Good morning,

Thank you to everyone that replied last week with feedback on the multimedia additions to these letters.

This week includes another video explainer, plus a podcast.

Let’s jump in! 🦘

1️⃣ ONE BIG THING

CEO of your life: a conversation imagined.

Imagine Clayton Christensen and Peter Drucker having a long conversation about life.

Each had developed influential theories on business innovation and management. As they aged, they observed human tendencies and varied outcomes among friends and colleagues. Both explored how to apply business theory to personal life, spreading these ideas through speeches and publications.

I imagined the two of them deeply engaged in conversation over coffee, seated at a quiet corner table in a well-loved Boston bookstore, the shelves surrounding them and the city bustling just outside.

My letter today draws on this imagined conversation, focusing on what practical lessons we might take from Drucker’s Managing Oneself and Christensen’s How Will You Measure Your Life?

I put this together in three formats:

1. Simulated podcast.

2. Video explainer.

3. A written summary.

CEO of your life: the podcast.

CEO of your life: a video explainer.

CEO of your life.

Christensen and Drucker sit down for a chat over coffee.

Christensen opens with a question that lands hardest on high-functioning people:

“How do capable, decent people end up with lives that don’t feel like theirs?”

He’s talking about gradual misalignment: work expands, relationships get postponed, health becomes “later,” meaning gets deferred until things calm down.

Drucker nods and translates it into a structural fact: in the modern world, nobody is managing your arc for you.

You’re your own CEO. Drift is common. Drift is also correctable.

Your life already has a strategy—because you already have an allocation.

Christensen replaces inspiration with mechanism, saying “Your real life strategy is what you fund.”

Your currencies are time, attention, energy, and emotional availability. That’s the budget your life runs on.

Work provides fast feedback loops—completion, praise, progress. Other domains (relationships, health, community, purpose) compound slowly. Their costs are easy to ignore until midlife makes them visible.

So the simplest audit is your calendar.

What did you “buy” with last week?

The hidden villain is the scorecard you didn’t choose.

Drucker introduces the question that slices through a lot of midlife fog:

“Who gave you the measurement system you’re using?”

Most of us absorbed a default scorecard early: status, money, productivity, being needed.

Those metrics can build a life. They can also crowd out quieter measures that matter more later: trust, integrity, health capacity, creative output, presence, contribution that actually feels like yours.

Drucker’s “mirror test” is his blunt shorthand: can you respect who you are when you’re alone with yourself? If your values and your environment are out of sync, friction becomes your baseline.

Christensen adds a second layer: the biggest shifts usually happen by inches. “Just this once” becomes a habit. A reasonable story becomes a pattern. Over time, you don’t simply make choices—you become a person who makes those choices.

Midlife gets loud when your scorecard starts contradicting itself.

Self-knowledge is the second act advantage.

Drucker takes the conversation somewhere refreshingly unromantic: strengths, performance, fit.

Most people are wrong about what they’re good at. His fix is simple: feedback analysis.

Write down what you expect will happen when you make an important decision. Revisit it months later. Compare expectation to reality. Patterns emerge: where you create results, where you sabotage yourself, what you consistently misunderstand.

Then Drucker pushes three questions that matter more in midlife than in your 20s:

• How do I actually work best? (reader/listener, solo/team, decision/advice, structured/chaotic)

• What values am I unwilling to trade away?

• Where do I belong now, given the person I’ve become?

Christensen likes this because it matches real strategy: you don’t win by trying to be well-rounded. You win by placing your resources where you’re strong and where the returns matter.

The second half of life rewards alignment.

Drucker says the “midlife crisis” is often boredom wearing a dramatic costume. You’ve mastered your role, your learning curve flattened, and you still have decades of runway.

Christensen reframes boredom as feedback: your investment mix is outdated.

Drucker offers three classic paths for the second half:

• A second career (a real pivot)

• A parallel career (meaningful contribution alongside your current work)

• A social venture (building something that serves beyond you)

Christensen adds the constraint that keeps all of this grounded: the second act gets built by weekly allocation. The future shows up in the budget.

Three ways to apply this right now:

1) Run a “Governance Audit” of your time and money.

Your life strategy isn’t what you say matters. It’s what you consistently fund with your time, energy, and money. High achievers drift because work pays fast rewards (progress, praise, promotions) while family, health, and friendships compound slowly and quietly.

This month, do a governance audit:

• Review your last 30 days of calendar and spending. Don’t rely on self-talk—use the data.

• Spot the mismatch between what you claim is important and what you actually prioritised. If your family is “number one” but gets only leftovers, your real strategy is different from your intended one.

• Watch for “just this once.” Small exceptions feel cheap in the moment, but they create a trajectory. Standards are easier to hold 100% of the time than 98%.

2) Start “Feedback Analysis.”

Most people think they know their strengths and working style, but they’re often wrong. You can’t build a great second half on weaknesses. You build it by compounding strengths—and designing work around how you truly perform.

Begin now:

• When you make a key decision, write down what you expect will happen.

• List what must be true for your expectation to be right. Ask: “What evidence do I have?”

• Set a review date (90 days is fine to start; 9–12 months is ideal for bigger decisions). This prevents you from rewriting history later and reveals patterns in what you do well—and what you should stop doing.

• Name your natural mode: reader or listener, writing/talking/doing learner. Working against your nature is a quiet path to underperformance.

3) Use “Jobs to Be Done” in a key relationship.

Many relationships fail because we give what we want to give, not what the other person actually needs. Treat your spouse/child/friend like a “customer” in the best sense: what are they trying to solve right now?

• Ask: “What job are they hiring me to do today?”

• Remember: the same person has different jobs at different times—problem solving one day, simple empathy the next. If you offer solutions when they need understanding, you miss the job.

• Then do the job, even when it costs you something. Sacrifice is often the mechanism that deepens commitment.

Do these three things and you shift from hoping for a better life to deliberately building one.

Thanks for reading this week.

Have a great week.

Kevin

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