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[New Insider Program] Why am I not happy?

What Feels Tolerable at First Eventually Becomes Intolerable.

…Sooner or Later,
You Have to Act.

I want to highlight the beginning of the release of a new 14-part program “Why am I not happy? How can I be happy?” available to Insiders and Legacy members. The first 2 episodes can be accessed here.

Also, only during the next 4 weeks period we will be taking questions for this program. As an Insider or Legacy member, you are welcome to email us a question for this program. If there will be some common questions that will be helpful for all Insiders and Legacy members, we may add additional episodes addressing these questions.

If you are a Legacy member, your question is guaranteed to get answered as an audio recording, taking into account your unique situation. Please ensure you submit it on 30th of April or 15th of May, including “Legacy question” as an email subject line. Those are the next 2 days during the upcoming 30 days when we will be taking Legacy members’ questions.

For Insiders, those questions that would be most relevant to the broader community will be considered, and we may create follow-up episodes addressing them.

If you have ever stopped to ask yourself, “Why am I not happy while others assume I have everything?” … you might find these reflections relevant.

Over the years, I have worked with senior partners from major consulting firms, private equity leaders, and CEOs of small, medium and large organizations. Some came right out and told me they felt stuck in a rut. Others never said it aloud, but small details, like needing 3 packs of cookies to get through the day, every day, hinted at a deeper discontent. They had all the outward signs of success (big expensive house, beautiful car, prestigious background, millions in their bank accounts), yet it was clear they weren’t happy.

Perhaps you have sensed something similar. Relentless achievement does not always translate into a genuine sense of contentment, let alone sustainable feeling of wellbeing and happiness.

Happiness is a feeling. It cannot be easily rationalized, it cannot be analyzed, deconstructed, or reconstructed. You are either happy or you are not.


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We live in a world where everything is measured and scrutinized, yet our feelings rarely respond to that kind of analysis.

I recall someone in one of our results clinics (part of the executive coaching program) asking, “How can I be happy? Why am I not happy?” and realizing that dissecting happiness into data points led nowhere.

It is like trying to enjoy a certain food just because it is popular. As Michael mentioned in one of the recent programs:

“If I do not like pizza in America (deep dish, thick crust, processed cheese), I do not torture myself asking, ‘How do I make myself like it?’ I just stop eating it.”

The same principle applies to a role, a project, or an entire career path. If you are forcing yourself to stay in an environment that never felt right, tolerance will eventually turn into frustration.

And if you are like me, before you know it, you will start getting signals from life, nudges at first, then stronger and stronger signals, indicating that something must change.


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Yet, the decision to walk away is not always so straightforward.

A slight variation in what you do and how you do it, as well as in your perspective, can make an enormous difference. Some of the most talented people I know left investment banking after one difficult experience, only to discover later there was a different niche where they could have done very well. They felt regret and that they had wasted an opportunity to create generational wealth and have a more successful career.

Others believed they were not suited for leadership, simply because they tried one rigid style. A minor shift made being a leader enjoyable for them.

We often attempt to measure what, by its nature, cannot be measured.

A feeling often cannot be explained easily.

It cannot be easily:
– rationalized
– analyzed
– deconstructed

Some choose to ignore it. You can mute it for a while, but then it comes back with a greater force.

So, it is important to listen to what feels right and what does not.

And, the change required is not always radical. Sometimes, it is a shift in perspective and then small adjustments.

In many situations, the answer is not, “Quit your job and head to a beach.”


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Instead, we guide clients to look more carefully at the patterns and assumptions that might be steering them away from genuine sense of wellbeing without them realizing it.

Reflect on this key insight:

Moving on does not necessarily mean abandoning everything you have built. Sometimes, it is about finding a better fit within the same broad space.

One small variation can reveal a new sense of alignment you did not know you were missing.

And sometimes it is about changing perspective.

If any of this resonates with you, there is an opportunity to explore these ideas at a deeper level with the new “Why am I not happy? How to be happy?” program for Insiders and Legacy members.

It is possible to blend ambition and drive with the kind of satisfaction you cannot measure on a spreadsheet. You do not have to choose between success and contentment. You can have both, once you recognize that happiness is not something you force. It is something you discover by recognizing your own natural preferences. As Steve Jobs said, find what makes your heart sing.

The first 2 episodes of the 14-part program was released for Insiders and Legacy members. Don’t let another program pass you by. The insights we share are unique, powerful, timely, and battle-tested. There is a reason we have many members who have been with us for years and years. As one of the long-term Insiders said in a recent conversation with me:

“The content is getting better every time… The thing with all the content here is that we kind of have to go through them. When you are put into that situation, you kind of like, okay, I picked up this concept from here. I review it because each person’s situation is different. But I know where to find them, and I always get results when I apply what I’ve learned.”

If you’re an Insider or Legacy member, this program is now available in your account on StrategyTraining.com.

Not a member yet? Enroll here: www.strategytraining.com (scroll to membership options and select Insider or Legacy level to immediately access this and other advanced Insider programs).

If you have any questions, feel free to reach out at [email protected].

Thank you for being a part of the StrategyTraining.com community.

Access First 2 Episodes

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