We’ve all heard the adage: “Failing to plan is planning to fail.” It’s sound advice that holds true in business and life. But I’ve come to believe there’s a crucial precursor often overlooked: a plan is only as productive as your destination is clear. Planning is critical, yes, but only if you first know, with reasonable clarity, where you’re actually trying to go.
The Tale of Two Travelers: Clarity vs. Ambiguity
Consider two individuals planning a trip. The first has a clear goal: visit New York City, see the Statue of Liberty, explore Central Park, catch a Broadway show. The second traveler is equally determined to go somewhere for a four-day getaway but hasn’t settled on a destination.
If both set to planning, their outcomes will diverge dramatically. The first traveler will meticulously plan their itinerary: book show tickets, arrange ferry rides, secure suitable accommodation, and map out transportation. Their trip is likely to be smooth, enjoyable, and fulfill their objectives, with an ability to handle minor disruptions in stride.
The second traveler, despite diligent planning; packing for all eventualities, mapping a general route, gassing up the car; drives off… but to where? Even if they serendipitously end up in New York City, they’ll be ill-prepared. The best shows might be sold out, attractions fully booked, and desirable hotels unavailable. Their well-planned journey lacks a well-defined purpose.

Applying This to Your SMB: Vision First, Then Tactical Planning
This analogy directly applies to business. While detailed five-year strategic plans can be challenging to etch in stone in today’s rapidly evolving environments, having clarity on your 6, 12, and 18-month objectives is essential. Beyond that, directional guidance for your 24, 36, and even 48-month aspirations provides the “North Star” for your shorter-term plans.
Even though these longer-term targets might shift as your journey unfolds, simply trusting that meticulous short-term planning will magically lead to your desired future is a gamble. As your fractional CIO, I often work with SMB leaders to first define that clear technological vision and its alignment with business goals, before diving into detailed IT project plans. Without that overarching “where,” even the best-laid IT plans can lead you astray.
The Peril of Directionless Motion
In almost every industry, the pace of change is accelerating. Businesses are either constantly striving to define their industry or risk being left behind by more agile or visionary competitors. A plan without a clear destination isn’t much of a plan at all. It’s motion without direction. As another old saying wisely cautions, “If you don’t know where you’re going, any road will take you there.” The problem? You just might not like where “there” is when you arrive.
A More Powerful Approach: Vision + Plan = Success
Combining these timeless pieces of wisdom offers a more powerful formula for success:
A clear destination, coupled with a well-thought-out plan, is key to achieving your desired outcomes. Without both, you might find yourself on an active, perhaps even initially enjoyable, journey that ultimately misses the mark.
What’s Next
Before diving deep into your next planning cycle for your SMB, whether it’s for business strategy, technology adoption, or market expansion. take a crucial step back. Ask yourself and your team: “Where are we really going?” Defining that destination with clarity is the essential first step to ensuring your plans are not just busy work, but purposeful steps towards helping your business “Succeed Sooner.”
Is your SMB’s strategic planning grounded in a clear, shared vision of its destination? If you’re looking for a partner to help you define that vision, align your technology roadmap, and create actionable plans to get you there, let’s connect with Succeed Sooner Consulting.


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