Thinking of retiring at 50. After I retire, what are some of the small gigs I can do to get some cash flows and enjoy retirement, without going throght the full 50 hour a week grind?

For context, a 44 year old MD. I think by 50 I'd have enough saved to last the lifetime, but don't want to be doing "nothing" while I travel for most part of the year.

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I’m thinking about retiring when I am 50. My plan is 1.) own and run a few rental properties, 2.) pick up a hobby (like learning to play violin), 3.) clean, cook and bake daily, 4.) work out daily, and 5.) travel regularly.

likeuplifting

Usher at a performing arts venue (Lincoln Center/Kennedy Center/etc.)

likeuplifting

I do this now too - a couple performances per month. I enjoy it a lot

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Starbucks barista. Perma vacationer

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Yeah, that’s too much work for sure

Hey there - just be aware of health insurance costs if you retire early. You won’t be eligible for Medicare until 65 (I think, honestly don’t know but it isn’t 50…). At most “laid back” employers (e.g. barista at Starbucks) require an hourly minimum before they cover health. Starbucks is 240 hours in a 3 month period, for example and they do a check every 6 months even after you meet the minimum. Not sure how easy it would be to, say, be a barista in Miami for 3 months while you enjoy the beach, then move that gig to Anchorage for the summer. This would likely prove difficult - but would be cool to know for folks that want to travel.

Anyway, I’m here at McK because of health insurance (and I like my colleagues). Despite McK’s reputation for burning out people, I took an (internal) role that is flexible, low effort, and lets me work from anywhere. Even in a role similar to mine - others get burnt out. I don’t because the folks around me know I am working for fun so frankly don’t ask me to do stupid shit that has no value.

likeupliftingsmart

Wells Fargo…a big part of planning is designing income “flexibility” to gain subsidies…i.e., how much of your nest egg is in Roth, how much is in taxable account (and what percent of that is cost basis), and what amount is in Traditional? The three main tax buckets will determine what your income can be on a given spending budget…ultimately, if you’ve got 25 times spending in investments(4% rule, as an example)…that might be 5 Roth, 5 taxable(with 2/3 imbedded cost basis) and 15 Traditional…thus, you would be taxed on 2.88% roughly of your 4% withdrawal with proportional withdrawals…or you can compare that baseline withdrawal strategy with withdrawing just enough from pre-tax Traditional to allow for a maximum subsidy…you can also look at what “tax-gain harvesting” or partial Roth-conversions in the year before retirement would do to your future strategy…it’s just an optimization calculation across multiple dimensions.

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Start a small business that you like and put in as much time as you want and have other people manage it when you’re not there.

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I plan to work at/manage a small nonprofit 40 hours a week. Even that would feel like retirement compared to law firm hours.

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Seasonal tax prep!

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Started at $9 in college and they did base pay up to $25 (guarantee 75% with 25% additional bonus) was averaging more than my B4 internship hourly. Would recommend more seasonal CPA or remote work it’s not that bad if you’re experienced. What would I know though considering B4 seasonal at my level is now 3 digits hourly.

uplifting

You should look into gig economy - Airbnb a room out or your house when you are traveling, lyft/Uber. I have been mentoring women in tech for free, I may start charging a small fee to keep the income coming. That’s my plan. I will do this under my Llc so I can get health insurance as an employee of my own Llc.

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Read 4 hour work week by Tim ferriss

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That’s about starting a business, right?

You can start a small company to do consulting at your own pace. Maybe become a qa director and remote in from anywhere

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Quality Assurance director. MDs with tons of experience will be checking the project stats periodically and provide guidance to other MDs on the firm/Sr. Leadership.

Can you teach anything?

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Livestock

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Livestock will limit travel mobility, and I want to continue to be living in the city. So, this won't work I guess

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Congratulations on being close to retirement! I'm currently in my late 20s and doing the calculations. I know this isn't your question, but I'm curious, at what age did you make MD and what level of MD are you currently at (e.g CL1-4)

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I think about this frequently, too, as I'm 40 and have hit my FI number. I think in my case (consulting) the most likely next step is independent contracting, and being incredibly picky about which projects to take (client/culture/location). I could reasonably transition into an individual contributor role, and dial the stress way down, and still have periods with something interesting and mentally challenging to work on.

As others have said, my biggest question is (sadly) health insurance. There's currently a cap on ACA plan premiums to not exceed 9% of MAGI. (It's also not permanent, though it's something this administration would like to change.) This is pretty reasonable if living on a retirement budget of mostly capital gains, but a harder pill to swallow if I do consulting projects for 12-18 month stints that create lumpy income streams.

I'm in a bit of wait-and-see mode as covid hopefully disappears, and I see the state of the emerging economy - and my investments - but I'm definitely approaching an inflection point, too.

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Substitute teacher

Go to graduate school to earn a passion degree with hopefully scholarship and healthy insurance?

You could do volunteer or short duration doctoring at a ski resort or a base camp or something else where it’s fun but people get hurt sometimes. Adjust teaching.

Did I miss something? If the premium is capped, it sounds like you can pay a capped amount, which seems a good thing.

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