Jean Genet
Grant and I met a really lovely young couple last weekend while staying at a bed and breakfast. They’re both in medical school but neither of them have decided what they want to specialize in. They know they want to be doctors, but do they want to: work with kids or adults, handle emergencies, clock crazy long hours, have a family? They keep rigorous schedules and take tons of difficult exams, giving up most of their free time and living in separate cities in order to achieve something that doesn’t yet have a name.
They are walking forward, trusting that by the time they have to make a decision, they will know the answer.
Anyone who’s ever pursued something challenging, changed career paths, followed a dream or created in any capacity–writing, painting, composing–knows this feeling well.
It’s an urge, a compulsion to do something great without the aid of a blueprint.
Last week, as I was taking a long walk with my friend Humaira (who has a very cool blog, Thoughts are Dots), we got to talking about uncomfortable change and what it feels like to head towards something when you don’t know exactly what that something is.
This is a topic I’ve been thinking about a lot over the last couple of years. How do you get from point A to Point Z when you don’t know what the letters in between look like and Point Z is a bit fuzzy?
So many worthwhile things are hard. Like really, really hard. Becoming a surgeon or a writer or an entrepreneur or a da Vinci is (obviously) not a cake walk. It would be a heck of a lot easier to stick to the tried and true and live in the light of the familiar–familiar job, familiar town, familiar hobbies, familiar, clearly marked path.
On that long walk, I told Humaira that, for me, taking a leap of faith into the unknown of a new career or creative project feels a lot like entering a pitch black room:
At first, you don’t know where the heck you are. You bump into furniture, you feel a bit panicked. What does the room look like? Where is the light switch? What if this is the completely wrong room?
But then, if you don’t bolt for the first exit (give up, try something easier, default to your old habits), your eyes begin to adjust. It’s still a dark room, but it’s not as scary anymore. You can move around without knocking into chairs and tables. You can hear yourself breathe.
If you stay in that dark room long enough, poking around, feeling the outline and shape of things, you lose some of that initial fear and begin to trust yourself.
Eventually, you evaluate all of the doors that will lead you to the next room, your goal. When it’s time to open one of those doors and step through to the other side, you’re able to make a decision that isn’t based in fear or peer pressure or “shoulds.”
Most people who pursue challenging, uncertain paths want to give up and bolt through any old safe, light-filled door at some point on their journey. I don’t think we talk about that often enough–about how successful people had to recommit to their dreams and learn to live with uncertainty, especially when people called them crazy or the siren song of easier money came calling.
Steve Jobs, J.K Rowling, Oprah Winfrey: these people tasted a lot of defeat before they became the icons we know today. (Here’s an article about 15 people who failed before they made it.)
Dreaming big is about more than boldness and planning and payoffs. At its core, it’s about embracing uncertainty. It’s about confronting fear and stepping into that pitch black room, trusting that you will (eventually) find the door to the other side.
Are you working towards something challenging and uncertain? How’s it going?

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