It’s more fun to be a pirate than join the navy

Bill Cushard
5 min readJan 13, 2023

One experience that inspired me to explore the idea of being a rebel intrapreneur is a conversation I had on Helping Sells Radio with Tendayi Viki, author of Pirates in the Navy: How Innovators Lead Transformation and Associate Partner at Strategyzer.

We talked about his book and about how someone can drive innovation inside an organization. This is not an easy thing to do considering that organizations are designed to optimize for the existing way of doing things and NOT transforming itself.

Not easy at all.

On the other hand, as Viki starts his book with a quote from Steve Jobs:

“It’s more fun to be a pirate than join the navy.”

The implication here is that being “in” the navy compels one to follow the rules, the culture, the way of doing things. To be restricted. Constrained. Limited. Hand-cuffed. Boring.

“Geez, Bill. It sounds dreadful, when you put it that way.”

Agreed. But what if we can be a pirate “in” the navy?

Viki defines a pirate in the navy as an intrapreneur, which is an employee “who works on entrepreneurial ideas inside a company.” The charter of the pirate in the navy is to “innovate for the future, inside a machine designed to run the current business. It is the management of the current business that tends to get in the way of innovation. The bureaucracy and incentives of the organization are all geared towards improving and exploiting the currently successful products and business models.”

How’s that better than just being in the navy? A pirate in the navy is drawn towards to the pull of innovative for the future, while accepting the challenge of working inside the machine designed to run the current business.”

So, as in all things in life. It’s a choice.

It is the innovator’s choice, as Viki calls it. There are three choices to make in order to become a pirate in the navy.

Choice 1: Do you really want to work inside a company?

The first choice to make is whether you want to be an entrepreneur or work for an entrepreneur. If you want to work inside a company and be a pirate inside that company, you must accept that you are “in the navy.” The navy (the company you are choosing to work for) is a traditional institution. In your pursuit of innovation in the company, you will need to continuously navigate the norms of the company. The company will decide on its own how and whether and how much it is willing to “tolerate your pirate behaviors without having the change itself.”

If we have an interest in innovating and creating new things, but cannot imagine working inside a company to do it, we must chose to be an entrepreneur. If we have an interest in innovating and creating new things, and are drawn to the mission of a particular company, we must make the choice to work there.

The choice provides clarity.

So that’s the first choice you need to make: whether you really want to be working inside a company.

Choice #2: Choosing growth versus transformation

Once you have decided to work inside a company, the next choice is whether you want to be a high performing employee or a pirate in the navy. Viki frames it as a choice between pursuing growth or pursuing transformation.

A high performing employee pursues growth. Growth of existing products. Creation of new products in pursuit of the existing company way. A high performing employees wants to help make this railroad company the best railroad company it can be. This is a good pursuit.

A pirate in the navy pursues transformation, which is to lead the organization towards new processes, new tools, and new business models that will drive innovation. A pirate in the navy wants to make this railroad company the next interstellar transportation company that can beam customers from one planet to another in seconds.

Viki makes a clear statement. Pirates in the navy pursue transformation. Transformation is a different type of job than growth. A a pirate in the navy makes a clear choice and does not pursue both.

Choice 3: Do you want to be a pirate in the navy

The third choice you must make is a confirmation choice. It is the cross roads. The Rubicon. The point of no return. The third choice is whether you want to commit to being a pirate in the navy. If you chose to work inside a company and pursue a transformation career path, it means you intend to be a pirate in the navy.

Are you sure you want to do this? If so, you will face the following seven paradoxes, as Wiki describes in his book:

  1. Searching while executing
  2. Create new products, manage existing products
  3. Deliberate strategy, emergent strategy
  4. Decentralized decisions, increased transparency
  5. A single company, not a single business model
  6. Fail fast, make money
  7. Impatient for profits, patient for growth (Clay Christensen)

If these paradoxes sound like just what the doctor ordered, then you are pirates in the navy material.

The point of all of this is the choice. It’s a question of being true to ourselves. To know what we are getting into. The more clear our choices, the most fulfilled we will be. That’s what’s its all about.

Rebel Intrapreneur is a podcast for a different kind of high performing employee. For people like you who want to make a difference. For people like you who believe that the best answer to a why question is who. For people who want to challenge the status quo, who see things to improve everywhere, who want to further the missions of the organizations they serve.

Check out our guest line up and rebel intrapreneurs at

Originally published at on January 13, 2023.



Bill Cushard

Building @dragonboat_io for outcome-focused product teams | Rebel Intrapreneur podcast | "Elite" reversed-sponsored ultrarunning athlete.