  • Pension options

    compare lump sum and annuity and review survivor benefit elections.

  • Part time work or consulting

    decide if you will supplement income and how that affects taxes and Medicare.

  • Inflation planning

    model income needs under different inflation scenarios.

  • Stress test portfolio

    model portfolio strength against past downturns and review the likelihood of plan success.

  • Emergency fund in retirement

    target six months to one year of cash or liquid reserves.

Taxes

  • Roth conversions

    build a year by year plan to lower lifetime taxes, increase tax free inheritance, or create more flexible income.

  • RMD schedule

    required age is 73 for those born 1951 through 1959 and 75 for those born 1960 or later. Calculate the impact and coordinate withdrawals.

  • Qualified Charitable Distributions

    give directly from IRAs to reduce taxable income.

  • Donor advised funds

    bunch deductions and set up a giving strategy.

  • Capital gains management

    harvest gains and losses with intention.

  • Tax efficient investment placement

    decide what belongs in Roth, Traditional, or taxable.

Health Care and Insurance

  • Medicare

    shop at age 641/2, coverage starts at 65.

  • Medigap or Medicare Advantage

    compare plans, costs, and coverage.

  • Health Savings Account

    if you have one, use it tax free for medical expenses.

  • Long term care planning

    evaluate insurance options or a self funding plan.

  • Life insurance review

    determine if it is still needed for income replacement or estate goals.

Risk and Protection

  • Portfolio review

    match allocation to risk tolerance and income needs.

  • Sequence of returns risk

    create a buffer for early years to avoid selling during downturns.

  • Fraud protection

    freeze credit, monitor accounts, and beware of scams that target retirees.

Other Planning Items

  • Required documents organized

    store in a secure but accessible place: will, trust, power of attorney, health care directives, and insurance policies.

  • Financial power of attorney

    ensure someone can act if you are incapacitated.

  • Health care surrogate or directive

    make wishes clear for medical decisions.

  • End of life planning

    funeral preferences and legacy documents.

  • Technology setup

    make sure spouse, children, or loved ones can access digital accounts and passwords.

Lifestyle and Personal

  • Housing decisions

    downsize, relocate, consider a second home, or age in place.

  • Home maintenance and safety

    plan for accessibility with grab bars, ramps, and similar updates.

  • Transportation

    decide how long to drive and identify alternatives like ride sharing or relocation.

  • Daily routine and purpose

    hobbies, volunteering, and community involvement.

  • Travel plans

    take bucket list trips early while healthy, then adjust for energy and mobility later.

  • Family engagement

    time with kids and grandkids and caregiving responsibilities.

  • Friendships and social circles

    stay connected to avoid isolation.

My MOO is provided for informational and educational purposes only and should not be considered financial advice. Users are encouraged to consult with a qualified financial professional before making any decisions, as the tool does not account for all aspects of an individual’s financial situation. Use of this tool does not create an advisory relationship. While efforts are made to ensure accuracy, no guarantees are made regarding the results.

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