How much $ do I need in my 401k to retire comfortably (2 vacations per year, maybe a new car) at 65 assuming I own property? In the Bay Area (Los Altos) vs Chicago?

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$1m, oh wait, you said Bay Area, $45m, used car…

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given the type of lifestyle you mentioned you wanted, this is WAY out of line. You don’t need 10 millie to retire at 65 lol that’s like a conservative $400-500K you can take out per year to not even dip into your principle

Work backwards and you can calculate that yourself

1. Determine how much money per year it would take to have that lifestyle

2. Divide that annual number by the safe withdrawal rate (usually 4 or 5%)

3. Adjust for inflation by taking projected inflation rate and number of years till retirement

4. Assume taxes that will need to be paid if traditional 401k. Personally I assume one tax bracket above what it is now since I expect taxes to go up

5. Take that number and subtract what you already have. Divide that by number of years remaining. Evaluate: does this look doable based on conservative estimates of stock market returns?

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It depends. There are some helpful websites that will show, but this is all based on assumptions about market growth until retirement and then through retirement, as well as how much you’ll spend during retirement and how long you will be retired (which includes both how long you expect to live and the age at which you retire).

There are a few rules of thumb here - the 4% rule says you should plan to withdraw 4% of your savings in your first year of retirement and adjust that number each year for inflation without running out of money for at least 30 years.

Fidelity says you want the following milestones:
1x salary by age 30
3x salary by age 40
6x by age 50
8x by age 60
10x by age 67

LEK is exactly right. It's important to think of retirement in terms of expenses, not salary.

Whatever you calculate x3 because you couldn’t figure this out on your own.

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