When You Feel Lost in Creative Work & Business

I got lost last week. Again. I was zooming down the same winding country roads in the verdant Hudson Valley to the same house-school where I have picked up my daughter each Wednesday and Friday afternoon for the past 7 months. But somehow, not 2 miles from my destination, I wound up on a road I’d never seen.

How did that happen?

The steady rhythm of no-traffic driving among green trees with dappled sunlight leading the way lets me “check out” of driving (still watching for deer and children, mind you) and check in with the latest creative idea buzzing in my mind and brain.

At some point – some several minutes past the turn I was supposed to make – a faint signal went off that said, “You’re lost.”

It’s not an unfamiliar feeling. That signal goes off about every seven years as my creative callings unfold in new iterations. And it goes off every few weeks when I’m in the middle of a project.

What to do? Here’s what I’m realizing.

First, there’s no shame in getting lost.
I have no ego-armor about being a man who wanders his way to truth, freedom, exhilarating creativity, and gratifying enterprising.

From an existential standpoint, letting myself get lost demands my wits wake up. And so does my faith, as in my confidence (with-faith-ness) in the messy process of creative questing.

From a creative process standpoint, it’s one of the wonders of the human mind and brain that we can wander deliberately and stumble upon an idea or two worth keeping. In this age that valorizes uber-focus, I’m obsessed about how we focus and how we wander as creatives. I continue to research how it happens in my and others’ experiences.

There’s little use in getting freaked out about getting lost. Okay, I do cuss at myself usually if someone else is in the car or if someone else is depending upon me for a service or is waiting for me to show up for a talk (it’s happened!).

But if it’s just you and your best self sorting through ideas or the next iteration of your creative calling, then remember it’s part of the process. You can muster the tools and gather the allies that work to help you keep centered amidst the mess and uncertainty.

There’s no shame in asking for directions.
When it comes to driving, I’ve never had a problem doing so. By the time I stopped to ask a guy (luckily) standing in his driveway where I was and how to find my little girl’s house-school again, I had fully articulated in my mind an idea for a book chapter and resolved a client’s creative problem.

Check one for me on the male thing.

But when it comes to my creative projects and my business enterprises, it took me a long time to realize there was no shame in asking for directions. I now have a stellar business mentor plus a smart executive wild pack who help keep me on track and who keep me honest along the way.

I’ve seen talented minds go to waste out of sheer stubbornness, pride, and shame.

Fitzgerald edited Hemingway’s first serious novel manuscript (The Sun Also Rises). “Cut the first 40,000 words,” he wrote him in a letter. Both Fitzgerald, Hemingway, and Tom Wolfe ended up having the best writer’s guide available, the exceptional editor Max Perkins at Scribner’s. Perkins’ editorial letters to Fitzgerald show his genius assistance in shaping The Great Gatsby and in mentoring an eager, talented writer.

Every thriving enterpriser I know and have studied has a mentor and a group of trusted allies.

I love mentoring; and I also love being mentored in areas where I flail.

When you’re lost, ask.

And when all else fails either pull out a map or make a map.
I have two white walls (walls with whiteboard material) in my studio. One helps me sort through “big picture” stuff for my business, my book, my presentations. The other helps me map out ideas for some of my clients’ projects and goals.

During the past two weeks, six clients felt huge relief by our co-creating maps:

• Three clients defined their taglines and brand strategies for their creative enterprises and/or their online author platforms that then defined how they would grow their best selves’ work in the world.
• One client drafted a “four-act” synopsis of the anchor story that holds together her scholarly memoir/creative nonfiction book that catalyzed her to re-write her proposal.
• One client and I mapped out a “three-act” outline for her memoir – in about 30 minutes – that then catapulted her to draft further with confidence.
• Another client defined the singular elegant idea that holds together his ten years’ worth of teaching and research for his book idea. Now onto drafting.

Pull back. Grab a sketch book or a flip-chart and some markers. Draw. Sketch. Think in pictures and arrows and funny forms to sort through your project’s parts. And then put the map aside.

I thrive on shaping ideas, books, enterprises. I’m an obsessive map-maker. But I’m also committed to tucking the map in the pocket and forgetting about it along the way – trusting my wits – until I get utterly lost.

Note: When I finally arrived, ten minutes late, to pick up my three-year-old little girl, she didn’t seem bothered. She and two other girls squealed buck naked as they splashed in a toddler swimming pool.

By the way, this weekend if you’re in the Greater New York area, visit me in Woodstock where we’ll explore numerous tools for your creative quest. You might be surprised by how organized a wandering poet-enterpriser can be.

See you in the woods (I’ll be the one following breadcrumbs),

Jeffrey