The Pivoteer Manifesto

When I started this newsletter, I had no expectations of a pivot coming my way, but life is funny. As I was writing this issue, a series of events happened over 48 hours that caused a chain reaction of “put up or shut up” moments.

An unexpected fight with my roommate left me without a place to live, and 60% of my income disappeared. These were “fire under the ass” moments, and it was “go time.”

I ended up reconciling with my roommate the next day, but in-between the fight, I found an Airbnb that would take my dogs where I could war-room next steps. It wasn’t too far away or too expensive and more manageable than going to La Quinta, the only hotel chain that will reliably take Rottweilers. Crisis one handled.

I then found a new client to rotate in that wasn’t a full-on replacement but could fill the income gap short term. I also looked at my business and came up with a new niche-down on my current model that will allow me to do more turn-key work at a higher price point. Crisis two handled.

When these things happened, I didn’t freak out or lose my shit because, like Liam Neeson, I have a particular set of skills, and I employed the right tools for the right jobs and got things handled quickly, calmly, and efficiently.

Before the tools comes the mindset, and thus is born The Pivoteer Manifesto! This manifesto will be a living document, and as we go through this career hopping adventure of discovery, I’m sure we’ll all learn from other epic Pivoteers and add their teachings.

The Pivoteer Manifesto

MacGuyver was an amateur.

A Pivoteer Is Always Learning

It doesn’t matter if you’re an autodidact or someone who learns from structured classes and teachers; a Pivoteer is ALWAYS LEARNING! Every day is a new opportunity to acquire new skills or hone the ones you already have.

Never go to bed without being more valuable to the world than when you started the day.

Some people keep a gratitude journal, but I’ve started a skills journal for this project. I have a goal to learn at least one new thing a day. It doesn’t matter the size of the skill, but there has to be something in my journal every day. If I find myself lacking, I’ll either open up one of the many online course sites I subscribe to and watch a video class or read a manual on something that I’m in the middle of mastering.

Before bed, I have a set of productivity rituals such as checking my calendar and setting up my to-do list for the next day. These aren’t so much a Pivoteer thing but something that lets me sleep anxiety-free. And the last thing I do before lights-out is catalog my learning for the day.

Since you’re always learning, you should have multiple irons in the fire at any time that you can go back to when your mood and time opportunities align. Writing down at least one thing a day (you can have multiple items, but you need at least one) gives you a linear progression you can look back at and see your progress.

And not all learning is active. You can passively learn from anything you experience in a day. I am a fan of spending my evenings watching mind-numbing cooking competitions on the Food Channel. If I discover a new technique for a dish or fresh ingredients for a sauce, I’ll pause the show and jot it down in my cooking notebook for another day. That counts as long as you remember it.

Remember, passive learning means NOTHING if you never act on it. It’s empty brain calories otherwise. Don’t try and justify that watching The Real Housewives will expand your mind if you learn about a new hairstyle. Unless, of course, you’re a hairstylist! You get my drift.

A Pivoteer Reads the Fucking Manual

When learning a new skill that will be important to your working career, you want to aim for being, at the very least, in the 80th percentile of skills. That starts with reading the manual. The maker of the tool you are learning has provided a vast amount of knowledge. By simply reading the instructions, you will be far superior compared to the impatient masses who jump in and “figure it out as they go.”

Reading the manual gets you to basic proficiency faster. While your peers are trying to figure out what ding dong A is doing or where widget B goes, you’re already on to intermediate skills and zooming past them on your way to 80%.

Why do I say go to 80%? Because if you do some back of the napkin bullshit statistical analysis, you can inaccurately quote Pareto’s Principle to say that only 20% of the competition gets to 80% proficiency, and so your odds of landing a job in that field are much higher. The truth is that 100% of what I just said is bullshit. No principle or law says that 80% is statistically or quantifiably meaningful.

After a lifetime of working in highly professional environments, I’ve personally found that approximately 5% of people get to 80% proficiency. Most civilians learn as little as possible and get by with the bare minimum to do their jobs.

Pivoteers strive for 80% because it’s not much harder to get a leg up and your longer-term path will be more accessible, and your rewards will be greater.

