Playing it safe


Uncertainty, comfort, and regret are all absurdly expensive.

If there’s one thing I’ve learned — especially over the last few years — it’s that we need to operate to minimize our regret as much as possible. By virtue of playing it safe we will only ever be rewarded with the same. Rewarded with the same paycheck each week. Rewarded with unrequited love. Rewarded with an overall lack of fulfillment.

And like I said, that cost is expensive. Life doesn’t handsomely reward those that succumb to comfort. There’s an incredible quote attributed to Steve Jobs back in the 90’s suggesting that our lives become broader when we realize that everything around us was made up by people not smarter than ourselves.

And that’s just the thing! We’re all presented with the same opportunity to craft the world around us. And when we play it safe, when we succumb to comfort, we receive the same bag of rewards mentioned earlier.

And so how do you craft the world around you? How do you stop playing it safe? How do you responsibly put it all on the line in aspiration of greener pastures?

You consistently shake it up

In Ryan Holiday’s Trust Me I’m Lying, he shares a story about a framework he invented called “Trading Up The Chain”. When he couldn’t get media press from nationwide audiences, he crafted a plan. By publishing with a conglomerate of small blogs, Ryan could leverage this press into additional press until his story was on bigger desks.

This was fairly unheard of. The tried and true process was rubbing enough elbows. It doesn’t take a genius to realize that media companies operate for page-views. And so with an ounce of credibility, and a proven story, one can get expensive press for free.

Shake up the tried and true.

I have a friend that I once worked with that was consistently told to stay in his lane. Despite this he pressed forward each day, much to the chagrin of the team, consistently questioning bad quality and poor process. He would later go on to be one of the most valuable employees they ever had and one of the brightest minds I know.

Companies — whether they say it or not — are constantly looking for diamonds in the rough. They hire for a (hopefully) descript and narrow role, and simultaneously hope they may have placed a budding, future CEO. And all you have to do is try.

So operate to respectfully shake it up at all times. Speak up for better process, operate outside of your lane, and respectfully abolish the tried and true.

You stop doing what everyone else is

Ultimately, the point is this: doing what everyone else is doing is bogus.

  • Don’t apply for jobs by shoving your resume into the Indeed engine, effectively rolling your dice as many times as possible. Do create a personalized pitch deck on why they should hire you, and consider offering up free analysis and suggestions alongside it. Send bold emails to hiring managers.
  • Don’t wait for your dream house to go on the market. Do knock on it and ask them to call you first when it’s available.
  • Don’t wait for your annual raise. Do prove your worth and make a substantiated, evidence-based argument on why you should be paid more.
  • Don’t build a sales team around fumbling a dial-pad and jamming down a list in the CRM. Do build an optimized content engine and an aggressive email drip/marketing campaign to match.
  • Don’t accept a missed deadline and a higher price-tag. Do email and ask kindly for a discount.
  • Don’t fall into the routine of performing repeatable tasks each week. Do document and hand them off to virtual assistants.
  • Don’t apply for jobs you don’t want to do exclusively because you’re qualified. Do get hired to do jobs you love by doing free work.
  • Don’t wait to get training through the sands of time. Do cold email and message hundreds of people and ask for their time over a cup of coffee.

I’ve gotten jobs and received opportunities to do things I never thought possible because I took risks. Being fairly non-confrontational, I’ve sent emails that still surprise me to this day. It’s hard but it’s rewarding. And ultimately, we should always be optimizing to maximize reward and reduce risk.

The danger of playing it safe is opportunity cost.

Albert Einstein once said that the definition of insanity is doing the same thing over and over again and expecting different results. And yet...