One idea I've covered quite a few times before is the extent to which the options market does not give money away for free. Marketwatch had a look at a trade chronicled at Reddit and executed through Robinhood called a box spread. The short explanation is that it is a combination of options such that it should be directionally neutral and you should get to keep the net premiums.
The trader putting this on had one of the options he sold, assigned and ended up owing more money to the brokerage firm than he first started with. Basically he had to buy the underlying at a price (the strike price of the option) that was much higher than the prevailing market price.
Marketwatch said that the trader bragged that the trade could not fail but one of the Reddit group moderators urged him not to do the trade. A good starting point for how to assess some options trade that appears to be wildly lucrative is to assume you're missing something or there is something you don't understand and of course, the options market never gives money away for free.
White Coat Investor had a good primer on Health Savings Accounts. I've written countless times about HSAs, we've been contributing to one almost since the beginning. Arguably, in the right circumstance (White Coat goes into what the right circumstance is) it is the second most important retirement vehicle you can contribute to with number one being your 401k up to the employer match. If you are unable to max out your 401k then getting the match and then funding your HSA makes a lot of sense.
White Coat addresses the tax favorability, saving receipts from today to take tax free withdrawals in the future and one that I didn't know, he says you can use your HSA funds to cover Medicare premiums. I got very excited for a moment, wondering if that might include supplemental Medicare but it looks like that is not the case. It appears to just be ok for regular Medicare. This could come in handy if you're 65 but not yet taking Social Security (usually Medicare is deducted from your SS payout) and I would add if you're lucky enough to not have chronic medical issues that you have to pay for. That last bit is yet another instance where modified behavior (diet and exercise) could make your retirement expenses cheaper.
Circling back to a post from Farnam Street about ten ways to live an antifragile life. Where antifragile means benefiting from disorder or other tumult, not all of the ideas seem to fit the bill even if they are good for enhanced resiliency. The one I like the most is "keep your options open." It can be antifragile but doesn't have to be.
I write about optionality a lot. Keeping options open or creating new options can make every other aspect of your life easier. I've told the story many times of getting laid off at Schwab in 2001 and how, professionally speaking, it was probably the best thing that ever happened to me. I had a sense it was coming about a year and a half ahead of time and began to do things that created some optionality for myself. This was long before antifragile became a term and while it did take a couple of years for it to become the best thing that ever happened, by virtue of having created more options it was not a stressful time.
Sticking with this, one nagging aspect of the job market since the tech wreck is the extent to which many people have been underemployed relative to their skill set or had to retrain for an entirely new field. This has created awareness of ageism as manifested by the difficulty people older than 50 have in finding work on par with what they'd been doing previously. You may disagree with the magnitude of this issue but there is no denying it exists to some degree.
If you worked in an office setting making $75,000 or $100,000 and then found yourself out of work in your 50's and could not get essentially the same job somewhere else, would you have options? Have you cultivated anything entrepreneurial that you could do, have you monetized a hobby, are you physically capable to doing some sort of labor (this could include something where you have to stand all day)? There are no doubt other examples.
In addition to optionality you also are living a more interesting life and continuing to learn new things is a key component to successful aging; increased healthspan.
Finally a Tweet from @AJA_Cortes that resonated, about what freedom in the 21st century looks like. The two points that really hit home for me were total control of your time and living where you want to live.
These things both tie into optionality. They are achievable by hustling, staying curious, living below your means and figuring out how to be good (or even just good enough) at something you love doing. I don't think there are short cuts here, there (probably) needs to be dues paid but never discount the role luck plays in anything, especially the life you create for yourself.