Can a brand have regrets?
We highly recommend reading these. Should we start a book club?
Beth and I recently realized we were exploring the same theme from two different angles. She was reading The Collected Regrets of Clover; I was reading The Brilliant Life of Eudora Honeysett. Both novels settle into the quiet, heavy weight of human regret.
At Root + Rigor, we believe that strategy is a system built on human truth. And that fiction (novels) are often best at bringing those to light. In life, as in fiction, humans are often defined by their regrets, which got us thinking: why would we presume brands are any different?
The Regret of Inaction: As leaders, we are trained to avoid the regrets that come as a result of action. We fear the failed launch, the polarizing campaign, the wrong choice. To mitigate risk, we play it safe.
But we would argue the most dangerous regret for a brand isn't the mistake you made. It is the white space you left open for a competitor to occupy.
The missed pivot: You saw the shift coming, but your current systems were too rigid to move.
The unnamed villain: You were too polite to call out market inefficiencies, letting the status quo continue to define the rules.
The lost audience: You hesitated to be "messy" or innovative, so your audience found a new home with someone who was. Or maybe worse, you tried to be all things to all people and in doing so, lost across the board.
In business, the status quo isn't a neutral position. It is just regret in the making.
Regret as a Signal: Many leaders treat past failures like skeletons to be locked away. We prefer to see them as signals - clear guidance on how to proceed.
When we partner with brands, we look for the ‘embarrassing’ truths. We ask the hard questions: Why did the last initiative stall? Why did a team’s blueprint never actually come to fruition? That lingering sense of regret is rarely a character flaw. It is usually just a sign that your strategy and your execution are out of alignment.
If you’re feeling that friction, use it to your advantage. Take these three steps to turn that regret into an asset:
Examine the Regrets: Identify three things you wish your brand had done in the last 24 months but didn't.
Identify the Friction: Determine if the failure was caused by a lack of consensus, a fragmented system, or the fear of leaving the safety of the status quo.
Apply the Rigor: Use those regrets to help identify and define what and where you need to systematize so that next time you're ready.
We don’t want our clients to end up like the characters in our books - looking back on what “didn’t” get done or “didn’t” happen, and wondering what might have been. We’re here to bridge the gap between ambition and execution. Because we believe that the only thing more expensive than a bold mistake is the regret of sticking to the status quo.