Stepping Back: The Untold Side Of Letting Go

We often talk about succession as if it is a baton race. One hand lets go, the other takes hold, and the race continues. Simple.

In practice, it is rarely like that. The handover is messy. The baton wobbles. And more often than not, the founder is still running alongside long after they said they would stop.

What we do not talk about enough is why.

Why Founders Struggle To Let Go

For many founders, the business is not just something they built. It is who they are. Their role has been their identity, their purpose, their community, sometimes even their family. Letting go of that is not about moving away from a job. It is about moving away from a life.

That is why stepping back feels so different from retirement in a corporate world. A career executive can finish on a Friday, hand back the laptop, and begin a new chapter on the Monday. Their identity was never fully tied to the business they served.

For a founder, it is different. Their name may be above the door. Their decisions have shaped every success and failure. Their fingerprints are on the people, the products, the culture. To let go of that is to let go of part of themselves.

And so, even with the best intentions, many find themselves caught in one of two traps.

Trap One: Ghost Leadership

The first is what I call ghost leadership. The founder steps down in title but not in influence. They are no longer the CEO, but they still chair the operations meeting. They “just” send the FD a note about cash flow. They offer “helpful” thoughts on hiring or pricing. Sometimes they do not even need to speak; a raised eyebrow or a glance can carry more weight than a formal instruction.

From their perspective, they are supporting. From the perspective of the successor, it feels like interference. And for the wider team, it creates confusion. Who is really in charge?

Trap Two: The Void

The second trap is the void. This is when the founder really does step out, but without something meaningful to step into. At first, the freedom feels exciting. But soon the days become long, and the habits of decades are hard to break. The business becomes both the comfort and the cage. They drift back, not because they are needed, but because they cannot stay away.

The irony is that both traps come from the same place: care. Founders care deeply about the business, the people, and the legacy. But unless that care is channelled differently, it risks doing harm to the very thing they want to protect.

What Families Can Do Differently

The families who manage stepping back well do not treat it as a moment in time. They treat it as a process.

That process starts with honesty. A recognition that stepping back is not only a structural decision, but an emotional one. It takes clarity of roles, written down and respected. It takes a proper outlet for the founder, whether that is a Chair position, a board seat, a family council, or structured check-ins that keep them informed without pulling them back in.

It also takes support. Letting go is hard. Stepping up is just as hard. Coaching, mentoring, or external facilitation can give both sides a safe place to explore frustrations and expectations before they spill over into the day-to-day running of the business.

And sometimes, it takes something very simple, and very difficult: the founder leaving the room. Not because they are not valued, but because their presence makes it impossible for others to lead with confidence.

Beyond Control: Finding New Purpose

What often sits beneath the struggle to step back is a deeper question: if I am not leading the business, what am I doing?

For years, maybe decades, the founder’s answer to “what do you do?” has been obvious. They are the leader of the business. Take that away, and the question is harder to answer. Without something meaningful to turn to, they risk drifting.

The families who thrive across generations are the ones who help founders find a new sense of purpose. That may be a Chair role, philanthropy, community involvement, investing in others, or simply more time with family. The activity itself matters less than the fact it is meaningful.

Something that makes the founder feel their energy and experience are still valuable, just in a different way.

The Courage To Step Back

At its heart, stepping back is not really about power. It is about courage.

The courage to accept you are no longer indispensable.

The courage to trust others to carry the business forward.

The courage to define yourself not by what you built, but by what you choose to do next.

That courage is what separates the families who continue to thrive across generations from those who stall at the very point they should be strongest.

Stepping back is not the end of the story. It is the beginning of a new one. And when families approach it with honesty, clarity, and courage, it is a story that can be every bit as rewarding as the one that came before.

About the Author - David Twiddle is the Founder and Managing Partner of TWYD & Co, a specialist executive search and leadership advisory firm working exclusively with family enterprises. Drawing on his own multi-generational family business background, and over 25 years advising leaders, David helps families appoint, develop, and align the right people at the moments that matter most.