1. How much after-tax income do you need?

Most people start with the wrong benchmark:

The old “70–80% of your working income” rule of thumb.

That’s far too generic.

What you really need is clarity on your monthly after-tax lifestyle spending.

For example:

• Housing (mortgage, rent, property taxes, insurance)
• Health care (premiums, out-of-pocket, future long-term care)
• Travel and leisure (grandkids, vacations, hobbies)
• Daily living (food, utilities, transportation)

Once you know the after-tax number that funds the life you actually want, the rest of your planning becomes much clearer.

2. How much income do you want guaranteed?

The #1 risk in retirement isn’t inflation or taxes — it’s sequence of returns risk.

If the market drops early in retirement, and you’re drawing from your portfolio at the same time, the math can spiral quickly.

A bear market in your first 5 years of retirement could cut your long-term income by 30–40%.

That’s why pensions, Social Security, and annuities matter so much.

They provide a floor of guaranteed income you can’t outlive — no matter what the market does.

3. How comfortable are you with market risk without a paycheck?

A funny thing happens when you stop working.

When the market drops while you’re still earning, it’s “paper money.”

You can ride it out.

But once you’re retired, those same drops feel like existential threats — because your withdrawals lock in losses.

Many people overestimate their risk tolerance heading into retirement.

Part of planning is being honest with yourself:

How will you really feel if your $1.5M nest egg drops to $1.1M in a single year?

4. What’s your long-term care plan?

Seven out of ten couples will face some form of extended care need.

And costs can range from $80,000 to $120,000 per year — per person.

The hard truth is this:

Without a plan, a care event can wipe out assets meant for a spouse’s income or for legacy goals.

Some people self-fund.

Others use long-term care insurance, hybrid life/annuity products, or Medicaid-compliant strategies.

But ignoring the question isn’t an option.

5. How tax-efficient is your withdrawal strategy?

Taxes don’t end in retirement — they often become your largest ongoing expense.

The order in which you tap accounts matters:

• IRAs/401(k)s trigger ordinary income
• Roth IRAs grow tax-free
• Brokerage accounts can be managed for favorable capital gains treatment

A tax-smart withdrawal strategy can help you:

• Stay in lower brackets
• Avoid or minimize IRMAA surcharges on Medicare
• Control RMDs later in life
• Preserve more wealth for heirs

This is where strategies like Roth conversions can be game-changers if done in your “golden window” — those years between retirement and RMD age.

6. What’s your longevity plan?

Retirement isn’t a 5- or 10-year vacation.

It’s a 25–35 year journey.

A couple at 65 today has a 50% chance one spouse will live into their 90s.

That means your income plan has to last three decades, through multiple recessions, tax law changes, and health events.

Longevity risk is the silent killer of many retirement plans.

Planning for age 95 or even 100 is no longer pessimistic — it’s realistic.

7. How will your plan handle market surprises?

Markets never move in straight lines.

There will be shocks — good and bad.

The key isn’t predicting them, but building flexibility into your plan:

• Portfolio Guardrails that adjust withdrawals up or down
• Buckets that protect short-term income from market swings
• The ability to pivot between taxable, tax-deferred, and tax-free sources

Without flexibility, every surprise feels like a crisis.

With flexibility, surprises just feel like adjustments.

The Bottom Line

These seven questions aren’t just checklist items — they’re the foundation of a retirement that actually works.

The best retirement plans aren’t about chasing the highest return.

They’re about clarity, confidence, and adaptability.

If you can answer each of these with confidence, you’re far more likely to enjoy retirement on your terms — with the peace of mind that comes from knowing both your income and your lifestyle are secure.