• Contact
  • My Account
  • Log In
  • 0Shopping Cart
thoughtLEADERS, LLC: Leadership Training for the Real World
  • About
  • Services
  • eLearning
  • Team
  • Blog
  • Clients
  • Books
  • Contact
  • Menu Menu

Build your skills! Take our eLearning courses on TITAN!

World-class eLearning courses with videos, exercises, downloads, and a certificate of completion. Get started today!

Structured Thought: Problem Solving
Structured Thought and Communication
Strategic Business Planning
Principles of Chart Design eLearning Course
Engagement Management
Deliberate Decision Making
Breakthrough Innovation
Everything is Negotiable
Leading through Change
Storytelling for Leaders
Storytelling for Salespeople
Building Leadership Resilience
Compelling Executive Presence
Coaching for Impact
Building Personal Resilience
Building Personal Resilience
Wide Banner SPS
Wide Banner STC
Wide Banner SBP
Wide Banner PCD
Wide Banner ENM
Wide Banner DDM
Wide Banner BTI
Wide Banner EIN
Wide Banner LTC
Wide Banner SFL
Wide Banner SFS
Wide Banner BLR
Wide Banner CEP
Wide Banner CFI
Wide Banner BPR
Wide Banner TMM
previous arrow
next arrow

How to Innovate Like Captain Jack Sparrow

April 25, 2011/7 Comments/in Innovation /by Mike Figliuolo

Is your organization struggling to be more “innovative” and create new ideas? There’s an “Innovation Agenda” but all that’s on it are status meetings to review the “idea pipeline” which is nothing more than a stale list of ideas that make the business incrementally better?

Yeah. That.

If you really want to innovate and shake things up, you can learn a thing or two from Captain Jack Sparrow. Aside from being some of the coolest movies ever made based on a lame amusement park ride that now kicks butt, the Pirates of the Caribbean’s star anti-hero can teach you a few things.

Sure – it seems everything Captain Jack does works out. All his crazy ideas end up looking brilliant even though at inception they’re a bit hare-brained. It’s a movie folks. Realize not all your ideas will work out well. You will have failures. That said, if you’re truly serious about being innovative, you have to accept some risk if you want the rewards that go with it.

Here’s what I think you can learn from Captain Jack Sparrow:

Forget the rules

For Captain Jack, there are no rules. Everything is in play. Heck, even the sacred Pirate Code is “more of a set of guidelines.” Captain Jack operates outside the rules. In doing so he creates new degrees of freedom that enable him to act in ways that someone encumbered by rules cannot. In that space outside the rules are some pretty interesting solutions.

Sure, you risk getting in trouble for breaking the rules and some rules should never be broken. However, don’t be afraid to at least intellectually explore the space outside your current “rules” and see if any creative ideas are lurking out there. When you find them you have a compelling case you can make for breaking the rules.

And if you simply decide to act like Captain Jack and break a rule because in that moment you saw an opportunity, you’ll find people are much more forgiving of a rule transgression when you demonstrate the value you captured by ignoring the rule in the first place.

Don’t Overlook the Simple Solutions

With all the data and information we have at our disposal we like making ideas all complexified because we think the more difficult they are to understand the better they might be.

Wrong.

Look at some of the great solutions Captain Jack and his crew come up with in their journeys. Most of the great ideas are born from simple items directly at hand. The key is in seeing that simple solution in the first place.

Don’t overlook the obvious. Simple solutions can succeed more frequently than complex ones because the team can actually understand and execute the simple solution.

Experiment

When Captain Jack fights Barbossa over Cortez’s gold, he gives being cursed a try. He steals a piece of gold to see if it too will make him an immortal skeleton pirate zombie (which is awesome). Had he been wrong and the curse didn’t work, he would have been dead when Barbossa ran him through with his cutlass.

Instead, he became immortal and was able to compete with a competitor who was initially much better positioned to win.

It was a risk. He experimented. Something cool happened. When was the last time you experimented? Try something new just to see what will happen. Many times our hypotheses and the conventional wisdom are wrong.

Be Bold

No one in their right mind would accuse Captain Jack of not being bold. When he decides to take a risk he does so with gusto. He throws his entire being into it and absolutely commits all his energy to making whatever crazy idea he’s pursuing work.

