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You wrote, Is this an annual election? Are you suggesting contributing 40-50% of your paycheck year round? Can your budget afford that? I think from your post you are suggesting large contributions until you reach the $19,000 limit for 2019, then changing your elections to not contribute anything the rest of the year.

For me, that's a gamble. You achieve a lot more dollar-cost-averaging if you spread your purchases throughout the year. …

I'm sorry, but I think you are looking at this through the lens of your own situation. The only real gamble darrellquock is taking is locking up money in tax-advantaged accounts sooner instead of later. The problem really has little to do with investment returns or market performance.

Also this is only a gamble if you don't have the reserves to handle having little or no income for a while. But if you are considering this option, it's probably not a problem for you. Note: I have about 10 years worth of living expenses in liquid, taxable assets (cash and investments), so I'm in a situation to do this too.

In addition if you have cash and want to invest it in the stock market, statistically it's better to put it in sooner rather than later.

Finally, the main reasons to prefer a (Roth) IRA contribution over a 401(k) contribution are:

1. No matching incentive, and
2. Investment options are inferior.

These two items are not a given, so for a lucky subset of the populate a 401(k) contribution could be preferable. And even if investment options are inferior, front-loading your contributions to max-out the company match as early as possible is still an option.

- Joel
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