Chapter 1

1. Monday Morning Malaise

“America’s Professional Elite: Wealthy, Successful, and Miserable.”

—The New York Times headline, February 21, 2019

“Sunday Night is the New Monday Morning, and Workers are Miserable.”

—The Wall Street Journal headline, July 7, 2019

February 2011—I flew to company headquarters in Los Angeles with the expectation and giddy hope that I would be fired. There were rumors that another round of corporate restructuring was around the corner, and I detected subtle signals. I wanted it to happen. I needed it to happen. I was confident it would happen.

My boss scheduled a 5 p.m. meeting on a Friday afternoon, my last session that week in LA. An encouraging sign, I thought. A classic HR move. All week I gleefully anticipated that meeting the way a child looks forward to Christmas morning. I eagerly awaited a golden parachute. I fantasized about how I would play the victim. How I would suppress the joy of terminating a seventeen-year work relationship. Seventeen years. That was nearly half of my life. I fantasized about how liberated I would soon feel.

The 5 p.m. conversation on that Friday did not go the way I expected.

It was a business-as-usual meeting. I received more projects to tackle and things to do. “Is there anything else we need to talk about?” I asked my boss, hopefully, at the end of the meeting.

“Have a good flight” was all I got in response.

My head exploded as I left his office. Instead of liberation, I got perpetuation.

I hated that soul-sucking job. I did not know how I could face another day in that organization. Every morning my stomach churned as I drove to work. I hated the office politics. The “always-on” expectations. The 10 p.m. conference calls. The bureaucracy.

I hated everything about that job except for the paycheck. Then I hated myself for not having the guts to walk away from that paycheck. I felt as if I gave a small piece of my heart every time I walked into my very nice office, with its expansive views and modern furniture. I was a wage slave. Trapped. Stuck inside a “good” job at a high-profile company in a sexy industry. I had a decent personal balance sheet, but my assets were unproductive. I did not have independent cash flow. I depended upon that salary. Although most other aspects of my life rocked, the unhappiness at work polluted everything else.

An enriched life, this was not.

The Many Work Mindsets

Think back to last Monday morning.

During your commute into work, what was your frame of mind? Were you looking forward to the day? Or looking forward to the day being over?

If you are lucky, perhaps your thoughts were optimistic…

Financially Secure Mindset: The new project excites me. It could game-change the company and my career. Sure, it’s risky, but we have a shot at making a big difference in the market. This opportunity energizes me while I work my butt off to make sure we get it right. If we do not greenlight the project, everything will be okay. I can afford to take a chunk of time off. Heck, I would enjoy some time off. Either way, I win.

Alternatively, were you less upbeat last Monday morning? Perhaps this is more familiar…

Hanging-On Mindset: I need this job. I have a kid in college and another on the way to University. I have years left on my mortgage and I’m years behind in my retirement readiness. I am screwed if the market does not recover. If the rumored restructuring happens, I’m also screwed. I have to suck up to Bob to make sure I will be safe. I can’t make any ripples. Gotta make sure I survive this. I need that December bonus.

Or maybe your commuting thoughts last Monday morning were along these lines…

This Sucks Mindset: I hate this job. I cannot believe I missed seeing my son score that goal on Saturday because of that stupid conference call with my boss. I wish Margaret would get a life so everyone else could have one, too. That fire drill last week with the Boston client. What a waste of time. My wife is still pissed that I missed dinner because of that farce. I need a drink already, and it is not even 9 a.m. I hope I can get through this bloody day without losing my mind.

Then there is that other prevalent mindset, the This-Job-Is-Everything Mindset.

My first encounter with this archetype occurred more than two decades ago, and it set off a personal chain reaction. Barely thirty at the time, I noticed a Japanese colleague, whom I will call Watanabe-san, standing forlornly by the window. He vacantly watched the frenzied streets thirty-two floors below. Known as a lifer in the company, Watanabe-san had recently learned the company no longer needed his services. He was in his early fifties. His career was over. To Watanabe-san, his career was everything.

“What am I going to do now, Todd-san?” he asked me. “I’ve worked for this company for my entire life. What else is there?”

I understood my colleague’s sense of nihilism entirely. Not long before, I also had a work crisis, one that shook me to the core and turned my views about work and life upside down.

It was my first job out of Columbia Business School. My dream job working for a Hollywood studio. Back then, I often laughed on paydays. It seemed outrageous to earn money from doing something I found so exciting and personally rewarding.

Then I tumbled.

I negotiated a deal with a Taiwanese company. The agreement was so important that the division president directly called me for updates. Closing this one deal would be my moment to shine.

So, what did I do? I did what any ambitious, newly minted MBA would do. I negotiated aggressively to prove myself. Too aggressively, it turned out. At 6 p.m. on a Friday, I received a terse message that said, “Thank you for your efforts, but the gap is too big. The deal is off.”

F@%#!

I scrambled through a flurry of desperate calls to my counterpart on the other side of the negotiation. It was too late. The weekend had officially begun, and this was before the age of cell phones. Reaching the client over the weekend would prove impossible. The only thing I could do was wait for a miserable Monday morning.

That weekend was excruciating. I couldn’t sleep or function. I only could replay the negotiation repeatedly in my head, each time blowing the deal even more spectacularly. Why had I pushed so hard on a deal that I could not afford to lose? That weekend I sat motionless on my living room floor, propped against the couch, staring blankly at a white wall. The shame of blowing this deal was almost unbearable.

Sixty very dark hours later, Monday morning arrived, and so did a second chance. I groveled to the client and salvaged the deal.

Surviving that painful experience changed me, personally and professionally.

I quickly realized that the transactions would only get bigger and the stakes higher as I progressed in my career. To maintain sanity, I needed to develop a concrete system for staying grounded when things fell apart at work, as surely they would. I needed a mechanism to keep perspective on what is most important.

I resolved never to allow work to define my self-worth and Identity. I would not defer the things that fire me up. I would not accept the default setting. A thriving career was no longer adequate. I demanded an enriched life.

I would be ready for the guy at a cocktail party who asks, so what do you do?

But that was not enough. As focused as I was on life goals, back then I failed to appreciate the importance of accelerating financial security. I was a rising star at work and quickly climbing the corporate ladder. At the time, I loved my job and my company. Financial security never even crossed my mind.

A decade later, financial insecurity handicapped me, and I realized that economic security is foundational. Upon this realization, I hustled to fast-track financial freedom.

Less than five years later, using the principles in this book, I achieved outright financial security. I was no longer a wage slave. Though I continued to work for several more years, employment became optional. When you choose to work, you anticipate Monday mornings.

Over the years, I have encountered many versions of Watanabe-san, many Hangers-On, and many This Sucks types. These are frequently recurring characters in the corporate world. Among the independently employed, variations of these archetypes also abound. Sometimes the corporate executive gets the wrong end of a restructuring, or a high-flying career hits a speed bump. Sometimes the workaholic lawyer burns out chasing billable hours, or the stay-at-home mom confronts an...