I had a call last week with a woman I'll call Sarah. She's been a Director at a large foundation for seven years. Manages a €20M portfolio. Built partnerships across three continents. By every external measure, she's successful. "I keep thinking I should figure out what's next," she told me. "But I never actually sit down and do it. I tell myself I'll think about it this weekend. Then the weekend comes and I'm catching up on emails, dealing with the kids' activities, grocery shopping. The moment never arrives."
She paused. "And honestly? I'm not even sure where I'd start."
I hear this constantly from people who are succeeding but feeling increasingly misaligned.
The Pattern I Keep Seeing
After mentoring 50+ professionals through career transitions, I've noticed something: the most stuck people are often the most capable ones. They need clarity about what they actually want. And they're trying to figure it out in the gaps between meetings, in the margins of already-full lives, without any structured way to think it through.
Here's what I keep hearing:
"I feel stuck, but I don't know what I'm stuck on."
They know something feels off. The work that once energized them now feels heavy. But they can't articulate what's wrong or what would be right.
"I have no time to think about this."
Work is demanding. Kids need attention. Aging parents need support. By the time there's a free moment, they're too exhausted to engage with big questions. Career clarity gets perpetually deprioritized.
"I started this career with clear values. Now I'm not sure they still fit."
At 28, you wanted to travel the world, conferences, field visits, being where the work happens. At 42, you want longer stays, deeper relationships, and being home for your kids' bedtimes. Or you're tired of being three layers removed from the communities you went into this work to serve, stuck in internal politics and bureaucracy instead.
"The sector is changing and I'm being forced to reconsider."
With funding shifts and organizational restructuring across the ODA world, roles are disappearing. People are being pushed out or pushed sideways. Suddenly you have to decide: more of the same somewhere else, or something fundamentally different? But how do you know?
"I don't know who I am beyond my current title."
You've been "Director at Organisation XXX" for so long that it's become your identity. If you left, who would you be? What would you say you do? It takes real work to excavate who you've actually become over 15 years.
Why This Matters Now
Last year, I facilitated a co-creation process that started with weeks of online work. Then we met in person in Kenya for three days. The shift was stunning. The quality of thinking when people had space to be fully present. When they could build on each other's ideas without phones buzzing or kids interrupting from offscreen.
Career transitions deserve that same spaciousness.
You can't figure out the next 10-20 years of your life in the cracks between other commitments.
How I Actually Approach This Work
After a year of cohorts and one-on-one mentoring on career transitions and authentic positioning, here's what creates real breakthroughs:
1. Start with what actually energizes you
I use the Ikigai framework combined with a Wheel of Life assessment. The honest version.
- What do you actually enjoy doing? What makes time disappear?
- What are you naturally good at, what are the things that feel easy to you but hard for others?
- How balanced are the different parts of your life? Work, relationships, health, personal growth, fun?
Most people discover they've been optimizing for "good at" and "world needs" while completely ignoring "love" and "paid for." Or they realize their Wheel of Life is wildly lopsided, work consuming 80% while everything else fights for scraps.
2. Unpack your backpack
This is experience mapping meets belief examination.
- What have you carried with you through your career? What beliefs about work, success, leadership? What roles and sectors? What experiences shaped you?
- I ask people to map their career timeline, peaks, valleys, turning points. When were you most energized? Most depleted? What patterns emerge?
- Then: What do you want to double down on? What do you want to avoid? What's missing that you need?
One participant realized she'd been carrying the belief that "leaving the organization means failing the mission." Once she named it, she could question it. Another discovered she lights up doing capacity building but has spent five years in grant management because it seemed more serious.
This process separates what you've accumulated from what you actually want to carry forward.
3. Define your North Star
This is the work that changes everything. Your North Star is your directional career purpose, the thing that guides decisions for years. It answers: What impact do I want to have? How do I want to work? What are my non-negotiables?
One mentee's North Star: "Strengthening education systems in fragile contexts through evidence-based approaches that center community voice, while maintaining time for deep relationships and creative work."
That's a compass. She can evaluate every opportunity against it. Does this move me toward my North Star? What would I gain? What would I sacrifice?
4. Build your decision-making compass
Once you have your North Star, you need a framework for assessing concrete options. Questions like:
- Does this move me toward my North Star?
- Would this energize or deplete me?
- Can I authentically stand behind this choice?
- What would I gain and what would I sacrifice?
- Does this honor my current life needs?
This compass works for everything: job offers, consulting opportunities, staying and shifting your role, launching a side project as a passion project.
5. Explore actual pathways
Now you can look at concrete options through your compass:
Traditional employment: More strategic roles in your sector, such as foundations, implementing organizations, multilaterals
Consulting: Building your own practice, choosing clients, pricing your expertise
Portfolio career: Multiple income streams, seasonal models, integrating different passions
Your path can evolve. But you need clarity on which direction to explore first.
6. Create a realistic action plan
You need:
- Brave first moves by "putting yourself out there" (the thing that scares you a bit)
- 30-day milestones (so you can see progress)
- 90-day roadmap (far enough to create momentum, near enough to feel doable)
- Accountability (someone who will ask "did you do the thing?")
And sometimes: concrete outreach plans. Reaching out to five specific people this month to have discovery conversations about X.
7. Work on your authentic positioning
Once you have your North Star, this becomes easier.
How do you talk about yourself? What's your unique perspective? How do you show up on LinkedIn, in networking conversations, when someone asks "what do you do?"
I've been experimenting with AI companions for this, among other aspects, having mentees work with an AI mentor between our sessions to dig deeper into their Ikigai, backpack, leadership stories and what it means for their positioning. This way, they can practice articulating their value, work through limiting beliefs.
Here's what I've learned: you can't position yourself authentically until you're clear on your North Star. Everything else is tactics without strategy.
Why It Has to Be Prioritized
Here's the uncomfortable truth: You will never "find time" for this work. There will always be another urgent email. Another meeting. Another crisis. Another weekend consumed by life logistics.
Career clarity requires:
- Separation from your daily routines and demands
- Spaciousness to think without interruption
- Structure so you're making progress
- Peer reflection with people who understand your context
- Expert guidance from someone who's navigated these transitions
This is why I'm bringing my cohort work to Greece in September. Physical separation from your inbox, your obligations, your routine momentum creates permission to ask: What do I actually want?
Three days. Eight women. Morning workshops on North Star, pathways, compass, action planning. Free afternoons to integrate. Evening storytelling circles.
Our first registered participant is a founder who's giving it to herself as a birthday present. After 10+ years building her organization, she's ready to figure out what's next. She's succeeding and wondering what else might be possible.
What It Actually Takes
I've watched people circle these questions for months, sometimes years, trying to figure it out alone, in the gaps between everything else. Then they spend three focused days working through it, and they have clarity.
Because transformation requires conditions.
You need space to think. Structure to work through it. People who understand your trade-offs. Someone who can ask the questions you're asking yourself. The alternative is continuing to tell yourself you'll figure it out this weekend. Next month. When things calm down.
Things won't calm down.
Your career is too important to keep deprioritizing. Because you spend more time on it than with your kids.