Sometimes, Your Job Is Just to Cheer

When I first caught the entrepreneurship bug, I tried to light every similar spark in other people. If someone told me they were thinking about starting a blog, quitting their job to freelance, or launching a startup, I always encouraged them to do it. Blank-check optimism.

One reason, other than that I am a blank-check optimist, was that I thought these people must encounter enough downers when sharing their aspirations, and so I wanted to provide some counterweight to society’s usual choir of “you can’t.”

As I got older, however, my takes became more balanced. “Do you think that’s really you?” “Don’t jump off a cliff without a parachute.” “That’s not gonna work because X.” For one, my sense of what’s a real aspiration vs. just a pipe dream got better, and for another, I myself had chased enough pipe dreams and burned my hands enough times to want to help people avoid my mistakes. So while I still leaned towards encouragement, I would add more disclaimers.

A few years later, I now realize there’s a time and place for both approaches: Under normal circumstances, you should make sure your friends keep their head on straight. Don’t let euphoria carry them away like a hot air balloon. Otherwise, they’ll crash and burn, and whether they would have taken your advice or not, they’ll definitely ask: “Why did no one warn me?”

When a loved one is down in the dumps, however, don’t burn the rope they have mounted in hopes of climbing out of their hole. In cases of grief, depression, or burnout, it doesn’t matter what that rope looks like or even if it will last them all the way. The point is that they themselves have chosen to get better — and who are we to thwart their first attempt? Now’s the time to show them unconditional love.

Most of the time, we can be helpful by pointing out the signs our friends are missing, but sometimes, our job is just to cheer — for as long as someone encourages us to get back up, we’ll always rise after we fall.