Episode 09: Work In Progress - Olly Haddock

💬 SummaryIn this episode of Work in Progress, we speak to Olly Haddock – solicitor, innovation specialist at Weightmans and founder of The Careers Edit – about redefining success, building careers that feel authentic and why networking desperately needs a rebrand.Alongside his legal practice, Olly helps lead innovation projects at Weightmans, creating tech-driven solutions to make law more efficient and client-focused. Through The Careers Edit, he’s built a global community of over 50,000 professionals, known for its fresh approach to events that swap stuffy boardrooms for spaces that encourage real conversations and meaningful connections.We explore why pressure can sometimes be a positive driver, how to pivot when a career path isn’t what you expected, and what the happiest professionals Olly meets have in common. Plus, we dig into the myths of networking, the skills we’ll all need in an AI-driven future, and how younger generations are reshaping the world of work.💡 TakeawaysPressure isn’t always negative – it can push you to achieve your best workNetworking is really just relationship building – and needs a total rebrandThe happiest professionals see work as more than tasks; it’s about experiences and relationshipsEmployers who empower their people to network externally show real confidence and trustBeing honest with yourself about what you actually want is key to defining successEmployee personal branding is becoming as powerful as company brandingAI will reshape roles – curiosity and self-motivated upskilling will be non-negotiable🕒 Chapters00:00 – Who is Olly Haddock and how does he introduce himself?01:23 – The story behind starting The Careers Edit03:51 – Early career plans and the importance of flexibility06:54 – Questioning the traditional checklist of success09:23 – Pressure as a motivator and driver of achievement11:16 – Why some professionals feel unfulfilled despite appearances12:15 – Backing instincts: moving into innovation in law16:34 – What the happiest professionals have in common18:32 – Co-working, connection, and the value of community19:41 – Why networking needs a rebrand22:39 – How careers really progress: word of mouth and relationships24:42 – Unconventional connections that shaped Olly’s career26:00 – First steps if your job is draining your energy28:45 – The rise of portfolio careers, purpose, and flexibility33:39 – The skills we’ll all need in an AI-driven future35:27 – How the right people around you shape your career36:50 – What excites Olly about Gen Z in the workplace39:02 – Personal branding, hustle culture, and side hustles40:30 – The widening gap between what people want and what companies offer43:18 – How employers can support people without massive budgets45:10 – Rethinking education and career guidance from school onwards47:28 – Imagining the workplace of the future48:59 – Olly’s one piece of advice for finding or transforming your dream role🔗 Follow OllyThe Careers Edit: https://www.thecareersedit.com/The Careers Edit Instagram: https://www.instagram.com/thecareersedit/LinkedIn: https://www.linkedin.com/in/oliver-haddock-2b316a106/Follow Favourite Positions on LinkedIn and Instagram, connect with Alex here.