Career Crossroads: What’s Your Next Strategic Move?
You’re not lost. You’re at a crossroads.
If you’re a woman of color or underrepresented leader in social impact, you know what it’s like to give everything to your work — and still wonder if you’re in the right role, the right organization, or even the right chapter of your career.
The sector is shifting fast. Funding is contracting. DEI is under attack. Organizations are restructuring. The job market is saturated. Colleagues are burning out or quietly leaving. And in the middle of all of it, you’re supposed to keep leading.
But what do YOU actually want? What’s the strategic move that serves both your mission and your life?
This free workshop will help you find out.
What You’ll Walk Away With
✅ Your Career Crossroads profile – Clarity on which crossroads you’re at: Strategic Exiting, Strategic Staying, Intentional Growth, Exploration, Transition Planning, or Fast-Track Seeking
✅ A values-priorities audit – Cut through the noise and identify what you actually need from your next chapter
✅ Your strategic path forward – A concrete, values-aligned next step — not a vague goal, but a real decision
✅ Frameworks for navigating transition – Tools grounded in your reality as a leader in systems not designed for you
✅ Community connection – Peer leaders who understand your reality
✅ Completed workbook – Your Career Crossroads guide to keep working with after the session
What We’ll Do Together (90 Minutes)
Career Crossroads Diagnosis (20 min) Take stock of where you actually are — not where you think you should be. Name your crossroads without judgment.
Values-Priorities Audit (20 min) Strip away others’ expectations and get honest about what you need your work to give you right now.
The Strategic Path Tool (20 min) Map your real options, name your constraints, and identify the move that fits your life — not just your ambition.
What’s Next (15 min) How to sustain this momentum + ways to continue working together.
Q&A (15 min)
This Workshop Is For You If…
✓ You’re a woman of color or an underrepresented leader in social impact, philanthropy, or international development (Everyone is welcome)
✓ You’re quietly wondering whether to stay, pivot, or leave — and can’t get clarity on your own
✓ You’re tired of career advice that ignores systemic pressures, emotional labor, and the complexity of leading while marginalized
✓ You want practical tools, not just inspiration
✓ You’re curious about values-aligned, equity-centered approaches to career strategy
About Your Facilitator
Maya Hasan, Founder & CEO of Fearless
I support women of color and historically marginalized leaders to lead with intention, navigate career pivots, and build sustainable practices in social impact work.
My approach centers trauma-informed practices, nervous system regulation, and community care — because we can’t lead powerfully when we’re operating from survival mode.
Based in Puerto Rico. Child of South Asian refugees with lived experience across 5 continents. Over two decades strengthening civil society leadership across 15+ countries. Committed to feminist, decolonial, equity-centered leadership development.
What You’ll Receive
Before: Zoom link, workbook, Career Crossroads Quiz (optional but recommended)
During: Live facilitation, breakout discussions, interactive activities
After: Recording with transcript (available for 7 days), workbook and resource guide
What Happens Next?
This workshop is designed to give you immediate value and introduce you to ways we can continue working together:
Flourish Fellowship – A low-cost membership community for mid-senior women of color leaders in social impact (and allies!). Live weekly sessions including workshops, guest speakers, peer coaching, and co-working with peers who get it. Plus 24/7 community platform access.
1:1 Coaching – Highly personalized 1:1 leadership, executive, and career coaching with Maya. (Free 30-min strategy session to see if it’s right for you.)
Learn more: fearlessproject.co
Accessibility
Live captions • Recording with transcript • Breakout room accommodations available • AI notetakers by request only
Questions or accessibility needs? Email: [email protected]
Limited to 300 Participants
This is an intimate, interactive workshop. When spots fill, registration closes.
Register now to secure your spot.