Where do I go from here? Exploring fractional, freelance & flexible paths in ops
As work evolves, priorities shift and traditional paths become less clear, it’s easy to chase the next opportunity without stepping back to ask: Is this really the way I want to work?
Join us for a thoughtful, peer-led roundtable designed to create space for real conversation about portfolio careers, flexible work, and designing life and work on your own terms. Whether you're already building a fractional/freelance/portfolio career or just starting to consider it - this space is for you.
This is a peer-led space, not an expert-led session.
Instead of formal advice, you’ll find honest conversation, shared reflections, and real connection. You’ll leave with a deeper sense of belonging, some shared language for your experience, and the comfort of knowing you don’t have to figure it all out alone.
This session will help you...
💬 Feel heard and supported by peers also exploring the portfolio path
💡 Explore what’s surfaced as you reimagine your work and your time
🪞 Reflect on your priorities and how fractional work might support them
🤝 Connect informally with others in a similar phase, building clarity and confidence
You should join us if you...
✅ Are exploring or actively navigating fractional, freelance & flexible paths in ops
✅ Want to connect with peers who are asking similar questions
✅ Are looking for insight through shared experiences - not structured advice
✅ Crave a space to explore new ways of working, with real talk and real people
You’re unlikely to benefit if...
🚫 You’re currently employed and focused on advancing in a traditional role
🚫 You’re actively job searching or recently unemployed and seeking immediate next steps
🚫 You’re looking for expert instruction or a highly structured learning session
To help shape the conversation…
We’ll open with this ice breaker question:
What are your priorities in life and work, and is a fractional, freelance, or portfolio career the way to get there?
We’ll also use your responses from the registration form to surface a few key prompts. At the start of the session, you’ll vote as a group on which feels most relevant to explore further.
Facilitators will be announced soon.
Are you interested in supporting a breakout room?
Each session will be led by a main facilitator, but we’re also looking for supportive individuals to help moderate a breakout room during the session. If you're someone who can hold space with empathy and curiosity, we’d love for you to express your interest during registration.
As a breakout room moderator, you would:
Gently kick off the conversation and help it flow naturally
Ensure everyone has a chance to speak, if they feel comfortable
Create a welcoming and inclusive space for all
Encourage sharing of experiences – not coaching or advice-giving
We’ll confirm at the start of the session if we’ll need your support, depending on final numbers and how many breakout rooms we’ll be running.
Event details 📝
🕒 60-minute roundtable
(Agenda & timing may be adjusted slightly)
Welcome & Session Framing | 10 min
Icebreaker | 5 min
Vote on question to discuss | 5 min
Breakout Room Discussion | 25 min
→ An open conversation guided by shared experiencesRegroup & Reflect | 10 min
→ Emerging insights, themes, and reflectionsWrap-up | 5 min
This is a confidential space: no recordings, no coaching, no pressure. Just real talk, mutual support, and shared humanity.
Key takeaways and anonymised themes will be shared afterwards with ON community members via Disco.
Additional information
This is the second session in our 3-part “Where do I go from here?” series. Designed to meet you where you are - whether you're in between roles, rethinking how you work, or exploring what growth looks like next.
Join the session that is most relevant to your current chapter:
🔍 In-between roles
🔄 Rethinking work as a fractional operations leader (this session)