How do you make a strategy when the terrain keeps changing underneath you?
We often want a map to tell us what will happen next. But maybe that’s asking a map to do the wrong job.
In this episode of Technically Joyful, Gabrielle Kohlmeier explores what maps can teach us about navigating uncertainty: from her children learning to find their way around Berlin to Cold War ghost stations, an infamous story about lost soldiers carrying the wrong map, to her own experience leading transformation when no reliable route to the destination existed.
Even the best map does not eliminate uncertainty. It does give us the directional energy to make a choice, pay attention to what happens, and adjust.
That distinction matters in the AI era, when leaders are being asked to make decisions about technology, organizations, careers, and investment without knowing exactly what the terrain will look like a year from now. There is no complete map for where AI, work, or our organizations are headed. But we can still map forward: identify what we know, decide what matters enough to become our North Star, name our assumptions, sketch plausible routes, make a move small enough to learn from, and watch for signals that tell us when to change course.
Gabrielle also examines the limits of maps. Every map reflects choices about what gets included, what disappears, and whose experience of the terrain is represented. Organizations have their own “ghost stations”: capabilities people cannot access, knowledge that does not move, and people close to the problem who were never invited to help draw the map.
And this is where joy becomes useful. Fear can make every blank space feel dangerous. Joy and curiosity can widen the field enough to notice another route, another person who sees something we don't, or another possibility worth testing.
The goal isn't to know exactly where the route ends.
It's to have enough agency to take the next step, learn from the terrain, and keep drawing the map forward.
In This Episode
- Why a map can create agency without creating certainty
- What Berlin's transit system taught Gabrielle about orientation and independence
- Why even an imperfect map can interrupt paralysis
- How maps reveal some things while making others disappear
- The “ghost stations” that can exist inside organizations
- Why speed is not the same thing as agency, but paralysis isn't safety either
- Why asking what isn't going to change can be as useful as predicting what will
- What strategy under uncertainty actually looks like
- Why there is no complete map for the future of AI or work
- How joy and curiosity widen the routes we are able to see
- Using AI to uncover assumptions, missing routes, and signals for change
Your Transformation Gym Rep: Draw a Small Map
Pick one change you're navigating right now: organizational, professional, or deeply personal.
In the center, write “You are here,” and underneath it write three things you know to be true, not what you predict and not what you fear.
At the top, write your North Star: what you're moving toward or what matters enough to protect even if the route changes.
Draw two possible routes, with one reasonable next step on each.
Then mark one blank space, something important you don't know yet, and one signal that would make you update the map.
Show your map to an AI tool and ask:
- What assumption am I treating as fact?
- What plausible route am I missing?
- What signal should I watch that might tell me to change course?
Don't ask AI to choose your destination. That's your job. Use it to widen the map. You don't need to listen to it or believe it. It's there to open up your perspective.
Then pick one small move to make this week.
Sources & Resources
Data Feminism, by Catherine D'Ignazio and Lauren F. Klein A powerful examination of how power shapes what gets counted, represented, and omitted - and how data practices can help challenge unequal systems. The book is also available in an open-access edition.
Same as Ever: A Guide to What Never Changes, by Morgan Housel A book about using the things that remain consistently true - especially patterns of human behavior - to navigate an unpredictable future.
The map of the Pyrenees story The story of Hungarian soldiers finding their way through the Alps with a map that turned out to depict the Pyrenees was popularized in organizational thinking by Karl E. Weick. Its earlier source is Miroslav Holub's poem "Brief Thoughts on Maps," based on a story attributed to Hungarian scientist Albert Szent-Györgyi. Its precise historical status is uncertain, so it is best understood as a parable about orientation, action, and sensemaking rather than documented military history.
Berlin's ghost stations After the Berlin Wall was constructed in 1961, Western S-Bahn and U-Bahn trains continued to travel beneath East Berlin on certain lines, but they passed slowly through sealed stations without stopping. The dimly lit platforms were guarded by East German border forces and became known as "ghost stations."
Ways to Connect with Gabrielle
Subscribe to Technically Joyful on Apple Podcasts, Spotify, and YouTube: technicallyjoyful.com
Newsletter: technicallyjoyful.com
GK Strategic Advisory: gkstrategic.com
LinkedIn: linkedin.com/in/gabrielle-kohlmeier
