The Unintuitive

The Unintuitive

The Alchemy of Aliveness: Stop Sleepwalking

151: Why most people spend their lives miserable.

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BOSS
Aug 08, 2026
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Humans know what makes them feel most alive, and then they don’t do it most of their lives. - Patrick O’Shaughnessy

After starting this year off strong and planning our goals without a clear vision. Overachieving everything we had set for ourselves. We have found ourselves in a position where we didn’t know what to do. At the same time, there is this feeling that gives you joy and energizes you. Knowing you have achieved what you planned before you were supposed to do it. But on the other hand, there is this feeling that you know you have planned things poorly and underestimated what you are capable of. Finding ourselves in a loop in which we don’t know whether we should be happy or sad because we managed to do it.

From a young age, we have all been convinced that chasing goals should be standard. Mandatory. Something that, if you are not doing it, is wrong. Without having someone else explain to you that once you achieve that big vision and what you have planned for yourself. There will be a BIG disappointment at the end. The emptiness of a big vision you had.

After a few months, some thoughts and sleep on it. The conclusion and the reason we were not feeling the way we should is that the goals we were after were giving us a sense of aliveness. Why were we doing the things we were doing. What it was all about and why it mattered. All packaged into the form of goal(s).

What came out of that was the idea that all of us, instead of chasing goals and building out the system to achieve them. Our time would be better off optimizing for a sense of aliveness and doing everything we can to keep that feeling alive. On the long-term horizon, it makes much sense to know what you desire and how to align that desire with who you want to become. More so than relying on a checkbox (your goal) you might or might not optimize everything to mark off.

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Aliveness vs. The Grind

We found this documentary, Comedian - thanks to this masterpiece of a post. It shows the perfect example of our point. It follows Jerry Seinfeld and young up and coming comedian Orny Adams.

After taking 2 hours and watching the documentary. The simple conclusion is that Seinfeld is in an eternal pursuit of aliveness, to the point that he is the eternal student of the game. He is one of the most successful comedians in history, well over 9 figs at that point. To see him going to small clubs day after day. All around town. Practicing how to get back into the game and get his groove on.

Orny Adams is the complete opposite. So hungry to the point that he ends up looking miserable because of the fake self-confidence he projects throughout the movie. Mixed with that hunger he has for success and his wondering what others will say about him. The result? It looks like desperation, as the director positions him. Thinking the end goal is the only thing that matters, based on how much effort he is putting in. Ignoring the REAL reason why he should be doing what he is doing.

We would recommend you give this a watch and pay attention to the differences.

Based on this video alone, you can see the approaches both of them take to the same craft. Night and day difference. Orny is completely transactional about his craft, thinking that because he is crushing his goal, doing the things day in and day out. He deserves to make it. Once you watch the documentary, you realize it gets much deeper than that. Everything he does that is not related to comedy feels like failure to him. He feels he is wasting his time by not doing what he should. Making himself more and more miserable in the process. Again, something you will notice if you watch it. Seinfeld’s approach? Infinite game. Eternal student. Addict to the game. Winner. The difference between the two? Massive. The one if you are not understanding yet. Will click as you read this further.

Goals and YOU

Since the early days of your life. Your teachers, the media, and even your parents have sold you a lie that chasing goals should be your 24/7 priority. To the point that if you do not have goals or are not 100% sure what you want... You are a loser. There is some truth to that, in the sense that you have to have an outline of where you are planning to go or what your end destination looks like. Not a complete picture. Just enough to keep you down and working toward it.

Why so much talk about goals? Because they are great. Great for those starting or trying to improve themselves. We even published our own guide on goal setting last year to make it more practical and show how to pull it off. Let’s say you are getting into fitness and want to change how you look and feel.

There is nothing wrong with having a bunch of small, realistic checklist-type goals you can get over in the next month. Just starting to lift weights and wanting to increase your lifts by 10 lbs? It is not that hard. Would this same approach work for someone who has spent 2 decades working out and is already at the top of his physical capabilities? Not really. Just adding 5 lbs to the shoulder press is HARD work, and everyone who’s done it knows it. This is where those goals shine. When you can see progress on a week to week (if not even day to day) basis.

But once you are past that stage and into more serious territory, progress gets much slower. This doesn’t mean you can’t structure your goals once you have moved beyond the beginner phase. It means they are much harder to position correctly and often lead you toward things you shouldn’t be doing in the first place. Usually wasting your time over-optimizing something that isn’t worth it in the end. Wasting your precious time and energy while ignoring the rest of the picture, giving you more space to do things wrong.

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