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401k with paltry match or SPY ETF?
Answers: 1. Is this a good idea? Is it really risky? What are the pros and cons? Yes, it is a bad idea. I think, with all the talk about employer matches and tax rates at retirement vs. now, that you miss the forest for the trees. It's the taxes on those retirement investments over the course of 40 years that really matter. Example: Imagine $833 per month ($10k per year) invested in XYZ fund, for 40 years (when you retire). The fund happens to make 10% per year over that time, and you're taxed at 28%. How much would you have at retirement? 2. Is it a bad idea to hold both long term savings and retirement in     the same investment vehicle, especially one pegged to the US stock     market? Yes. Keep your retirement separate, and untouchable. It's supposed to be there for when you're old and unable to work. Co-mingling it with other funds will induce you to spend it ("I really need it for that house! I can always pay more into it later!"). It also can create a false sense of security ("look at how much I've got! I got that new car covered..."). So, send 10% into whatever retirement account you've got, and forget about it. Save for other goals separately.  3. Is buying SPY a "set it and forget it" sort of deal, or would I need     to rebalance, selling some of SPY and reinvesting in a safer vehicle     like bonds over time? For a retirement account, yes, you would. That's the advantage of target date retirement funds like the one in your 401k. They handle that, and you don't have to worry about it. Think about it: do you know how to "age" your account, and what to age it into, and by how much every year? No offense, but your next question is what an ETF is! 4. I don't know ANYTHING about ETFs. Things to consider/know/read? Start here: http://www.investopedia.com/terms/e/etf.asp 5. My company plan is "retirement goal" focused, which, according to     Fidelity, means that the asset allocation becomes more conservative     over time and switches to an "income fund" after the retirement     target date (2050). Would I need to rebalance over time if holding     SPY? Answered in #3. 6. I'm pretty sure that contributing pretax to 401k is a good idea     because I won't be in the 28% tax bracket when I retire. How are the     benefits of investing in SPY outweigh paying taxes up front, or do     they not? Partially answered in #1. Note that it's that 4 decades of tax-free growth that's the big dog for winning your retirement. Company matches (if you get one) are just a bonus, and the fact that contributions are tax free is a cherry on top. 7. Please comment on anything else you think I am missing I think what you're missing is that winning at personal finance is easy, and winning at personal finance is hard