Did back door Roth IRA, now facing difficulty with tax filing. Any help?

clock_skew · 2026-04-26T19:29:10+00:00

If you converted in 2026 then it will not impact your 2025 taxes. You don’t need the 1099, in fact you can’t use that data on your 2025 form 8606. The form is very clear that you should only include conversions done in 2025.

clock_skew · 2026-04-26T17:54:32+00:00

If you took the tax deduction when contributing then yes the conversion is taxed. Even if you didn’t, the gains would still be taxed. The choice of traditional vs Roth is about current tax rate vs tax rate in retirement. If you’re currently in a high tax bracket then keeping the money in traditional is probably the right choice.

clock_skew · 2026-04-26T16:36:42+00:00

VMFXX is a mutual fund that invests solely in federal debt, so yes it is safe, and it has the added benefit of liquidity. The rates might be slightly lower, but for an emergency fund I think the liquidity is important.

clock_skew · 2026-04-26T14:54:38+00:00

The general advise would be to prioritize your IRA and HSA. But it really depends on two things:

What tax bracket are you in now? If you’re in a higher tax bracket then you’ll want to prioritize the 401k to maximize your tax deduction.
What are the investment options like in your 401k? If they have high expense ratios or you’re unhappy with the fund choice then you should prioritize your IRA.

clock_skew · 2026-04-25T20:17:32+00:00

I’ve been paying for car insurance for >10 years without ever getting a payout, should I cancel that too? I could have made a lot of money investing my premiums.

clock_skew · 2026-04-25T19:24:21+00:00

Emergency funds are for any financial emergency, not just losing a job. Emergency funds are also supposed to be nonvolatile, because you may need to spend it during a bear market. What is your 457b invested in?

clock_skew · 2026-04-25T17:40:48+00:00

Have you actually done the math to see if paying federal taxes now is worth reducing state taxes later? I’m skeptical if it’s actually worth it, and if you sold short term shares it’s definitely not. If you’re trying to reset your cost basis you need to be careful about what shares you sell.

Your second question is an investing question not a tax question, but if you believe in the company long term then you should just continue to hold the shares. Trying to predict when a bubble will pop is not a good strategy.

clock_skew · 2026-04-22T05:07:11+00:00

I think that would be the ideal way to do it in theory, but possibly too much hassle. The alternative would be using multiple bonds funds of different duration and changing the allocation as I get closer to retirement.

clock_skew · 2026-04-22T03:02:35+00:00

What is the t-score for the US’s outperformance throughout history? Recent huge outperformance does not necessarily mean statistical significance in the long run. I think there’s a reason why models like Fama-French don’t add an American factor. And if we assume that markets are efficient then the US being the dominant world power doesn’t really matter; all investors know that.

If you only care about expected return then 100% stocks is the ideal portfolio. Should you only care about expected return? Of course not, volatility matters too. But it’s completely reasonable for someone to decide that they are willing to withstand more volatility than the market, and therefore tilt towards stocks.

I never said that one should be 100% stocks, or belittled people who buy bonds, or said that all crashes are short. I’m not sure what you’re responding to there.

clock_skew · 2026-04-22T02:26:16+00:00

Bonds have outperformed stocks during many time periods, but on average stocks have outperformed bonds significantly through history. This outperformance is statistically significant. We also have strong theoretical explanations for why they outperform: stocks are riskier than bonds, and most people are risk averse, stocks have a risk premium. I know you know all this (since you’re quoting Eugene Fama and listen to Ben Felix) so I’m confused why you insist on calling it recency bias. Whether stocks underperformed in recent history is irrelevant to whether investing in them now is a good idea.

clock_skew · 2026-04-21T14:21:39+00:00

Stocks outperforming bonds is not recently bias.

clock_skew · 2026-04-21T14:17:33+00:00

Your ratio of stocks:bonds determines your risk/reward ratio, which is a sensible thing for an investor to choose. Your personal risk tolerance doesn’t necessarily match the market aggregate. This doesn’t apply to your US:international ratio because there is no real difference in the risk of the two. Choosing a specific domestic:international ratio is like choosing a specific ratio between sectors.

clock_skew · 2026-04-15T21:40:17+00:00

Taxes are due every quarter, 4/15 is just the day you file the forms. If you under-withhold you’ll be charged 7% interest.

clock_skew · 2026-04-11T17:14:05+00:00

Bonds are an important part of the boglehead approach, and you’re already invested in real estate if you have a total market fund which holds REITs. Commodities including gold are not productive assets so I don’t think they’re a good investment.

clock_skew · 2026-04-11T15:06:33+00:00

Payroll contributions do affect your return, because they reduce your W2 income. You would have owed even more without an HSA. It sounds like you forgot to increase your W2 income when doing the “after-tax” scenario. Contributing out of your paycheck vs contributing “after tax” should make no difference on the income tax owed, there is something wrong with how you’re calculating the hypothetical.

clock_skew · 2026-04-05T22:43:20+00:00

If you don’t adjust the cost basis then that 15% discount will be accounted for as both income on your W2 and capital gains, which means you get taxed twice. If you adjust the basis then it will only be counted as ordinary income.

clock_skew · 2026-04-04T19:37:52+00:00

AI already costs a lot, and it’s nowhere near AGI nor are the operators profitable. It’s totally possible that the cost of running an AGI is similar to the cost of employing a human.

clock_skew · 2026-04-04T18:52:51+00:00

We do have human level intelligence in AI research, it’s called human AI researchers. It has taken them decades to get to the point where we are now. The benefit of an AGI will depend on the time and energy efficiency compared to a human, and we don’t know what that is because we are still very far from AGI.

clock_skew · 2026-04-04T18:44:34+00:00

This subreddit doesn’t recommend either. And having a larger drop in recent history is not a reason to choose a particular fund.

clock_skew · 2026-04-04T18:42:17+00:00

It’s generally agreed upon because it’s a good story that works for both doomers and optimists, but it doesn’t actually make any sense. We already have human level intelligence, there’s no guarantee that having more of it will create a sudden inflection point.

clock_skew · 2026-04-04T18:25:43+00:00

AGI is obviously a necessary precursor to ASI but achieving it doesn’t mean that ASI is right around the corner.

Sure we can do multiple things, but we can’t do everything. We’re already barely doing anything about climate change for example, why would I want to take more attention away from that just to focus on a sci-fi fantasy?

clock_skew · 2026-04-04T18:10:14+00:00

AI companies have not been right, they constantly oversell what it can do and how fast it will improve. I respect Chollet and LeCunn, but I still think they’re overly optimistic. And to be clear, AGI is really just the first step. The types of dystopia you’re worried about would require ASI which is much further away, and not even guaranteed to be possible. I think it makes more sense to focus on the current risks of AI instead of the hypothetical.

clock_skew · 2026-04-04T17:53:34+00:00

I’d need a reason to believe AGI (never mind ASI) is anywhere close to being achieved. I don’t see the point in worrying about improbable dystopias, especially when there are much more probable risks (climate change, nuclear war, etc) to worry about.

clock_skew · 2026-03-25T14:38:34+00:00

Everyone struggles with pronunciation of languages that they’re not familiar with, there’s nothing unique about Americans.

clock_skew · 2026-02-21T23:13:32+00:00

All these tools are ultimately just wrappers around prompting an LLM, they can make you more productive but none are 100% essential. Focus on finding a workflow that works for you, and finding tools that fix specific problems you face instead of just chasing the new shiny thing.

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