The Art of Unfolding – A Leadership Experiment on Wheels
For years, my default setting has been Plan Everything. Meticulous spreadsheets, color-coded itineraries, contingency plans for my contingency plans. As an ex-project manager, this level of control was basically my learnt personality trait.
But this year, I’m testing a different approach. Instead of detailed planning, I’m embracing unfolding, a way of moving through leadership (and life) with a balance of clarity and adaptability. And I’m using my upcoming two-month motorhome trip across Europe as an experiment in this very concept.
We set off on 10th March, covering 10 countries in 8 weeks, and here’s the kicker: aside from two ferry crossings, we’ve booked nothing.
Yes, I - a former queen of spreadsheets - am letting the route emerge as we go. No fixed stops, no rigid plan, just a direction, a loose outline, and an openness to what unfolds.
Why? Because the most exciting things in life often happen off-plan.
The same is true in leadership and startups. It turns out that the ones that thrive aren’t the ones that rigidly follow their initial blueprint, but the ones that learn, adapt, and pivot with clarity and purpose.
🚗 Driving a Motorhome vs. Driving a Train (A Leadership Metaphor I Didn’t Expect to Make)
Most traditional leadership (and life planning) looks like driving a train. The track is laid out in advance, and your job is to follow it exactly. There’s comfort in knowing exactly where you’re going, but the problem?
If an obstacle appears, you’re stuck.
If conditions change, the tracks don’t move (or it takes too long to lay new tracks).
The only way forward is to keep going, even if it’s no longer the right path.
But leading with an unfolding approach is more like driving a car, or a motorhome in our case:
You have a destination (a North Star) - you know where you’re headed.
You have a rough route, but the ability to take detours if something more interesting appears.
You check in regularly, adjusting based on: fuel, weather, or an incredible local bakery that simply must be visited.
And most importantly, YOU control the vehicle, not the road: you stay in charge of the journey, but remain flexible to adjust your path as conditions change.
For our trip, the only planned things we have are:
The start date
The finish date
Two ferry crossings
10 countries we want to visit
Everything else? Completely open to discovery.
And we’re treating our North Star as the kind of experience we want to have - adventure, cultural immersion, and freedom on the road. But also, finding more ways of being together that create deeper connection. Last year, we made sunrise watching a ritual and loved it. This year, we want to explore what other shared experiences bring us that same kind of magic.
This translates perfectly to startup leadership:
Instead of over-planning every detail, define the vision and values that guide decisions.
Instead of assuming you already know everything, embrace real-time learning and iteration.
Instead of locking in an inflexible roadmap, build in room to pivot based on emerging insights.
This isn’t abandoning structure—it’s choosing dynamic clarity over rigid certainty.
🎯 Clarity in the Midst of Unfolding
If we’re embracing an unfolding approach, what keeps us from spiralling into chaos?
Here’s what I’ve realised are the three key elements that create stability even when the path unfolds:
1️⃣ Admitting When You Don’t Know
Startups, like road trips, involve a lot of uncertainty. Instead of pretending to have all the answers, the best leaders (and travellers) admit what they don’t know and stay open to learning.
For our trip, here’s what we don’t know yet:
Where we’ll stay each night.
The exact route we’ll take.
Whether we’ll love or regret some of our stops.
But that’s okay! Because what we do know is that we have the tools to figure it out along the way.
In business, great leaders operate the same way:
They test hypotheses instead of betting everything on one assumption.
They listen, observe, and adapt based on feedback.
They see uncertainty as a space for learning, not a leadership failure.
A Leader who says, “I don’t have all the answers, but I trust our ability to figure it out together,” builds far more confidence than one boasting they have all the answers.
2️⃣ Having a North Star (So You Don’t Just Drive in Circles)
A clear North Star ensures you’re not just drifting, you’re unfolding in the right direction.
For our trip, our North Star is the kind of experience we want to have: adventure, cultural immersion, and deeper connection.
In leadership, your North Star might be: 🚀 A clear company vision, e.g.: "Make financial services more accessible." 🎯 Strong values, e.g.: "We prioritise learning and customer-first decision-making." 🏆 Defined success measures, e.g.: "We want to double user engagement within six months."
With these in place, you can adapt without losing your way.
3️⃣ Clarity on Roles & Responsibilities
Unfolding doesn’t mean abdication. On our trip, even with a flexible plan, we still have clarity on who does what:
My partner drives the motorhome.
I manage logistics and ensure he lives on more than just caffeine, meat, and craft beer.
Together, we make route decisions daily.
In leadership, unfolding doesn’t mean lack of accountability, it means defining ownership while allowing flexibility in execution.
🛠 Actionable Practice: Experiment with Unfolding
If you want to explore a more adaptive leadership approach, try this:
1️⃣ Pick one project and reduce over-planning.
Define the outcome, but allow the how to emerge, and let your team tell you how!
2️⃣ Hold a “Sense-and-Respond” Forum.
Instead of rigid quarterly planning, run a session where your team discusses:
What’s changing in our market or business right now?
What opportunities or threats are emerging?
What should we double down on, tweak, or stop?
This practice ensures teams aren’t just following outdated plans but actively shaping strategy as they go.
3️⃣ Try an OODA Loop Approach (Observe → Orient → Decide → Act).
This tool helps leaders make small, iterative decisions instead of massive all-or-nothing ones. Experiment with shorter planning cycles, rapid decision reviews, and frequent reassessment instead of locking in a 12-month strategy.
Let’s Be Honest…
I may have written this entire newsletter just as an excuse to brag about my road trip.
But if you take away one serious thing from all of this, let it be this:
The best leaders aren’t the ones who always know the answers. They’re the ones who know how to navigate without them.
Whether you’re leading a team, a company, or an epic European motorhome adventure, the key is this: ✨ Set a direction, stay adaptable, and enjoy the ride.
Your Turn:
Do you naturally lean toward rigid planning or unfolding?
How do you create clarity in the midst of uncertainty?
Have you ever resisted a shift, only to later realise it was exactly what you needed?
Let’s start a conversation—drop your thoughts in the comments!
Love,
Dag
P.S. If you’re a leader or tech startup executive exploring how to embrace adaptive leadership, let’s talk. Visit my website dagmaraaldridge.com, email coaching@dagmaraaldridge.com, or use the ‘Book a Meeting’ button on my LinkedIn profile. Let’s explore what’s waiting to unfold. 🚐✨
