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What you'll learn:
How to learn new skills by jumping in first, then studying - this builds deeper understanding than following tutorials
Why connecting AI tools to Notion creates powerful automation without needing technical skills or complex systems
How small startups can reach $10M revenue with fewer than 10 people using generalist team members and AI tools
Why "context engineering" is the secret to building AI agents that stay smart throughout their work processes
How to start with simple AI automations like email sorting and lead generation that give quick wins
Why tools like Lovable now let anyone build custom apps just by describing what they want in plain English
How combining different skills creates better career opportunities than becoming an expert in just one area
Why following your interests beats trying to predict what skills will be valuable in the future
Some takeaways:
Learn by doing first, then studying.
Use Notion as your AI control centre.
Build lean teams of multi-skilled people, not big specialist departments.
Master context engineering for better AI performance.
Start with simple automations that give quick wins.
Build custom software without coding skills.
Combine skills instead of specialising deeply.
Follow your interests instead of guessing future trends.
Aim for higher revenue before raising big funding rounds.
Where to find Sawyer
Linkedin: https://www.linkedin.com/in/sawyer-middeleer/
Where to find Milly
Linkedin: https://www.linkedin.com/in/milly-tamati/
Website: http://www.millytamati.com/
Generalist World resources:
Podcast: https://open.spotify.com/show/0qbGzMUMDCK5v3XbvRANmD?si=b1d7af51c24e43ee
The Generalist Quiz: https://www.generalistquiz.com/
Essays: https://www.generalistcareer.com/
Upcoming events: https://lu.ma/generalist.events
Positioning Guidebook: https://www.generalist.world/positioning
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What You'll Learn:
How to transform from viewing generalism as a career liability into recognising it as a competitive advantage
The four-stage framework for generalist professional development and career progression
Client-centred sales approaches that prioritise understanding over convincing techniques
Strategic methods for transitioning from transactional sales roles to relationship-based account management
Future-proofing career strategies by developing AI-resistant soft skills like empathy and facilitation
Psychology-based communication techniques for converting skeptical prospects through empathetic engagement
How to avoid the "perpetual learning trap" that prevents generalists from taking decisive action
Networking strategies that build genuine long-term professional relationships rather than superficial connections
Some Takeaways:
The Generalist Development Framework operates through four distinct stages
Client-centred sales philosophy fundamentally shifts focus from persuasion to understanding.
The transition from B2C sales to account management represents a strategic career evolution
Future-proofing careers requires focus on distinctly human capabilities
The "dark side of generalism" involves using community and learning as avoidance mechanisms
Psychology principles applied to professional communication create breakthrough moments
Strategic networking emphasises relationship depth over quantity
Simplification strategies become essential as businesses and careers grow in complexity.
Building a personal brand requires consistent vulnerability and authentic self-expression in professional contexts.
Where to find Ramiro
Linkedin: https://www.linkedin.com/in/ramiro-oosting/
Where to find Milly
Linkedin: https://www.linkedin.com/in/milly-tamati/
Website: http://www.millytamati.com/
Generalist World resources:
Podcast: https://open.spotify.com/show/0qbGzMUMDCK5v3XbvRANmD?si=b1d7af51c24e43ee
The Generalist Quiz: https://www.generalistquiz.com/
Essays: https://www.generalistcareer.com/
Upcoming events: https://lu.ma/generalist.events
Positioning Guidebook: https://www.generalist.world/positioning
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What you'll learn:
How to create your own role by raising your hand for interesting projects and linking development needs to work assignments
Why moving from "driver" to "navigator" mindset helps generalists thrive in uncertain environments
How to use energy audits to make better career decisions about people, projects, and opportunities
Why healthcare as a "red thread" helps explain diverse career moves from neuroscience to finance to HR
How to leverage apprenticeship programs to gain qualifications while solving real workplace problems
Why systemic thinking from neuroscience applies to organizational change and resistance patterns
How to network effectively by saying yes to community events and following up immediately
Why entrepreneurship will surge as traditional hiring becomes more difficult and impersonal
Some takeaways:
Build spiral careers, not linear ones.
Craft roles by linking personal development to business needs.
