The Generalist World Pod

Leaning into wintering

Alice Montgomery on natural cycles, sustainability, and bridging disciplines. 📚What You'll Learn How generalists move from isolated expert silos to becoming bridges between disciplines that create stronger solutions Why building career decisions around a problem you care about works better than chasing job titles How assuming positive intent transforms communication and relationships across cultures, backgrounds, and misunderstandings ✍️ Some Takeaways Transferable skills matter more than job title match. Assume positive intent; give everyone grace. Surround yourself with people aligned to what matters to you. Lean into natural cycles instead of fighting them. Where to find Alice Montgomery https://www.linkedin.com/in/alicemontgomerystem/ Where to find Milly https://www.linkedin.com/in/milly-tamati/ Generalist World Resources: Podcast: https://open.spotify.com/show/0qbGzMU... 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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Environments are disabling, not people

Zahra Hedges on choosing values over money, designing for neurodiversity, building better teams. 📚What You'll Learn Why pattern recognition in your own career is more reliable than external validation or "shoulds" How neurodiversity shows up differently in every person, and why diagnosis is about removing shame, not changing who you are The practical difference between designing for inclusion versus designing "reasonable adjustments" ✍️ Some Takeaways Your wanting to leave is reason enough. Values only matter when they cost you something. High-functioning is masking, not capability. Lower the floor, raise the ceiling; don't force people into your box. Where to find Zahra Hedges https://www.linkedin.com/in/zahrahedges/ Where to find Milly https://www.linkedin.com/in/milly-tamati/ Generalist World Resources: Podcast: https://open.spotify.com/show/0qbGzMU... 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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Play and curiosity as core values

Mildred Cheng on gut feeling, connecting people, and why feedback matters. 📚What You'll Learn How running on gut feeling and knowing what you like leads to better decisions than trying to please everyone Why trust is a self-fulfilling prophecy in teams and organisations How identity shifts require pruning and loss ✍️ Some Takeaways Feedback is so radical that it feels shocking when it actually happens. Binaries are false idols and everything lives in nuance. Save your compliments and revisit them when doubt creeps in. Work is a construct, what matters is time and the people you spend it with. Where to find Mildred Cheng https://www.linkedin.com/in/mildred-cheng/ Where to find Milly https://www.linkedin.com/in/milly-tamati/ Generalist World Resources: Podcast: https://open.spotify.com/show/0qbGzMU... 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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Fear of irrelevance can drive burnout

Ellie Pyemont on holding things lightly, the generalist edge, and experiments over outcomes. 📚What You'll Learn How genuinely egalitarian partnerships enable ambitious, multifaceted careers that wouldn't otherwise be possible Why specialisation made sense in predictable times but generalists thrive in ambiguity and change The power of tinkering and holding things lightly; small experiments over grand plans ✍️ Some Takeaways Every role taught you what you needed; the lack of a plan was actually the plan. Equal partnership with your spouse changes everything. Fear of irrelevance can drive burnout, stepping into it can free you. Tinkering and holding things lightly is where real learning happens. Where to find Ellie Pyemont https://www.linkedin.com/in/elliepyemont/ Where to find Milly https://www.linkedin.com/in/milly-tamati/ Generalist World Resources: Podcast: https://open.spotify.com/show/0qbGzMU... 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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Take ‘Chief of Staff’ off the pedestal

Courtenay Hallwood on generalist superpowers, learning through discomfort, and self-belief. 📚What You'll Learn How to build self-belief through proving capability to yourself, not through external validation Why generalists are uniquely positioned to navigate early-stage startups and organisational scaling How AI cannot yet orchestrate the brain of an organisation, making human judgment still essential ✍️ Some Takeaways Throw yourself into things to learn they're learnable. You can do anything, but not everything at the same time. AI solves for speed and output, not orchestration. Chief of staff isn't a pedestal role, it's a skill-set match for generalists. Where to find Courtenay Hallwood https://www.linkedin.com/in/courtenay-hallwood/ Where to find Milly https://www.linkedin.com/in/milly-tamati/ Generalist World Resources: Podcast: https://open.spotify.com/show/0qbGzMU... 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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Don't fit the template

