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When Frugality Is A Fault: Certified v. Regular Mail

So I recently started the 401k to IRA rollover process [3], moving my assets from my former employer’s 401k plan to a Rollover IRA at Vanguard, and just today I received the check for the value of my assets that I would be sending off to Vanguard. The check is easily the largest single legitimate check I’ve held in my hand (beating a check that was the down payment for my house a year and a half ago) and I kind of wondered why the plan administrator would mail something so important in regular first class mail.

Anyway, I was very very tempted to just slap a thirty-nine cent stamp on the letter and mail it off but I thought better of it. While I’m pretty sure that there was a 99% chance the letter would make it there without any problems (I have faith in the USPS, even if Nick doesn’t [4]), do I really want to deal with the hassle in that 1% case?

Let’s compare…
99%: I save myself a few bucks.
1%: I’d have a headache. First, it would take me a little while to learn that the check was lost, then I would have to request that my 401k plan administrator void the original check and reissue a new check. That request would likely come with some sort of (unreasonable) fee. Then, after I lose about three or four weeks of appreciation on a pretty sizable sum (to me anyway), I’d send it via certified mail this time. So… I think certified the first time is the route to go.

So, frugality can be a fault and in this case, saving a few bucks could potentially cost me a lot in terms of time, hassle, and money.