When Perfect Plans Block Your Perfect Career
What I Learned From Killing Miss Planning
Miss Planning died last summer.
No one really died, of course. Just the part of me convinced that everything in my life needed a plan. And with Miss Planning gone, I discovered something key about career transitions: the difference between having no direction and leaving room for direction to emerge.
For years I made Excel spreadsheets for everything: projects, holidays, even groceries. I was convinced that following the plan from A to Z would protect me from the fear of change and that happiness would be waiting at Z.
But happiness never showed up.
That's when I realized: I didn't need to abandon planning entirely. I needed to stop planning so rigidly that I couldn't see the opportunities right in front of me.
The Moment I Created the No-plans Plan
It took months to understand what had actually changed. While rereading old journals, I found the clues: a slow experiment that began with a sabbatical, moved through leaving my corporate job, and taught me the skill that now defines how I coach others through career transitions.
I call it the No-plans Plan —having direction without setting a specific destination.
My Experiment: A Sabbatical With Intention, Not Itinerary
Lucky enough to afford a three-month sabbatical, I decided to try something radical for a chronic planner: set an intention instead of an agenda.
My intention was simple: create space to understand what I actually wanted, not what I thought I should want.
I had only one plan: and that was to have no-plans.
For once, I didn't make an itinerary. No list of must-see places, no "productive" accomplishments to check off. I allowed time for the unexpected, which showed up as a last-minute flight home to spend time with my parents—and became the catalyst for my entire career transition.
But bear in mind, it wasn't easy - Miss Planning was fiercely trying to sabotage the experiment daily. I had to fight hard to break the pattern, while at the same time don’t falling into wandering aimlessly.
This is what I now help my clients do differently.
What I Actually Learned About Career Transitions
Once I clearly felt that chapter of my professional life was ending, I didn't rush my exit from corporate life. But I also didn't just wait passively.
Instead, I practiced what I now teach: the no-plans patience. I stayed present, observed what opportunities emerged, and positioned myself to act when the right moment came. Not when I felt uncomfortable because I had no plan.
This mindset shift was the real game changer: I learned resilience and adaptability—the ability to hold a vision while remaining open to how it unfolds. These are the exact skills I help clients develop, because they're essential for navigating today's unpredictable career landscape.
When I finally left with a severance package instead of the quick resignation my need for control would have pushed me toward, I didn't immediately hunt for a new job. But I did give myself structure to continue moving forward: reflection time, values understanding, and networking—just without forcing a predetermined outcome.
Living With a No-plans Plan in Amsterdam
Amsterdam runs on a tight schedule. A coffee with a friend requires two weeks' notice; a Tuesday dinner needs a month's lead time.
Choosing spontaneity in a culture of planners means accepting you might sometimes be alone. A Saturday might go unplanned. Boredom might knock at the door.
But what once felt like drama now looked like opportunity for personal growth.
Why Boredom Is Actually Career Research
Instead of scrambling to fill the gap that a cancelled yoga class or friend bailing would create, I treated it as a sign to pause and reflect on my path.
Real boredom shows us what we actually want, not what we think we should want based on societal expectations or past versions of ourselves.
This is why I now include boredom into my own process. It's not about having no plan at all—it's about creating space for the path to emerge before you commit to the next big move.
And trust me, no one ever died of boredom.
Redefining Success on Your Own Terms
That first experimental summer taught me something I now help every client discover: you need far less than you think to be fulfilled, but you need to be very clear about what that "less" actually is.
For me, it was work-life balance over yearly promotions, outdoor time over hours in a conference room, and autonomy over big titles.
A simpler life with a little less money and more free time makes me sleep better than a big job title with a fat paycheck ever did.
That’s me, but it doesn’t have to be you. You define what you want from your career.
Something to keep in mind is, I didn't stumble into this realization by wandering aimlessly. I discovered it through intentional experimentation with structure light enough to hold me but not so rigid it crushed what was trying to emerge.
What This Means for Your Career Transition
If you're a chronic planner facing career change (like I was!), you probably don't need to abandon planning entirely. You need to plan differently.
Here's the approach I now use with clients— the No-plans Plan in practice:
Set intentions, not destinations - Know your values and priorities, but stay open to how they manifest
Create boundaries, not maps - Define your non-negotiables (minimum income, work-life balance, location) without dictating the exact role
Build in reflection time - Schedule space for boredom and self-discovery; it's the most strategic thing you can do
Experiment before committing - Test options through side projects, conversations, and small bets before making big leaps
Trust the process you've designed - The unknown is scary, but you can create a process for navigating it
The best career opportunities still happen when you least expect them—but you're far more likely to recognize and seize them when you've done the inner work first.
When Old Patterns Resurface
Some weeks I notice my calendar packed into tight time slots again. Miss Planning has resurrected, trying to protect me from uncertainty by controlling everything.
When I catch this pattern, the work isn't to drop everything and give up. It's to stop and ask: “Am I planning because it helps, or am I planning because I'm scared?”
The results couldn't be more different.
The Real Difference Between Getting Lost and Having Direction
Through this journey, I learned what I now help clients understand: many of us confuse control with clarity and rigid plans with real direction.
You don't need a detailed map of the entire journey. You need:
A clear sense of your values and priorities
Enough structure to feel safe taking the next step
The flexibility to adjust as you learn
Support to stay grounded when uncertainty spikes
Fear taught me that letting go of rigid planning feels like being lost. Experience proved that a No-plans Plan is actually the fastest path to finding authentic work that aligns with who you've become.
Your Career Transition Doesn't Need to Be Chaos or Control
If you're facing a career transition and feeling stuck between over-planning and wandering aimlessly, there's a third option: No-plans Plan guided by someone who's navigated this path before.
I help chronic planners redesign their careers without sacrificing the structure that makes them feel safe—while creating enough space for unexpected opportunities to emerge.
Because the goal isn't to have no plan at all. It's to have the right no-plan: one that guides without restricting, that provides direction without demanding a specific destination.
Ready to explore what a No-plans Plan could look like for your career transition? Let's talk about how to navigate your next chapter with both intention and openness.