Sakshi Shukla on narrative depth, human solutions, and the long game. 📚What You'll Learn Why story is the first technology and how every business is fundamentally a narrative inviting people into a new reality How transferable skills from working across sectors create deeper empathy and storytelling ability than any single niche ever could Why pursuing your own authentic narrative beats chasing algorithms and templates every single time ✍️ Some Takeaways Don't fit templates because not fitting is actually your competitive advantage. Narrative takes years, not months. Tech is never the singular answer; some problems need human solutions. Awareness of your own process is your superpower. Where to find Sakshi Shukla https://www.linkedin.com/in/thesakshishukla/ Where to find Milly https://www.linkedin.com/in/milly-tamati/ Generalist World Resources: Podcast: https://open.spotify.com/show/0qbGzMU... 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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Learning as a transformational tool

Eva Košćak on distilling knowledge, personal perspective, and what makes learning stick. 📚What You'll Learn The framework for finding and owning your point of view: Known, Own, Tone How to distill expertise into digestible, actionable learning without cognitive overwhelm Why learning outcomes as "guiding north stars" prevent feature creep and keep design focused ✍️ Some Takeaways Three to five learning outcomes max; more than that breaks adult brains. Teach, show, do is a repeatable structure that creates transformation. Explain it to a six-year-old; don't overthink. Story and personal honesty are what make content land. Where to find Eva Košćak https://www.linkedin.com/in/ekoscak/ Where to find Milly https://www.linkedin.com/in/milly-tamati/ Generalist World Resources: Podcast: https://open.spotify.com/show/0qbGzMU... 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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Get comfortable being uncomfortable

Aliénor Hunter on getting comfortable speaking, breaking the cycle of avoidance, and and accepting imperfection. 📚What You'll Learn The massive gap between how nervous you feel internally and how you actually appear to others Why being yourself on stage feels riskier but creates true connection and confidence How human connection becomes more critical as AI handles the technical work ✍️ Some Takeaways Exposure therapy works; just get into speaking situations regularly. Half of your nervous symptoms are invisible. Don't berate yourself after speaking; build positive feedback loops instead. True confidence is accepting you might bomb and being okay. Where to find Aliénor Hunter https://www.linkedin.com/in/ali%C3%A9nor-hunter/ Where to find Milly https://www.linkedin.com/in/milly-tamati/ Generalist World Resources: Podcast: https://open.spotify.com/show/0qbGzMU... 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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You can do anything, but not everything

Supanuch Yik on decision-making, co-creation, and finding purpose across borders. 📚What You'll Learn How generalists and connectors bridge communication gaps between specialists by using active listening and clear shared goals Frameworks for finding purpose when you can't define yourself: ikigai, quizzes, and self-coaching tools How to make strategic choices when you want to do everything ✍️ Some Takeaways Communication breaks down when goals aren't clearly set and shared between generalists and specialists. Each yes is a no to something else; treat decisions like choosing ice cream flavours. Impact requires understanding the full system of input, process, and output. Don't wait for external confirmation or the perfect title. Trust yourself and take risks. Where to find Supanuch Yik https://www.linkedin.com/in/supanuch/ Where to find Milly LinkedIn: https://www.linkedin.com/in/milly-tamati/ Generalist World Resources: Podcast: https://open.spotify.com/show/0qbGzMU... 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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Choosing people over job titles

Chavi Pande on collaborators, removing metrics, and letting things unfold. 📚What You'll Learn Emergence as a design philosophy that extends far beyond products into process, work, and decision-making Why team culture and people matter infinitely more than company prestige or job titles How generalists build careers by staying curious, saying yes, and creating community ✍️ Some Takeaways Stop tracking metrics; follow energy and joy instead. Choose collaborators over job titles. Not defining things gives you more options. Community is a safe testing ground for experiments. Internet Archive: https://archive.org/ More on Bauhaus: https://en.wikipedia.org/wiki/Bauhaus Four Thousand Weeks: https://www.oliverburkeman.com/fourthousandweeks Arrival: https://www.imdb.com/title/tt2543164/ Where to find Chavi Pande LinkedIn: https://www.linkedin.com/in/chavi-pande/ Chavi's Website: https://chavi.net/ Where to find Milly LinkedIn: https://www.linkedin.com/in/milly-tamati/ Generalist World Resources: Podcast: https://open.spotify.com/show/0qbGzMU... 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

