Gig Mindset: Reclaim Your Time, Reinvent Your Career, and Ride the Next Wave of Disrupt

By Paul Estes

Tim Ferriss had it right: you can work with virtual assistants to escape the grind of eighty-hour workweeks. Ferriss was ahead of his time in predicting how entrepreneurs would work today and we have discovered that the benefits of the gig economy now extend to employees and business owners. You don't have to quit your job to live a balanced life, reskill, unlock new opportunities, or start that side hustle you can't stop thinking about.

You just need Gig Mindset, and Paul Estes is here to help you adopt it. For years, Paul struggled to balance his home life with fast-moving jobs at Dell, Amazon, and Microsoft. Hiring his first virtual assistant transformed his life—and it can do the same for you. Paul will help you get started with freelancers by utilizing the TIDE Framework: Taskify, Identify, Delegate, and Evolve. He also shares stories from interviews with leaders at NASA, GE, and Topcoder on how they're transforming their organizations using gig economy strategies.

If you're ready to re-energize your work, Gig Mindset is what you need.

• Language: English
• Publisher: BookBaby
• Release date: Jan 14, 2020
• ISBN: 9781544506333

Book preview

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Copyright © 2019 Paul Estes

All rights reserved.

ISBN: 978-1-5445-0633-3

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Contents

Foreword

Introduction

1. Standing in Quicksand

2. The Gig Mindset

3. Resetting Your Default

4. The T.I.D.E. Model

5. Taskify

6. Identify

7. Delegate

8. Evolve

9. Making the Elephant Dance

Conclusion

Appendix A—Fifty Tasks for Work

Appendix B—Fifty Tasks for Home

About the Author

Acknowledgments

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I trust you will treat humanity kindly. At the end of the day, at least for now, it is the individual’s skills and abilities that have value. I hope the process that rates and assigns future work is honest and level.

My generation will not yield easily to artificial intelligence algorithms. Our grandchildren may have no choice. You have chosen—or been chosen—to stand on the leading edge of disruption, and I know and trust that honesty and character will guide you.

—John Estes

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Foreword

When Dick Fosbury was in high school, he was fascinated with the high jump. The problem was that he wasn’t particularly good at it. Neither of the commonly accepted jumping techniques—which involved sailing over the bar face down—allowed him to get any higher than six-feet-three.

When he got to college at Oregon State, which had foam landing pads instead of the sawdust and wood chips common at the time, Fosbury tried something new. As he jumped, he turned over, sailed over the bar upside down, and landed on his back in the foam. He soon cleared six-feet-ten and went on to win an Olympic gold medal with a record-setting jump of seven-feet-four.1

High jumpers had been going over the bar face down for a hundred years until Fosbury decided to flip his orientation and reach new heights. Today, the Fosbury Flop is the only technique high jumpers use.

That’s precisely what Paul Estes is doing today; he is flipping the paradigm and finding new ways to tackle problems and improve results. He uses democratized technology and open innovation to find the best people to find novel solutions.

Paul is a pioneer of the Gig Economy. His pursuit of the Gig Mindset not only changed the way he works and lives, it set him on a new path. Now he uses his passion and experience to help companies make these changes as well. His agile, open-system approach is outpacing the work of dinosaur managers who limit their knowledge to people on the payroll.

Paul and I share a passion for this approach. I have also used gig tools to start companies and compete with incumbents. While sometimes this was a financial necessity, hiring freelancers also made my companies more nimble and efficient than our old-school competitors. My ad agency, Victors & Spoils, had twenty-five employees but curated the work of more than 7,000 freelance creatives, allowing us to find prompt and potent answers unencumbered by corporate circumspection. I worked from the outside looking in, so when I met Paul and learned he was using the same approach from the inside looking out, we hit it off right away.

The Gig Economy embraces the idea that we are all entrepreneurs responsible for our own career journey. Paul gets this. He may have spent his career in Big Tech, but he has the mindset of an ambitious small business owner. He values entrepreneurs as problem solvers and independent thinkers who work with urgency and brisk execution, and with this book, he reveals the secrets to taking advantage of that world. Entrepreneurs see the possibilities, not the limitations, and so does Paul.

The benefits are far reaching. Shifting to a Gig Mindset and building broad networks of freelance experts and gig workers brings joy back to our work. Entrepreneurs don’t have time for a lot of talk. They like to do. Working with people like that invigorates you, allowing you to rediscover your energy and passion.

It’s also a generational issue. Millennials entering the workforce have grown up in this democratized, connected world, and they don’t want to work in the same command-and-control environment their parents and grandparents worked in. They are focused on outcomes and getting work done. They aren’t interested in sitting in meetings. They aren’t interested in working on an assembly line. They want to be on teams that collaborate and solve big problems.

