A lot of the advice posted above is correct.

The most important thing is: Max the 401k out! If you do it early or spread it out, just max it out!

The next thing is to watch the fees. Big fees add up more than people realize. If you are investing with an advisor that charges the standard 1% and they put you in funds that have fees up to 1%, you are getting absolutely killed. A 2% total fee after 30 years will cut your money by about 1/3. Do not do that crap.

Statistically, you are better do front load and get the $19,500 in as early as possible. But if the market is due for a correction, it might be a good time to think about spreading it out. The markets historically do 10% a year, so you should normally be better off getting it in there asap at the start of every year. But, with markets really high now and possible in store for a correction, I think spreading it out is a fine idea for this year.

Lastly, if you are not near retirement, you should be in stocks and not bonds. Bonds are yielding such low rates right now, that with inflation, you'll likely be going backwards. If you have 5 years left, you'll want to start protecting your money, but if you are in your 30s or 40s, you should be all in in stocks. Bonds aren't a good choice for younger folks right now.

Also. Don't take financial advice on a forum. But, you can listen to me

Tax brackets can be a helpful gauge. For example, if your single and a mainline captain (or even fo if your in the 200k’s) your more than likely paying 35% tax on the entire 19,500 if you do it as a Roth. I’m fairly confident that won’t be the case in retirement. Based on the today’s same chart it would be 24% to withdraw up to 83k-163k and the amount below 83k is taxed even less. Not only that you just put yourself closer to the AMT.

I think I'd rather be taxed 35% on 19.5 than 24% on 50 or 70 (assuming doubling every 7-10 years and 15-30 years before drawing much more than RMDs from the Roth). AMT is another factor, for sure.

except it’s not 24% on the first 50-70. That would be 10% on the first 10k, 12% next 10-40, then 22% 40-85k. Somewhere around 15% tax to take out 85k. That’s AGI as well. Could probably pull 100k for an average of 15% or pay a guaranteed 35% now. Roll into a Roth when your in a low tax bracket for whatever reason. There’s no real right answer but if your in a high tax bracket it should be a factor in your decision. My current tax guy likes to keep it non Roth and max a Roth IRA with the 6k tax savings. Best of both worlds for the same $.

It is certainly a good idea to transfer funds to a Roth during low income.
Another thing to keep in mind is that Roth income does not count against social security income.
Social security ( depending on your age) is full retirement at 67 and increases 8% a year until 70. You can make an account online and see what you will make at depending on when you collect.
Tax strategies in retirement are a whole new ballgame.

I’ve been able to roll 30/40k or so twice into my Roth sub 20% tax. First year at a mainline and back in 2008ish when everyone was taking pay cuts as an fo.

That works when below the income and contribution limits. Once you hit the limits, there is an argument for pre-paying taxes so you have more spendable income in retirement. If your retirement funds are in a traditional IRA, you are using retirement funds to pay taxes. If your retirement funds are in Roth accounts, you are using retirement funds for retirement.

understood. Zero $ in traditional Ira, it’s all in a roth ira via conversion, rollover, or original contribution when in lower tax brackets. That’s the one no brainer after contributions are no longer tax deductible. I guess you could say I paid 35% on the back door Roth conversion contribution and that would be correct but it was all tax savings to begin with.

You don’t pay tax on Roth earnings. So even in a high tax bracket now it’s worth putting in Roth. Let’s say you put $19,500 in a Roth 401k today and it gets taxed at 35%.

Let’s say that $19,500 is worth $100,000 in retirement when you decide to withdraw it. My understanding is that entire amount is withdrawn tax free. So I’d rather get taxed at 35% on $19,500 now than get taxed 15-20% on $100,000 as I would on a traditional tax deferred 401k

Ideally, by the time you retire you’ve paid off all your mortgages and loans. You can probably live on $80,000/yr to pay for just utilities, travel, and your retirement goal hobbies. $7000/mo without a mortgage or car payment can get you pretty far. Currently the federal tax bracket for married filing jointly is 12% up to $80,250.

Roth is an amazing vehicle, but your 401k rates at retirement should’ve spook you out to avoid loading it up. Especially if the $19,500 is going to be taxed at 28% this year.