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In regards to the 401k, I disagree. Unless your employer only offers really crappy funds it's in no way gambling.

First off, your employer match is essentially free money. It's foolish to ignore that. The tax benefits can also be significant. For instance, I contribute 25% of my pre-tax salary to my 401k. That works out to $1500 a month but because my taxable income is lowered my monthly net is only decreased by about $950. That's $550 a month into savings that I wouldn't have previously had due to taxes.

If you follow the investing philosophy of John C. Bogle, founder of Vanguard, you'll likely do just fine. Assuming you're young, you just split your 401k between four index funds: total bond market, total domestic stock market, total international stock market and real estate investment trusts (REITs). I do 20/45/25/10. Yes, in the short term you might take a big hit but in the long term (>20 years) this is historically shown to perform very well. As you get closer to retirement you increase the proportion of your portfolio in bonds so as to lower your risk.

Indeed. With a historical performance of 9% a year returns and a 100% employer match, you'd have to be pretty pessimistic about the future of the economy to not have a 401k. (Though one could argue that taxes will be higher in the future, and so paying taxes now might be better than paying taxes when you take the distribution.)

You don't even have to manage the split yourself, there are plenty of mutual funds that target certain retirement year changes and rebalance the portfolio as appropriate (basically: less risky investments as your retirement date nears). There are fees for this, of course, but for my fund they amount to $90 per 10 years per $10,000 invested. I think that's worth it if you don't want to actively manage your retirement portfolio.

You still have to be pretty pessimistic to think taxes will rise faster than your rate of return!

The point of 401k is that you compound the growth on the deferred tax money, and then pay much less /present value/ tax once you retire. Index funds and high yield bond funds give you low overhead with almost no "gambling" element. Drawbacks: Limited maximum contribution, very long deferred gratification, vulnerable to future policy changes.

Exactly. I keep all of my 401k in index funds, same with my Roth IRA. I have other non-tax-advantaged accounts I use to investing in individual stocks.

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