I found a few posts that relate to risk taking in various aspects of life.
First is this comment is related to investing that comes from Richard Zeckhauser a professor at Harvard who was featured by Tren Griffin;
> ... I am willing to make some bets where you say it is 20% likely to work but you get a big pay-off if it works, and only has a small cost if it does not. I will take that gamble.
This is along the lines of comments made by Nassim Taleb a long time ago that I have referenced here numerous times. The idea of concentrating a lot of risk into a small portion of your investment portfolio. I chronicled my personal trade in Grayscale Bitcoin Trust (GBTC) back in November. I'd tried to learn as much as I could (this is still an ongoing process) and while I was skeptical that Bitcoin could go to $400,000 or any of the other massive price targets placed on it, I did not want to watch it go that high from the sidelines so I bought a very small amount. It rocketed up so fast I sold it thinking I would get in later but have not done so yet and don't know when or if I will. It is not something I think is appropriate for clients; there is nothing underlying it and as I have said many times all the favorable attributes projected onto Bitcoin could easily accrue to some yet to be created cryptocurrency.
That anecdote though captures appropriate sizing for what amounts to a lottery ticket (I bought less than one year's Roth IRA contribution). I've made a similar investment in stock of The Maven (MVEN), this website. I bought it after it went down a lot and then it dropped a lot more. The investment is tiny. The story is intriguing but then the story is almost always intriguing with nano cap stocks. I have absolutely no idea if the story as presented to the writers will pan out and I never considered buying it for clients. I've heard the story several times and I don't want to watch it go up to some astronomical market cap knowing what I know. Everything here is public, I heard the story for the first time last December the day after it was presented at an investor conference. This could be described as a form of FOMO but the dollars are inconsequential if it goes to zero but very life enhancing if it goes to $50 which is not a prediction. Again, I view this as a lottery ticket and am not buying for clients. But it is a great example of a lot of risk concentrated into a small position. You might be exposed to things/companies in your life where you've learned some things about a company (ies) and would not want to watch it skyrocket without you. If you do, keep the speculation small enough that it cannot hurt you but can help you if it actually pays off.
The next risk relates to career risk as noted by Mark Baker who Tweeted an excerpt from his book Gang Fit which talks about how depressing it is (his opinion) to have some mundane job that you commute to all because you were told this is how things should be done. He basically calls this a miserable existence, click through to check it out.
In my adult life I've had very few jobs, I tend to stay a long time in one place but there have been three times where I have taken risks that I believe were calculated in pursuit of where I wanted to end up. The way I have framed Mark's idea is to not want to sit in a cubicle wishing the week away to get to the weekend. I view that as an awful way to live. James Altucher likes to advise people to QUIT YOUR JOB TODAY which isn't practical for too many folks. Quitting a job you don't like should involve some planning. How long can you go without your paycheck, do you have a specific plan of what you will do, if that means going the self employed route, how long will it take to generate income, is there a point where your new self employed venture should be deemed a failure and there are more questions you should answer for yourself.
Somewhere in there is the line between taking a risk and being reckless. The path to where you want probably involves taking a couple of risks, calculated risks, without QUIT TODAY recklessness.
I've told the story of my layoff from Charles Schwab many times. I got laid off in late September 2001 about two weeks after 9/11. I knew in the spring of 2000 it was going to happen but did not know when. I stopped putting money in my 401k and let my vacation time build up so that I would have a robust "war chest" that along with my severance would last for hopefully a long time, if we needed it. The catalyst for my knowing it was coming was then CEO Dave Pottruck leaving a company-wide voicemail gushing about the stock's price hitting $100 while at about the same time opening yet another call center in Austin, TX. Getting laid off was one of the two or three best things to happen to me professionally but it probably would not have been so had I let it catch me off guard. Whether you love what you do or hate it you need to stay curious and engaged to have the best shot of being out in front of something adverse occurring which then gives the best shot of making something that appears to be bad actually a huge positive.
The final article talks about letting children take risks when they play. I won't attempt to tell anyone how to raise their children but I don't think people would disagree that kids from the 60's, 70's and into the 80's collectively took more risks when they played.
Pivoting to adults and risk taking, we are better off for enduring the stress that goes with certain types of risk and succeeding in the face of that risk. One example could be something it involves balance or agility where the consequence is falling, not falling off a cliff but maybe scraping yourself up if you lose your balance. Doing something on a ladder could be risky to a certain extent. Arguably, volunteering as a firefighter is a way to take the sort of calculated risks that can make you stronger and healthier. There are many opportunities to take calculated risks as a firefighter (potentially good for you) and opportunities to be reckless (which at the very least is not good). Again the concept of risk versus reckless is very important to understand.
I would differentiate this type of stress/risk from the type of stress of having a big monthly nut and a lumpy income, or the stress that goes with getting angry every day in traffic commuting to work or having deal with coworkers and/or bosses who seem to delight in making you miserable.
The call to action here is to learn more about positive stressors and negative stressors, what kinds of risks are appropriate for you and how you can benefit health-wise, career-wise and financially from the right kinds of stress and risk.