Paul isn’t suggesting you take work away from an internal employee who writes one hundred lines of code a day and give it to an external worker to do the same job. Real success is when you engage with an expert freelancer who has figured out how to use AI to write ten million lines of code a day. That’s an exponential return. Imagine if that same internal employee now coordinates with ten similar freelancers.

If you’re a business owner or a CEO reading this, it’s incumbent on you to create the new structures and systems for taking advantage of this. Some of you might see this as an existential threat, but if you find yourself on a treadmill, running faster each day to try and make analog systems work in a digital age, the Gig Economy is a way to get your life and work back. Technology is getting faster, and that’s increasing everyone’s workload, regardless of the industry you’re in. The amount of work some of you are going to be in charge of is so overwhelming that you will have no choice but to turn to freelancers. Those who learn the skills that Paul talks about in this book are going to be the winners in this world of open systems and open tools.

The Gig Mindset will pull back the curtain to reveal the landscape of this world. It’s a future where entrepreneurs don’t follow a career path but mark their own path through the power of open innovation. I’ve been in the world for some time now, and I can tell you that the friction has been removed from all our systems and we are free from the analog constraints that many of our industries were built on. We’re no longer limited to the knowledge of people we hire. The digital age gives us radical abundance, opportunities, and tools, but we need books like this one from Paul Estes to learn how to best use them.

—John Winsor

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1 This Day in History, History.com, October 20, 1968, https://www.history.com/this-day-in-history/fosbury-flops-to-an-olympic-record.

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Introduction

Your profession is not what brings home your weekly paycheck. Your profession is what you’re put here on Earth to do, with such passion and such intensity that it becomes spiritual in calling.

—Vincent Van Gogh

On a cold October morning in 2015, my boss asked me to join him for a cup of coffee. A quick one-on-one was nothing out of the ordinary, but he’d never invited me out for coffee before. Something was up.

Honestly, our relationship had been off for a while, and there were serious challenges in the overall business. Our office culture was unhealthy and spiraling into toxic. Without a clear path forward, the team floundered.

This wasn’t a place for anyone to do their best work. My boss and I couldn’t agree, and our strained relationship put even more pressure on the team. He came from the engineering side; I came from the business side. He thought we were a few features away from unlocking scale, and I wanted to make drastic changes to our business approach.

We’d butted heads since the beginning. He wanted to add more features and call it a day, but I thought we needed to address the core business challenges that were limiting engagement and usage. I pushed the team in one direction while he shouted down to go the other way. I knew it wasn’t compatible. He knew it wasn’t compatible. Yet we worked day after day to get toward the end goal. Honestly, I saw this cup of coffee as an olive branch. A chance to get back on track, to focus on the company’s goals, and to work as a team.

After we ordered our drinks and sat down, he told me plainly, It’s not working out. You’ve got three months to find a new role.

I don’t know how long I sat there in shock. I had just lost my role at a Big Tech company. Sure, there were other opportunities at the company. I wasn’t out of the fight, but I’d definitely had the wind knocked out of me.

What made the sting so much worse was that this was supposed to be a great week. My first daughter was due in a few days. This was going to be an amazing time for my family, and my boss knew that. Such is the audacity of the corporate world.

That was it. My career ended before my coffee had a chance to cool off. What the hell had just happened? You have three months to find a new role. I’d never heard those words before, and they banged around in my head like a bull in a china shop.

I’ll be the first to admit I wasn’t always a perfect employee. Sure, my track record was solid. I put in the hours and made sure I could stand out as an employee and contributor. I had always delivered what was asked, and I’d been praised for my hard work and the product I delivered. My boss and I had disagreements about methods, but after fifteen years working in tech, I never saw this coming.

It shook me. This wasn’t how it was supposed to be. This wasn’t the path I had envisioned my entire life.

But why did I think this was the only way?

A Company Man

I’m a third-generation company man.

My grandfather served as a drill sergeant in the US Army during World War II. When he came home from overseas, he sold insurance. He worked hard, going into the office every single day, and he built a social contract with his company. When he retired, he had a pension from the insurance company and a few benefits from the Army.

My father worked for the FBI before moving to the private sector. He worked security at Shell Oil, climbing the ranks until he ran the entire division. Again, he put in the years and the hard work, and when he retired, he had a pension waiting.

That was the promise sold to me and everyone in my generation: if you work hard and show up, you can keep the same job your entire life and retire with benefits. The company wasn’t just a place you worked; it was a part of your life. You grew with them, rising up the ranks, getting your chance to make an impact.

That was the model I lived by. That was the foundation for my life plan. I wanted the company life.

