Favourite Positions
Work has changed and so should the way we think about it. Favourite Positions explores modern careers, leadership and human skills so you can move forward with intention and confidence.
Hosted by Alex Young, the podcast brings honest, thoughtful conversations with founders and leaders who are reshaping how work works. From practical career insight to big ideas about purpose and growth, each episode helps you think differently about your next step, whether you’re early in your career, switching paths or leading others.
Favourite Positions is part of a broader platform supporting people and organisations to build careers they love and workplaces that empower them. With no fluff, real-world tools and a community of people who value clarity and curiosity, this is your go-to space for inspiring stories and practical guidance.
Favourite Positions
Episode 09: Work In Progress - Olly Haddock
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💬 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/
Follow Favourite Positions on LinkedIn and Instagram, connect with Alex here.