Use energy audits to guide career decisions.
Position yourself as a bridge between technical and human systems.
Healthcare technology needs systemic solutions, not just personal responsibility apps.
Community membership accelerates professional identity formation.
Start with genuine pain points when implementing healthcare innovation.
Mass layoffs will drive an entrepreneurship wave.
Partnership between technology and healthcare systems creates the biggest impact.
Where to find Roxana
Linkedin: https://www.linkedin.com/in/roxana-seifer/
Where to find Milly
Linkedin: https://www.linkedin.com/in/milly-tamati/
Website: http://www.millytamati.com/
Generalist World resources:
Podcast: https://open.spotify.com/show/0qbGzMUMDCK5v3XbvRANmD?si=b1d7af51c24e43ee
The Generalist Quiz: https://www.generalistquiz.com/
Essays: https://www.generalistcareer.com/
Upcoming events: https://lu.ma/generalist.events
Positioning Guidebook: https://www.generalist.world/positioning
Hosted on Acast. See acast.com/privacy for more information.
Hosted on beehiiv. Read the full Privacy Policy at beehiiv.com/privacy.
What you'll learn:
How to apply reframing philosophy to transform challenges into growth opportunities and learning experiences
The fractional CTO model for serving multiple startups simultaneously while maintaining strategic impact
Why focusing on female founders creates unique business development and market positioning advantages
How to bridge the gap between technical capabilities and business strategy for faster execution
Community networking strategies that convert connections into partnerships, customers, and professional opportunities
The democratisation of technology experimentation for non-technical entrepreneurs and business builders
Methods for maintaining human-centered approaches while leveraging advancing technology capabilities
Strategic positioning for the emerging trend of business-tech hybrid professionals in startup ecosystems
Some takeaways:
Reframing adversity as strategic advantage
Fractional CTO positioning in startup ecosystems
Female founder market specialisation
Community-driven business development
Technology democratisation for business builders
Business-technology hybrid positioning
Human-centered technology advocacy
Global mobility as competitive advantage
Impact-driven technology consulting
Where to find Katherine
Linkedin: https://www.linkedin.com/in/katherinemora/
Book Kath as a speaker or for a workshop on the tech and AI space: https://www.amanzi.io/speaking
Have an idea or need guidance on your tech direction? Chat with Kat: https://www.amanzi.io/contact
Where to find Milly
Linkedin: https://www.linkedin.com/in/milly-tamati/
Website: http://www.millytamati.com/
Generalist World resources:
Podcast: https://open.spotify.com/show/0qbGzMUMDCK5v3XbvRANmD?si=b1d7af51c24e43ee
The Generalist Quiz: https://www.generalistquiz.com/
Essays: https://www.generalistcareer.com/
Upcoming events: https://lu.ma/generalist.events
Positioning Guidebook: https://www.generalist.world/positioning
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Hosted on beehiiv. Read the full Privacy Policy at beehiiv.com/privacy.
What you'll learn:
How to make faster decisions by trying things instead of overthinking them
How to lead teams by taking care of everyone while still getting work done
Why joining professional groups helps you learn and contribute right away
How people with many different skills can succeed in startups
How to build your first product without knowing how to code
How to help others in your network from the very beginning
How to use communities to feel more confident about your career choices
How people with varied backgrounds can start their own companies
Some takeaways:
Jump into professional communities right away Groups like Generalist World show that you don't need to lurk for months before participating. Within just two weeks, you can both get help and help others. This creates valuable relationships that benefit everyone involved.
There's no single "right" career path Professional communities reveal that people with diverse skills can build successful careers in many different ways. This takes pressure off finding the "perfect" path and gives you permission to follow your actual interests.
You can build products without coding skills Modern tools let non-technical people create real, working products. If you're good at understanding systems and user needs, you can build a business without hiring programmers or spending tons of money on development.
Your diverse background is actually an advantage People with experience in different areas can spot opportunities that specialists might miss. Your ability to connect ideas from different fields helps you find gaps in the market and create innovative solutions.
Your existing skills transfer to entrepreneurship If you're good at seeing the big picture, building relationships, and solving different types of problems, you already have many of the skills needed to start a company. Early-stage businesses need people who can handle multiple responsibilities at once.
