We’ve all been there—riding high on the momentum of something that used to work. Maybe it was a marketing strategy that got your business off the ground or a leadership style that energized your early team. But here’s the truth: the very strategy that led you to success might be the one that will eventually drag you down.
Think of it like parenting. What works to calm and guide a toddler isn’t going to cut it when you’re raising a teenager. The context changes. So must the approach.
This is true not just in business, but in every area of life. I’ve seen it firsthand as a soccer coach for seven years. During practice, I might raise my voice to grab attention or push players to their limits. But during a game? That same intensity can rattle them or shut them down. What motivates in one scenario can demoralize in another.
The challenge is that success breeds confidence—and sometimes, that confidence makes us cling too tightly to the playbook that got us here. It’s easy to assume that if something worked before, it will work again. But in a dynamic business environment, that kind of rigidity can become your downfall.
Consider the tech world. BlackBerry once dominated the smartphone market. Their keyboard-first design and enterprise security features were once cutting-edge. But when Apple introduced the iPhone in 2007 with a touch screen and app ecosystem, BlackBerry didn’t adapt quickly enough. What was once a strength—security and physical keyboards—became a liability as the market shifted. Their previous success blinded them to what was coming next. (More on that here: Harvard Business Review on Why Big Companies Cam’t Innovate
The same can happen to your business. Maybe you once turned down digital marketing because word-of-mouth was enough. Or perhaps you rejected hiring a virtual assistant, believing only you could handle the details. But now, are those choices still serving you?
Sometimes, we need to dust off the strategies we once dismissed. What didn’t fit your startup phase might be perfect for your scale-up phase.
Here’s a quick gut check:
Is your current system struggling to keep up with your growth?
Are you solving new problems with old tools?
Do you find yourself saying, “But this always worked before”?
If so, it may be time to rethink.
One helpful approach is to schedule quarterly “strategy audits.” Pull out a whiteboard and write down everything you assume is still working. Then challenge each point: Is it helping? Is it hurting? Is it still aligned with your goals? If you can, bring in an outside perspective—mentors, advisors, or even your team. They might see things you’ve become blind to.
Here is a ChatGPT prompt that I have found helpful:
Using the first principles method, can you deconstruct my business by questioning all underlying assumptions and then re-evaluate how it operates? Please also suggest innovative approaches to rethink its functionality and strategy.
Adaptability is the name of the game in long-term business success. The best leaders aren’t just great at making plans—they’re great at changing them.
So, before you double down on what worked last year, pause.
