One of the most eye-opening conversations I’ve had recently was with Conor Pendergrast, a career coach, consultant and seasoned leader with over 15 years of experience. He shared his personal journey through career transitions, parenthood, and the challenges of balancing it all. What struck me the most was how openly Conor discussed the realities of managing these transitions while maintaining a thriving career. His insights resonated deeply, especially for anyone going through major life changes—whether you’re a new parent, changing jobs, or managing a growing team.

In this blog post, I want to share the lessons from our conversation that can help you navigate your own transitions and prepare for what’s next in your career.

1. Navigating Career Transitions with Confidence

Conor left Expensify after ten years and embraced a significant career transition. What stood out in our conversation was how prepared he was to face this change. For Conor, it wasn’t about resisting the transition but acknowledging that change is inevitable and that being flexible and open can ease the process.

"I think transitions in your career or personal life are about accepting that things will change and preparing yourself mentally for it. You might not have all the answers, but it's okay to trust the process."
— Conor Pendergrast

This really hit home for me because transitions can be overwhelming, especially when you're juggling work, life, and family responsibilities. Conor’s approach of trusting the process and preparing mentally is something we can all take away.

2. Leading with Empathy

Leadership isn’t just about managing tasks—it’s about supporting people through change. Conor emphasized how important it is to provide empathy, especially when your team members are going through significant transitions like parental leave or new career challenges.

"As leaders, it’s our job to recognize when our team members are going through big life transitions. It's about being empathetic and flexible, helping them navigate those changes without feeling overwhelmed."
— Conor Pendergrast

This resonates with me because, as leaders, we often forget that our team members are going through life outside of work. Offering support and creating a space where they feel understood is key to building a strong, resilient team.

3. Preparing for Parental Leave: A Practical Approach

One of the most valuable pieces of advice Conor shared was around preparing for parental leave. He spoke from his own experience about the importance of documenting responsibilities ahead of time to make the transition smoother.

"Before going on leave, I took the time to document my responsibilities. I wrote down all the processes I handled and worked out who would take over while I was gone. It eased the stress, knowing everything was in place."
— Conor Pendergrast

This is such a practical tip, and it’s one I wish more people implemented. By creating a clear transition plan, you not only make it easier for yourself but also for your team, ensuring continuity while you’re away.

4. Balancing Parenthood and Work

As a parent myself, I really appreciated Conor’s honest take on parenthood and work-life balance. He shared how essential it is to divide responsibilities at home and work collaboratively with your partner to make sure both family and professional needs are met.

"When you’re a parent, you need to be realistic about your energy levels. Planning how to divide responsibilities with your partner makes everything smoother. It’s all about communication."
— Conor Pendergrast

This struck a chord with me because balancing work and family life is a challenge we all face. It’s important to plan ahead, communicate openly, and set realistic expectations for yourself and your partner.

5. Giving Yourself Grace

One of the most important messages from Conor’s story is to give yourself grace during transitions. Whether it’s becoming a parent, starting a new job, or taking on more responsibility, it’s essential to be kind to yourself.

"There’s no perfect way to handle big changes, especially when you’re juggling multiple roles. It’s about giving yourself grace, knowing that you won’t get everything right all the time—and that’s okay."
— Conor Pendergrast

I think this is something we all need to hear. We can be so hard on ourselves during periods of change, but Conor reminds us that it’s okay to make mistakes and learn along the way.

Key Takeaways:

1. Prepare for Change – Anticipate life transitions and create a plan to navigate them smoothly, both at work and home.

2. Lead with Empathy – As a leader, recognize when your team members are going through life changes and offer flexibility and support.

3. Document Your Responsibilities – Before going on parental leave or stepping away, clearly document your processes and hand them off to the right people.

4. Balance Parenthood and Work – Communication with your partner and dividing responsibilities is crucial to maintaining a healthy balance between family and work life.

5. Give Yourself Grace – It’s okay not to have everything figured out during transitions. Be kind to yourself and trust the process.

Conclusion: My conversation with Conor was a refreshing reminder of how important it is to embrace transitions, both in your career and personal life. His insights on parenthood, leadership, and career growth offer practical advice for anyone going through a period of change. Whether you're preparing for parental leave, moving into a new role, or simply trying to balance work and life, Conor’s approach will inspire you to do so with empathy and grace.

If you’re navigating big changes in your life, I hope you’ll tune in to this episode and find as much value in Conor’s story as I did.