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As entrepreneurs, we’re simultaneously expected to be dreamers but never succumb to the slumber of inaction. We’re supposed to be able to snap our fingers, fall into a trance, dream of some marvelous future, then awake to cast vision in a compellingly contagious way to our teams, and then martial pragmatic, organized marching orders. But shifting gears like that can be tough, especially at a blistering pace in an age of distraction.
I’m inspired today to examine these three separate stages, which can each lull us in with their siren song and keep us stuck for far too long. Let’s explore these three entrepreneurial responsibilities and the inflection points between each.
The “Dreaming”
Some of us are natural dreamers. We collect concepts like keepsakes, and our heads stay in the clouds — incessantly flipping puzzle pieces and looking for previously undiscovered connections. This is how genuine innovation comes into the world. We must spend uninterrupted time putting things together.
It reminds me of Bill Gates at the height of his career, taking “think weeks” where he’d disappear for two weeks to amalgamate a dozen random books and recent learnings into fresh insight for Microsoft’s future. Maybe this feels very natural for you, and if it does, make sure you don’t get stuck here. Dreams in business are only helpful if you do something with them once you wake.
Related: 10 Surprising Facts About Bill Gates
The “Dramatizing”
And then it’s time to share. When you wake, how do you articulate your dream? And beyond that, how do you bring others into your idea? How do you compellingly tell the story that people understand and can even begin to own themselves? Some people are gifted communicators, and storytelling is second nature. But for those who need pointers, here’s what I’ve found helpful — a distillation of the hero’s journey.
Your dream is likely solving some tangible problem people are plagued by. Introduce that person as the story’s main character, with hopes and dreams of their own, only to be burdened by some impervious obstacle. They have a problem they can’t solve on their own, and this problem is preventing them from achieving their own dream. They need help, and you are perfectly positioned to help them. Your personality is exactly the kind they connect with (perhaps even an inverse of their own personality, offsetting their negative personality traits), and your guidance speaks to both their head and their heart, encouraging and inspiring them to take action. You end by sharing a clear articulation of what’s at stake (“What’s the worst that could happen?” by them not taking action, followed by “What the best that could happen?” with your help).
Related: A Brand Story Is What You Need to Share Your Entrepreneurial Vision.
That story formula will always resonate, no matter your audience or industry. And by telling it as a story, it’s far more likely to be remembered and shared contagiously throughout your network. People remember and love telling stories, especially when they’re easy to remember and have an emotional payoff.
The “Doing”
But now it’s time to get moving. How does this baby giraffe of an idea take its first steps? Slowly — that’s how — with great intention. In my fifteen years of entrepreneurship, I’ve found that milestones are great but that inchstones are even better.
In your mind’s eye, put yourself a year down the road. At that point, you’ve arrived at some new inflection, which will require another cycle of dreaming. Now, give yourself 3-4 milestones you need to hit between now and then. Don’t worry about flowery language, and don’t focus on feelings.
Be as plainly pragmatic as possible when describing those milestones. Use phrases like, “We raised enough for 24 months” and “We have our first paying customer.” And when you’ve got those milestones down, break each into 3-4 inch stones. Baby steps, if you will.
This may seem wildly uninspiring or unrevelatory, and that’s the point. When wrestling our wispy, aspirational brain into action, it’ll feel like we’re robbing our work of all its romance — and we are — but our future selves will thank us.
When that final milestone comes into view, it’s time to dream again. Gather everything you’ve collected since your last dream, absorb it, take a break from your typical routine, and let yourself fall into a dream state again.
There you have it — the three primary hats most entrepreneurs are expected to joyfully vacillate between from day to day deconstructed in plain language. It takes extraordinary discipline to follow this flow and not jump back to dreaming again once you’ve shared an idea. As a point of confession, my biggest fault is over-dreaming and under-doing, so this process becomes my guardrail. And trust me, my team is grateful for it. There are only so many times you can jerk the wheel before people onboard get seasick and want off.
Founders don’t need to keep all three hats on as companies grow, thank God. As we experience a bit of success and hire to replace ourselves, we can slowly nuzzle into what we love most (the Dreaming, the Dramatizing, or the Doing). But in the first stages of entrepreneurship, we’re likely going to have to wear all three hats.
And it’s quite the dream.
