Description

💬 Summary

In 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.

💡 Takeaways

• Pressure isn’t always negative – it can push you to achieve your best work
• Networking is really just relationship building – and needs a total rebrand
• The happiest professionals see work as more than tasks; it’s about experiences and relationships
• Employers who empower their people to network externally show real confidence and trust
• Being honest with yourself about what you actually want is key to defining success
• Employee personal branding is becoming as powerful as company branding
• AI will reshape roles – curiosity and self-motivated upskilling will be non-negotiable

🕒 Chapters

00:00 – Who is Olly Haddock and how does he introduce himself?

01:23 – The story behind starting The Careers Edit

03:51 – Early career plans and the importance of flexibility

06:54 – Questioning the traditional checklist of success

09:23 – Pressure as a motivator and driver of achievement

11:16 – Why some professionals feel unfulfilled despite appearances

12:15 – Backing instincts: moving into innovation in law

16:34 – What the happiest professionals have in common

18:32 – Co-working, connection, and the value of community

19:41 – Why networking needs a rebrand

22:39 – How careers really progress: word of mouth and relationships

24:42 – Unconventional connections that shaped Olly’s career

26:00 – First steps if your job is draining your energy

28:45 – The rise of portfolio careers, purpose, and flexibility

33:39 – The skills we’ll all need in an AI-driven future

35:27 – How the right people around you shape your career

36:50 – What excites Olly about Gen Z in the workplace

39:02 – Personal branding, hustle culture, and side hustles

40:30 – The widening gap between what people want and what companies offer

43:18 – How employers can support people without massive budgets

45:10 – Rethinking education and career guidance from school onwards

47:28 – Imagining the workplace of the future

48:59 – Olly’s one piece of advice for finding or transforming your dream role

🔗 Follow Olly

The Careers Edit: https://www.thecareersedit.com/

The Careers Edit Instagram: https://www.instagram.com/thecareersedit/

LinkedIn: https://www.linkedin.com/in/oliver-haddock-2b316a106/

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