11 conversations that'll shape your 2026 - vol.1

As 2025 wraps up, we’ve been reflecting on the incredible conversations we've had on The Generalist World Podcast. They are just FULL of insights which we thought could help you! From fractional careers to AI integration, from career pivots to building sustainable businesses.

We’ve organised the episodes by what you might want to work on in 2026. Jump to whatever resonates most with where you are right now. Whether that's exploring new career models, sharpening your skills, or building something from scratch.

So let’s dive in! 🤿

^{For those exploring flexible work arrangements, multiple income streams, or considering the leap into fractional roles.}

Ep 1: She spills the tea on fractional marketing

Terra Milo opens up about the world of fractional marketing, revealing how this model allows for deeper integration with teams while maintaining flexibility. She discusses the art of cold outreach with empathy, thriving as an introvert in video and public speaking, and why authenticity trumps polish in today's marketing landscape.

Best for: Marketing professionals considering fractional work or anyone curious about building genuine client relationships

Key takeaway: Pricing should reflect the value you provide to clients, not just your personal financial needs

Ep 2: She's built a FIRE portfolio career & shares what's working right now

Taylor Elyse Morrison shares her journey through coaching, facilitation, and even a PhD program, all while maintaining a portfolio career. She emphasises the power of curiosity, the importance of asking good questions, and how to find community as a generalist navigating multiple interests.

Best for: Anyone juggling multiple roles or considering a portfolio approach to their career

Key takeaway: Starting small projects can lead to a fulfilling portfolio career—you don't need to have it all figured out at once

^{For those in transition, exploring new industries, or rethinking their career path entirely.}

Ep 3: Take the 'side door' (career hack!!)

This episode with Li Si Wong explores diverse career journeys, focusing on transitions between industries and the concept of 'side doors' in career opportunities. Learn about the role of generalists in product management, the importance of asking the right questions, and how AI is reshaping job titles and roles.

Best for: Career changers and anyone feeling stuck on the 'traditional' path

Key takeaway: There are multiple paths to success, not just one right door—embrace the side entrances

Ep 4: 20 yrs in one org to Design Ops Strategist!?

Lucy Nersesian shares her journey from theatre design to operations, emphasising the need for generalists to connect the dots across teams. She discusses the evolving role of design operations, the importance of empathy, and how continuous learning is essential for personal and professional growth.

Best for: Anyone considering a major career shift or struggling to define their career identity

Key takeaway: It's important to define oneself beyond job titles—your skills and perspective matter more

^{For founders, aspiring entrepreneurs, and anyone building something new from the ground up.}

Ep 7: Ex-chief of staff builds her startup with no coding experience

Alison Y. shares how to build products without coding skills using modern tools, why diverse backgrounds are actually an advantage in entrepreneurship, and how to make faster decisions by trying things instead of overthinking. She discusses jumping into professional communities right away and how existing skills transfer to entrepreneurship.

Best for: Non-technical founders and chiefs of staff considering entrepreneurship

Key takeaway: Your ability to understand systems and user needs means you can build a business without hiring programmers or spending tons on development

Ep 11: The road to $10M (from a chief of staff in NYC!)

Sawyer Middeleer reveals how small startups can reach $10M revenue with fewer than 10 people using generalist team members and AI tools. He discusses 'context engineering' as the secret to building AI agents, how to start with simple automations for quick wins, and why tools like Lovable now let anyone build custom apps just by describing what they want.

Best for: Startup operators and founders looking to scale efficiently with AI

Key takeaway: Learn by doing first, then studying—this builds deeper understanding than following tutorials

^{For those looking to strengthen relationships, improve their networking game, or rethink how they approach sales and community.}

Ep 10: Organisational Psychologist on selling without the ick

Ramiro Oosting shares how to transform viewing generalism as a career liability into recognising it as a competitive advantage. He discusses client-centred sales approaches that prioritise understanding over convincing, psychology-based communication techniques for converting skeptical prospects, and how to avoid the 'perpetual learning trap' that prevents decisive action.

Best for: Anyone who struggles with sales or feels 'icky' about self-promotion

Key takeaway: Client-centred sales philosophy fundamentally shifts focus from persuasion to understanding

Ep 13: Stop applying for jobs & do this instead

Simran H. reveals how to get jobs by building relationships instead of filling out online applications, ways to juggle multiple projects without burning out, and why future workers will either be super specialised or really good at many things. She discusses how to test out new career ideas with small experiments instead of making big commitments.

Best for: Job seekers tired of the application black hole and professionals building their network

Key takeaway: Building relationships beats sending tons of job applications—invest in your network before you need it

^{For those seeking better work-life integration, alignment with their values, or more sustainable ways of working.}

Ep 16: She quit the 9-5 to build a business around alignment

Ishita Agarwal discusses how to identify misalignment through body awareness and journaling, the framework for transitioning from traditional employment to entrepreneurship without rigid planning, and methods for balancing masculine and feminine energy cycles in business decision-making. She shares strategies for 'batch cooking' work sessions to optimise productivity.

Best for: Those feeling misaligned in their current work or considering leaving traditional employment

Key takeaway: Vision-over-process entrepreneurship—focus on where you're going, not rigid plans

Ep 18: She's a top voice who's been working remotely since 2012

Nola Simon shares how to advocate effectively for flexible work arrangements, why trust is the foundation of successful remote work policies, strategic approaches to building flexibility that cascade through entire organisations, and why surveillance and micromanagement create compliance issues rather than solving productivity concerns.

Best for: Remote workers advocating for flexibility and leaders designing remote policies

Key takeaway: Effective flexibility advocacy requires precision and preparation, get clear on your needs and organisational obstacles

^{For those wanting to understand AI's impact on work and position themselves for the future.}

Ep 6: your ‘figure-it-out’ ability is a career asset!

In this episode, Jiten R. explores the advantage of moving between high concepts and diving into details, how to find the 'red thread' of your career, and why being the person who puts their hand up for difficult jobs pays dividends. Jiten discusses how to get better at breaking down complex ideas like AI into something everyone understands and how to thrive in environments of extreme ambiguity.

Best for: Problem-solvers and those navigating uncertain environments

Key takeaway: Build a reputation as someone who knows 'how to figure it out'—your adaptability is your greatest asset

We'd love to hear which episode resonates most with you and what you're working on heading into 2026. Share your thoughts in the poll, your journey inspires us all.

Stay tuned for next week’s podcast roundup!