I am working on another project that looks at some of the thinking we need to embrace at each age chunk. For example, I’m turning 54 next month. What should I (we) be working toward in this glorious 50s era? What are some of the Grand Planning dos we should have at least be knowlegable about by now? There’s so much to learn and plan for, but breaking it down in chunks — like chewing and digesting our food well — can help turn our anxious planning worries into manageable cud. (Gross, haha) I hope to share this Grand Plan repackaging with you soon.

Until then, let me swallow my cud and break Grand Planning in the 50s down for you.

Here we go. As a general measure, the 50s is a time to get aware and be knowledgeable on and accepting of what’s ahead. The first fact? That we are aging during an unprecedented demographic shift: by 2035, there will be more adults over the age of 65 than children in our country. The second is that we’re living much longer than any other time in human history. 100 years is the number we should all be planning for financially and socially. The third fact? More than 70 percent of us will need some form of expensive long-term care during our lifetime. So to give you the cud so to speak, there are a shiz ton of us older adults, living longer and needing expensive care than ever before. This is the reality-based backdrop we must plan against during our 50s.

So let’s jump into the nitty gritty. I took some of the best practice measurements from CFP, elder and estate law, insurance, health and wellness, senior housing, decluttering and other experts in the older adult ecosystem and with the help of ChatGPT blended it with my Grand Planning resources to build a rough checklist of what gold star grand planning should look like in different stages of life. This is 50-ish, ya’ll — we can do this:

1. Legal Authority: Lock It In and Keep It Current

What to do:

• Have all core documents in place:
  • Will
  • Durable Power of Attorney
  • Healthcare Proxy
  • Living Will / Advance Directive
• Review after any major life change (marriage, divorce, move, death, asset change)

Best practice check:

• Documents updated within last 3–5 years
• All decision-makers still appropriate and informed

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2. Financial Readiness: Know Your Numbers (Not Just Your Intentions)

What to do:

• Calculate where you actually stand
• Increase savings rate if needed
• Align lifestyle expectations with reality

Best practice benchmarks:

• Retirement savings ≈ 6x your salary by age 50
• Savings rate ≈ 15% of gross income (including match)

Your score:

• Salary multiple = retirement savings ÷ salary
• Savings rate = annual contributions ÷ income

If you don’t know these two numbers, you are not yet “on track”—you’re guessing.

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3. Long-Term Care Planning: Face the Reality Early

What to do:

• Research local costs for:
  • Home care
  • Assisted living
• Compare those costs to your future income

Run the math:

• Home care: hourly rate × hours/day × 30
• Assisted living: monthly cost – guaranteed income

Why this matters:

• ~70% of adults will need some form of care
• Medicare does not cover long-term custodial care

Goal:

• Understand your monthly care gap before it becomes a crisis

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4. Housing: Test Your “Aging in Place” Assumption

What to do:

• Evaluate your current home honestly:
  • Stairs?
  • Bathroom accessibility?
  • Transportation dependence?
  • Proximity to services?

Compare two paths:

• Cost to stay:
  • Home modifications
  • Transportation alternatives
  • In-home support
• Cost to move:
  • Senior living entry + monthly fees

Best practice:

• Make this a side-by-side financial comparison, not an emotional decision

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5. Organization: Build a System Someone Else Can Use

What to do:

• Create your “In Case Of” / Grand Planner / death binder
• Include:
  • Bills and accounts
  • Insurance summaries
  • Tax contacts
  • Medical info and medications
  • Passwords and device access
  • Pet care instructions

Reality test:

• If you disappeared for 30 days…
  • Could someone run your life without chaos?

If not, your system isn’t ready.

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6. Communication: Close the Gap Between Plans and People

What to do:

• Talk to your chosen decision-makers about:
  • Their roles
  • Your wishes
  • Where everything is located

Best practice:

• 100% of named agents have had a real conversation

Why it matters:

• Documents without conversations = confusion under pressure

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7. Health & Function: Protect Your Future Independence

What to do:

• Build habits now that protect later autonomy:
  • Strength training
  • Balance training
  • Cardiovascular activity
  • Sleep optimization
  • Hearing and vision checks

Baseline targets:

• Weekly movement (moderate activity)
• 2+ strength sessions/week
• Balance work incorporated regularly

Why it matters:

• This is the decade where future fall risk, mobility, and independence are shaped

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8. Benefits, Insurance & Strategy: Know Your Options Early

What to do:

• Evaluate:
  • Long-term care insurance or hybrid products
  • Veteran benefits (if applicable)
  • Medicaid planning considerations
  • Benefits screening tools

Best practice check:

• You’ve explored all 4:
  • LTC insurance
  • VA benefits (if relevant)
  • Medicaid implications
  • Public benefits screening

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9. Retirement Reality Check: Are You Actually On Track?

What to do:

• Estimate future spending
• Compare assets to need

Quick planning formula:

• Target assets ≈ 25× annual retirement spending

Your score:

• Adequacy ratio = current assets ÷ target assets

Interpretation:

• Below ~70% → requires serious adjustment (timing, spending, housing, work)

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10. Life Continuity & Legacy: Reduce the Burden on Others

What to do:

• Clarify:
  • Burial vs cremation
  • Service preferences
  • Key contacts
  • Obituary starter
  • Payment/insurance details

Best practice:

• Someone else could carry out your wishes without guessing

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This decade is about turning intentions into systems.

You should leave your 50s with:

• ✔ Clear legal authority
• ✔ Known financial position (not assumptions)
• ✔ A realistic long-term care plan
• ✔ A tested housing strategy
• ✔ A fully usable life-organization system
• ✔ Shared understanding with your people
• ✔ Health habits that protect independence

Ready, set, go! This sounds like a lot, I know… but the earlier we think about all these details and imagine the “what ifs” of our next decades, the better prepared we’ll be to handle it thoughtfully and with our own preferences guiding the decision-making. Most importantly, the better off our kids, caregivers and loved ones will be to support us without unexpected stress. One in four of us are caregivers today, according to recent studies. This thinking impacts MOST of us. What can you do today that will make the next decades of your life easier and representative of your vision? What can we do today that will be more loving for the people who will support us on the journey?