My Sabbatical Didn’t Make Me Happier

I am currently figuring out the next iteration of a sabbatical group. You can read about our last one here and you’d like to sign up for the waitlist for what might be next, you can do so here.

Last week, I was talking with a group of professionals about AI and what it means to live inside this particular moment, with all of its promise and disruption sitting right next to each other. There is real upside in what AI may unlock. There is also real loss in what it may displace. The acceleration can feel energizing, especially for those of us who like building, learning, and imagining what becomes possible when constraints start to fall away. It can also feel unsettling when you consider what it means for work, identity, expertise, creativity, and the many ways people have learned to feel valuable in the world.

As the conversation unfolded, I noticed how quickly AI pulls people into binary positions. Are you thoughtfully outsourcing or simply offloading? Excited or afraid? Building or resisting? Accelerationist or doomer? That framing has started to feel less useful to me because it asks us to simplify something that is not simple. The more honest place is the one where we can acknowledge the full reality of what is happening without collapsing into a single stance too quickly.

What surprised me in that discussion was my ability to sit with the tension.

That ability is newer for me than I would like to admit. It did not come from reading more about technology or developing a sharper point of view about the future of work. It came from my sabbatical. More specifically, it came from the part of my sabbatical I did not expect. I thought the time away from work would help me feel happier. What it actually gave me was more peace, more spaciousness, and a greater capacity to hold more than one truth at a time.

When I stepped away from work, I had a fairly clear expectation of what that time would give me. I expected relief from the pace and responsibility of my previous life. I expected my energy to return. I expected space to think, read, write, and eventually shape whatever would come next. Underneath all of that was another expectation I had not fully examined: I expected to feel happier.

There was a logic to it. If the pressure was removed, if the calendar opened up, if I no longer had to carry the constant weight of executive responsibility, something lighter should emerge. With enough rest and distance, I imagined I would return to myself in a way that felt joyful and clear. I may not have used those exact words at the time, but that was the assumption underneath the plan.

Of course, I had a plan. I approached the sabbatical the way I had approached most things in my professional life. I read extensively. I tried to make sense of the phases I was experiencing. I looked for structure, models, and frameworks. Some part of me believed that if I could understand the map, I could move through the terrain with some efficiency.

That is not how it worked.

The early weeks looked productive on the surface. I kept myself busy, closed loops, had conversations, and started thinking about what might come next. Then my energy dropped in a way I could not override. My days became smaller and simpler: sleep, kids, walks, reading, writing, meals, more sleep. The fatigue was deeper than tiredness. It was the kind of exhaustion that does not respond to effort because effort is part of what created it in the first place.

At first, that felt disorienting. Later, I understood it as the beginning of the work.

The shift that happened during my sabbatical did not arrive as a single revelation. There was no dramatic moment where everything suddenly made sense. It was gradual enough that I almost missed it.

I began to notice that I felt steadier. Not happier in the way I would have defined happiness before. There was not a constant sense of lightness or excitement. My days were not suddenly filled with obvious joy. Many of the external markers I would have used to measure whether I was “doing better” were absent.

What changed was my baseline.

There was more space in my thinking. I had more patience with questions that did not yet have answers. I felt less urgency to fix, decide, optimize, or move something forward before it was ready. I could notice competing truths without immediately trying to reconcile them. I could grieve the identity I had left behind and feel real curiosity about what might come next. I could miss parts of my former life without wanting to return to it.

At some point, I realized the sabbatical was not making me happier. It was making me more peaceful.

I still value happiness. I feel it in small moments with my family, in good conversations, in the right kind of work, in a walk when the light is just right, in the rare stretch of time when nothing feels particularly urgent. Happiness is lovely when it arrives, and I notice it more now than I used to.

The problem is not happiness itself. The problem is making happiness the primary measure of whether a life transition is working.

Happiness is more dependent on conditions than we often want to admit. It can be affected by the weather, a conversation, a difficult email, a child’s mood, the state of the world, or the amount of sleep we got the night before. During a sabbatical, or any meaningful transition, happiness may come and go. If we make it the goal, we can start to believe something has gone wrong every time it disappears.

