NEXT CHAPTER

From Hero to Mentor: The Mid-Career Shift That Changes Everything

John Bailie

February 24, 2025

Obi Wan Kenobi was once a young and impetuous Jedi Knight.

The wise and peaceful King Solomon was once a brash young king who made war, expanded an empire, and aggressively purged his rivals.

Haymitch Abernathy, the skillful trainer who prepares Katniss Everdeen for the Hunger Games, was once the most renowned reigning victor of that deadly trial.

Spending a lifetime in business leadership is every bit an adventure – a hero’s journey where we all begin as inexperienced upstarts with a dream and a big bag of goals. We fear we won’t live up to expectations, imposters playing a role we’re not ready for, and that the dragons we’ll face are too big and powerful. I felt that way as the first person in my family to go to college, then doubly so when I entered my PhD program, when I helped to create a freestanding graduate school virtually from thin air, building an international training and consulting business, becoming a young president, and sitting in my first board meeting – not to mention getting married and becoming a dad.

However, with time, sacrifice, and plenty of scars, we acquire the reps, experience, and wins needed to prove ourselves to the world and eventually (hopefully) to ourselves. At mid-career this can be immensely satisfying. It also brings a new crisis. Namely, what now? We’re no longer working to prove ourselves. We know our capabilities, strengths and weaknesses. We already have a metaphorical (or literal) chest full of medals. We made change in the world. But… we still have plenty of gas in the tank and time left to fly. What’s our place in the world?

In the Hero with a Thousand Faces, Joseph Campbell, describes the critical moment in hero’s journey when the young hero meets “the mentor” – the one who helps them break through their wall of fear, lack of skills, and crushing uncertainty. We can all think of those people in our careers, who appeared when we were ready, and helped to make us who we are today.

The Leadership Shift: From Hero to Mentor

Here’s the thing… Obi Wan, Solomon, Haymitch weren’t born as mentors. They were once unsteady heroes themselves. However, at some point they decided to become mentors. This is the heart of the mid-career Next Chapter – the move from dragon-slayer to knight-trainer. Our businesses are full of young heroes that desperately need a battle-tested mentor. Great senior leaders are not star performers. They’re star mentors. This is the good-to-great hurdle, the “level-up’, at mid-to-late career.

The double bonus for family business leaders is that we’ll often be mentoring the next generation of our own family – our children, nieces, and nephews. One of the most common challenges we help clients with is the experienced senior family member/leader who can’t make the jump from hero to mentor. We have a responsibility to not hang onto the spotlight too long, to make space in the arena for the next generation of would-be family heroes. This isn’t easy to do. It requires courage, humility, and often, experienced support.

Making the Shift: What It Takes

Transitioning from front-line leader to mentor doesn’t mean fading into the background. It means stepping into a new, equally powerful role—one that focuses on legacy, long-term impact, and equipping the next generation to lead effectively.

But let’s be honest: this shift isn’t easy. It requires:

• Letting go of the need to be the sole decision-maker – Trusting others to step up and make their own mark.
• Fostering a culture of learning and accountability – Creating space for younger leaders to develop their own leadership style.
• Redefining personal success – Recognizing that legacy isn’t about personal accolades but about the success of those who follow.
• Having the courage to embrace change – Understanding that leadership evolution is not a loss but an opportunity for deeper impact.

It’s a move from center-stage to director, protagonist to narrator, achieving to serving. It’s a beautiful opportunity, that can also be as painful as it is exciting. Though experienced, we need to allow ourselves to feel uncertain again – to recognize that one chapter is ending and another is beginning. Though we now know the map of our world, it’s a conscious choice to take yet another unknown path – and that’s always a little scary.

You Don’t Have to Do It Alone

Like any new challenge, this transition is best navigated with support. Just as we sought mentors early in our careers, we benefit from guidance at this stage, too. Whether through peer networks, coaching, or strategic leadership programs, investing in this next chapter is what separates those who leave a lasting impact from those who merely hold on.

If you’re ready to turn the page and start your mid-career leadership transformation, to become the mentor your company—and your next generation—needs, an executive coach or next chapter plan can provide the roadmap.

Your biggest legacy won’t be the battles you fought. It will be the leaders you helped shape. Are you ready for your next adventure?