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Jesse Cramer

The Three Demons of Overconfidence 👹

Published about 15 hours ago • 1 min read

Good morning!

Today's email includes:

--a podcast episode about overconfidence

--an argument for early Social Security claiming

--great articles about "fear vs. prep," hiring an advisor, and umbrella insurance ☔️

FIRE and Early Retirement Misconceptions

In this podcast episode, we draw on ideas from psychologist Daniel Crosby to show how common overconfidence biases show up in everything from stock picking and market timing to insurance decisions, retirement dates, spending plans, and expectations about our future selves.

We dive into concepts like the illusion of control, the planning fallacy, focalism, immune neglect, and projection bias to show why seemingly rational financial decisions can become distorted by overconfidence.

The Social Security Youth Discount?

Should we consider claiming Social Security earlier to squeeze more life out of it?

Or, put another way, is there a subjective reason why $2000 per month at age 62 is actually more valuable than $3500 per month at age 70?

And is that subjective reason so powerful that it’s worth locking in those lower payments for life?

…so powerful that it overcomes the objective reasons to delay?

The Top 3...

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

​Fear vs. Prep​

There's a fine line between preparing for an uncertain future vs. living in fear of all that life might throw at you. In this article, the author describes it this way:

Preparation is: “Something may go wrong. I should be able to handle it.”

Fear is: “Something may go wrong. I should arrange my life around that possibility.”

​5 Lessons from Hiring an Advisor​

WSJ writer Brian Hershberg shares his lessons after hiring a financial advisor (after being a DIYer for 25+ years).

All his lessons are good, but I especially liked Lesson #1 - "the fit goes both ways."

I'd encourage any of you to remember that you can/should look for a "best fit" advisor, just as advisors look for "ideal clients." It cuts both ways.

​On Umbrella Insurance​

I've had a couple of good client conversations recently about umbrella insurance, so I wanted to share a bit more here.

Many of you reading this are either high earners and/or high net worth.

Umbrella insurance might be an important component for your financial plan.

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

Smart ideas about money and retirement.

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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