Create your own opportunities As traditional jobs change, people who are comfortable with uncertainty and have multiple interests will be better positioned to create their own work rather than waiting for the perfect job to appear. This entrepreneurial mindset becomes more valuable as the economy keeps evolving.
Links:Where to find Alison
Linkedin: https://www.linkedin.com/in/ally-syeung/
Where to find Milly
Linkedin: https://www.linkedin.com/in/milly-tamati/
Website: http://www.millytamati.com/
Generalist World resources:
Podcast: https://open.spotify.com/show/0qbGzMUMDCK5v3XbvRANmD?si=b1d7af51c24e43ee
The Generalist Quiz: https://www.generalistquiz.com/
Essays: https://www.generalistcareer.com/
Upcoming events: https://lu.ma/generalist.events
Positioning Guidebook: https://www.generalist.world/positioning
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Hosted on beehiiv. Read the full Privacy Policy at beehiiv.com/privacy.
What you'll learn:
The advantage of being able to move between very high concepts and also dive into the weeds of an idea
How to find the ‘red thread’ of your career
Why being the person who puts their hand up for the difficult job pays dividends
Why a great manager changes everything
How to get better at taking complex ideas (like AI) and breaking it down into something everybody understands (like pizza)
Some takeaways:
Worst case scenario thinking - face it , demystifies it, fear looses power and you can focus as a mental model for stressful situations.
Build a reputaion as someone who knows ‘how to figure it out’
How to thrive in environments of extreme ambiguity and chaos
AI will become normal, just like a few years, unlocking your phone with your face was not a thing, AI will just be how things work
Generalist will become more sought after, new jobs likely to emerge, and you need to be able to adapt quick and learn fast. As complexity increases, need people who can see patterns.
Solo travel as a career reset mechanism
Where to find Jiten
Linkedin: https://www.linkedin.com/in/jiten-rama/
Where to find Milly
Linkedin: https://www.linkedin.com/in/milly-tamati/
Website: http://www.millytamati.com/
Generalist World resources:
Podcast: https://open.spotify.com/show/0qbGzMUMDCK5v3XbvRANmD?si=b1d7af51c24e43ee
The Generalist Quiz: https://www.generalistquiz.com/
Essays: https://www.generalistcareer.com/
Upcoming events: https://lu.ma/generalist.events
Positioning Guidebook: https://www.generalist.world/positioning
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Shern Tee is a lecturer, researcher, physicist and coder who specializes in all molecular dynamics simulations weird and unusual. Currently, he teaches and conducts research while advocating for cross-disciplinary thinking in traditionally specialized academic environments. Previously, he has worked across various educational institutions, developing his philosophy of "irrational optimism" about student potential. His work spans from designing engaging curriculum to fostering student curiosity to exploring how human connection intersects with academic learning. Shern also researches the evolving role of AI in education while maintaining focus on the fundamental importance of human relationships in learning environments.
What you'll learn:
How "irrational optimism" about student potential can transform teaching approaches and outcomes
Why generalist thinking is valuable in specialized academic environments and research settings
Strategies for increasing student engagement through curiosity-driven teaching methods
How exploring opposite perspectives can lead to breakthrough insights and learning
The importance of confidence-based networking versus transactional relationship building
Why human connection remains critical even as AI transforms educational landscapes
Practical approaches to fostering exploration and discovery in academic settings
How to navigate uncertainty in both networking and career development
Where to find Shern
Linkedin: https://www.linkedin.com/in/shern-tee-phd-8172241b3/
Where to find Milly
Linkedin: https://www.linkedin.com/in/milly-tamati/
Website: http://www.millytamati.com/
Generalist World resources:
Podcast: https://open.spotify.com/show/0qbGzMUMDCK5v3XbvRANmD?si=b1d7af51c24e43ee
The Generalist Quiz: https://www.generalistquiz.com/
Essays: https://www.generalistcareer.com/
Upcoming events: https://lu.ma/generalist.events
Positioning Guidebook: https://www.generalist.world/positioning
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Hosted on beehiiv. Read the full Privacy Policy at beehiiv.com/privacy.