I worked hard in high school so I could get into a good college. Now, I wasn’t an A student, but I did well enough. What I didn’t have in grades, I made up for with life experience. I was a competitive swimmer, a radio DJ, and the student body president. Then I went to grad school, making myself more marketable for the type of business I wanted to land. Then I got a job in my field, with the intent to work hard and earn my way up the ladder.

Learn by doing. It’s how I was raised, and it’s how I lived my life. That was the surest path to job security that I knew, and it’s exactly how I lived my life for the next fifteen years.

Everything I worked on was about experimentation and learning, but I knew I had safety in the golden path my father had outlined.

In the back of my mind, I kept thinking about my daughter. She was days away. All I wanted was to give her the world, to be the provider my father had been for my family.

So that moment, sitting across the table from my soon-to-be former boss, I felt like the foundation of my life was crumbling beneath me. I was going on forty, about to be a father, and my life plan had just been shattered.

I took a few days to gather myself. There, at one of my lowest moments, my wife delivered one of my highest.

My daughter was born a few days later. She was a gift, a wonderful miracle that reset every priority in my head. All at once, I was elated and terrified for the future. I stayed in the room with my wife and newborn, basking in a feeling I hoped would last. Then reality came creeping back in, along with that familiar anxiety. That night, I took a walk to get some fresh air while my wife and newborn slept.

What was I going to do? Find a new company, pledge my loyalty, and try to climb the ranks again? That path no longer felt so secure. I stood in the cold night air, trying to make sense of the last few days.

I felt overwhelmed by a new sense of personal responsibility. I’d spent so much energy trying to do a good job, hunting for that next promotion, and toiling away every hour I could spare. Suddenly, I had time. I had space. I had agency to reinvent myself and chart my own path forward. The question was what should I do with that opportunity?

In that moment, thinking of my growing family, I started a new journey to find my story. The second my daughter came into this world, everything changed. They were my world, and our life became my sole focus. The skills I had, the job I worked, and the life I provided all surrounded them. I needed to find a path that wasn’t just safe but kept me relevant and skilled to continue working and growing.

I had to say goodbye to that old mindset. Goodbye to relying on the company to provide a safe and secure path. It was time to chart my own course, to question the norms and radically change the way I worked.

Forging a New Path

Over the next three months, I ran through my options. One of the first things I did was engage with a career coach.

Okay, this is a bit of an aside: why don’t more people hire career coaches? When you’re sick, you go to a doctor. When you’re training for a sport, you work with a coach. When you’re in legal trouble, you go to a lawyer. There is an entire industry out there to help you orient yourself toward the best career. Why don’t more people take advantage?

My career coaches (I had two) were amazingly helpful as I went on this journey. They provided me with the confidence and clarity to charge forward.

I could take the skills I already had and apply them somewhere else. I went on interviews with large companies and startups, and even got a few offers. It was tempting, but there was no guarantee I wouldn’t find myself in a similar situation in a few years’ time.

I could invest some capital and start my own business. I had friends who worked as entrepreneurs, and they were always excited about their new ventures. I was impressed with the clarity of their goals and the Herculean efforts they managed in order to be successful.

Back in February of 2014, Satya Nadella took over as CEO of Microsoft. He brought a great new energy and voice. The culture felt different, which encouraged me to try and stay. My challenge was to find a new role, and quick.

Not long after, I found myself sitting across from a senior executive interviewing for a chief of staff position. I really wanted the job. It wasn’t just security; it was a way for me to keep in the same mindset, to keep the status quo.

I’d had good and bad years at the company, but with good reason. I liked to put myself in places where I could provide value. I took innovative and often ambiguous roles, and the company was constantly changing. That level of flexibility gave me time to shine, but it also led to inconsistent reviews.

I remember telling the senior executive, If you’re looking for someone who wakes up every day and tries to play the ratings and review game, I’m the wrong fit. If you’re looking for someone who will work hard, take risks, and bring energy to work, then let’s get started.

I got the job, but tech is an inherently unstable industry. Innovations come every news cycle, and even big tech companies had to transform and reorganize constantly to adapt to a highly competitive market and changing customer needs. I’d been in the business long enough that it felt familiar, but I didn’t have the certainty about where that left me.

There might not be a perfect job, but I knew what I wanted in life: I wanted a career that challenged and excited me, I wanted to provide value and impact in my company and industry, and—most important of all—I needed to be able to support my family and be a part of our journey.

I also had to find the answers my family would need when they entered the workforce. I wasn’t going to convince my daughters to follow the same path as my father and grandfather. They would one day need to understand the evolving, hybrid workforce of the future. They would need to know how to make time to reskill, to stay relevant. In order to teach them to follow this path, I would have to first learn these lessons myself.

Why