In this episode of Life Matters More, Philippa speaks with Dana Dennis-Smith OBE, founder of Obelisk Support, about what it really takes to build a more flexible, human way of working in a profession that has long rewarded tradition and endurance.
Together, they explore the gap between what organisations say about flexibility and what people experience in practice, especially at the point where careers and life collide. Dana also reflects on the principles behind creating a business designed around experienced talent, and what “human first” looks like when it becomes a standard rather than a slogan.
You’ll hear them touch on:
- The moments that shape a career, and what can change when you step away and come back
- The subtle barriers that keep skilled people on the margins, even when the intention is “support”
- What flexible work can look like when it is built properly, not treated as a perk
- Why values matter most when they cost you something, not when they are convenient
- A perspective on progress that feels practical, not performative
- Dana’s work on the national campaign, “First 100 Years” celebrating the centenary of women in law in 2019. And the “Next 100 Years” championing those in positions of leadership to encourage the next generation of aspiring lawyers to pursue their ambitions.
It’s the kind of conversation that stays with you because it isn’t trying to impress you – it’s trying to tell the truth about work, life, and what happens when we stop pretending those two things live in separate worlds.
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