Keep your hobbies or lose yourself

Rachel Fenton on the messiness of pivots, curiosity as the thread, and making things with your hands. 📚What You'll Learn Why staying connected to multiple identities and hobbies is essential insurance against work consuming everything in your life How the career gap is often messier and less linear than the polished LinkedIn stories we see, and what that realistic timeline looks like What "the right size" means for your career and why growth isn't always the answer ✍️ Some Takeaways When work becomes everything, leaving becomes impossible because you've lost all your other selves. Career moves are pragmatic sequences of small decisions, not pivotal moments. The career gap is messy and turbulent, even with privilege and safety nets. Making things by hand is medicine for a life spent on keyboards, and it's non-negotiable. Where to find Rachel Fenton https://www.linkedin.com/in/rachel-fenton/ Where to find Milly LinkedIn: https://www.linkedin.com/in/milly-tamati/ Generalist World Resources: Podcast: https://open.spotify.com/show/0qbGzMU... 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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If it sucks, you can leave; the world is as we've made it

Tyler Sellhorn on showing up whole online, identity stacking, and life’s seasons. 📚What You'll Learn Why "if it sucks, you can leave" is the foundational belief that changes everything about how you approach work and life How to think like a remote-first leader who sees whole people, not disembodied profiles What makes AI genuinely transformational versus where it falls apart completely ✍️ Some Takeaways An identity stack keeps growing and reordering based on seasons, unlike fixed frameworks that suggest you're a finished product. Showing up as your whole self, online and offline, is how you actually build community and have real influence. You're never actually stuck; that's a lie that gets passed down by people who are also stuck. AI is exceptional at compression and code generation, but it's subtractive technology everywhere else because feedback loops don't exist for most human work. Where to find Tyler Sellhorn https://www.linkedin.com/in/tyler-sellhorn/ 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/0qbGzMU... 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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Your easiest thing is your truest thing

Avi Love on alignment, play in difficult moments, and creativity as nervous system medicine. 📚What You'll Learn Why deep conversations and containers matter more than ever in a shallow, algorithm-driven world The difference between therapy and coaching, and why coaching is experiencing a renaissance right now How polyvagal theory explains why play is literally a survival and innovation skill ✍️ Some Takeaways Denial about your calling is always rooted in making things hard for yourself—we're taught that what comes naturally must be suspicious. Monetise when the world asks you to, not when you preemptively decide it's viable. Fear and heartbreak are signs you're in alignment, not out of it; they point to what's deeply meaningful to you. Play is the foundational nervous system skill that enables everything else: connection, resilience, and breakthrough innovation. Where to find Avi Love https://www.linkedin.com/in/avi-love/ 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/0qbGzMU... 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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She got fired. Then she wrote a book about empathy.

Jessica Bozsan on getting blindsided, building a web of people who root for you, and why empathy is the most underrated business strategy right now. 📚 What You'll Learn Why getting fired can be a catalyst and the one practical move that helped Jess rebuild her confidence and career faster than she expected. The difference between tacit and explicit knowledge and why making empathy explicit is one of the most important things we can do right now as AI takes over the processy stuff. The Kindly Framework: a five-step approach any brand, solopreneur, or team can use to treat their customer like a real person, not a data point. ✍️ Some Takeaways When your world gets too small, a crisis can force you to rebuild it better. Empathy is a skill, not a personality trait, and most organisations are letting it go invisible. The Kindly Framework: five steps to stop treating your customer like a demographic. Posting, journaling, frameworks - it's all the same muscle. Where to find Jessica Bozsan https://www.linkedin.com/in/jessica-bozsan/ 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/0qbGzMU... 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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She helps first-time leaders survive the identity crisis nobody warned them about

Valeria Collu on putting her financial career on hold, coaching yourself like your best friend, and why becoming a leader is nothing like getting promoted. 📚 What You'll Learn How to run "time experiments" to figure out what energises you without blowing up your career in the process. The calculated-risk question that makes scary transitions way less terrifying: "Can I go back if this doesn't work out?" Why getting promoted into leadership is a completely different game and why most organisations fail their people right at that moment. ✍️ Some Takeaways When you stop being challenged, that's information, not a sign to stay put. Reframe failure as data, and make the risk feel smaller. Burnout doesn't announce itself, and by the time it does, it's usually too late. The first-time leader identity crisis is real and almost nobody talks about it. Where to find Valeria Collu https://www.linkedin.com/in/valeriacollu/ 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/0qbGzMU... 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 happens when work identity and self-identity become the same thing

