A simple way to estimate this is to take the annual income you want in retirement and multiply it by 20. That gives you a rough target for your portfolio using the income approach I use with clients. If you’re using the traditional 4% rule, you’d multiply by 25 instead.

Social Security, pensions, and annuities can reduce how much your portfolio needs to provide, so those should always be factored into the plan.

As a rough benchmark:

• 10 years before retirement: ~10× your income saved
• 5 years before retirement: ~14× your income saved
• At retirement: ~20× your retirement income

That often means saving at least 15% of income into Roth accounts or around 20% into pre-tax accounts like a traditional 401(k), depending on your situation.

To get a quick read on whether you’re close:

1. Start with your desired annual income in retirement.
2. Subtract Social Security, pensions, and any annuity income.
3. Multiply the remaining amount by 20.

If your current portfolio is in that range, you may be in a good position to retire. From there, we stress-test the plan and confirm it’s built to last through good and bad markets.

The biggest risk isn’t just market volatility, it’s sequence of returns — getting bad market years early in retirement while you’re drawing income.

I use a guardrails income approach, which adjusts withdrawals based on what markets are doing. The goal is to:

• Reduce the risk of running out of money
• Avoid underspending and dying with a large unused balance

We use clear rules around when to hold income steady, when to trim back slightly, and when it’s safe to give yourself a raise.

Many retirees have most of their assets in pre-tax 401(k)s and IRAs, so tax planning becomes a major part of the strategy. Depending on income, a reasonable ballpark for total taxes (federal + state) is around 20%–30%.

Good retirement tax planning might include:

• Managing which accounts you draw from each year
• Strategic Roth conversions when they make sense
• Keeping the investment mix tax-efficient

If you’re planning to use Medicare at 65, a reasonable estimate is around $7,000 per year per person, including premiums and prescriptions.

With chronic health conditions, that can rise closer to $14,000 per year per person. Long-term care facilities can easily cost $100,000+ per year, with an average stay of around four years.

A solid retirement plan builds these possibilities in so healthcare surprises don’t derail the rest of your life.

In general, the fewer fixed expenses you have in retirement, the more flexibility we have with your investment strategy and income plan.

Even with low mortgage rates, many wealthy families prefer the peace of mind of a paid-off home instead of trying to squeeze extra return out of a low interest rate. It’s less about “beating the rate” and more about simplifying your life and cash flow.

Retiring at 60 and living 25–30+ more years means your money still needs to grow. Going too conservative can actually increase the odds of running out of money.

A common starting point I use is:

• About 70% in growth-oriented investments
• About 30% in preservation/defensive assets

A 70/30 portfolio might see roughly a 30% drop in a 2008-style event and take a few years to recover — which we plan around. Some clients prefer 50/50 or more conservative mixes; we design the guardrails and income plan around your comfort level.

The default advice is “delay to 70,” but the right answer depends on your portfolio, health, and income needs.

General guidelines:

• Delay the higher earner’s benefit as long as realistically possible, ideally to age 70.
• The lower earner’s benefit is more flexible and can often be taken earlier.
• Avoid claiming at 62–64 if possible due to permanent reductions.
• Aim to claim at or after full retirement age (66–67) when we can.

This is something you want sorted out long before you ever have to live through it. When a spouse passes away:

• You keep the higher of the two Social Security benefits; the other stops.
• Annuities may be reduced, end entirely, or pay a lump sum, depending on the contract.
• Pensions may be reduced or eliminated if they weren’t set up with a survivor option.

Part of my planning process is mapping out what income, taxes, and cash flow would look like for the surviving spouse so there’s a clear plan already in place.