Paranoid Optimism

You can assume that everything that can go wrong, will, and still be an optimist. Trust me, I’m a pro at it.

Flash back a few years ago to early 2014. At work, my division was growing like wildfire. Like a thorny weed. Like bunny rabbits. Heck it was growing so fast we couldn’t remember who was on the team. We were extremely bullish about the outlook for our division and even more bullish about the industry we were helping to create. “Coding bootcamps” as an industry didn’t exist before 2012, and we were at the forefront of this burgeoning world in education. We were helping people change their lives (someone actually told me that I saved their life, a surreal moment I’ll never forget) and we woke up each day with a great sense of purpose.

That said, I attribute much of our success to our ability to plan for the worst and react to unforeseen issues quickly. At night I played through disaster scenario after disaster scenario in my mind. The instructor wouldn’t show on the first day. A student would arrive on campus with a weapon. A student would claim I misled them. I could go on and on. Many of these things did actually play out in reality in addition to many many more that we did not see coming.

These experiences instilled a mental toughness in our team but never dissuaded us from continuing to push forward toward a wonderful future. We became paranoid optimists.

The key to understanding paranoid optimism is to understand that it’s not an inherent contradiction. In fact, I firmly believe that healthy bouts of short term paranoia actually protect and even enhance one’s ability to be optimistic over the long term.

Basically if you prepare for worst case scenarios and assume anything that can go wrong, will, you’ll put processes in place to ensure your short term initiatives succeed, thus enabling your long term vision. You’ll also likely to consistently have a positive view of the future just by thinking about all the precautions you’ve put in place.

I’ve thought about what this tactically looks like day to day based on my experiences, and here are some of my top tips for being a paranoid optimist in business:

  • Learn which of your key contacts (coworkers, partners, or clients) always do what they say they’ll do. Observe and analyze those who don’t. Never believe that the people who don’t always deliver, will deliver if your plans depend on it.
  • Create back up plans for everything. This goes without saying.
  • Train your teammates to think with a lens of paranoid optimism, especially in the context of managing up and in matrix management.
  • Write out all your assumptions for a project, and then have other teammates review the assumptions you’ve listed.
  • Fact or gut check your assumptions checklist against industry standards – if you’re way off from industry standards you need to have a clear reason why.
  • Under promise, over deliver – this old adage is especially helpful for short term paranoia
  • Remember no good comes from wallowing over the fact that something bad has happened. When something bad happens paranoid optimists go “man should have realized that, okay let’s figure out how to fix it….”
  • When you think someone won’t respond, let them know you’ll follow up with them in a few days, and set a reminder to do so (I love the gmail plugin Boomerang). Giving a preview as to how often you’ll follow up makes following up less annoying to the other person

Paranoid optimism is a mental approach to an uncertain yet wonderful future. It’s good for life, even better for business.

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