Playing it Dangerous

If you play it too safe, it could be more dangerous in the long run

I’m just gonna play it safe.

I’ll just take the sure thing.

I went with the sure bet.

These phrases are all just similar ways to express the same desire to not take too many chances, lest something bad might happen. And, in many instances, taking the “on paper” safe path is probably the right call. Whether it is deciding not to wrestle an alligator, bet your life savings on a game of H.O.R.S.E. with Lebron James, or take the wheel after a few cocktails, there are moments where taking a safer path will literally keep you safe from physical harm.

And in those cases, I am in no way advocating that making a riskier choice is the right way to go (but if you did take those chances and come out ahead, they’d make for a helluva story. But a story is not a reason to endanger yourself…usually).

But I think the “safe path” is a trap oftentimes. Because there comes a point when if you want any sort of return on your choice investment, you will have to make some moves that could leave you vulnerable to pain and loss.

For example(s):

-You could play it safe with your money and keep all your savings in cash. Sure, you’d never lose money, but it would also never grow had you invested it with the chance you could “lose” some along the way (this is not investment advice, but if you read the wonderful book The Simple Path to Wealth by J.L. Collins, you’ll see that simply investing in total stock market index funds is a likely path to growing your nest egg). I put lose in “ “ marks because if you don’t sell when the market is down, and wait for it to come back up you don’t really lose money. But I digress.

-You could play it safe and never ask that girl/guy out on a date. Sure, you’d never feel the pain of rejection, but you’d also then have the pain of not finding an awesome partner to share your life with.

-You could play it safe and take the “sure bet” career path. Sure, it may not be what you love, like, or even tolerate, but then you’d have the pain of regret, wondering what you could have done or been had you done anything remotely closer to what you enjoy for a vocation.

And it’s that 3^rd point that sticks especially hard with me. Pharmacy was something I picked because it was more a sure thing. Go to college. Get the degree. Get the job. Get paid. A very logical series of choices for a career from my brain that has been annoyingly logical since I was a little kid. Now, my other career “plan” was pitching for the Chicago Cubs, and despite the struggles of their bullpen, I still probably did not have a chance of making that career dream happen.

Also, I don’t want to sound ungrateful for a career choice that has led me down a path to a pretty cool life. Because pharmacy has provided an educational base that has had me meet some very smart and interesting people, help a lot of patients, and has helped shape who I am. But in retrospect, there were a number of things that I had more interest in than pharmacy:

-sports

-history

-comedy

-aviation

But even back at 17 when I made the logical choice to pursue pharmacy, these career paths seemed too “risky.” And so yes, even though many people live by the motto “no regrets,” I do have some tinges of regret that I didn’t go after one of these things that was calling me harder. It’s a dichotomy, because I would not want to trade my life now with the people, family, and friends I have, but it does serve as a lesson to myself, and you, for now and in the future to not limit your belief in what you can do because something could be “too risky.”

And, this is a balance. I am glad that despite my 6 figure student loans, I got a career that I could pay those off and support myself and family. There is a risk of an expensive education that doesn’t provide a career as well.

To put it simply: risk and regret is a balance.

You can’t put all your money in bitcoin, infinitely date new people “in case” a better person can come along, or change career paths every 3 months. Well, you could, it probably just wouldn’t work out great for you in the end.

So, what is your risk tolerance?

That is a question only you can answer. But as I have grown older, I have come to realize my youthful overly safe approach has brought more pain than some of the moderate risks I have decided to take. Advocating for more risk is not a conventional set of advice, but it simply comes down to this in any decision:

What will you regret more?