Nobody Knows Their Expiration Date (...So Plan Like It) 📅


Good morning!

Today's email includes:

--an important lesson about the unintended consequences of assuming your age at death.

--a throwback to one of my favorite podcast episodes

--three great articles from others about Social Security, tax planning, and momentum

--a community member wrote a book! One of us! One of us!


"End of Plan" - A Vital Planning Decision

Small change, giant impact.

One challenge in financial planning is when a “small” decision creates something much bigger than we assumed.

“End of Plan” is one such decision.

Some planning software might call it “planning horizon” or “life expectancy” or any number of other euphemisms for “when might you die?”

Yes, death is scary to consider.

And it’s obvious how our lifespan affects our finances. The longer we live, the more money we need to live a successful retirement.

But there’s so much more!


Reset Your Portfolio Expectations!

Peter Lazaroff is one of my favorite voices in the investment management space.

Sharp. Interesting. A great teacher.

In honor of Peter's new book (!!), I wanted to throw things back to Episode 112, where Peter and I discussed the psychology and strategy of investing during uncertain times.

Our topics include international diversification, sequence of returns risk, and why consistency in strategy beats chasing performance.


The Top 3...

I enjoyed this content recently. I hope you do too.

​The Loooong History of Social Security​

Social Security might be ~90 years old in the US.

But the *idea* of Social Security is much, much older.

This great article from Humble Dollar explains the long historical arc of Social Security and points us toward better SS decisions today.

​Early Retirement? More Tax Planning​

This is a great conversation between Morningstar's Christine Benz and Ed Slott...

The big takeaway:

MOST of the time, your earlier retirement years are great for tax planning.

Plenty of nuance. Some corner cases.

But make sure you contemplate good tax planning for those early years.

​Trend Following / Momentum Investing​

Indexing is a wonderful investing strategy.

Some of us are then exposed to "add-on" ideas.

Trend-following and momentum are interesting examples. In short, the idea is:

Assets moving in one direction will keep moving that way

Ben Carlson breaks it down succinctly in this post.


How Close Are You To "Time Freedom?"

One of our very own newsletter members, Brian Herriot, just published his new book, Time Freedom.

He even put together a nifty nine-question quiz to help you decide whether his book is for you. It took me ~90 seconds:

If the button doesn't work, try:

​https://timefreedom.life/score

The book is a good reminder that the trade-off between time and money does NOT have to be delayed to one single "retirement age." It's a series of decisions that starts much earlier.

Congrats Brian!


I Help People Retire (Even) Better

I'm a Partner at a fee-only fiduciary retirement planning firm.

We work with clients all over the USA.

If you know someone who needs help, visit PlanWithJesse.com and let's start a conversation.


Until Next Week...

Thank you for reading, listening, and writing back. People like you send me questions every day.

I'd love to hear from you. ​​

All the best,

Jesse Cramer


Jesse Cramer

Retirement is a different game. You’ve spent decades building wealth. Now comes the harder part - turning it into a paycheck that lasts. I’m Jesse Cramer. I help DIY investors turn their savings into a clear, cohesive retirement plan. Join 4000+ weekly readers and 20,000+ podcast listeners.

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