I’m kicking off with a little shameless self-promotion.

If that’s not your thing, skip it, unsubscribe, whatever you like.

But there’s a reason I’m bringing it up, so hear me out.

I advise executives at retailers, brands and at various retail-adjacent companies.

When I started this work, I assumed most conversations would be about merchandising strategy, process innovation, growing wholesale accounts, product creation and so on.

Which is absolutely the case.

However, there is a topic that routinely comes up which, at first, I did not anticipate talking about so much….

Legacy Creation.

It’s easy to talk about roles in retail (Chief Merchant, CEO, etc.) how they’ve evolved and what it takes to succeed today.

And of course, talking about what constitutes success in the role is a necessary conversation. Also, roles will always continue to evolve and a pressing topic today is the impact of AI.

Candidly, this conversation is a bit overplayed. Because what we don’t discuss enough is what success looks like after the role.

(For completeness, there’s also a “before the role” discussion but that’s for another day.)

Many leaders have a clear aim for what they want to be known for in their roles: strong leadership, profit growth, developing talent and so on.

But as they do that work, a quiet anxiety creeps in about what happens when the role ends, whether it ends on their own terms or not. The feeling starts as a whisper that you can ignore, until one day it hits like a bolt of lightning.

Plenty want to serve on boards and keep contributing. If that’s not lined up, even high performers can feel unmoored when suddenly there is so much free time on their hands.

Then, cue the guilt: “Am I doing enough? Am I working hard anymore?” “Maybe I should have networked more aggressively while I was working!”

All of which is completely valid. I remember when I was working as merchant, I focused hard on doing the best job possible. Meanwhile, I did not spend the energy on the bigger picture and where my retail career would take me. In fact, a chance meeting helped steer my path towards consulting at Accenture.

You could say that our jobs interfere with our careers.

Complicating this, people at the top rarely have true peer support inside the organization to talk about these things. I mean, think about it, the headlines are all about layoffs and “become an AI power user or else.” It’s hard to find a safe internal space to explore what life looks like after your time with the company is over. No wonder I hear about it so often.

I’m raising this because the conversation needs more oxygen. It’s also a nudge for you to invest some time now in what comes next, so your legacy isn’t an afterthought but a deliberate choice.

After all, we do our best work when driven by a bigger mission.