I don’t care that my personal finance posts never resonate, I will continue to write about it when the spirit moves me. Deal with it.

Nick Maggiulli could teach me a lot about how to write about personal finance. His first book, Just Keep Buying, sold 400,000 copies. And his brand new book, The Wealth Ladder, is getting tons of attention on several of the pods I listen to.

The inspiration for this post is a friend, let’s call him, IE. IE is planning to retire in the spring of 2027. He appears to have his personal finance shit together. Good paying job. Lots of passive income. And he’s been riding equities up.

On the downside, he’s showing signs of irrational exuberance. He seems to think the stock market, near all-time highs, will continue its run. Or maybe he’s just trolling us in the group text?

His target retirement date was carefully determined based upon his normal “spend rate” combined with lots of planned post-retirement traveling.

I’m guessing he hasn’t modeled exactly what a market worst case scenario might do to his plan. Before retiring, model exactly what a market worst case scenario might do to your total net worth. Put differently, don’t tip-toe around “sequence of returns” risk, dive head-first into it.

How to do that? Calculate your net worth, excluding your residence(s)* because as the saying goes, you have to live somewhere. Adding in any home equity only makes sense if you plan to seriously downsize upon retiring.

Next, take the total amount of money you have invested in equities and divide it by two as if there was a 50% correction. So, in IE’s case, let’s make a wild ass guess and say he has a net worth of $3m, $2m in equities, $800k in fixed income, and $200k in cash.

IE would create a second spreadsheet showing his adjusted net worth after a 50% correction in the stock market. He’s “post-market correction” net worth would be $2m or one-third less than today. Print the “Bear Market spreadsheet” and let it sink in.

Only then can can IE determine 1) whether his asset allocation makes sense and 2) whether the spring 2027 timeline still makes sense.

Because he’s a friend, I will not be charging him for this advice. Some, no doubt will say, my advice is worth what I’m charging for it.

*plural if your DDTTM and have an extensive real estate portfolio