Chasing an idea half-heartedly will doom you to failure. If you don’t commit and you aren’t bold, it will show through to your team. Your trepidation will manifest itself in counterproductive ways that undermine your chances of success. If you’re truly committed to innovation, pursue it boldly. The force of will is a force to be reckoned with.

You too can innovate like Captain Jack Sparrow. Forget the rules. Pursue simple ideas. Experiment. Be bold. I refer to him as “Captain” throughout this post because he always corrects people who leave it off as he sees that as a sign of disrespect. I respect the man’s audacity and innovation. You should too.

An administrative heads-up

Pretty soon we’ll be moving this blog to a new address. This site is (finally) being combined with our main thoughtLEADERS site as well as the site for my upcoming book One Piece of Paper. Just keep an eye out for our moving announcement. I think you’ll love the new look and layout. More soon…

– Mike Figliuolo at thoughtLEADERS, LLC
– Get the latest updates on my upcoming book One Piece of Paper – CLICK HERE

https://www.thoughtleadersllc.com/wp-content/uploads/2022/04/logo.png 0 0 Mike Figliuolo https://www.thoughtleadersllc.com/wp-content/uploads/2022/04/logo.png Mike Figliuolo2011-04-25 07:00:002018-06-26 09:24:45How to Innovate Like Captain Jack Sparrow
7 replies
  1. Mark Henson
    Mark Henson says:
    April 25, 2011 at 7:09 am

    Mike,

    Great article! I love the pirate code idea: more like guidelines, really. The people who really innovate are the ones who take things to the edge of "the rules", then see what happens when they bend, break, or step over the line.

    The next time I sense a rule getting in my way, I'm going to say "argghh", put on my pirate hat, and swashbuckle past it just to see what happens.

    Thanks for the fun (and powerful) thought to start my Monday!

    Reply
  2. Elena Patrice
    Elena Patrice says:
    April 26, 2011 at 6:41 am

    And either look like or hire someone that looks like Captain Jack and you're all set! ;) Kidding! Really Mike, great post! Strong points and definitely something we can learn from. Thanks so much!

    With kindness,

    Elena

    Reply
  3. Steve
    Steve says:
    April 26, 2011 at 7:59 pm

    Definitely good to shed a little light for the less-enlightened.

    In some cases pushing the rules on a regular basis will get you isolated because your a "cowboy". The key is to have the confidence to push back and cover all your bases to leave no ground available for opposition. If you experience this type of pressure you should sincerely consider moving on. A negative environment will sooner or later erode your positive outlook and that would be the real tragedy.

    Reply
  4. t0hierry
    t0hierry says:
    May 11, 2011 at 8:24 am

    Everybody agrees on no rules, until something goes wrong and the company is sued. First things lawyers look at, are the rules. Watch their face as you explain there are none…

    Reply
  5. Mike Figliuolo
    Mike Figliuolo says:
    May 11, 2011 at 8:27 am

    @t0hierry I'm not advocating stupidity however if we constantly run around afraid of attorneys and lawsuits, we'll never take a risk. On top of that, if your intent is good and your business practices are solid, you can actually win a lawsuit. Don't get me started on an attorney rant. I only have 6.5 hours left in my day…

    Reply
  6. April
    April says:
    May 26, 2011 at 10:09 am

    LOL! Captain Jack Sparrow, was not about experimentation, he was about strategy. Those movies are like a chess game in play. He was always a step ahead of everyone. He had each move and even the opponents- multiple opponents- moves all figured out. The gold piece creating zombies was a proven fact, which is why he was strategic in purposely pocketing one to ensure his life–not experiment. He also did stay within the rules, helping the other pirates and crews, despite coming off as self serving. In the end, other people benefited from his actions. He in then end always did the right thing (giving up position in the third movie to will so that he would not perish, instead of stabbing the heart himself so he could sail eternally as he had wanted. In business are you thinking like him? Are you figuring out your opponent's moves? Your customer's moves? Getting to know each piece of the puzzle so you too can play the business game with gusto? Are you doing what is right/working ethically?

    Reply
    • Kirana
      Kirana says:
      November 19, 2011 at 7:07 am

      yep – i see his moves as strategy arising from chaos. it’s fascinating. but i also think he does improvise well – he often gets in trouble he didn’t expect, but he recognises opportunity and seizes it creatively to get out of it. like when he escaped from prison, and steals the navy ship, stayed alive in the cannibal village etc.

