An Intentional Life — Part 2: Stumbling into My Operating System

This post is part of a series. You can find Part 1 — the introduction — here.

There are a several moments in my life that led to the development of my operating system. The four most important are described below, as context to why I developed the operating system and the problem statements it is designed to tackle.

“What matters most to you, and why?”

1. Going to business school.

The admissions application for business school at Stanford has a challenging, but insightful question: “What matters most to you, and why?”

To write that essay well — and I’ve given this feedback to almost everyone who has asked me to read their first draft — you need to go uncomfortably deep. You need to ask “why?” at least 5 times to get to the core of what drives you. (Coincidentally, getting to that place is where the essays get interesting.) Because of the way it forces deep introspection, the essay writing process itself is a powerful experience.

But when I arrived on campus and faced the deluge of academic, extracurricular, and social opportunities, I definitely was not focused on what mattered most to me. I was responding to what professors and others thought I should be doing rather than taking control and figuring out what I wanted to do.

This experience led to one of my key insights: if I don’t control my agenda, others will.

The first step I took to take back control was to put a sign on the back of my door that said, “What matters most to you?” It was a daily cue to reflect upon what I really wanted to do. Soon thereafter, I wrote down a statement of my values and started to try to align my time with the dimensions of the values statement. By the start of the second year of business school, I took a seminar called “The Quest for Happiness.”

And with that, the operating system was born.

“Why run on a treadmill when you can run on the open road?”

2. Increasing privilege.

My parents were both educators. We were never rich, but we had everything we needed to survive and thrive. In fact, it never occurred to me that there was any reason not to be content with that state.

Then, I went to Harvard. And then I worked at a consulting firm and visited the posh homes of the senior partners. And then I went to business school and became friends with people who had already had multiple years of earning six-figure salaries.

All of this changed my mindset. My mental goalposts for “being comfortable” or having “enough money” or having a “nice home” all changed. My 18-year-old self certainly would not have recognized my 27-year-old’s view of life.

Hence my second big insight: social influences can warp my view on what matters, so watch out.

For me, shifting one’s goalposts is particularly dangerous because it’s never ending. Before we got married, I told my wife that I did not see much value in a luxury car. But once I got a BMW, I become more annoyed at the minor design flaws of our Mazda (which is still a nice car!). We bought a comfortable rowhouse on Capitol Hill in Washington, D.C. Then I started looking at those corner lots, with houses that are twice as wide, and thought, “it’d be nice to upgrade eventually.”

When I was a consultant, I worked with a Partner who claimed that he had as much money left over at the end of each month now as when he was an Associate. I wondered how that could be. Then, he showed up to a team event (attending a cricket match) in his Porsche, toting his high-end watch and high-end camera. Basically, even though he had made more money each year, he had also increased his spending in the same amount.

In contrast, I once developed a financial model for my life. The key question it aimed to answer: when could I switch to a job in the public or nonprofit sector and still be comfortable?

The key finding: as long as my spending didn’t meaningfully escalate, everything would work out just fine. I could retire at a decent age, pay for kids to go to college, and afford good childcare for when the kids are young and still have a long career in service.

In fact, the model only didn’t work in the scenarios in which I bought nicer and nicer cars and a bigger and bigger house. If I did those things, I would need an ever-increasing private sector salary until I retired. It would feel like running on a treadmill, chasing a monetary goal that’s never in reach.

That point felt like the exact opposite of privilege. What’s the point of having lots of professional opportunities if you can never take them? Why run on a treadmill when you can run on the open road?

“Professional priorities have a natural advantage over personal to-dos.”

3. Having a demanding job.

My first job, in addition to a roughly 60-hours per week work schedule, carried the expectation of traveling to the client’s office four days each week. As a 22-year-old, I was happy to work hard and happy to travel. But there were several complications.

A trivial one is that my definition of a “good” hotel changed. Even when I traveled for personal reasons, I’d want to stay at a nice hotel, and would actively complain if that were not possible. I also came to have clear opinions on the merits of Four Seasons vs. Ritz-Carlton, which is just not the kind of guy I want to be :).

More importantly, because I was traveling or working well into the evenings, I missed out on the kinds of social events most normal 22-year-olds in a big city were attending. And on the weekends, I often didn’t have the energy to plan something or go out.

Hence, the next insight: Professional priorities have a natural advantage over personal ones.

This happens because most of our professional tasks come with deadlines, monetary incentives, and someone monitoring our performance (i.e., the boss, the client, the customer). For me, the only way to succeed in a way that was consistent with my values was to keep my personal priorities on the same level as my professional ones. And where, possible, put deadlines and a “boss” on my personal priorities.

“…progress came from inviting feedback and spending time reflecting…”

4. Starting my own business.

For about three years, I had my own fledgling start up business. And for a good part of that time, it was mostly a one-man band. I was chief developer, designer, strategist, accountant, and office manager.

Because of that it was easy to get buried in the weeds. And when things weren’t going well, it was often easier to take on busy work— like playing around with colors and fonts on the website— than really face the business issues that mattered.

This meant that there were weeks at a time that I did not make meaningful progress. In contrast, the times I made the most progress were when I had external feedback and spent time reflecting on what I really needed to accomplish.

Thus, another insight: if I don’t proactively generate moments of feedback and reflection, it’ll be hard to accomplish my goals.

So to recap, the insights that formed the basis of my operating system:

• If I don’t control my agenda, others will.
• Social influences can warp my view on what matters, so watch out.
• Professional priorities have a natural advantage over personal ones.
• If I don’t proactively generate moments of feedback and reflection, it’ll be hard to accomplish my goals.

All of those insights are key parts of why my system is the way it is. Again, everything is designed to fix everything I’m bad at. There’s no one system for all people for all seasons, and yours should be different from mine.

In Part 3, I describe the 5 Design Principles of the operating system.