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Know when to hold 'em, fold 'em: Timing the market for retirement in harsh times

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Updated Nov 10, 2022

With all the worry over 2022's new federal regulatory proposals, diesel prices and availability reaching dire straits, and spot rates a mere shadow of where they were a year ago, it's increasingly common that packing it all in and retiring comes up in conversation with owner-operators. 

But nobody wants to leave the table on a losing hand. With stocks firmly in bear market territory -- the bellwether S&P 500, for example, is down 20% year-to-date -- even successful owners who wisely squirreled away funds for retirement may be in for a shock when checking account balances. 

Recent polling underscored impacts to the negative when comes to retirement investments and plans for Overdrive's mostly owner-operator readers. 

While the wide majority have been hurt by recent swings, some have benefited on the whole. That's what market uncertainty means, you might say, similar people doing similar work making relatively similar investments and finding wildly different outcomes.

If you've recently retired and you're reading this, there's a chance (indeed a hope) that in the midst of the pandemic, you sold your equipment for peak, previously-unheard-of prices, cashed stocks at the top of the COVID recovery phase and maybe even sold your home well above asking price as office workers fled cities for exurbs and rural areas. If you did, you're made in the shade, as they say. 

Yet if you held on just a few months more and saw home and truck prices moderate, and prospective cost of living in retirement balloon under unchecked inflation -- heaven forbid, some health problem pops up. ... You'd be fully justified to be frightfully stressful about the situation looking toward retirement.