091: Why the ‘Perfect Moment’ Never Comes (and What to Do Instead) with Donna Robertson
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.
About the host
Connect with Sandra Lewin on LinkedIn
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