The Things We Keep

I’ve always been curious about something. Is it harder to create the thing, or to know when it’s time to walk away?

We’re surrounded by these decisions every day. One could say we know them all too well.

Taylor Swift re-releases her own music with additional songs and extended versions. Clearly there was more to say, and somewhere along the way those words hit the editing room floor.

And then there’s the other side of it.

Andy Bernard spends seasons becoming a better version of himself, only for that growth to slowly unravel as The Office kept going. A character on an upward trajectory was pushed back toward the very behavior that had made people resent him in the first place.

It happens to television characters all the time. A show runs a little too long, the original arc has run its course, and the writers need somewhere to take the character. Instead of letting him keep evolving, they pull him back toward an earlier version because it’s familiar, easy, or funny.

Success can create its own trap. The things that made something work become the things we’re most reluctant to let go of. Sometimes the original thing was good. Sometimes it was great. Sometimes we just keep going long after the thing that made it great has passed.

I’ve started noticing the same pattern in my own work.

You’re asked to optimize a digital experience, but you’re working inside a system you inherited. The navigation, the workflows, the business rules. Years of decisions that may have made perfect sense at the time.

That last part matters. It’s what creates many of the legacy products so many of us are now trying to enhance. Most of the things we call “legacy” exist because someone made a reasonable decision with the information, technology, and business they had in front of them. The problem is that businesses change, customers change, and technology changes. The original reason for a decision disappears long before the decision itself does.

We spend a lot of time asking how to make an existing experience better. Improve the search, simplify the navigation, remove a few clicks, make the page faster. All worthwhile. But at some point you have to ask a more uncomfortable question: are we actually improving the experience, or are we just getting better at maintaining the past?

That question is harder than it sounds, especially in B2B. The systems are complicated for real reasons. Customers, sales teams, operations, finance, supply chain, product data, ERP systems, integrations, and decades of business rules all sit underneath what looks like a simple button on a screen.

Every piece of complexity has a story behind it. Someone needed it, someone requested it, someone built it, someone depended on it. Over time, though, “because we need it” can quietly become “because we’ve always had it.”

That’s where product work gets interesting. The job is to understand why something exists well enough to decide whether it still should.

That doesn’t mean everything needs to be thrown away. Quite the opposite. Some things deserve to be preserved, some need to be rebuilt, and some need to be allowed to end.

We celebrate creation. New products, new features, new platforms, new ideas. There’s a real excitement in putting something into the world that didn’t exist before, and walking away from something rarely feels like progress. But there’s a difference between preserving something valuable and preserving something familiar.

The customer doesn’t care how long a workflow has existed or what system sits behind it. They care about the job they have to do.

Which brings me back to where I started. Is it harder to create the thing, or to know when it’s time to walk away?

Creation has everything on its side. Launches, announcements, something new in the world. Nobody throws a party for the workflow you retired.

But think about the writers who pulled Andy Bernard backward. They weren’t trying to ruin him (or maybe they were, I’ve heard the rumors). They were going back to a well that once worked. That’s the trap: loyalty to a version of the thing that no longer exists.

“No man ever steps in the same river twice. It’s not the same river, and he’s not the same man.”

Heraclitus

The product is the river. The customer is the man.

The work is admitting that both have already changed, and building for what’s actually in front of us.

Creating is the fun part. Walking away is the work.