Success Leaves Clues: Ep 301 - If Not Now, When? Reinventing Yourself in Midlife with Brenda Benard, COO at Benard + Associates
Episode Details

What if the most meaningful chapter of your life hasn’t happened yet? 


In this episode of Success Leaves Clues, Robin Bailey and Al McDonald sit down with Brenda Benard, COO at Benard + Associates, to explore midlife reinvention, overcoming self-doubt, and finding the courage to create a life that reflects who you are becoming.


Brenda never planned to become a business leader. After turning down an opportunity to study theatre, struggling with low confidence, and believing her happiness would come from other people, she spent years moving through life without a clear sense of what she wanted. But a quiet voice continued reminding her that she was capable of more.


Brenda shares why walking into a room filled with CEOs changed how she saw her own value, what her professional-athlete daughter taught her about self-belief, and how perimenopause affected her confidence, identity, and mental health. She also explains why asking “What’s the worst that could happen?” can make intimidating decisions feel possible.


Robin, Al, and Brenda discuss intentional aging, protecting your health, listening to the whispers that tell you something needs to change, and refusing to postpone meaningful experiences until someday.


Whether you’re questioning your career, navigating midlife, rebuilding your confidence, or wondering whether it’s too late to make a change, this episode is a powerful reminder that today is the youngest you will ever be again.


You’ll hear about:

  • Why Brenda calls herself the “reluctant COO”
  • How self-doubt shaped Brenda’s early life and career decisions
  • Why she turned down her dream of studying theatre
  • Becoming a police officer at 33 while raising two young daughters
  • How to recognize the quiet signs that you are capable of more
  • The question that changed Brenda’s outlook on time and opportunity
  • Why taking responsibility can be more empowering than assigning blame
  • The moment Brenda realized she deserved to have her success celebrated
  • How other people may see strengths you cannot yet recognize in yourself
  • Overcoming feelings of inferiority around senior leaders and executives
  • Why even the most accomplished leaders are still figuring things out
  • How perimenopause can affect confidence, identity, and mental health
  • What Brenda’s daughter taught her about making her younger self proud
  • How evaluating the worst-case scenario can help you move through fear
  • Why health and longevity have become central to Brenda’s next chapter
  • The power of trading expectation for appreciation


We talk about:

00:00 Introduction to Brenda Benard and rethinking success in midlife

03:43 Self-doubt, abandoned dreams, and expecting happiness from others

05:02 Listening to life’s whispers and becoming a police officer at 33

08:41 “If not now, then when?” and why someday may never arrive

11:31 The moment Brenda decided she deserved to have her success celebrated

13:53 How Brenda’s employees saw strengths she couldn’t recognize in herself

21:06 Walking into a room of CEOs and overcoming feelings of inferiority

26:00 Perimenopause, self-confidence, and navigating the dark years

27:52 What Brenda’s daughter taught her about honouring her younger self

29:42 Using the worst-case scenario to move through fear

31:02 Raising courageous daughters and refusing to waste more time

33:10 Intentional aging, protecting your health, and living while you can

38:57 Trading expectation for appreciation


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Episode cover art for Success Leaves Clues: Ep 301 - If Not Now, When? Reinventing Yourself in Midlife with Brenda Benard, COO at Benard + Associates
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