I donate the max to my HSA, which I then invest in commission-free ETFs, with the plan of using this money for health care costs in retirement. My employer contributes a certain amount but that is not predicated on my contribution, so I don't have to worry about matching like I do for a 401(k). In the enrollment election I am allowed to enter a monthly contribution amount. However, since the general long-term trend is for my ETFs (ITOT, IXUS, AGG) to increase in value, would it be worth the trouble to call to try to do the whole contribution in one or two paychecks? I could afford this and wouldn't have to sacrifice my 401(k) contribution and matching, health insurance premium, etc., but is it worth the trouble? I don't believe I can time the market but it does seem quite high right now--would that be reason to stick with contributing throughout the year in case of a pullback? Are there any studies looking at the effects of investing at the beginning of the year versus throughout the year versus at the end of the year?

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    Are you saying that you are treating the HSA as a long term investment? Not planning to use it up most years? Commented Nov 26, 2013 at 17:21
  • @JoeTaxpayer Correct. I plan to use it for health care costs in retirement, and anything left over will be treated as an extension of my 401(k) and IRA.
    – Craig W
    Commented Nov 26, 2013 at 17:33
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    Got it. The question boils down to Jan 2 lump sum VS DCA. We need to find it, but DCA has been thoroughly addressed here. On average, January will be lower by the average market return. But not in every year. In down years, or choppy years, DCA is better. I'd have to ask, "do you feel lucky? Well do you, punk?" (A Movie reference. I know you are not a punk.) Commented Nov 26, 2013 at 23:37

1 Answer 1


The Mad Fientist has an article on this. He gives these following benefits:

  • Stocks go up more than they go down when you're in for the long haul (which you claim you are). So front-loading gets a bigger piece of the up-trend.
  • Postpone Taxes. HSAs are tax deductible, allowing your to put more money in investments at the beginning of the year. You'll still pay the same taxes, but they will be delayed towards the end of the year.
  • Front loading allows more tax-free growth. (His words, not mine.)
  • If you lose your job, you've got your contributions maxed out, and possibly your employers match too!

He also gives the caveat that your employer may not match things in their entirety. Like you mentioned, this mostly applies to 401(k)s and not to HSAs where the employer tends to contribute a fixed amount (in my experience).

Anecdotally, my wife and I front-load our IRAs; but not our HSA and 401(k) because we don't have that option. In the comment section of the linked article, several big-name early retirees confess to front-loading before it was cool.

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