Charting the Map Is the Work (Part I)

Picture two people, both standing at the beginning of something.

Maybe it’s a career pivot. A creative project. A leadership role they’ve never held before.

Person A does what most of us are taught to do: they get ready. They close their office door and work on a plan. They do their research — investigating possible next steps, trying to anticipate obstacles — and slowly, they build a plan that’s going to help them take on this new something.

Then there’s Person B. They take steps that look, from the outside, a little messier. They start to take action on this new something — not because they’re ready, but because they want data. Each small experiment helps them chart the map of their new something.

A month later, Person A is still refining their plan.

Person B is already somewhere new.

For the kind of work that asks us to do something new — the projects that have never been done quite this way before, the leadership challenges that don’t come with a manual — our instinct might be to hole away and create a map before we begin; that way, we know where we’re heading.

But for some somethings, the answer to “where we’re heading” may not be a question we can answer before we start.

Person A isn’t wrong for wanting a map. That instinct comes from a good place — even a considerate place. From care, from not wanting to waste anyone’s time or resources, including their own — those are good things.

And it’s not a bad approach in the right scenario. If you’ve done this before, if the path is established, if the data is good — then map it carefully and execute.

But… what if the path forward isn’t established? If the data isn’t clear and reliable, or isn’t relevant to your context? If it’s a brand-new territory?

Professor Saras Sarasvathy at the University of Virginia’s Darden School of Business has spent decades studying expert entrepreneurs. She wanted to understand how they thought. What she found led her to coin a term: effectuation.

Here’s an excerpt from her article, What Makes Entrepreneurs Entrepreneurial?:

“The word ‘effectual’ is the inverse of ‘causal.’ In general, in MBA programs across the world, students are taught causal or predictive reasoning — in every functional area of business. Causal rationality begins with a pre-determined goal and a given set of means, and seeks to identify the optimal — fastest, cheapest, most efficient — alternative to achieve the given goal… A more interesting variation of causal reasoning involves the creation of additional alternatives to achieve the given goal. This form of creative causal reasoning is often used in strategic thinking. Effectual reasoning, however, does not begin with a specific goal. Instead, it begins with a given set of means and allows goals to emerge contingently over time from the varied imagination and diverse aspirations of the founders and the people they interact with.”

Effectual thinking asks a different first question. Instead of “what’s my goal, and how do I get there?” it asks: “what do I have to work with, and what’s possible from where I am now?”

It’s less about plotting the end destination and more about trusting that if you start moving from where you are — with the skills, resources, and relationships already in your corner — the path will become clearer as you walk it.

The causal approach works when the destination is clear and the data is reliable. It works beautifully in stable, predictable environments. (Packing for a trip is a perfect example: you know your destination, you check the forecast, you plan your suitcase. Goal clear. Data available. Map accordingly.)

But many of today’s interesting problems aren’t like that.

Our ambitions, our leadership challenges, our strategies for navigating whatever’s coming next — these rarely come with a fixed destination or reliable/relevant data. We might have a challenge in mind: find a new job, launch something, figure out what’s next. But can we really know, in advance, where that challenge will lead us?

If we’re stuck in a causal approach when our something has a lot of unknowns, the hesitation can sound like:

• I’ll tell my network I’m open to something new once I know what I’m looking for.

• I’ll start the podcast once I’ve figured out the format.

• I’ll pursue the hobby once I know it’s worth my time.

• I’ll pitch the idea once I’ve thought it all the way through.

• I’ll announce the new org structure once I’ve created it.

Each of these is reasonable on its surface. But each of them could also do a great job of keeping someone stuck. Because when we’re working through challenges with a lot of unknowns, waiting for the complete map has a high cost. Every week spent planning is a week without data. Without feedback. Without the small, clarifying, course-correcting surprises that only come from being in motion.

What if, instead of holing yourself away trying to chart the path forward, you started walking?

Pulling from Professor Sarasvathy’s research, we can explore an effectual approach to help us navigate through new challenges and unknown futures.

Here’s how it might look in practice.

Imagine a leader who’s just been promoted and handed an ambiguous charge: figure out the new organizational structure for your department. The causal instinct is to disappear into a spreadsheet — mapping roles, reporting lines, and org charts — and emerge weeks later with a polished proposal. The effectual instinct is different. She starts by talking to her team. She runs a few small experiments with how work gets assigned. She pays attention to what’s working and what’s creating friction.

The structure doesn’t come first. It emerges from what she learns. That’s effectuation in action.

Here’s how it might show up for you:

• Tell someone where you are, not where you’re going. You don’t need a polished pitch. Share what you’ve been working on, what’s energizing you, what you’re curious about. Show up with genuine curiosity, not a goal in mind. (EXAMPLE: You’re thinking about changing jobs. Rather than waiting until you know exactly what you want, start talking to the most trusted people in your network. What have they noticed about your work? What trends are they paying attention to? What do they think of the market right now?)

• Make something small — then show it, post it, share it. A rough draft, a pilot episode, a first attempt, an outline of products or services. Not to launch — to learn. Focus on your skills, not your goals. (EXAMPLE: You want to start a podcast but have no idea what format it should take. Hit record on one conversation with someone you find fascinating. Listen back. What surprised you? What do you want to do differently next time? Share it with a few trusted folks. What’s their feedback?)

• Try the hobby before you justify it. You don’t need to know how it serves you. Follow the pull. Interests have a way of connecting to things you couldn’t have predicted. (EXAMPLE: You keep thinking about taking a ceramics class but can’t articulate why it would be “worth it.” Sign up anyway. See what it does for your brain after a week of hard meetings. Don’t be demanding of results; be open to what might come next for your skills, resources, and network if you stay in this space.)

• Pitch questions, not answers. Share what you’re exploring and ask for reactions. The feedback you get in that conversation is data you can’t generate alone. (EXAMPLE: You have a half-formed business idea. Instead of waiting until it’s airtight, learn more about the target audience. Approach 2-3 people you think this business would serve: “Here’s what I’m thinking about — what’s your gut reaction?” You’ll learn more in those three conversations than in three more weeks of solo planning.)

• Have the conversation you’ve been postponing. With a potential client, mentor, a peer, someone who’s done something adjacent to what you’re considering. Not to get a roadmap — but for a real ask, to get a data point. Make the ask, not the inquiry. (EXAMPLE: You’ve been thinking about pitching your services as a consultant. Instead of researching indefinitely, reach out to a few potential clients and ask for a 20-minute call to explore fit. The worst they can say is no — and that’s also a data point.)

• Set a small, low-stakes deadline. Not to finish something — to start something. Commit to one step by Friday. Then see what you learn. (EXAMPLE: You’ve been “about to” reach out to that contact for three months. Put it on your calendar for Thursday at 2 pm. Write the message. Send it before you can overthink it.)

We’re not being reckless; we’re not skipping any strategic planning. We’re just doing our strategic planning in the world — where it can bump up against reality, get refined, and become something truer than what we could have anticipated in the planning stage, alone in a room with a whiteboard.

The map you’re waiting for? Maybe for you, that “map” would be the moment when you feel prepared enough, ready enough.

Maybe it’s not something you work out in the planning stage. You may have to walk your way into it.

What’s something you’ve been mapping instead of starting? What could a few first steps, a few small experiments, look like?

You’ve got this. 🫶