Sniper Alley
One of the more striking things that surfaces in conversations with leaders approaching the end of long operating chapters is how many of their peers are getting sick.
Not in abstract terms. Personally. The colleague who had the heart event at 62. The friend diagnosed with something the doctors said had been developing for years. The person who seemed fine – more than fine, thriving by every external measure – until they stopped. And their body finally had the space to tell them what it had been holding.
There is a phrase that captures this pattern: sniper alley. The idea that high-achieving leaders mask physical deterioration through sheer force of intensity. The adrenaline of the role, the momentum of the work, the identity built around performance – these things function as analgesics. They suppress the signal. And for years, sometimes decades, the body sends messages that the mind is too occupied to receive.
Then you slow down. And the signal comes through.
This is not a coincidence. The health event that arrives in the first year of transition, or just before the decision to leave is finally made, tends to carry a message that was overdue. The body has a way of enforcing the transition that the mind kept postponing.
The intensity that made you effective over 30 years also had a cost. Some of that cost was visible – the missed dinners, the travel, the years that went by too fast. Some of it has been accumulating quietly in ways that will not show up until the pace changes and the stillness arrives.
Taking your health seriously in this season is not a concession to aging. It is a recognition that the second half of life – which for most leaders in this position still contains 20 or 30 years of active runway – deserves the same investment you made in the first half.
Pay attention to what your body has been trying to tell you. It has been trying to tell you for a while.
How You Leave Shapes What You Leave Behind
The exit is a leadership act. Most people treat it like a finish line.
How you transition out of a company – who you choose to carry it forward, how you hand it off, how you manage the space between the announcement and the departure – has consequences that extend well beyond the transaction. For the team you are leaving. For the successor you are handing to. For the culture you spent years building.
The most common failure mode is not malice. It is ambiguity. Leaders who leave gradually – whose involvement dims over time without a clear line being drawn – tend to create organizations stuck between two centers of gravity. The new leader cannot fully lead because the old one is still present. The team does not know who to orient toward. The departing CEO, often with the best intentions, continues to be available in ways that make clarity impossible.
The counterintuitive truth is that a clean exit is a gift. Not just to the organization, but to the successor. It creates the conditions in which they can actually lead – build their own team, establish their own culture, make their own decisions – rather than spending their first year managing the shadow of the person who came before.
Choosing the right successor is part of this. Not the person most like you, or the most loyal, but the person who has what the business needs for its next chapter. That requires a level of self-awareness that not everyone brings to the process. It means being honest about what the business needs that you could not or would not give it, and finding someone who can.
The leaders who are remembered well by the companies they built are not always the ones who performed best at the peak. They are often the ones who left with grace – who made it as easy as possible for what they built to continue without them.
That is its own kind of legacy. And it deserves the same intentionality you brought to everything else.
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