Peace operates differently. Peace does not require everything to be settled before you feel grounded. It can make room for uncertainty without turning uncertainty into an emergency. It can hold grief for what has ended and openness toward what is emerging. It can allow concern, ambition, hope, fear, gratitude, and loss to coexist without requiring one of them to win.

That is the expansiveness I did not know I was looking for.

A sabbatical sounds spacious from the outside. It sounds like rest, freedom, and time. Those things can be true, but they are not the whole story. For someone who has spent decades moving quickly, producing consistently, and using achievement as a stabilizing force, spaciousness can feel deeply uncomfortable at first.

The structure that used to organize your life is gone. The identity that used to explain you to yourself and others becomes less reliable. The calendar opens up, which sounds wonderful until you realize how much noise had been protecting you from certain questions. Without the familiar pace, you have to encounter what is actually there.

That is where the real work begins.

I’ve described the sabbatical in phases: rest, reconnect, reimagine, rebuild. I still believe that map is useful. It gives language to an experience that can otherwise feel vague and unsteady. Yet the map can make the process sound cleaner than it feels. In reality, the phases overlap. You may feel rested one week and completely depleted the next. You may experience clarity in the morning and doubt by dinner. You may believe you have released an old identity, only to discover another layer of attachment waiting underneath it.

The work is learning to stay present anyway.

Over time, that practice changes you. You stop needing every question to have an immediate answer. You stop assuming discomfort means something has gone wrong. You build trust that something can be unresolved and still be moving. You begin to understand that clarity forced too early is often just control in disguise.

This is why the AI conversation stayed with me. It reminded me that the capacity I built during my sabbatical was not limited to my own transition. It applies to any moment where the old markers are breaking down before the new ones are fully formed.

AI is one of those moments. So is midlife. So is a career transition. So is parenting teenagers. So is aging. So is stepping out of a role that once gave you status and structure. So is trying to build a different kind of life when the old one no longer fits.

These moments ask something different from us. They do not only ask for intelligence, strategy, or speed. They ask for discernment. They ask for presence. They ask for the ability to see clearly without reducing the complexity simply because complexity is uncomfortable.

I can see the promise of AI and the risk. I can be interested in what it makes possible and concerned about what it may erode. I can believe it will create new forms of work and also understand that many people will experience a real loss of identity as old forms change. I do not have to choose one truth in order to be credible.

That feels like a more mature place to operate from. It also feels like a more human one.

For anyone in the middle of a sabbatical or significant transition, the distinction between happiness and peace can be reassuring. There is often a point when you begin to question whether the experience is working because you do not feel better in the way you expected. You may have more awareness but less certainty. More honesty but less momentum. More clarity about what no longer fits without knowing what does.

That can feel like regression. It may actually be expansion.

The ability to hold more truth often arrives before the ability to act on it. First, you see more. Then you feel more. Then you learn how to remain steady inside that increased awareness. Only after that can you begin to make choices from a different place.

This is not as satisfying as a clean breakthrough story. It does not make for a neat before-and-after narrative. It is slower and less dramatic than that. It is also more durable.

The other side of my sabbatical has not been a permanent state of happiness. I do not wake up every day feeling light, clear, and certain. I still have complicated days. I still experience doubt. I still get pulled toward urgency, overthinking, and old patterns.

The difference is that I recover more quickly. I can see myself more clearly. I can engage in work without disappearing into it as completely. I can care about outcomes without attaching my entire identity to them. I can sit in a conversation about a complicated future and resist the urge to make it simpler than it is.

That may sound subtle, but for me, it has become a kind of superpower.

I used to think the goal was to build a life that made me happy. I still want happiness in my life. I want joy, pleasure, ease, laughter, and delight. I also know now that those are not strong enough to carry the full weight of being human in a complicated world.

Peace has more strength in it. Spaciousness has more utility than I understood. The ability to hold multiple truths at once may be one of the most important capacities we can build.

My sabbatical did not give me the happiness I thought I was chasing.

It gave me the ability to live with more of what is true.

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