091: Why the ‘Perfect Moment’ Never Comes (and What to Do Instead) with Donna Robertson

100 Women in Insurance Summit 26th March 2026

A day and evening event to celebrate 100th podcast episode. Expect plenty of learning, networking and celebrating opportunities.

Get your tickets here.

Summary

In this episode, Sandra speaks with Donna Robertson about what it really means to trust yourself when the timing feels inconvenient and the decision is uncomfortable.

Donna shares a moment many women will recognise. On paper, everything looked great. Seniority, experience, strong results. But while pregnant with her second child, she realised that waiting for circumstances to improve felt harder than being honest. The timing was far from ideal, yet staying silent no longer felt sustainable. Instead of waiting for certainty or the “right time,” Donna chose transparency, handed in her notice at eight months pregnant, and trusted her gut.

Together, they explore why so many women slow down mid-career, particularly after having children. Not because ambition fades or capability is lost, but because the perceived cost of getting it wrong increases. Donna challenges the way maternity leave is often treated as a career risk, despite being a predictable, manageable event.

The episode closes with what Donna chose to build instead. A brokerage shaped by values rather than volume, where trust, transparency and long-term relationships matter more than commission or incentives. She talks about leadership, flexible working and why selling does not need pressure to work when it is rooted in clarity and doing the right thing. This is a conversation about backing yourself before everything feels ready, and choosing alignment when certainty never quite arrives.

Takeaways

• When the internal resistance becomes louder than the external risk, it is often a signal to reassess rather than push through
• Transparency early on can save time and emotional energy later on
• Waiting for certainty can keep you aligned to roles that no longer reflect who you are becoming
• Values-led businesses create stronger loyalty than incentive-led models
• Selling works best when it is rooted in trust, education, and long-term relationships
• Flexible working succeeds when outcomes matter more than optics
• Being open early on, helps see which environments are genuinely supportive, and which are simply familiar
• Choosing alignment may feel uncomfortable in the short term, but it creates far more sustainable careers over time

About the Guest

Connect with Donna Robertson on LinkedIn.

Find out more about Squared Insurance Brokers. 

About the host

Connect with Sandra Lewin on LinkedIn

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