A Pivoteer Is Constantly Prepared

New situations don’t scare a Pivoteer because planning is a core competency. Pivoteers expect the best but plan for the worst. If they lose one job, they have three options on standby at all times. If they lose their home, they know how to use the system to survive until they can reacquire stable lodging. And in preparation, a Pivoteer often discovers opportunities that they weren’t aware of before.

A Pivoteer Isn’t Afraid of Adventure

Adventure brings opportunity for growth. Whether the chance is financial, spiritual, social, or something else, a Pivoteer never wastes an opportunity for experience. Some adventures are grand with travel and danger, and some are small that you can have from home. A Pivoteer is a master of identifying adventure and takes full advantage of it.

A Pivoteer Rarely Uses the Front Door

Pivoteers don’t queue or follow the crowd. They find the cracks in the system. They are experts at exploiting what the masses would see if they looked just a little deeper at how the world works. Pivoteers rarely have traditional career paths, but they navigate the corporate structure like a mongoose hunting a cobra. They don’t rely on quarterly reviews for upward mobility. They move diagonally inside the organization, eschewing the tired thinking of old business. Using relationships and deep knowledge of how a company works, a Pivoteer can go from the mailroom to the boardroom in record time. There is no such thing as an unfair advantage. It’s just an advantage, and Pivoteers use them as often as they can.

A Pivoteer Always Belongs

There is a super-power that resides in everyone, and it’s the ability to look like you belong almost anywhere. Pivoteers cultivate this skill and are fearless in deploying it.

Gatekeepers are an annoyance that you can bypass with enough hutzpah and skill. We had an incredible security team when I worked on the lot at a major movie studio. One of my more adventurous co-workers and I would regularly try and go where we were most definitely were not allowed. After getting kicked out more than a few times, we developed the super-power of simply looking like we belonged. The skill I cultivated sneaking into Star Trek soundstages 25 years ago still serves me to this day in life and business.

A Pivoteer Cultivates a Network of Super-Advocates

All people collect acquaintances, friends, and enemies as they move through life. Some people are networkers, and others are not. No matter how adept a Pivoteer is at networking, they accumulate a stable of Super-Advocates. Super-Advocates are usually connectors with extensive personal and professional networks who are intimately aware of a Pivoteer’s unique skills and can connect them with other people who need those skills. SA’s need to be cultivated and treasured.

A Pivoteer Craves Novelty

A Pivoteer is always on the lookout for new paths and adventures and gaining skills to make informed decisions on which way to travel. When an opportunity arises, or the unexpected interrupts your life path, the Pivoteer is capable and ready.

Career paths don’t exist anymore. Even if you are on a track that you think will last forever, something will happen. You may get tired, bored, or jaded from the same scenery. An external force may block the road, and you’ll be left scrambling to find a way around the rock or over a mountain you have no skills in climbing.

A Pivoteer is curious and a lifelong learner. We take the sum of our unique experience, and we seek paths that will allow us to grow and learn and find adventure along the way. Some adventures turn into misadventures, but the Pivoteer is prepared to face these situations. Pivoteers don’t stay on the same path longer than they want or have to; instead, they crave novelty and growth over stagnation and routine.

Take this list as a starting point, start that skills journal, and we’ll talk next time about how to take these traits and expand them into actionable skills.




A no-bullshit approach to changing your career and life by the people who have done it.

Love podcasts or audiobooks? Learn on the go with our new app.

Recommended from Medium

Book Review: Principles by Ray Dalio

In Order to Have Business Success You Must Become Comfortable with Risk

Intern at Freshdesk

Five critical things to consider in all-remote work

Flawless Tips & Tools for Team Leads to Manage Remote Workers

Three Things

When Your Work Changes, Take These 5 Steps

Want to Know How to Run a Remote Team?

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
The Pivoteer by Jason DeFillippo

The Pivoteer by Jason DeFillippo

A no-bullshit approach to changing your career and life by the people who have done it.

More from Medium

Happiness #9 — Conquering Unhappiness

Negative Value Hires (and How to Avoid Them)

What’s What in Education? №7 Boredom Kills!

A Journey with Passion and Purpose - Eneida Roldan