Madalina Buzdugan on career breaks as privilege, generative AI's climate problem, and prompt efficiency. 📚 What You'll Learn Why work identity has become dangerously entangled with self-identity for millennials, making career breaks feel taboo and risky How generative AI can't have positive climate impact due to resource consumption, but predictive AI and machine learning are creating impressive climate solutions Why batching your prompts and being concise can dramatically reduce AI's energy consumption and environmental impact ✍️ Some Takeaways The taboo around taking time off stems from work identity being entangled with self-identity, especially for millennials who were told "work hard and everything will work out." Shift how you react to career breaks by responding with "Congratulations" instead of concern, and seek out people who've taken time off to understand their experience. Generative AI cannot contribute positively to climate goals, but predictive AI and machine learning are creating impressive climate solutions that deserve more capital. You can reduce AI's environmental impact immediately by batching prompts into single requests and being as concise as possible to eliminate guesswork. Where to find Madalina Buzdugan https://www.linkedin.com/in/madalinabuzdugan/ 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/0qbGzMU... 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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Why your transferable skills don't care about your industry

Natalie Hoop on squiggly careers, the confidence problem, and multi-unit retail as training ground. 📚 What You'll Learn Why your transferable skills don't disappear just because you're sitting in front of a new audience, industry, or type of work How confidence is a learned skill that comes from taking ownership of who you are and what your secret sauce is Why rejection isn't personal - when someone says no, they're saying no to their vision of what fits that spot, not to you ✍️ Some Takeaways We've been programmed to believe we need specialisation to succeed, but humans naturally keep growing and developing - it's odd to think we'd do the same work at 60 that we did at 18. Women especially have been trained that humble is the way to go, that accepting compliments is ego-driven and frowned upon - but learning to take ownership of your abilities is essential for communicating your value. Multi-unit retail experience teaches foundational transferable skills that apply across industries and roles you never imagined pursuing. Life happening to you rather than being designed can be the path to where you need to be - intentional design often only becomes possible after you've accumulated unexpected experiences. Where to find Natalie Hoop https://www.linkedin.com/in/nataliehoop/ 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/0qbGzMU... 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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The accidental glue person: How community work kept finding her

📚 What You'll Learn Why "glue people" are valuable in organisations and how spotting the best in others helps you connect the dots The difference between transactional networking and the "be a villager" approach of showing up consistently without expecting immediate returns How to identify your unique superpower by noticing what keeps magnetising toward you without you seeking it ✍️ Some Takeaways Portfolio careers don't require launching multiple streams simultaneously - start with one extra thing and build slowly over a year or more. Your effortless skills can transform outcomes for others - volunteer what feels easy to you but impossible to someone else. The "be a villager" mindset transforms community engagement by focusing on consistent contribution rather than transactional exchanges. Being a glue person means seeing the best in people and understanding how they prefer to interact, then connecting those dots within teams. Where to find Nicola Earle https://www.linkedin.com/in/nicola-ruth-earle/ 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/0qbGzMU... 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.

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From screens to streets: Why local community work is the future

📚 What You'll Learn Why the "back to the 90s" prediction suggests internet-era careers will be massively disrupted as AI forces us to reconnect with our physical communities How AI is acting as a mirror that prompts us to think deeply about what we value as humans, not just economically but in terms of our core values Why building micro-communities and leveraging AI for local, hands-on work might become the new career path as digital work becomes automated ✍️ Some Takeaways The internet era of careers is ending as AI automates digital work, potentially forcing a "back to the 90s" shift toward local, physical community work. Community will become essential for navigating AI disruption because isolated individuals struggle while connected groups adapt together. AI is prompting us to examine what we value as humans, forcing decisions about whether we let it replace us as people or use it to enhance life. Values need directional energy behind them (valences) to create meaningful action and build a positive future. Where to find Jon Saltzman https://www.linkedin.com/in/jonsaltzman/ 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/0qbGzMU... 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.

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How to go fractional (the realistic version)

📚 What You'll Learn What a fractional role actually is (a senior embedded leader working part-time for multiple companies, not just consulting or freelance work) Why the fractional job market is harder than people think and can take 3-9+ months to land your first role, requiring network building while still employed How to balance being the founder of a free community with the reality of needing to pay yourself and avoid resentment ✍️ Some Takeaways A fractional role is a senior embedded leader position, not synonymous with part-time consulting or freelancing. Landing your first fractional role is harder than it looks and requires strategic network building while you're still employed. Going fractional means becoming your own boss with all the administrative responsibilities nobody talks about. Community monetisation requires balancing giving value with sustainability, especially when resentment starts creeping in. Where to find Karina Mikhli LinkedIn: https://www.linkedin.com/in/karinamikhli/ 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/0qbGzMU... 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.

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