I just came back from my MBA 10-year reunion, and before going, I decided to re-read Clayton Christensen’s book "How Will You Measure Your Life?" as I remembered that it started with him reflecting on the difference between his classmates at their 5-year reunion versus their 10-year reunion. Early on, everyone looked successful. Great jobs, prestigious careers, strong momentum. But by the 10-year mark, some of the cracks had started to show. Some relationships had broken down. Some people looked deeply unfulfilled despite all the external signs of success.

And after coming back from my own reunion, I found myself thinking about his observations a lot. The interesting part? My generation looks very different from his. Curious to hear what I found? Keep reading.

Tip of the Week: Your life already reflects your priorities, you just have to look at where your time, energy, and money are going.

Side Note: Trying to be reflecting about one´s life is extra hard when the world around you doesn´t stop and communication overflow seems to be getting out of hand.

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The Theory Behind

We allocate our lives the same way companies allocate resources. One of Christensen’s core ideas is that companies become what they invest in, and people do too. We like to think our values are defined by what we say, but in practice, they’re revealed by where we consistently invest our time, energy, and money. If we say we value family, health, friendships, or giving back, those things should show up in our calendars, habits, and spending decisions. Otherwise, we may be optimizing for something completely different without realizing it.

Small exceptions compound over time. Christensen writes about how dangerous “just this once” thinking can become. One missed dinner, one skipped workout, one extra weekend working. In isolation, none of those decisions seem significant. But repeated over years, they shape our lives. Somebody once told me that it’s easier to stay aligned with your values 100% of the time than 99% of the time (and now I know they were paraphrasing Christensen). I’ve always remembered that line because small compromises have a way of becoming patterns, even if we tend to minimize them when they occur.

The metrics we optimize for change over time. Early in our careers, success is usually measured through visible milestones: titles, promotions, compensation, prestige. But reunions have a funny way of exposing how much the scoreboard changes over time. Ten years later, conversations start shifting toward health, relationships, meaning, freedom, and peace of mind. The external metrics still matter, but they stop being sufficient on their own. Christensen noticed this in his reunions too: many people who looked successful on paper weren’t necessarily fulfilled. Over time, most of us start realizing that the quality of our lives depends on much more than career momentum alone.

What I’ve Learned

What surprised me most is that my reunion felt very different from the one Christensen described in his generation. He found classmates already dealing with divorces, broken relationships, and the consequences of years spent neglecting other parts of life. What I found instead was a generation that already seems highly conscious of balance, health, and meaning much earlier on. People were talking about wellness, parenting, nutrition, purpose, therapy, skincare, relationships, and designing intentional lives. Many of the lectures we received were actually centered around living a meaningful life, so maybe this shouldn’t have surprised me as much as it did.

I was also pleasantly surprised by how many people told me they read this newsletter and that it feels “authentic.” That word stayed with me. Because the older I get, the more I realize that authenticity is probably just alignment over time. When your work, your values, your interests, and the way you show up start pointing in the same direction, people can feel it. And honestly, hearing that mattered more to me than any title update ever could!

Make It Happen

1. Run a “calendar reality check.” Look at your last two weeks of calendar activity. Your priorities are probably hiding there more honestly than in your goals document.

2. Separate your “anchors” from your “batteries.” Anchors drain your energy. Batteries recharge it. Start noticing which people, meetings, habits, and environments consistently do each. Then ask yourself a hard question: does your life currently contain enough batteries to sustain the anchors?

3. Create a personal scorecard. Define 3–5 metrics you actually want your life to optimize for: meaningful conversations, family dinners, workouts, uninterrupted focus time, time spent creating, etc. If you don’t define your metrics, the world will define them for you.

4. Schedule relationship maintenance before you need it. Don’t rely on reunions to reconnect. Create recurring reminders to reach out to people you care about. Most relationships don’t end dramatically, they slowly drift through lack of intentionality.

5. Audit your “just this once” decisions. Weekly, review all the small exceptions (usually they are the real system). What keeps repeating eventually becomes your lifestyle.

6. Create life review moments. We review businesses quarterly and projects weekly. Very few people review their lives with the same intentionality. Build reflection points into your year before life starts drifting on autopilot.

Sometimes the most important metrics in life don’t show up until years later.

Measuringly,

Jorge Luis Pando

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