59.5 comes pretty fast. I completely agree with diversifying but if you can't afford to max out your tax advantaged accounts then you shouldn't be investing heavily anywhere else. You should be making enough to max everything out and have some side investments. Most guys who say they want to invest elsewhere don't do the math on the tax advantage of 401k's and IRA's.

I know a retired major airline pilot that has out of pocket medical related expenses of $7000 per month despite being heavily insured.
Nobody will lend money for health care or retirement like they will for school.

Thanks guys, great advice all around.

I plan on fully investing in the company retirement plan. I am doing 5% extra right now on first year pay, then plugging some more in next year. That will put me at about 26% of my w2 in retirement savings, which when I plug it in as a rough estimate shows me at around 7 million bucks. Next year alone should net 39k in retirement contributions, equaling 9 years of fully vested company matching and contributions from my regional days.

I just think that if I have a second gig I wont be putting 53 k MORE! into retirement vehicles, rather reinvesting into other areas like real estate, etc.

There should be a pilot investment club, all the FO's buy the Captains beer while they tell them all the things NOT to do! (and what worked)

It's called a PCRA at Schwab. I have brokerage accounts on both the 401k and PRAP.

You can even have a third party manage the PCRA investments.

Morningstar is who I use.

How have they been? I just started with Retirement Advisors of America.

Wiser Wealth. Former Airline pilot and ALPA R&I guy. Highly recommend talking with him.

Out of curiosity, what calculator are you using?

I think your being overly optimistic on your average return over the next 30 years. Not saying its impossible, but not a high probability. I would use 5-6 percent in your calculators. Don't forget also in 30 years at 3% annual inflation your money will be worth roughly 2.5 times less than it is today. I'm maxing my personal contribution out and am 70% likely will be around 6 mil at the end of my 33.5 year career. Thats only 2.4 mil in todays dollars. Better to be overly prepared than under prepared. Especially when we don't have the ability to work longer if we need to.