“I Feel Directionless”

“I feel directionless.”

One thing I enjoy about advising people on their businesses is the way this work continuously invites me to challenge my assumptions.

A new client came to me recently saying, “I feel directionless.”

Immediately, my brain goes to the big picture. Vision, goals… “Oh!” I think, “They must not be clear on where they’re headed, I can definitely help with that.”

Except that’s not what they meant at all.

For them, feeling directionless was about the day-to-day. They knew what they wanted long-term but didn’t know what to be doing each week to build towards that. They didn’t have systems they trust.

See what happened? My brain went to the big picture because that’s what “feeling directionless” means to me, and it’s what I’ve seen more commonly in others. But it’s not what it meant to them, so thank goodness I kept asking questions.

This is a great illustration of a principle that underpins my work: don’t expect yourself in others.

When we hear something, we often interpret it through our own experience—what we would think, do, or believe in that scenario. That’s human, but it leads to disconnection. And in a context like this, it’s how we’d end up solving for the wrong problem.

If you have your own word or phrase that keeps circling in your head or between your team, do yourself the kindness of getting specific about what you actually mean.

Three questions can help:

  1. If you had to describe the experience without using that word (i.e. directionless), what would you say? This gets at how you’re being impacted by the problem, which more accurately helps diagnose what it’s about at a deeper level.

  2. When you no longer feel this way, what will be true? Or, How will we know this is solved? This starts to define what success actually looks like for you, which will surface assumptions that may or may not be worth challenging, and will highlight any interrelated areas that need to be addressed as well.

  3. Why does that matter to you? This is where you find out if you're working toward something you actually want and fits with your values, or something you think you should want.

These three questions work at different levels of awareness and time horizons to help us get to “the thing under the thing.” It makes sure we’re solving for the right thing. Otherwise, you think you have a marketing problem when really you have a direction problem. Or you think you have a sales problem and it’s really a marketing or business model one.

This is especially important if you’re a team.

Shared language is foundational to growing in a mutually beneficial direction. If you keep bumping up against the same thing—“We’ve got to figure out X!!”—part of what’s keeping you stuck might be that you each have a different idea of what X even means, and therefore how to address it. Getting aligned on that before you jump to problem solving is what creates solutions that stick.

It’s hard to solve something you haven’t accurately named.

If you or your team have your own version of this circling sentence, I’d love to help you tease it apart. Especially if you’re a couple in business together or a small founding team of 2-3 business partners. That's what my advising and facilitation work is for—making sure your ladder is against the right building before you keep climbing. Reply to this email or get in touch with me directly here.

— Kate


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    Kate Smalley

    Kate Smalley is a small business advisor, facilitator, and educator based in Toronto, Canada. She writes about growth and business development for principled, industry-shaping entrepreneurs.

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