Learning to Ride Without Training Wheels
Thriving in Ambiguity
I stood there, paralyzed by the question I couldn’t answer: What next? My career, once structured by clear goals and opportunities, suddenly felt like an open ocean with no map. I was terrified.
Sounds familiar?
Ambiguity feels like freefalling. It’s the absence of certainty, the lack of guardrails to steady you. Early in our lives and careers, we’re given those guardrails—processes, mentors, and structured deliverables that act like bicycle training wheels. They help us balance, find our footing, and build confidence. But eventually, those wheels have to come off. The wobbles, the scraped knees, the spills—they’re all part of learning to navigate the chaos.
This essay isn’t about romanticizing uncertainty. It’s about learning how to work with it, to lean into it, and to discover the growth and freedom it offers when we stop clinging to the need for perfect answers.
The Allure of Certainty
Certainty feels like a warm blanket. It’s reassuring to have numbers, clear metrics, and structured plans to cling to. But what happens when certainty becomes a crutch? When we’re so focused on getting everything “just right” that we miss opportunities for growth?
Let’s look at two individuals, A and B, who tackle ambiguity in entirely different ways:
A waits for data: He wants all the numbers, reports, and perfect conditions before taking any action. Months pass, but A’s plans remain just that—plans.
B starts small: She dives in, running tiny experiments. She interviews a few people, creates a WhatsApp group, and starts building conviction through action. Her work isn’t polished, but it’s real.
Who wins?
B, of course. While A is stuck in analysis paralysis, B has gathered insights, refined her approach, and is leagues ahead in solving the problem. The lesson here is simple: you can’t plan your way out of ambiguity. You have to start somewhere, even if that somewhere is messy, incomplete, and filled with unknowns.
Expanding on ‘Permission to Act’
One of the biggest barriers to navigating ambiguity is the mental block of needing permission to act. Often, we wait for external validation—a job title, formal resources, or someone else’s approval—to start working on an idea. This hesitation doesn’t just slow us down; it keeps us stuck. The reality is, that permission is rarely given. It’s taken.
Consider the story of Sara Blakely, the founder of Spanx. Before becoming a billionaire, she was selling fax machines door-to-door. She didn’t have a background in fashion, formal training in product development, or the resources of a large corporation. But she had an idea: footless pantyhose that smoothed under clothing. Instead of waiting for permission from industry insiders or investors, she acted.
Blakely cut the feet off her own pantyhose, tested prototypes herself, and cold-called manufacturers until one agreed to work with her. She created a product sample, started selling it, and built a brand from scratch. Spanx became a global phenomenon, not because she had permission to enter the industry, but because she gave herself the permission to try, fail, and learn.
Waiting for permission is a safety mechanism—a way to avoid failure by deferring responsibility. But as Blakely’s story shows, stepping into action, however imperfect, is the only way to create opportunities that don’t yet exist.
Why Ambiguity Feels So Hard
Ambiguity triggers fear because it represents the unknown. Psychologists call this the “ambiguity effect,” where we avoid options with unclear outcomes, even when they could be beneficial. The brain craves certainty because it reduces cognitive load—decisions feel easier when the paths are clear.
But life and work rarely offer clarity. Negotiations become abstract. Success becomes diffusive. We must learn to define value on our own terms. And that requires rewiring our relationship with ambiguity.
Building Comfort with Ambiguity: Lessons from Consulting
The Art of Guestimation
Guestimation is about building a framework for action when perfect data isn’t available—and it’s a skill you can sharpen:
Practice Real Scenarios: Estimate simple things, like the number of coffee shops in your city. Break it into components: population size, coffee drinkers, and average shop capacity. The more you practice, the sharper your intuition.
Use Analogies: Compare your problem to something you already understand. Estimating fitness app downloads? Think about how social apps grew in similar demographics.
Validate Your Assumptions: After making a guess, check it against partial data or benchmarks. Did you overestimate? Underestimate? Refine your mental model with every exercise.
Debrief and Reflect: Reflect on what worked and what didn’t. Guestimation isn’t about perfection—it’s about improvement through iteration.
MECE Frameworks (Mutually Exclusive, Collectively Exhaustive)
Structure is key to tackling ambiguity. The MECE framework can guide you:
Define the Scope: Clearly state the problem. For example, “How can we improve customer satisfaction?”
Break It Down: Divide it into categories that don’t overlap but together cover the whole issue, like:
a) Product experience
b) Customer service
c) Post-purchase follow-upsTest for Completeness: Ensure no gaps or overlaps in your breakdown.
Address Each Component: Solve each area methodically.
Iterate as Needed: MECE evolves as you gain insights. It’s a tool for clarity, not rigidity.
SWOT Without All the Data
A full SWOT analysis is ideal, but even incomplete information can guide you:
Strengths: Identify what you’re already good at.
Weaknesses: Acknowledge pain points, even intuitively.
Opportunities and Threats: Trust trends and emerging patterns.
Trusting Your Gut
Intuition isn’t magic—it’s experience distilled into subconscious signals.
Learn from Past Decisions: Reflect on when your gut was right or wrong and why.
Seek Feedback: Validate your instincts through trusted mentors or peers.
Act Despite Fear: Confidence in intuition grows through use. Take small steps and build your trust in it.
This Isn’t Just Me Saying Things (As Usual)
Here’s a personal example. When I came back from China during COVID, I didn’t know what I wanted to do. I had an idea that I wanted to work in consumer tech, but I couldn’t see where I fit within the system. Instead of waiting for clarity to strike, I decided to act. I started talking to people—specifically small sellers on Instagram. I was curious about why they didn’t use platforms like Shopify to sell their products.
Their answers were eye-opening: technical barriers, costs, and a lack of understanding of the tools available to them. I took these learnings, mapped out their pain points, and built a very hacky (and in hindsight, woefully inadequate) market map. Then, I tweeted it out to Swiggy, pitching the idea. To my surprise, it worked. That tweet became the foundation for Minis on Swiggy, the first product I helped launch.
This experience taught me a critical lesson: you don’t need all the answers to start. What matters is being curious, taking small steps, and being willing to fail. Ambiguity isn’t a roadblock—it’s an invitation to explore.
Final Thoughts: Leaning Into Ambiguity
When the training wheels come off, it’s not going to be pretty. You’ll stumble, fall, and question why you ever thought you could navigate the mess of ambiguity. But every scraped knee adds to your experience. The lessons you gain from these moments become the guardrails you build for yourself.
Next time you face ambiguity, don’t wait for perfect data or permission to act. Start small. Experiment. Fail fast and learn faster. The guardrails will disappear eventually—but that’s when you truly learn to ride.