Withdrawal Strategies in Retirement

How to Take Money Out Without Giving Too Much to Taxes

Hey Coach,

Most retirement planning focuses on how to save.

But what really determines how long your money lasts is how you withdraw it.

Two coaches can retire with the same balances…
and end up with very different outcomes based solely on withdrawal strategy.

This week, we’re talking about the retirement endgame.

Why Withdrawal Order Matters

Not all retirement dollars are taxed the same.

If you pull money randomly:

  • You may pay unnecessary taxes

  • Trigger higher Medicare premiums

  • Increase taxation of Social Security

  • Run out of tax flexibility later

A smart withdrawal plan is defense against taxes, not guesswork.

The Three Buckets (Know Your Roster)

Most coaches have money in three places:

1. Taxable Accounts

  • Brokerage accounts

  • Savings or money markets

  • Capital gains taxes (often lower)

2. Tax-Deferred Accounts

  • Traditional IRA

  • 401(k), 403(b), 457

  • Every dollar withdrawn is taxable income

3. Tax-Free Accounts

  • Roth IRA

  • Roth 401(k)

  • Withdrawals are tax-free (if rules are met)

Each bucket plays a different role.

Last Time the Market Was This Expensive, Investors Waited 14 Years to Break Even

In 1999, the S&P 500 peaked. Then it took 14 years to gradually recover by 2013.

Today? Goldman Sachs sounds crazy forecasting 3% returns for 2024 to 2034.

But we’re currently seeing the highest price for the S&P 500 compared to earnings since the dot-com boom.

So, maybe that’s why they’re not alone; Vanguard projects about 5%.

In fact, now just about everything seems priced near all time highs. Equities, gold, crypto, etc.

But billionaires have long diversified a slice of their portfolios with one asset class that is poised to rebound.

It’s post war and contemporary art.

Sounds crazy, but over 70,000 investors have followed suit since 2019—with Masterworks.

You can invest in shares of artworks featuring Banksy, Basquiat, Picasso, and more.

24 exits later, results speak for themselves: net annualized returns like 14.6%, 17.6%, and 17.8%.*

My subscribers can skip the waitlist.

*Investing involves risk. Past performance is not indicative of future returns. Important Reg A disclosures: masterworks.com/cd.

The Traditional Withdrawal Order (Simple Version)

A common baseline strategy:

1. Taxable accounts first

2. Tax-deferred accounts next

3. Roth accounts last

Why?

  • Lets tax-free money grow longest

  • Keeps taxable income lower early

  • Preserves flexibility later in retirement

This isn’t perfect - but it’s a solid starting framework.

Why Roth Accounts Are So Valuable

Roth dollars are:

  • Tax-free

  • Not required to be withdrawn (no RMDs)

  • Great for large expenses or late-life flexibility

  • Powerful estate planning tools

Think of Roth money as your closer - not your first sub.

Where Social Security Fits In

Once Social Security starts:

  • Withdrawals can increase how much of it gets taxed

  • More income can trigger higher Medicare premiums

That’s why many coaches:

  • Spend taxable money first

  • Use lower income years to do partial Roth conversions

  • Delay Social Security strategically

Everything works better when coordinated.

What This Looks Like in Practice

A disciplined approach often includes:

  • Filling lower tax brackets intentionally

  • Mixing withdrawals across accounts

  • Avoiding big tax spikes

  • Adjusting year by year, not set-and-forget

Retirement isn’t one season - it’s a long series of adjustments.

Common Mistakes to Avoid

🚫 Withdrawing from one account only
🚫 Ignoring taxes until April
🚫 Forgetting Required Minimum Distributions (RMDs)
🚫 Treating Roth money like “spending cash”
🚫 Not planning before retirement starts

Once withdrawals begin, mistakes compound fast.

Final Whistle

Retirement success isn’t just about how much you saved.
It’s about how smartly you use it.

Know your account types.
Understand tax impact.
Withdraw with intention.

That’s how coaches protect their income long after the final buzzer.

Subscribe here → Wealth4Coaches Newsletter

Coach Mike Klinzing
Founder, Wealth4Coaches
"Coach smarter. Save better. Live freer."

1