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Reply to "Long Term Strategy vs Risky Short Term Returns"

It's typically advised to only contribute up to your 401k match. Once there is no longer a match, or in other words, free money, invest other funds into an IRA. The reasoning is 401 plans are typically limited in the investments you can choose and will be taxed upon withdrawal. However, it varies, so if you feel it is optimal for you to continue to invest in your 401k based on your analysis then continue to do so.

Regarding your logic with taking on more risk with after-tax dollars. Higher risk comes with a higher reward, but the risk persists. This means it is possible to further decrease the amount of money you have. It has already been taxed, then you risk the potential to lose it all or significant amounts by taking on additional risk. It can be argued that it is better to preserve the after-tax dollars since they have already been reduced by being taxed.

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