In this conversation, Milly Tamati and Lucy Nersesian explore the journey of being a generalist in the professional world, particularly in design operations. They discuss the importance of community, the challenges of defining one's career identity, and the evolving role of generalists in a rapidly changing technological landscape. Lucy shares her experiences, insights on collaboration, and the significance of continuous learning and understanding diverse perspectives.
takeaways
Lucy feels a deep connection to the generalist community.
The conversation highlights the importance of networking and serendipity.
Lucy describes her career journey from theater design to operations.
She emphasizes the need for generalists to connect the dots across teams.
The role of design operations is evolving and requires adaptability.
Lucy believes in the value of empathy and understanding others' perspectives.
Continuous learning is essential for personal and professional growth.
The community of generalists offers diverse insights and support.
Generalists will play a crucial role in navigating the future of work.
It's important to define oneself beyond job titles.
Links:
Follow Lucy: https://www.linkedin.com/in/lucynersesian/
Follow Milly: https://www.linkedin.com/in/milly-tamati/
Subscribe for free to Generalist World
Pre-register for the May Community Cohort
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Today we're talking diverse career journeys! From focusing on transitions between industries, to the concept of 'side doors' in career opportunities, to the role of generalists in product management. They discuss the importance of asking the right questions, the impact of AI on job titles and roles, and the future of work in a digital age. The conversation emphasizes the significance of relationships and personal branding in navigating career paths.
takeaways
The journey to product management can be non-linear.
Recognizing when to leave a role is crucial for growth.
Asking the right questions can open new opportunities.
Generalists can thrive in product management roles.
There are multiple paths to success, not just one right door.
AI will change job titles and the nature of work.
Building relationships is key to career advancement.
Digital footprints will become increasingly important.
Understanding motion versus busy work is essential for productivity.
Embracing change and being open to different opportunities is vital.
Links:
Follow Li Si Wong: https://www.linkedin.com/in/lisiwong/
Follow Milly: https://www.linkedin.com/in/milly-tamati/
Subscribe for free to Generalist World
Generalist World products:
Generalist World Lifetime Community Membership: https://www.generalist.world/pricing
Positioning Guidebook: https://www.generalist.world/positioning
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Milly Tamati interviews Taylor Elyse Morrison, who shares her journey through various business environments and her embrace of a portfolio career. Taylor discusses the challenges and joys of having multiple roles, including coaching, facilitation, and her recent venture into a PhD program. The discussion highlights the importance of curiosity, awareness, and balance in navigating a multifaceted career, as well as practical advice for those looking to explore similar paths. In this conversation, Taylor Elyse Morrison discusses her journey in pursuing education and career flexibility, emphasizing the importance of facilitation and coaching. She shares insights on developing presence, the power of asking questions, and the significance of finding community as a generalist. The discussion also touches on predictions for the future of work, particularly in light of AI advancements, and the joy of experimentation in professional growth.
takeaways
Taylor has worked in almost every type of business except nonprofit and government.
She thrives in startup environments where innovation is key.
A portfolio career allows for diverse interests and opportunities.
Many people are curious about the concept of a portfolio career.
Embracing a portfolio career can come with feelings of shame and uncertainty.
Starting small projects can lead to a fulfilling portfolio career.
The normalization of portfolio careers is increasing.
Clear value propositions for different roles can enhance branding.
Intimate content, like email series, resonates well with audiences.
Curiosity and awareness can lead to unexpected opportunities. I wanted to have more accountability and support in my academic pursuits.
It's so cool to be like, I would never have met you without this program.
There's a certain amount of ego death that happens in coaching and facilitation.
It's really not a situation where you're the star of the show.
You can just start to be more intentional about how you approach things.
I believe in having a growth mindset; presence can be developed.
A good question can change everything in a conversation.
What would be possible if we shifted our perspectives?
It feels like a space where I can take up space and share my journey.
If you can make it fun and bring others along, it just feels like play.
Links:
Follow Taylor: https://www.linkedin.com/in/taylorelysemorrison/
Follow Milly: https://www.linkedin.com/in/milly-tamati/
Subscribe for free to Generalist World
Pre-register for the May Community Cohort
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