How To Become A Corporate Pirate

5 min readJun 27, 2016

If you’re currently working at a large or established organization, think about those who work there. Can you think of a group of people who are seemingly growing discontent with the status quo? They’re usually quite driven, likes challenges, and are more often than not rather opinionated. They have a knack for identifying problems. They raise questions on how things are done, what rules are put in place, and why. Some of them may be more vocal than others, and it’s probably common for you to hear one of the vocal ones referring to something as “stupid”.

Maybe you’re part of this group too.

This group of people are excellent candidates for what I like to call Corporate Pirates. The more commonly-used term is intrapreneurs. Intrapreneurs are serial innovators — they take risks and exploit their creativity, strengths, and capabilities to implement new and effective solutions to problems, most of the time without being asked or without the proper authority, and sometimes even using resources which aren’t really theirs. They sound and behave just like entrepreneurs (they’ve probably dreamt of being one). They both have that hunger to make an impact — one of the main differences being that intrapreneurs aren’t necessarily in their own startups while they try to do it. While they may not be the owners of the company they’re working in, it doesn’t stop them from taking ownership of its direction and how they contribute to it. This pattern of behavior is consistent with what author Dan Pink describes in his book Drive as the new motivation model for the complexities of 21st century work, which consists of three main components: autonomy, mastery, and purpose. And intrapreneurs will take these whether it’s given to them or not.

Does this still sound like you? If you feel like you can identify with this exciting life of intrapreneurship, here are some things you can do to become a Corporate Pirate.

Keep asking “why?”

Why doesn’t this work? Why are we doing it this way? Why does this suck? — All valid whys. And whatever answer you get to that first why, go ahead and ask four more. If something doesn’t feel right, repeatedly asking “why” can help to unearth potential problems, and subsequently the root causes to those problems. Identifying problems and getting them right is just as important as getting the solution right. Just make sure to not only complain — you should also be contributing to the solution.

“If I had only one hour to save the world, I would spend fifty-five minutes defining the problem, and only five minutes finding the solution.” -Albert Einstein

Own it

Own those problems and solutions with a great passion. Treat them as if they were your own little ventures. Doing this will help to establish yourself as a leader in your organization, and having that experience may also come handy one day should you decide to cross the threshold into entrepreneurship (there are quite a few examples of intrapreneurship being a stepping stone to full-on entrepreneurship).

Rally others to your cause

What happens when you find that you can’t execute your little intrapreneurial venture alone? You need to bring others onboard. This will be your chance to do two things: test your idea for feedback (and refine your “ugly baby”), and test your pitching skills in making others believe that you’re saving the world. After all, to be a successful pirate, you’ll need your merry crew. There will also be times when what you need from others is their permission, which brings us nicely to the next item…

Know when to break the rules

“It is much easier to apologize than it is to get permission.” — Grace Murray Hopper

Pirates are good risk takers. They’ll find out what the rules are, then figure out which ones to break in order to get what they want. This is part of what makes them so resourceful. However, just as important as knowing which rules to break, they also have a good sense of what rules not to. They should be guided by a solid moral compass (hey, even pirates had a Pirate Code). Typically, this is the greater good of the company, even though others (aka naysayers) may not see it that way.

Get things done

“Real artists ship.” -Steve Jobs

Above all else, intrapreneurs are productive beings, and they follow-through to get things done. Ideas have almost no value when they stay in your head. Get them out by telling others, build it, ship it, and improve.

Fail fast and pivot faster

Like pirate ships of old, intrapreneurs are fast and nimble, knowing how and when to pivot when necessary. When something doesn’t work — and something is bound not to — brush yourself off, learn from it, and try something different. Some call this ‘failing forward.’

Look beyond the horizon

“Skate to where the puck is going, not where it has been.” -Wayne Gretzky

Say you’ve found your problem — something as small as an inefficient process, or perhaps something as big as exploring the development of a new cash cow for your organization — and you came up with an awesome viable idea, took the resources you needed to execute, convinced others to come on-board, possibly broke some rules in the process, and you shipped it and saved the world. Is that it though?

Never.

Intrapreneurs and pirates alike are almost never satisfied. Always have an ear to the ground to see what may be next — the next problem, the next improvement, the next unicorn.