August 28th, 2025
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Why Legacy Brands Fail at Rebrands (And How to Do It Right)

How to refresh a legacy brand without alienating loyal customers—or costing millions in mistakes.

Article

Rebranding isn’t about throwing away the past. It’s about honoring it while making space for what’s next. I’ve been trying to avoid chiming in on the Cracker Barrel fiasco that’s been swarming my LinkedIn feed this week. But here we are. My take isn’t about heckling Cracker Barrel; it’s about what this moment reveals about legacy brands and the tricky business of preserving heritage during a brand refresh.

As a brand designer, I work almost exclusively with companies in moments of transition: new offerings, rapid growth, pressure from competitors. In those moments, the subject of “brand refresh” comes up almost every time. Some companies approach it with curiosity. Others with dread. And given the public backlash we’ve seen against some high-profile rebrands, I can’t blame anyone for feeling hesitant. But here’s the thing: a refresh should be exciting, not terrifying. The key is knowing how to honor your past while building your future.

The Ghosts of Branding Past, Present, and Future

When I guide clients through a refresh, we always start with discovery. It reminds me of Charles Dickens’ A Christmas Carol: you sit down with the ghosts of your brand’s past, present, and future.

  • The past: what built your legacy, what made you recognizable, how you got big in the first place.
  • The present: where you are plateauing, what’s no longer working, the gaps that feel obvious.
  • The future: the trajectory you’re currently on and where you need to be if growth is the goal. Much like Dickens’ ghost of Christmas-yet-to-come, it often shows a bleak path if nothing changes.

This exercise isn’t fluffy. It’s essential. Too many rebrands jump ahead to “what’s next” without pausing to ask: What did we build our house on to begin with? Ignore that, and you risk ripping out the heart of your brand.

The Side Step: Understanding the Community

Once you know where you’ve come from and where you’re going, there’s an important sidestep, almost like a football play. You pause, take in the field, and notice the other variables in play: your audience.

And I don’t just mean your loyalists. I mean the whole community: the ones who wear your logo like a badge of honor and the ones who stuffed your brand in the back of their closet like an old sweater. Even if they don’t actively engage, they know you. They have a perception.

A smart strategy asks: how do we hold onto our die-hard fans while also opening the door to those on the periphery? This is where the art comes in.

Kissing the Line Between Familiar and Fresh

In consumer packaged goods (CPG), this balancing act is make-or-break. I call it “kissing the line between familiar and fresh.

Too much “fresh” and your product risks alienating people. I’ve seen brands swing so far toward “cool and hip” that the product ended up in the wrong category altogether, like hummus that looked more like baby food than something you’d actually crave. Too much “familiar” and you look dated, irrelevant, or easy to ignore.

Food is an especially good example because it’s tied to human instinct: survival, indulgence, comfort. People don’t just buy hummus, cereal, or crackers—they buy trust, memory, and familiarity. So when a brand identity suddenly changes without respecting that history, it feels like someone ripped up the rug under their feet.

That’s why people don’t just dislike a bad rebrand. They revolt.

The Feedback Loop: Too Many Chefs, or Not Enough?

Here’s where things get sticky. Once a rebrand is underway, opinions fly.

I’ve heard people say, “too many chefs in the kitchen ruins the meal.” But in my experience, when the stakes are high, you want a lot of voices. The job of a skilled brand team is to know when to listen, when to read between the lines, and when to double down or let go.

Sometimes that means scrapping the cake at 95% completion and starting over. Painful, yes, but a good baker knows when the toothpick comes out messy (or worse,the rise is off). The cake isn’t ready to be served.

The Real Cost of Getting It Wrong

One thing often overlooked in these conversations: rebrands are expensive.

A single shift in a brand’s core color can trigger millions of dollars in signage replacements across multiple territories. And that’s just signage. Add packaging, uniforms, vehicle fleets, websites, advertising—the bill grows fast.

That’s why you scope a rebrand like building a custom home:

  • Budget: Plan for 3x padding.
  • Timeline: Plan for 2x padding.
  • Expectations: Build in flexibility and refinement.

Yes, it sounds overwhelming. But if you give yourself that breathing room from the start, you end up leaner, smarter, and better positioned than if you try to run at max capacity from day one.

The Takeaway

Rebranding is not just design. It’s anthropology. It’s psychology. It’s economics. It’s listening and translating, while knowing when to defend the soul of the brand.

Legacy brands that succeed at refreshes don’t discard their heritage. They respect it, even when they need to grow past it. For founders and leaders in transition, the lesson is simple:

Don’t run from your past. Use it as fuel. That’s how you rebrand without the pitchforks.

Downloadable Strategy Sheet