Good morning! Today's email includes...

The 14 biggest risks in retirement - and how to beat them. [Part 2 of a two-part series]

A funny connection between investing and the weather - and our strange perceptions of both.

The 14 Retirement Risks - and How to Beat Them

In these two episodes, Jesse applies Charlie Munger's principle of inversion to retirement planning, arguing that instead of defining success alone, investors should first identify how retirement plans fail and then design strategies to avoid those outcomes.

In other words, retirement planning is improved by focusing on failure modes first.

Here's the most recent episode, featuring the second set of 7 risks...

And here's last week's episode, featuring the first 7 risks

Is the Summit "Good Enough"

I'm headed back to the Adirondacks in mid-June for two quick hikes with my older brothers.

Hiking asks an important question of you: how prepared should you be?

Preparedness requires research, time, and money. But it provides a higher probability of summiting the mountain(s), a more straightforward path, and the confidence of knowing you’ve done your homework.

Less preparedness is easier upfront. But is it easy in the long run? Likely not. “A stitch, in time, saves nine,” as Ben Franklin said. This idea rhymes with the concept of “Hard choices, easy life. Easy choices, hard life.”

Where do you want to fall on the preparedness spectrum? That's your call. There is no correct answer in general, but only a correct answer for you.

Hopefully we all reach our “ summit” either way. But your preparedness provides flexibility in how easy or hard that journey will be.

Retirement works the same way. Here's a terrific example explaining how.

What Are *Your* Questions?

My most popular episodes are the "ask me anything" episodes. Check them out here:

I'm collecting questions for AMAs 19 and 20.
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Reply to this email or send questions to jesse@bestinterest.blog​

Looking for a Financial Planner?

Retirement planning can be complex.

But I help!

I'm a partner and advisor at a fee-only retirement planning firm. I work with clients all over the USA.

If you'd like to learn more or explore working together, visit PlanWithJesse.com and fill out the form.

Until Next Week

Thank you for reading, listening, and writing back.

People like you send me questions every day.

Go ahead! I'd love to hear from you. ​​

Until next week,

Jesse