The Discomfort of Planning

I’ve been a strategist and a brand planner for many years now. The kind of years that earn you labels like “experienced,” “pro,” or—my personal favourite—“seasoned.”

But here’s a confession: working on any client strategy still makes me uncomfortable.

Last year around the same time, I was working on a campaign proposition for a global logistics company. The brief was clear: From the current perception of a ‘shipping giant’ reposition them as a tech-driven solutions partner. Simple, right?

Except I had no clue about freight forwarding, cross-docking, first-mile, middle-mile, or last-mile optimisation. My Google search history looked like I was preparing for a customs clearance exam. I had two weeks to figure out what mattered to CXOs, make sense of operational inefficiencies, and somehow string together a story that both the client’s C-suite and our creative team would find compelling.

There’s an unease that never fully goes away - trying to become a customer I’m not, looking at their world through borrowed eyes, search for something that is not obvious in datasets and reports. It amplifies when I step into a new category I’ve never worked in, and having to sound convincing in front of people who’ve live and breathe it every day.

And even before that to convince the creative team and say, “Here’s the insight, here’s the narrative, and here’s why this matters.”

This discomfort is not an impostor syndrome or false humility. It’s just the honest messiness of doing a job that requires you to be in a state of perpetual not-knowing—and then making something clear and confident out of it.

In the initial years, I always thought that the fault was within me. Maybe, I’m slow to grasp things. Maybe, I am not keeping my ears on the ground perpetually. Maybe, I’m not sharp enough. It was much, much later, a wise mentor told me that discomfort can be a secret weapon—if you know how to work with it. 

In Hidden Potential, Adam Grant writes that the most successful people aren’t always the most gifted—they’re the ones who are the most coachable. The ones who can navigate discomfort, stay curious, and keep iterating. Strategy isn’t about certainty. It’s about staying in that uneasy middle ground long enough to uncover something valuable.

In a world obsessed with strengths, comfort zones, and “zone of genius,” we forget that growth mostly comes from the exact opposite—moments where we feel out of depth, unqualified, and uncertain.

Here’s a 3-step framework that’s worked for me:

1. Lean into the “I don’t know” phase

In strategy, you’re often expected to be the “smartest person in the room.” But the truth is, you’re usually the most curious person in the room. You’re the one paid to not know, but to ask better questions.

The key is to normalise that blank slate. Enter industries like a student, not a consultant. Let go of the pressure to sound smart; instead, aim to learn fast. Say “I don’t know” early, so that “here’s what I found” lands stronger.

2. Get uncomfortably close to the customer

Strategy is empathy in action. And empathy doesn’t happen from behind a desk. Whether it’s hanging out in warehouses, joining sales calls, or reading Reddit threads for hours, browsing through various social media profiles and posts, immersing yourself in the customer's reality is non-negotiable. Discomfort here isn't a bug—it's a feature. If you're not a little out of place, you're not close enough to the truth.

3. Treat the brief as a working hypothesis, not a final answer

Your initial versions of the strategy are just placeholders. Let it be messy. One of the hidden skills of a strategist is being a translator—converting ambiguity into clarity for others. You must explain the messy 'why' behind a clean 'what.'

Use discomfort as empathy. If you struggled to make sense of the customer, the market, the brief—chances are the creative team will too. Instead of giving a prescription, bring them into the journey. Share the questions you asked, the blind spots you hit, and how you arrived here. The best briefs are not answers—they're provocations with a purpose.

If you're in the business of strategy, brand, or creativity, discomfort is your lifelong roommate. The trick is to make it your collaborator.

Instead of managing discomfort, learn from it. Instead of masking it, mine it. Because discomfort isn’t the thing holding you back. It’s the thing pushing you forward.

A great strategy emerges—from the friction between certainty and contradiction.