How to Solve a Dilemma
With real-life examples.
Dilemmas suck up time and energy, but almost all dilemmas come down to two paths: love and fear.
When you’re confronted with a difficult decision, try to recognize which path is rooted in fear and which is based on love. Choose love, but balance it with common sense. It almost always works.
Here are some examples from my own life:
Find a job or start Qtr?
After the layoff, I had to decide. Doing the startup meant bringing my vision to life and working with people I love. Finding a job would have stemmed from fear–what if the startup fails? I chose the startup.
Move out from California or stay in Bay Area?
Last year we considered relocating. Moving would have been driven by fear (what if CA gets unaffordable?). Staying was rooted in love:
friends, spiritual community, music and dance groups, and my photography circle…everything we cherish. We chose to stay.
My first job, back in 2005, in Tucson: quit or stay?
Great company and nice pay, but it wasn’t fulfilling. I missed my friends in Phoenix and wanted to work with folks my age. I chose love: I joined Software Architects in Phoenix. People thought I was crazy to quit the Tucson job since I was on H1B, had only a few weeks to find another job, and most likely would end up with a pay cut. But it’s still the best decision of my career.
But you have to apply common sense. Here’s an example of when the path of love didn’t work:
I quit Yammer in 2010 (before any of my stocks were vested) to work on my startup, 20 Questions (path of love). A few months later, Yammer was sold to Microsoft for 1.2B. Worst decision of my career.
Choose love when you have to make a difficult decision (it almost always works). Just balance it with common sense.
When I shared this with friends, Adam Perell, a former colleague, offered a beautiful insight:
Like a river, people gravitate towards the path of least resistance. If two choices seem equal with resistance included, then ignoring resistance, the path with more resistance will be superior. You could also view your career journey as choosing the path with more resistance.
If you’re interested in optimizing your life, check out Qtr, a new visual planning app designed for high performers.
