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Maggie is a former Deloitte consultant and Slack product marketer who walked away from the “good on paper” path to build a portfolio career—mixing retreats + events, marketing work, and community-building on her own terms. In this episode, we unpack the high-achiever pattern that quietly keeps people stuck: chasing the next title, the next company, the next “safe” move—until burnout forces a reset. Maggie shares how she used internal pivots, side experiments, and strategic networking to find clarity, build confidence, and finally make the leap (even without income lined up). In this candid conversation, Maggie explains: → The high-achiever trap: consulting looked “right” until loneliness + burnout exposed the cost. → The Slack leap: one LinkedIn message + referral changed her trajectory. → The pivot playbook: curiosity, relationships, and win-win projects to move internally (and externally). → The real unlock: coaching + side experiments to rebuild self-trust and find what actually fits. → The new model: portfolio career + long-game money mindset + boundaries for sustainability. Chapters 00:00 Early influences: practical path vs creative pull 03:45 Chasing the “best” internship + the consulting path 04:10 Deloitte reality + travel and exposure 08:20 The pivot trigger: lonely + bored + “do I want this forever?” 09:45 Jump to Slack: new role + learning curve 11:10 Imposter syndrome + what helped over time 14:15 Product marketing + internal pivots 16:00 How to switch teams: curiosity + “what’s in it for them?” 17:35 COVID wake-up + burnout + “same problems” 19:40 Career coaching + mindset + future self visualization 25:00 Using a job as runway: Pilates + first client + networking 31:05 Financial fear + long-term game 55:40 Redefining success: external → internal Host: Dar Patel, Founder of Little Pursuits Connect: / darpatel Join Our Founder Circle: https://98sg03uup7d.typeform.com/to/T... Upcoming Events: https://luma.com/calendar/manage/cal-... Newsletter: https://littlepursuits.substack.com/ Guest: Maggie Blackburn, Experience Designer & Career Strategist, Connect: / maggieblackburn