How to Reboot Your Thinking with Worst Idea Possible

by Jeff Hittner

As much as we’d like to believe we’re open to changing the trajectory of our careers, we are almost always searching for new solutions from the same mindset that got us stuck in the first place.

Why? We all carry with us the same general insecurities: judgment, doubt, and fear.

If we try to explore a new direction, one of them will start lingering behind the bushes. When it jumps out, we’re going to dismiss things that seem out of the ordinary, outside our comfort zone, and inconsistent with our past experiences.


Our past experiences got us stuck in our current thinking, yet they are informing us—through our fears and doubts—about what to do going forward.

“I can’t reach out to him, what if he doesn’t want to help…

They’ll be too busy.

She won’t respond to this.”

In our programs, we hear these rationalizations all too often. This is judgment — of ourselves and others. We judge ourselves unworthy and others as too inconvenienced. Our program participants discover most people are pleasantly surprised when they reach out. People like to help!

“When you’re convinced you can’t think of any new “good” options (in a world that is limitless!), chances are you’ve already narrowed your lens.”

With very few exceptions, we all fall prey to narrowing our options. Recognizing this requires a bit of self-awareness. When you consider a new idea and your immediate reaction is to shun it, do you sense a twinge of anxiety? When you’re convinced you can’t think of any new “good” options (in a world that is limitless!), chances are you’ve already narrowed your lens.


(None of them require you to perform psychoanalysis on your fears…)

  1. Find a friend with 20,000 unopened emails! This is my way of saying get advice from someone that has nothing in common with you (they could have a different education background or a different family background). If you’re the one with 20,000 unopened emails, find someone that is super structured. Ideal life hack: marry someone that thinks completely differently than you. Think about how many times your narrow point of view will be challenged then. Yes, I know from experience.
  2. Alter your mind! No, not in that way… Meditate, do yoga, go for a jog. Do something to physically change your brain chemistry a bit. Exercising is a common tool, but if you’re not into sweating, mindfulness works great, too.
  3. Throw away your phone! …just for a day. I call it the ‘tech Shabbat’. In Judaism, Shabbat is sundown Friday to Saturday, a time of deep reflection that is meant to be technology free. The best ideas come when we’re bored. When our minds wander they connect disparate concepts. With our phones, we don’t allow this to happen anymore. There’s too much news / WhatsApp videos / Instagram updates to go through.
  4. Create art! The act of tapping into your creative self—and we are all creative—has a profound effect on changing our perspective. Creativity is a conduit to everything we go through in life because, like with any creative exercise, our futures have no fixed outcomes. I suggest drawing your future fulfilled. Sketch yourself 20 years from now. It can be abstract: the goal is to visually create what a fulfilled future would look like.
  5. Write Morning Pages. Made famous by Julia Cameron, it’s a simple process of drafting 3 pages of longhand, stream-of-consciousness writing at the start of your day. I recommend getting an accountability partner to do it with you each morning. It can do wonders for clearing your head and helping you prioritize your life.
  6. Audit your network. Go through your community of friends, colleagues and barely-remembered contacts. How similar and how different are most of them from you? Reach out to the ones that think and act differently from you. You could easily go through a couple hundred names and reach out to only a dozen that you know are going to have a perspective of their own.
  7. Find the Worst Idea Possible – last and certainly my favorite. Take whatever topic you are stuck on and spend 5 minutes brainstorming the absolute worst ideas to change that situation. Bonus points if you can get several friends to join you. This exercise actively blocks out the barriers you have to new possibilities because we’re already framing them as crazy! For example, a participant in one of our programs was fearful about opening a coffee shop. She went through this process and came up with the worst idea possible: running a coffee shop from 9pm till 5am. Crazy, right? From this, she zeroed in on a unique opportunity: opening a pop-up coffee stand from 3-6am next to several early morning events. This is the next step. We look at our ideas and consider what aspects of them can be tweaked to actually experiment with.

Now you’re ready to shift your mindset and get unstuck. If any of these concepts peak your interest, tune into the podcast we did on the topic with Kylon at Successful Dropout.

Related: How to Reign In Fear and Invite Curiosity Instead

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