      Reply

Leave a Reply

Want to join the discussion?
Feel free to contribute!

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Get free blog posts by email NOW!

It’s the best 5 minutes a week you can spend on your development.

Subscribe HERE!

Get new posts FREE via RSS!
Follow thoughtLEADERS on LinkedInFollow thoughtLEADERS on twitter
This site contains affiliate links to products. We may receive a commission for purchases made through these links.
 

Check Out Our Courses

Our courses teach immediately applicable skills that have real impact on your business. From leadership to strategy and negotiation to conflict resolution, we have a broad set of course offerings that will drive immediate performance improvements.
OUR COURSES

Our Courses

Group of Business People Meeting
Puzzle Pieces
Glasses Looking Over Cityscape
Doors on a Wall
Cog Wheels
Man Reading Book
Fishing hook in the sea
Microphone in Lecture Hall
Charts on Blue Background
Wristwatch
Exploding Light Bulb
Man on Summit of Mountain
Lightning Bolts
Man Painting the Word Change on a Wall
Construction Cranes
Plant Growing in a Hand
High Performance Gears
Men Shaking Hands Closeup
Influence Definition
Sailboat at Sunset
Hanging light bulbs with glowing one isolated on dark blue background
Wagon Wheel
Risk
Strategic Client Engagement
Strategic Business Planning
Advanced Meeting Leadership
Building a Growth Mindset
Executive Communications
Structured Problem Solving
Creating Leadership Maxims
Leading inside the Box
Deliberate Decision Making
Simple Strategic Planning
Storytelling for Leaders
Storytelling for Sales
Executive Presence
Principles of Chart Design
Time Management Mastery
Breakthrough Innovation
Leadership Resilience
Conflict Resolution
Leading through Change
Project Management Reality
Coaching for Impact
High Performing Teams
Everything is Negotiable
Leading with Influence
Building Personal Resilience
thoughtLEADERSHIP
Engagement Management
Risk Management
Client Engagement
Strategic Business Planning
Advanced Meeting Leadership
Building a Growth Mindset
previous arrow
next arrow
 

eLearning Courses on TITAN

Structured Thought: Problem Solving
Puzzle Pieces
Structured Thought: Problem Solving

Clearly define a problem, scope all issues related to the problem, generate potential solutions, then analyze and select the best solution by using time-tested critical thinking methods and tools.

VIEW COURSE
Structured Thought and Communication
Group of Business People Meeting
Structured Thought and Communication

Craft clear and compelling recommendations that resonate with stakeholders. Get your ideas approved by using a proven method for delivering executive-level communications.

VIEW COURSE
Principles of Chart Design
Different Types of Line and Bar Charts
Principles of Chart Design

Create well-designed presentation charts that get your message across quickly and clearly to drive your audience to action. From data charts to concept charts, these methods help make your point.

VIEW COURSE
Engagement Management
Wagon Wheel
Engagement Management

Whether you’re an internal or external consultant or a project leader, learn proven methods, techniques, and processes to effectively lead consulting engagements that drive your client’s success.

VIEW COURSE
Strategic Business Planning
Cog Wheels
Strategic Business Planning

Use a straightforward and effective strategic planning process that shows how to craft a clear, compelling plan for your organization - not just one time, but on an ongoing basis year after year.

VIEW COURSE
Deliberate Decision Making
Deliberate Decision Making
Deliberate Decision Making

Make better, faster, and more effective decisions. Apply simple yet powerful decision making tools to define decision authority, manage risk, increase accountability, and drive execution.

VIEW COURSE
Everything is Negotiable
Men Shaking Hands
Everything is Negotiable

Become a better negotiator in all situations – from day to day interactions to hammering out large deals. Build the skills required to get what you want and strengthen relationships while you do.

VIEW COURSE
Breakthrough Innovation
Exploding Lightbulb
Breakthrough Innovation

Generate and select unique strategies that separate you from the competition. Construct bold and disruptive solutions then build and execute a plan for taking those strategies to market.

VIEW COURSE
Storytelling for Leaders
Man reading stories from a book
Storytelling for Leaders

Create business stories that inspire people, build connections with your audience, and ultimately advance your organization's goals by using a repeatable, straightforward method.

VIEW COURSE
Storytelling for Salespeople
Storytelling for Salespeople
Storytelling for Salespeople

Create and deliver stories that will take your sales efforts to the next level. Connect with and convince buyers in all situations using memorable stories. These stronger relationships drive more sales.

