Hare-Brained Schemes

I’ve found that if you create something trivial to be anxious about, it cancels out serious things that you might be anxious about.

Malcolm Gladwell, WSJ

The patriarch of a family that I advise gave me a call to ask my advice on an investment with a very low probability of success…

“Am I crazy to do this?

Should I simply toss it in the trash?”

We think alike and his questions were a reflection of my own thinking… no way you’re going to make this work, it’s likely a waste of money, yada yada yada…

My advice?

Go for it. Absolutely.


Here’s why…

The deal was in an area that’s far outside his core competency. Having the opportunity to learn, to make mistakes, to create is a lot of fun. When I’m having fun, I do all aspects of my life better (husband, father, consultant).

The deal has a limited financial and time downside. The risk of time is often overlooked – time spent worrying, time spent seeking to fix a low performer, time not spent working on a strength. My pal is very good at his strengths and has a young family. Spending additional time learning new skills is “worth” the small downsides.

As Gladwell notes, when we’re working on a modest hare-brained scheme, we are far less likely to dream up something that risks a material chunk of our net worth, have an affair, quit our job, or pursue any of the other areas of Human Misjudgment.


Related to the above, if you have trouble being financially sensible, or get a thrill from risk, then a smart way to manage yourself is to allocate a small portion of your net cash flow towards casino-type investing, or actual trips to the casino!

You’ll find that your brain doesn’t require a large stake to excite itself with anticipation and you can stay open to the creative side of your personality.

Call it your “Fund of Fun” and use if for Vacations, Luxuries and Hare-Brained Schemes.

Allocate a portion of your cash flow (and time) towards these schemes.

Keep the rest of your life sensible and run it on autopilot.


Personal note – I always know that I’m holding onto my “rules” too tightly when my wife starts telling me to “be more fun.”

Truth be told, I’m terrified of breaking the rules because there’s nothing I like better (in the moment) than a massive binge!

I need a “fun budget” more than anyone.

Binging is a clear sign of holding on too tightly.


Finally, pay attention to how “the things that you think will make you happy” make you feel. I’ve noticed a HUGE difference between what I think I need and what makes me content.

  • I’m fond of adversity in hindsight
  • More food, more alcohol, more sleep, more money, more fatigue – MORE is not my answer
  • It doesn’t take much of a hangover to negate the small marginal gain from extreme living.
  • We are naturally loss averse – the trick is to frame choices to take advantage of this tendency
  • I’m prone to forget the joy of serenity, stillness and simplicity

Anyhow, that’s my list. I sincerely hope that you take the time to write your own.

Don’t wait to start living.