There’s a moment in every journey where we stand at the crossroads, wrestling with the enormity of what lies ahead. We become tangled in the complexities of the “how” – how do we execute this plan, how do we ensure success, how do we avoid failure? But in my experience, this preoccupation with the “how” is often where progress stalls, and dreams remain unfulfilled.
In my professional life, spanning over two decades of strategy, design, and coaching, I’ve seen countless individuals and organizations stymied by this very obstacle. The quest for a perfect plan – a polished, foolproof strategy that anticipates every twist and turn – can lead to an analysis paralysis. It’s a condition where we become so obsessed with getting it right that we end up doing nothing at all.
But here’s the thing: the “how” isn’t always clear at the start, and that’s okay. In fact, it’s more than okay – it’s often the way it should be. What’s far more critical, in my opinion, is the “why.” The intent, the purpose, the driving force behind our ambitions – that’s where our energy, time, and effort should be dedicated. If we are comfortable with the “why,” if we understand and embrace the risks and the purpose, the “how” will eventually reveal itself, often in ways we never anticipated.
Let me share a personal perspective. When I first ventured into the realm of real estate, it wasn’t a straightforward decision. The “how” was murky – how would I transition into this new field? How would I bring value with my background in strategy and design? But I was driven by a powerful “why”: to help others navigate one of the most significant decisions of their lives, to bring my decades of experience to bear on an industry that has a direct impact on people’s futures.
I didn’t have all the answers when I started. I still don’t. But I knew that standing still, waiting for the fog to clear, wasn’t an option. So I chose a “what.” I picked something tangible – an action that would move me a few steps forward – and I ran with it. As I took those first steps, new possibilities and options began to open up. The “how” started to take shape, not because I had all the answers, but because I was willing to start the journey without them.
This approach isn’t about recklessness or abandoning planning altogether. It’s about recognizing that the perfect plan is a myth. The world is too complex, too dynamic for us to anticipate everything. But when we focus on the “why,” when we pick a “what” and take those initial steps, we create momentum. And momentum is powerful. It builds confidence, uncovers opportunities, and provides the clarity we sought in the first place.
I’ve seen this play out not just in my own life, but in the lives of those I mentor and coach. Whether it’s a young entrepreneur launching their first startup, a nonprofit leader scaling a mission-driven organization, or a student navigating the transition from academia to the professional world – the pattern is the same. Those who succeed are the ones who are willing to start, even when the path ahead is unclear.
We need to give ourselves permission to begin imperfectly. To understand that progress, not perfection, is the goal. The “how” will evolve, and it will often look different from what we initially imagined. But we’ll never discover that unless we take the first step.
So if you’re standing at the crossroads, overwhelmed by the enormity of what lies ahead, I encourage you to shift your focus. Dedicate your energy to understanding your “why.” If you’re clear on that, pick a “what” – any “what” – and start moving forward. Trust that the “how” will come into focus as you go. Because once you get started, the journey itself will guide you in ways that no amount of pre-planning ever could.
In life and in business, the fog of uncertainty is inevitable. But it’s only by stepping into it that we can begin to see the path forward. Don’t let the fear of the unknown keep you from starting. Embrace the power of just getting started, and let the journey unfold in its own time.