Simple Solutions, Hard Feelings
After reflecting on my learning on leadership and strategy, I asked multiple AI tools to “summarize my perspective on enjoying work and life” based on all five years of Monday Musings.
What Claude Told Me
“Your philosophy centers on making work feel less like work by designing life to minimize conflicts rather than optimizing time management. Most uniquely, you emphasize the ‘one-pot life’—integrating family, work, play, and health so they reinforce rather than compete. You focus on the Get-To/Have-To ratio, arguing that feeling ‘on the clock’ matters more than hours worked. You’re skeptical of competitive parenting and prestigious obligations that corrupt genuine joy. Critically, you believe we already have the power to create satisfaction—the constraint isn't resources but our willingness to define ‘enough,’ say no strategically, and recognize that most urgent work won't be remembered anyway.”
Solving the Emotional Challenge
As I reflected on that synthesis, I thought about the conversations I’ve had with clients when their work-life balance is off, and they feel stuck. I’ll often ask them, “If your good friend came to you with this situation, what would you tell them to do?” Almost every time, the solutions spill out quickly. In other words, it’s not a lack of knowledge of what they need to do to achieve a healthier life that keeps them stuck. It’s usually something emotional.
Simple solution: “I should spend more of my free time on activities that I authentically find enjoyable.”
The hard part: Many of the things that fill our “free” time are almost like work—i.e., meeting obligations for others and working on deadlines—but to shift behavior would require being “selfish” and disappointing others.
Simple solution: “I should spend more time at work on the activities that make it fun.” For example, if brainstorming with the team is fun, I should make sure the team invites me to those sessions, rather than just telling me about the results afterward.
The hard part: Eliminating “people at my level shouldn’t…” from their thought process. I usually hear it as, “People at my level shouldn’t do that kind of work,” or, “I’m too advanced in my career to take on an individual contributor role.”
I suspect what’s behind those statements is that we have endless scripts for climbing the ladder. We have almost no scripts for stepping sideways—or down—toward work that actually energizes us."
Ironically, I’ve recently met several people who see the benefits of giving up the fancy titles and getting back to what they really enjoyed about work in the first place. For example, a doctor friend told me that he’d only return to medicine if he could mimic the conditions that he had during a summer in a developing country—simply treat the person in front of you without having to deal with running the business or office politics. And I met a baker who talked more excitedly about his day making hundreds of baguettes than his previous career as a government executive.
Simple solution: “I need to hold boundaries more strongly and avoid taking on the company’s problems as my own.”
The hard part: Many of us have spent our whole careers—maybe our whole lives—being someone who takes responsibility and tries our best at everything, and that’s helped us succeed. Hence, it’s not in our self-conception to say, “It’s 5 pm, I’ve already done enough to justify my paycheck, and I’m moving on.”
In each case, shifting to a new relationship with work would require a more substantial change in mindset than the simple solution would suggest. All that said, what I’ve learned as an executive coach is that I can’t create that emotional shift for anyone. Nudging them on balance solutions only works when people are already leaning toward change.
Unfortunately, most people only change after something forces them to—a health scare, a crisis, a loss they can’t ignore. The real challenge is engineering those shifts before the crisis arrives, while we still have the luxury of choosing from strength rather than necessity.
What’s Interesting to Me Now
I’ve read a dozen books this year that predict an AI-apocalypse coming to the job market, an end of the American-led global economic order, or a collapse of a functioning democracy. Whether or not these predictions come true, the books pushed me to consider this hypothetical: “If next year is my last year earning at a decently high level, what would that mean?”
That question has obvious technical implications for financial planning, but it’s more interesting to me to think about what it says about my emotional relationship to work, status, and the things I consume.
How much of my self-esteem comes from having a job that society deems to be a “good job” or having an impressive title?
How much of my consumption is implicitly driven by social comparison rather than authentic enjoyment?
What would I do if I had to start from scratch?
I suspect that (a) those are the kinds of questions that are useful for everyone to ask in a moment where substantial disruption is possible, and (b) the people who proactively answer them and take action on the implications are much more likely to achieve an authentically balanced life, regardless of what happens.