Find the Path, Lose the Path: Hiking the Business Wilderness


Go as far as you can see; when you get there, you’ll be able to see farther-J.P. Morgan

A woman walks along a trail in the deep woods. Perhaps it has taken her a long time to find the path, but before her now lies a clear and meandering way. Having groped in the dark long enough, having gone a little hungry at times, and having gotten dangerously lost even, this time she feels prepared. She's brought her compass, some food and water, an extra sweater. 

Just as she's beginning to feel confident in her ability to trek this terrain, the cleared and well-maintained trail starts to get a little thick. The forest vegetation encroaches; the trees above grow shadowy. She follows as far as she can, until she is left only the faintest, snake-like deer trail. Before long, the deer trail becomes just a few trampled areas, and suddenly, she is lost again.

But, having her compass with her, knowing her general direction, she isn’t as lost as last time. So she steps and stumbles through the underbrush, gently moves aside thick and drooping ferns, balances across a stream on a string of stones.

She finds chanterelles for dinner, meets a crow who gives her clues, discovers that her boots need mending. Her courage mounts. She reaches a vista and sees two paths ahead: The one she was on, and one just a little to the north. The one to the north seems more open, a bit sunnier, wider, greener. It’s closer to the river. She adjusts her compass, and sets off on the more befitting trail.

*    *    *    *    *

So often, we have the ideas, the maps and songlines, the dream, but we are afraid to start or continue. How do we begin? Can we nurture our ability to benefit from getting thwarted on the professional journey?

In our fast-paced society, speed is over-valued. But no matter the deadlines and timelines we impose, when something about our business (or life for that matter) needs changing, it will make itself known.

Perhaps our sales dip. Perhaps we lose a client we depended on, a partnership deteriorates, or a new idea has stalled out. How will we respond? Will we go hungry? Will we have a compass with us? Will we be courageous?

It’s certainly no fun, and actually can be scary, to be “lost in the woods” business-wise. So here are some key take-aways from our girl in the woods ...

First, You Have to Decide.

You have to get out on the trail. However many ideas (paths) we have about our business itself or some aspect of it, we can only pick one, maybe two or three max, in any one year, month, day or hour. What path feels the best right now? Which steps? What is our ultimate reason for doing this work? What’s the next best outcome we would like to see?

Make some decisions. Flexible, but very strong. Deciding which trail to take and starting to walk is more than half the challenge in getting ourselves “out there.” It can be scary to decide. What if we miss an opportunity? What if this path doesn’t end with an epic vista? We won’t know until we choose. And the beauty is, for whatever we may be “missing,” my experience is that the act of choosing carries big, big magic.

Bring Supplies

As a small business owner, self-care, saving, and planning ahead for times when development is going to be more important than sales are nourishing business supplies. And what is the business equivalent of a compass? Perhaps a business plan! Even the simplest one will make a huge difference when the path disappears among the trees. And it always disappears, at some point.  

Gather a community of support around you. Who are your allies? Who can you brainstorm with, hire, or otherwise lean on? None of us exist in a vacuum, however alone the trail can feel. A compass is as much a friend as a friend is a compass.

Keep Going, with Caution

You can take some breaks, but no one lost in the woods can just stop going. You’ve got to re-discover the trail. One of the most common things to happen to entrepreneurs when we hit a wall is to let it slow us way, way down, or stop us all together. The cure is to find some task, some corner to keep developing, some client to keep working for, some tidying of finances or files … anything but stasis. We’ve got to keep that compass in hand and do what we can in these times so we'll emerge from the wilderness- maybe a little dusty- but nevertheless renewed and strengthened.

The other extreme of this is barreling ahead when what is called for is a time of searching, noticing, resting and planning. Surging forth on a path that doesn’t feel quite right is the worst you can do. In the woods, it often leads to those serious injuries that make all the romance of this metaphor take a dark turn. Trust your instincts: should I stop and re-group, or just go slowly forth?

If Your Eyes Are Open, You Will Emerge From Lostness (or detour) With More Resources, Courage, and a Clearer Path Forward than before you lost the trail.


“Lost-ness,” in and of itself, has lost appeal in our culture today. I am old enough to have gotten lost many times from childhood until my mid-twenties. I traveled the country for nearly two years with no cell phone. Gasp! It was one of the most inspired and invigorating times of my life.

Now, with google maps, google search, the ability to call for help at almost any moment from almost anywhere, we’re losing our thirst and our patience for getting lost, despite the strengthening of character it tends to bring.

Lost-ness is a beautifully instructional part of life, part of running a successful, innovative business and it’s part of being human.

So don’t be afraid of those times when you feel the overwhelming, unsettling over-growth professionally, or personally for that matter. Celebrate the fact you are out in the woods in the first place. Recognize this moment as not only an opportunity, but as a messenger- that some course-correction is needed in order for things to work a little better, or perhaps, infinitely better.

header photo: the girl outdoors