The Very Best Laid Plans
tl;dr
Plans will change and that’s okay; staying loose lets you learn on the fly and turn messy experiments into fresh business breakthroughs..
When Flip the Script hit a wall, CanWCC opened a waitlist, kept momentum, and showed small, quick moves can still build trust and community.
Every curveball is a mirror; it strips away vanity metrics, reminds you why you started and sharpens both your leadership and your product.
Humans plan; God laughs.
I’ve occasionally answered a coworker’s confused or frustrated “what happened??” with a Harold McMillan quote: “Events, dear boy, events...” (whether, in fact, a boy or not). Sometimes it’s the only answer you can give and retain your sanity, as an entrepreneur.
Everyone starts with a plan - perhaps a business plan, a strategic plan, a project plan or a research plan. Before long you’re on version five. Reasonable assumptions you’d made now sound like they came from left field. Contracts you’d drafted carefully suddenly reflect an entirely different purpose. You quickly learn how costly it is to pivot.
Entrepreneurship can be messy, and should be. Entrepreneurship is about testing theories, building and breaking, learning through experience, and iterating. The messiness is the primordial soup whence creativity is fuelled and businesses are born.
The problem, of course, is the fly in the soup and what we do with it.
FLEXIBILITY IS A MORE VALUABLE SKILL THAN FORESIGHT
You can spend an unreasonable amount of time trying to plan for every contingency. That’s the myth of control. It’s hubris to think you can or need to prepare for every eventuality.
A well-meaning (if blunt) investor once said to me, “Women are great planners when it comes to starting businesses. They always have their paperwork squared away. They just don’t get funding. So build your plan around that.”
I realized it comes down to a few basic steps: do your research, make sure you understand the potential risks and challenges, decide which you can do something about. Your flexibility is a factor of what you learn through research and applying your previous experiences.
And in the end, it’s not remotely glib to say that true leadership shows up in how you face challenges, not in whether you were able to accurately predict and plan for it or not.
SETBACKS REVEAL WHAT TRULY DRIVES YOU, NOT WHAT YOU’RE CHASING
Entrepreneurship is a powerful journey of self-discovery if you want it and let it be.
We build our plans with blueprints and spreadsheets, but life builds us with challenges, detours, and hopefully some grace. So when ‘events, dear boy’ blows everything up, don’t mourn the plan, meet the moment. That’s the uncomfortable place where true growth lives.
When your planning fails, you’re forced to ask: Who am I without this win? It’s a powerful reminder that your worth isn’t defined by outcomes or metrics, but by the values you carry through the fire. Each of those moments is a chance to strengthen your identity based on intrinsic values rather than external validation.
Setbacks don’t just test your resilience, they force you to reconnect with your purpose and get really clear about why you’re here and what you really want to build.
NET GAINS
Just like a katana is forged through repeated heating, folding, and hammering, meeting challenges that derail your plans shapes both you and your business through pressure and persistence. The process may be intense, but it creates something sharper, stronger, and built to adapt.
What feels like a setback can actually crack open a smarter, leaner, or more human-centered version of your product or service. Forced innovation can yield results no one would’ve thought to plan for, but everyone’s grateful for in the end.
And let’s not forget the most joyful reason, the beacon of silver lining in the rough seas of entrepreneurship:, aka Who We Meet Along The Way. Navigating uncertainty often leads to unexpected allies, collaborators, and mentors. These relationships, forged in the fire of challenges, can become the most cherished ‘assets’ of your journey.
NO ONE IS IMMUNE
We’ve experienced it too. For us at the Canadian Women’s Chamber of Commerce (CanWCC), it looked like this: we were so proud at our Beyond the Pitch Event to announce the launch of Flip the Script for general availability.
And then the roadmap got rewritten in real time. We’re still waiting to finalize execution on our Go To Market Plan so we can get this incredible skill training course out to women entrepreneurs who are looking to get funding.
What’s our workaround? We created a signup sheet so founders can sign up for first access once we’ve cleared our final hurdles. That’s what we can control, the best we can do in the present moment. We know you get it.
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