How To Keep Trying

There’s a moment every ambitious, talented person eventually reaches that doesn’t make it into their highlight reel: the silent, personal realization that a project isn't going to work or a dream simply isn't going to happen. It's failed.

Too often, instead of dealing well with these endings, we let the residue of disappointment carry over into the next season, weighing us down.

I was reminded of how easy this is to fall into a few years ago when I was out on a midday walk. I came across a dead butterfly by the side of the road and, strangely, felt compelled to bury it.

In that odd little ritual, I realized something important: sometimes our best next step is to give our failed dreams the dignity of a decent burial. Intentional closure can allow us to re-focus on the next season without resentment, disappointment, or regret.

Here are a few practical ways to do this:

Recognize Residue When It’s There

When a project, relationship, or business doesn’t pan out, it’s tempting to either steamroll ahead or pretend it never mattered. The reality is, we internalize those “failures” far more than we admit. They sneak into the way we make decisions, treat our new work, and even how we lead our teams. As Martin Seligman once wrote, we tend to make these setbacks permanent, pervasive, and personal. The first step, then, is simply to admit when we’re carrying the ghost of something that used to matter a lot.

Ask yourself:

• Where am I letting an old disappointment shape my reactions or risk tolerance now?
• Am I treating a past failure as a fact or as a personal defect?

Understand the Real Nature of Failure

As Steve Kamb, author of How To Try Again shared in this week's podcast episode, failure didn’t always mean a personal deficiency. It used to define an event, not a character trait. That shift matters. Failure is an inevitable outcome of aiming at difficult, worthwhile things, especially in creative work. If you try sufficiently difficult things, you are bound to fail eventually. The critical distinction is refusing to wear the failure as a name tag. You aren’t the failure; you’re simply someone who experimented and learned.

Make a Clean Shift, Not a Rash Rebound

"Try Try Again" is common advice in our "grind it out" productivity-obsessed culture. But Steve's “PACT” framework is worth keeping in mind:

• Pause and examine whether this is the right thing to return to, or if you should move on.
• Accept your actual context: your resources, limitations, and circumstances right now.
• Change your approach. Becoming a curious detective about why things didn’t work is far better than becoming your own harshest critic.
• Try again, but differently—this time, as an experiment rather than a referendum on your worth.

Bury the Butterfly

Sometimes, as difficult as it is, the best thing you can do is close the chapter. Creative legacies are built as much on what we let go of as what we accomplish. Give that aspiration, or failed project, an intentional ending. Mark it, mourn it if you must, and then permit yourself and your team to fully engage with what’s next.

Creative leaders set the tone for how everyone else on the team processes setbacks. Show your team how to properly end what’s over. By doing so, you make space for fresh energy, sharper focus, and the kind of clarity that chases down new breakthroughs. Don’t carry yesterday’s losses into the work that matters now.

Let’s all learn how to bury the butterfly so what’s next can fully live.

Have a great week!