Letting Go of "The Plan" to Maintain Creative Tension with "The Now"

There’s a seductive security in planning. It provides structure, focus, and a sense of control. As someone who often dwells at the intersection of innovation and strategic execution, I know the allure of a well-drawn roadmap. Plans, after all, are meant to crystallize ambition and give life to vision. But here’s the thing: life, innovation, and even personal growth rarely adhere to our plans. What if, instead of chaining ourselves to them, we allow space for the now to breathe, for the unexpected to happen, and for new opportunities to emerge?

In my previous posts, I discussed two core principles that underpin much of my thinking—“Consistency Drives Invention” and “Read broadly to cultivate insight” In both of these, the rhythm of intentional practice and the cultivation of curiosity stand tall as driving forces for creativity and progress. Today, I want to bridge these concepts with a more nuanced challenge: letting go of "the plan" without sacrificing the long-term vision or the energy to get there.

The Myth of Total Control

A few weeks ago, I was having a coffee + doggo meeting (my favorite kind, holler if you’d like to do one) with my dear friend and colleague Amish Patel, catching him up on life and work. I said in passing that my career was going according to my five-year plan, he stopped me and said, “But that doesn’t need to be the plan. It could be A, B, or C in a year, and you’d happily choose a totally different route.” His statement gave me pause, but I realized he was totally right. Despite my proclivity for five-year plans and weeks planned to 15-minute increments, my career has thrived on serendipity and meanderings.

We live in a world that often equates planning with progress, a world that encourages us to map every detail of our future. Yet, if there’s anything I’ve learned from building ventures, mentoring founders, and fostering creative ecosystems, it's that rigidity is often the enemy of progress. The moment we cling too tightly to our original plans, we risk suffocating the potential that exists in the present.

When I say "let go of the plan," I’m not suggesting we abandon foresight or discipline. Rather, it’s about recognizing that the most transformative moments happen when we embrace the unexpected. Whether you're building a startup, guiding a product team, or even recalibrating your own life goals, leaving room for the present to shift your course is essential.

Creative Tension: Holding Vision and Present Reality

This brings us to the concept of "creative tension." It’s a delicate balance between staying true to your vision (the plan) and remaining flexible to adapt to what’s happening in the moment (the now). It’s not about impulsivity or reckless deviation; it’s about maintaining a dynamic tension between the two.

Creative tension is like a bow and arrow: The string is taut because of the tension between the archer’s aim and the bow’s resistance. This tension fuels forward momentum. If you pull too tightly, the string breaks. Too loose, and you never hit your target.

The goal isn’t to lose sight of the destination, but to accept that the path is often winding, and sometimes, the detours lead to the most creative breakthroughs. Often, the rigidity of a plan can become a crutch, whereas letting go of the plan forces you to be hyper-attuned to the signals from your environment—the emerging trends, the sudden epiphanies, or the changing needs of your team or customers. Recall, you can’t force an insight.

"Consistency Drives Invention" Meets the Now

In my post on consistency driving invention, I emphasized that showing up regularly, practicing discipline, and committing to a process are critical for creativity. That still holds true. But what consistency does is provide a framework, not a straightjacket. It’s the muscle memory that allows you to act fluidly when the unexpected arrives.

Think of an athlete who has trained rigorously for years. It’s their consistent practice that allows them to adapt to game-day surprises, to pivot and seize the moment. In a way, consistency equips you to let go of the plan because you trust in the foundation you’ve built. You’re more nimble, not less.

Curiosity is Always Present

When I talked about the Bedside Book Shift—the idea of having a rotating selection of fiction books next to your bed to stimulate curiosity—I was highlighting a method for continuously engaging with new ideas. The plan is fluid, dictated by what grabs your attention in the moment. This is a metaphor for how we should approach our career and creativity: not as a set of rigid goals but as a journey guided by our evolving interests and challenges.

In practice, this means allowing the "now" to influence your direction. What are you reading, absorbing, or experiencing that feels like it’s pulling you toward something unexpected? Can you let go of your preconceived notions of how things should unfold and trust that this shift might unlock new avenues for growth or innovation?

Letting Go is Not Giving Up

For those of us who live by strategy and foresight, letting go of the plan can feel counterintuitive—almost like a surrender. But it’s important to understand that letting go is not the same as giving up. In fact, it often requires greater courage and awareness. It’s about acknowledging that sometimes the plan you created was based on old information or assumptions that no longer apply.

For me, letting go has been essential in both my career and in my personal life. Letting go of being a doctor when I quit pre-med in undergrad to focus on philosophy and entrepreneurship. Letting go of being an attorney when I failed the bar and instead threw all my effort into Fizzy Media. Letting go… It’s what allows for evolution, for serendipity, and for authentic growth. The magic often lies in the margins, where the plan ends and the unknown begins.

So, as you navigate your own creative endeavors—whether it's starting a business, writing that book, or simply managing a household—consider how tightly you're holding onto "the plan." Is it helping or hindering your progress? Can you create space for "the now" to speak to you, without losing sight of your overarching vision?

It’s in this tension between consistency and adaptability that true insight happens.