Good morning, Retirement Starts Today Community! Welcome to Every Day is Saturday, the newsletter reminding us that in retirement, every day is Saturday (including Thursday mornings).

​​Click here to view a recent video from my YouTube channel about If I Claimed Social Security Again, I’d Do This Instead

​Click here to work with us!

This holiday season tune in as we revisit some of our favorite podcast episodes of 2025.

Episode Breakdown:

• (00:00) Intro
• (01:16) Retirement Headlines: Five Key Retirement Challenges (and Solutions)
• (10:26) Listener Question

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​Listen on Spotify | Listen on Apple​

Retirement Headline

Retiring Doesn’t Mean You Should Claim Social Security

Many retirees assume they must take Social Security as soon as they stop working. In reality, delaying benefits can lead to significantly higher lifetime payouts, especially for couples. Strategic planning around this decision can maximize income and tax efficiency.

Waiting to claim can also create opportunities to fill income gaps with tax-efficient withdrawals, like Roth conversions or capital gains harvesting. Instead of locking in a lower benefit for life, retirees who plan ahead can give themselves more financial flexibility and security in their later years.

You’ll Likely Live Longer Than You Think

Retirement planning often relies on outdated life expectancy figures. By focusing on personal longevity rather than average statistics, retirees can better prepare for a future that could last 30+ years. Planning with a longer horizon helps prevent running out of money too soon.

Prepare for Retirement to Arrive Earlier Than Expected

Health issues, layoffs, or family responsibilities often push people into retirement years ahead of schedule. Running a “retirement fire drill” by adjusting plans for an earlier exit ensures financial security, even if work ends sooner than expected.

By assuming retirement could come three to five years earlier than planned, people can build more flexibility into their strategy. Whether that means boosting savings, paying down debt, or considering part-time work, early preparation can turn an unexpected retirement into a smooth transition instead of a financial crisis.

Short-Term Gains Can Lead to Long-Term Struggles

Decisions like taking a higher pension payout today or avoiding Roth conversions to minimize taxes now can backfire later. Optimizing for long-term security rather than immediate income helps protect against financial shortfalls in later years.

Resources

• ​Click here to view my YouTube channel, Even Better Retirement
• ​Click here to order my book, Retirement Starts Today: Your non-financial guide to an even better retirement
• ​​Click here to read Five Key Retirement Challenges (and How to Face Them Head On)

I need your help...

I will be starting a new segment on my podcast: Retire TO something, not FROM something.

The segment will be brief at the end of the show and will share a fun retirement idea, along with links to learn more. Volunteer work and part-time “fun” jobs will be a common theme.

​Click here to share your ideas!

That's it for our four hundred and ninth installment of "Every Day is Saturday." As always, I read (and usually reply to) every listener email. Got a question? Hit reply—you just might hear your name on the show.

Enjoy your “Saturday,”
​Benjamin Brandt

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