VIEW COURSE
Leading through Change
Leading through Change
Leading through Change

Lead your organization through the most challenging times using a proven change management process. Get people through the change and back to driving performance quickly and effectively.

VIEW COURSE
Building Leadership Resilience
Mountain Climbing Expedition
Building Leadership Resilience

Prepare your body and brain to be ready for and recover from your biggest challenges. Build approaches for overcoming stress, managing reactions to difficult events, and leading more effectively.

VIEW COURSE
Compelling Executive Presence
Compelling Executive Presence
Compelling Executive Presence

Build your ability to connect with your audience and convey your ideas in a clear and resonant way. Create meaningful connections between you and your audience to build buy-in.

VIEW COURSE
Coaching for Impact
Plant Growing in a Hand
Coaching for Impact: Foundation Course

Coach employees for performance and development more effectively by helping them identify and pursue their own solutions. Create the right environment and conditions to help them grow.

VIEW COURSE
Building Personal Resilience
Boat at Sunset
Building Personal Resilience

Build the habits and learn the behaviors required to manage stress, deal with adversity, and maintain your physical and mental wellbeing. Personal resilience is a key to your ongoing success.

VIEW COURSE
Time Management Mastery
Watches
Time Management Mastery

Learn techniques to manage your time, delegate, say “no,” and be more efficient. Balance your limited supply of time with the overwhelming demands that are placed on you every day.

VIEW COURSE
previous arrow
next arrow

Books You MUST Read

The Elegant Pitch
One Piece of Paper by Mike Figliuolo
Lead Inside the Box
10 Stories Great Leaders Tell
Getting Ahead
Sell with a Story
Lead with a Story
Mastering Communication at Work
The Hook
Innovative Leadership Fieldbook
Innovative Leaders Guide to Transforming Organizations
The Three Commitments of Leadership
The Littlest Green Beret
Storytelling in the Land of Oz
The Camino Way
Hiring Veterans
Disability is Human book
Race to Innovation
The Emergent Leader
Business is Simple
Business is Simple
The Elegant Pitch
One Piece of Paper by Mike Figliuolo
Lead Inside the Box
10 Stories Great Leaders Tell
Getting Ahead
Sell with a Story - Border
Lead with a Story
Leading from Your Best Self
Mastering Communication at Work
The Hook
Innovative Leadership Fieldbook
Innovative Leaders Guide to Transforming Organizations
20120318 Three Commitments
Leadership Vertigo
The Littlest Green Beret
Storytelling in the Land of Oz
The Camino Way
Hijacked by Your Brain
Outthink the Competition
Driving Innovation from Within
Hiring Veterans
Disability is Human
Race to Innovation
The Emergent Leader
Business is Simple
Global Mindset
previous arrow
next arrow
  • The Elegant Pitch
  • Disability is Human
  • Hiring Veterans
  • Race to Innovation
  • The Emergent Leader
  • Business is Simple
  • Global Mindset

Categories

This site contains affiliate links to products. We may receive a commission for purchases made through these links.

Our Course Offerings

Leadership Skills

Creating Your Leadership Maxims
Leading Inside the Box
Leading With Influence
Leading Through Change
Structured Problem Solving
Deliberate Decision Making
High Performing Teams
Simplified Strategic Planning
Strategic Business Planning
Coaching for Impact: Foundations
Coaching for Impact: Applications
Building Leadership Resilience
Engagement Management
Project Management Reality
Risk Management

Communication Skills

Communications: Foundations
Communications: Applications
Principles of Chart Design
Strategic Client Engagement
Storytelling for Leaders
Storytelling for Salespeople
Compelling Executive Presence
Advanced Meeting Leadership

Individual Skills

Conflict Resolution
Everything is Negotiable
Building a Growth Mindset
thoughtLEADERSHIP: Innovation
Building Personal Resilience
Time Management Mastery

Coaching & Consulting

©2026 thoughtLEADERS, LLC: Leadership Training for the Real World. thoughtLEADERS, LLC is a registered trademark of thoughtLEADERS, LLC.
  • Privacy Policy
  • Terms of Use
  • Cookie Policy
Getting Your Risk-Averse Boss to Take a Chance On Your Ideas 4 Failure Lessons You Should Learn from Google
Scroll to top