Yesterday, we had the first MasterPlan Annual (MasterPlan 365) session with the new group. The first session is always interesting.

At the beginning of the call, we explained two things we wanted to focus on. The first question was what was your trigger moment to enroll in the MasterPlan program? The second question was whether clients wanted to focus on the long-term track of putting together their Master Plan for the next 10, 20, or 30 years, or whether they wanted to focus on the short-term track where they are dealing with a particular problem or opportunity this year.

Those two questions helped us start gaining a deeper understanding of each client’s situation and how we can best help them identify points of growth.

One client said the trigger was that he felt stuck overall in his career, and no matter what he was doing, nothing was moving him forward. He had been speaking with people in his network, and they kept telling him they didn’t think he was clear on what he wanted to do next.

Eventually, he realized he needed help beyond his immediate network. And since he was an Insider for over 4 years, he naturally thought of a team that already helped him via Insider programs.

Another client described it slightly differently. He said he is relatively happy with where he is right now, but he doesn’t want to end up in coasting mode. He said he doesn’t want to get to a point where, in five years, he looks back and thinks that was half a decade he just wasted.

Another client described a very specific trigger moment. He received a phone call from his manager. The manager asked the client to stop working on a particular project that the client was working on in his free time, for the benefit of the organization. He said logically, he could just stop working on it and continue with something else. But the situation kept bothering him, and it was consuming too much of his mental bandwidth. Even when he was having dinner with his partner, he was still thinking about it. Something wasn’t right.

We discussed the difference between short-term planning and long-term planning.

Most people focus on the short term. One year. Two years.

But many people end up really unhappy later because they never planned where they needed to be in the long term. You can be very successful in the short term and still end up moving away from where you actually want to be in the long term.

Then the conversation moved to the fundamental thing we no longer teach anyone: how to be happy.

When you go to school, nobody teaches you how to be happy. When you go to university, nobody cares about it. When you interview for a job, the number one goal of society is to make sure you become a self-sustaining economic unit.

Someone who is not a burden. Someone who provides a surplus.

But nobody asks whether you are actually happy.

This leads to something we see again and again. People confuse happiness with achievement.

Happiness is a feeling. It is not something you calculate.

Many people look at what they have achieved and then decide whether they are happy. But that is not happiness. That is satisfaction or contentment. You are grading yourself.

And grading yourself is not the same thing as happiness.

You can achieve everything society asks you to achieve. The right schools. The right firms. Very senior levels. And still not be happy.

That happens to many people.

This is why the MasterPlan does not focus only on career. There are four primary elements we look at: health, wealth, relationships, and life’s purpose.

Wealth is only one of them.

Another thing we discussed during the session is something people often underestimate.

In life, you get a few major pivots. Each time you make a pivot, you may have to wait five to ten years before you see whether it works.

If it does not work, you may have lost ten years.

That is a long time.

That is why the MasterPlan is not about predicting the future. It is about understanding yourself.

Your motivations. Your capabilities. Your values. Your goals.

There is no point in creating a plan you cannot implement.

And the MasterPlan is not a static document. Think of it as a living document. Something you always iterate on and upgrade.

As you change as a person, your vision for the future will also change.

Very few people actually invest the time to do this. To really think through what they want in life and to put together a plan that helps them move in that direction.

MasterPlan is also about gaining momentum.

Many people feel stuck. They try different things, but nothing seems to move them forward. It feels like they are putting in effort, but the situation does not change.

One thing we see again and again is that people underestimate the importance of momentum.

When you start making decisions that move you in the right direction, even small ones, things begin to shift. You start having different conversations. Opportunities appear. People start seeing you differently.

Momentum builds over time.

And once you have momentum, it becomes much easier to keep moving forward.

Applications for the MasterPlan Annual are closed right now.

But if reading this made you think about where you are going, that usually means you have already started asking the right questions.

If you are not yet an Insider or Legacy member, you can enroll here and gain access to the programs our community uses to rethink their strategy, careers, and leadership decisions.

As I mentioned, MasterPlan Annual sessions officially started yesterday, and applications are closed. The discussions in the first session were fascinating, and I wish more people could hear them. We may open applications again later in the year.

Take care,

Kris Safarova