Stuck? Try facing downhill first

I still remember how I felt that morning. It was a beautiful, sunny day as I cycled on the country road just outside the city. I felt calm, confident, and ready for the challenge ahead: two climbs in a row. Not only did I know this route well, with each passing week I was improving my performance on these two hills.

That’s why what happened next was so jarring.

As I started the ascent on the first climb, I shifted gears and my chain fell off. My feet spun wildly, but I was able to act quickly and clip out of the pedals narrowly avoiding falling into the roadside ditch.

I caught my breath, moved safely off the road, and got to work fixing the chain. Once it was back in place, I was eager to re-start my ride, and that’s when I made a rookie mistake.

I attempted to start my ride on an incline, facing uphill.

And I wish I could tell you this is where I realized my error, but no, I proceeded to try again only to fail, again.

Then it hit me. Turn the bike around to face downhill first so I can get started easily, then once I’m in motion, turn the bike around and tackle the hill.

It worked like a charm.

But it doesn’t just work for cycling.

Starting uphill

It dawned on me recently I was in a similar situation to that sunny morning on the bike. Only this time, I wasn’t on a country road. Instead, I was looking at my list of projects.

For months, I was looking at a project I titled “Speaking Engagement Strategy & Pitch” and never making progress on it. It’s the kind of project that’s important but not urgent. I assumed the lack of a real deadline was the problem. But then I remembered the lesson from the bike and realized I was making the same mistake: I was trying to start while facing uphill.

My vision of the project included crafting the ideal strategy and the perfect pitch before I ever reached out to a prospect. It felt daunting. In my pursuit to figure it all out first, the weight of my expectations was keeping me frozen.

Facing downhill

Once I recognized I expecting far too much out of the gate, I turned my proverbial bike around and decided to face downhill first.

No perfect strategy or pitch. No finalized tracking system. Just start with the help of gravity.

I opened a fresh page and made a list of contacts I could comfortably reach out to without hesitation. This meant people who already expressed interest in having me speak or those who, even if they said no, would do so in a kind, respectful way.

Then, one-by-one, I started reaching out until I completed my list. I was finally in motion.

Embracing this approach meant letting go of overthinking and dropping the weight of lofty expectations. It doesn’t mean I won’t ever develop a strategy or refine an effective pitch. It’s just that first I’m turning my back away from those pursuits as I embrace gravity, get the wheels turning, and when I’m ready, turn the bike around to tackle the hill.

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