The Pioneer Process

Navigating the Wayward Path to Progress.

Exploration drives humanity forward. It’s the discipline of pursing the unknown and learning more about the loosely understood. Much of our human nature draws us away from this challenge because the unknown is dangerous, unpredictable, and outside of our control. Anything that pulls us away from the tribe could lead to harm or uncertain death. For the bold souls who reject these natural propensities and venture into the darkness, we bestow upon them the title Pioneer.

Drawing insights from Pioneers throughout history, we can see patterns emerge. More than the land they find or mysteries they uncover, they are defined by a tenacity and hunger for progress and adventure. Their journeys also follow a similar cadence. A process of sorts, that carries them through the highs and lows of discovery.

The Pioneer Process

The Pioneer Process highlights key insights to navigate the wayward path to progress. It provides no answers, rather a framework to illuminate the journey ahead. The steps are simple, but rarely easy.

  • Set a Target
  • Plan the Approach
  • Execute the Plan
  • Reflect and Recalibrate
  • Repeat

Few narratives that exemplify the process are more widely known than that of Christopher Columbus. As we unpack the Pioneer Process, we’ll parallel modern examples with those from the discovery of the western world.

Set a Target

Where are you headed?

Defining what success looks like is the cornerstone of progress. The destination will change and evolve, this is certain, but naming your target gives you something to anchor to and plan towards. In rallying support, a clear vision also keeps others aligned and working together.

As you choose a destination, evaluate the purpose. Why are you doing this? What do you hope to accomplish? Without a clear ‘why’, you’re unlikely to gather the support of energy need to withstand the pitfalls and challenges ahead. Or if you find the support, you’ll likely arrive to discover no one cares about the progress.

For Columbus, the target was a westward path to the East Indies (South and South East Asia). In pursuit of economic gain and imperialistic growth, discovering a new trade route would mean untold fortunes.

Caution: The ‘why’ is much more important than the ‘where’. The purpose will provide stability when things become difficult or go awry.

“People don’t buy what you do, they buy why you do it.” — Simon Sinek

Plan the Approach

How will you get there?

It’s not just about where you’re headed but how you plan on getting there. The key elements to any pursuit that should be considered and optimized.

  • Timeline. How long do have or need?
  • Resources. What money, tools, and supplies are available or required?
  • People. Who will be able to help?

In planning his journey westward, Columbus sought the funding and support of a number of government. After being rejected by the kings of Portugal, France, and England he eventually, he enlisted the aid of Spanish crown, which provided the resources needed to make the trip. From there began the arduous task of finding a crew, ships, and supplies to survive for months at sea.

Caution: When overemphasized, planning can become a tool for procrastination. Resist the urgent to plan for every contingency or over engineer a solution. There is expertise that can only be gained by taking action. If you wait too long, many of the original conditions you defined will begin to change.

“If I were given an hour in which to do a problem upon which my life depended, I would spend 55 defining the problem and 5 minutes solving it.” — Einstein

Execute the Plan

Take action.

With a clear target and a solid plan, it’s time to take action. Things will go wrong. Parts or all of the plan may be rendered useless. What matters is experience and keep in mind, not everything is going to work as expected. It will be messy and the plan will need to flex. It’s during execution where both failure and breakthrough occur. Learnings and survival are the primary goals at this point.

In 1492, nearly six years after arriving in Spain, Christopher Columbus began the journey west with his crew and their three ships. After years of preparation, it was now time to cross the ocean and plot their long desired trade route.

Caution: Much of how what we’re taught and what’s baked into our mind reinforces the notion that failure is bad. That’s wrong. Coupled with thoughtfulness, failure is required for meaningful growth.

“If I Fail More Than You, I Win!” — Seth Godin

Reflect and Recalibrate

What did you learn?

Without reflection, growth is stifled and process is limited. Assessing the journey’s progress provides more perspective that can lead to compelling insights. Without it, you run the risk of repeating mistakes or overlooking key patterns that have emerged.

A few questions can help drive the reflection process.

  • Which predictions were correct? Why?
  • Which predictions were incorrect? Why?
  • Which actions worked well? Why?
  • Which actions didn’t work? Why?
  • What needs to change?

With Columbus, the crew landed on October 12, 1492. Nearly 2 months after departing from Spain, they were confident their mission was a success. Over time however, they realized they hadn’t made it to the East Indies at all. Though the scope of their original charter was unfulfilled, this first journey yielded new opportunities for future trips. They could make another attempt at finding India or colonize this New World.

Caution: This is easiest part to skip or cut short but it provides some of the most helpful feedback for future improvement. Much like you wouldn’t ask a question without listening to the answer, reflection is all about taking inventory of what should continue and what needs to change. Choosing to ignore this information leads to repeating the same failures and prolonged discomfort.

“Education begins the gentleman, but reading, good company and reflection must finish him.” — John Locke


Where are you headed next?

Set a New Target
Plan the Approach
Execute the Plan
Assess Progress

Once you’ve reflected on the journey thus far, it’s time to set a new destination. Our teams work through this process every 2 week sprints. Before taking action, we determine where we are headed and plan the approach. Following each sprint, we reflect on the progress, course correct, and set the next sprints target. Time boxing in terms of weeks prevents anything from getting too far off course and forces a pause to readjust.

For Columbus, the remainder of his career as a Maritime Explorer was spent in pursuit of his longer desired route west. Meanwhile, the rest of Europe was ramping up colonization efforts to inhabit the new world. Setting the next target allows room for the team to regroup, adjust, or part ways if needed. Failing to establish a westward path to the East Indies didn’t mean the quest was over, it just meant some realigning was in order.

Caution: Some may define changing focus as quit. Regardless of how you define it, sometimes walking away is a wise decision. Rather than throwing good money after bad or allowing ego to cloud judgement, acknowledging ‘defeat’ can be the fastest path to the next great adventure.

“We are what we repeatedly do. Excellence, then, is not an act, but a habit.” — Aristotle


“A place for everything and everything in its place” — Benjamin Franklin

You’ll notice that only 20% of the process involves executing. While it’s hard for most to accept, planning and evaluating is far more important. If you have a clear picture of where you’re heading and how to get there, execution will be much simpler.

The Pioneer Process provides no guarantees. The nature of entrepreneurship and exploration can’t be separated from risk any more than a ship can sail without water. However, a deeper understanding of the process can help weather the storms.