What I Have Learned as a Serial Entrepreneur as I Get BOLDER

Written by Debra Olshan Cooper,
President and Founder of Your Career Design lab

In today’s fast-paced career landscape, advancement is no longer just about how far you climb the corporate ladder; it’s about how deeply you can build meaningful relationships. Reflecting on my own journey, I remember being 18 to 20 years old, believing that each job was “it.” Every role seemed like the pinnacle of my career, and I thought I had reached the zenith of my knowledge and skills. Now, in my 60s, I find myself marveling at the incredible network of people I know, all doing fascinating and impactful things with their lives. This leads me to wonder: is my generation becoming bolder, not older?

5 Lessons I’ve Learned

As I look back, I realize that these experiences have taught me invaluable lessons about careers and relationships. Here are five key takeaways:

1. It’s Just the Beginning

Every new role or connection is a stepping stone, not a final destination. Embrace each opportunity as the start of something new and exciting.

2. Build with Intent

Focus on building genuine relationships rather than just networking. Seek to understand and support others, and meaningful connections will follow.

3. Stay Curious

Never stop learning. Curiosity keeps your mind active and opens doors to new possibilities and collaborations.

4. Adapt and Evolve

The career landscape is ever-changing. Be flexible and willing to adapt. Evolving with the times ensures longevity and relevance in your field.

5. Embrace Your Wisdom

Leverage the intelligence, wisdom, and awareness that come with age. Your experiences are a treasure trove of lessons that can guide and inspire others.

How to Make Your 60s the New 30s

Resurrecting your career in your 60s involves harnessing the qualities that come with age—intelligence, wisdom, awareness—and continuing to grow and evolve. Here are some ways to achieve this:

  • Continuous Learning: Keep up with industry trends and advancements. Whether through formal education, online courses, or industry events, stay informed and adaptable.
  • Networking with Purpose: Engage in networking not just to expand your professional circle, but to build relationships that are mutually beneficial and meaningful.
  • Mentorship and Coaching: Share your knowledge and experiences with younger generations. Mentorship can be incredibly rewarding and offers fresh perspectives.
  • Personal Growth: Focus on personal development. This includes physical well-being, mental health, and emotional resilience. A balanced life enhances your professional effectiveness.

A Lesson in Perseverance for the Long Run

Perseverance is a key ingredient for long-term success. Here’s how you can cultivate it:

  • Set Realistic Goals: Aim for achievable milestones that keep you motivated and on track.
  • Stay Positive: Maintain a positive outlook, even in the face of challenges. Positivity fuels perseverance.
  • Embrace Change: View change as an opportunity rather than a setback. Adaptability is crucial for sustained success.
  • Celebrate Small Wins: Acknowledge and celebrate your achievements, no matter how small. They are the building blocks of your long-term goals.


Career advancement today is not just about how far you can get in your career, but how far you can get in building meaningful relationships. By embracing the wisdom and experiences that come with age, you can resurrect your career and make your 60s the new 30s. Stay curious, build with intent, and keep evolving. Remember, your journey is just beginning, and with perseverance, intelligence, and awareness, the possibilities are endless.

Questions about your career?

Let’s talk about it! Schedule a free 30-minute call with me:

Créditos de las imágenes

Imagen 1: Elnur / Canva
Imagen 2: Fotógrafo Vlada Karpovich / Pexels
Imagen 3: Fotógrafo fauxels / Pexels

Find your passion with our "Ta-Da" List

Excavate who you are, find your passion and discover your pursuits with my “Ta Da” List - Free to download. 

Join My Mailing List

To receive FREE tips and insights on how to get your Dream Career.
linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram