BOSS Letter

BOSS Letter

The Personality System That Actually Connects The Dots (+ Prompts That Do the Hard Part)

132: Personalities. System. Prompts. You.

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BOSS
Feb 26, 2026
∙ Paid

Welcome reader! This post is something we have never done before. Giving you a breakdown of how to figure out WHO you are. Requirements? Some background information, a few questions you should ask yourself, a few tests to help you, and enough energy. Plus some prompts that will provide you with insights you never thought about.

We have been talking about this for months.

What You Need To Run This

Things you will need:

  • Pen and paper. Not necessary… But it will help.

  • Space and some time.

  • Answer 21 questions about where you are and who you are. This will be 10x faster if you have already worked with the mindset workbook.

  • AI tool of your choice

AI tools

  • Claude - $20

Some tests are free (such as MBTI), while others are not (such as wealth dynamics). We will provide you with the links that are closest to the original stuff. By original, we mean the paid versions (official ones). If you do not care about it and just want the official ones… Here is what it would look like.

Cost breakdown

  • Free route: $0

  • Budget (AI + most important ones): $50 to $120

  • Complete (AI + official tests - overkill for most): $160 to $250

The next step is deciding how deep you want to go and what you want to get out of this. You need a clear answer to why you are doing this.

There are three possible scenarios

  • Level 1 - Takes about 4 hours.

  • Level 2 - Takes about 6 - 8 hours. Depending on how many tests you complete.

  • Level 3 - Takes about 10 - 12 hours. Overkill for most people. Something for those who want to take things to another level. There is an opportunity cost associated with this level.

This system will help you gain insights into things you never thought of before. Mostly coming down to awareness and connecting the dots. From your social life and why you behave as you behave, all the way to your career or running a business. Working around your pattern recognition mechanisms.

It is worth mentioning that:

  • This system serves as a personal operating manual. Giving you insights into who you are.

  • Without putting effort daily (in all areas of your life). This won’t matter.

  • Personality patterns are real. You can’t go against them.

  • The important part is to approach this from a fun perspective. Some tests will be life-changing and make you nod your head. Others might tell you something that is completely off from what YOU think about yourself. Pay attention.

When not to do this

  • You are feeling lost or in crisis mode (doing things that lead you nowhere).

    • This process will point you towards something that might not be the best for you… But best for the type of personality you have.

  • You do not have a few hours to spare.

    • The reason you do not want to rush this is that tests alone will take you a solid amount of time if you are really reflecting.

  • You have not done the first part - answering the questions.

    • This is key because it allows you to compare your beliefs and self-perception with your test results.

  • You are under pressure.


Choose Your Level

Level 1. - Getting To Know Who You Are

  • Time needed: 3 - 4 hours

    • Answering the initial questions: 30 min

    • Assessment (3 of them): 1 - 2 hours

    • AI Prompting: 1 hour

    • Analyzing + reflecting + Implementation advice: 30 min

  • Cost: $0 - $50

  • Who should do this?

    • Those who have never done something similar or have zero idea about their personality characteristics.

  • What you will be able to answer:

    • How you process the information and what type of work energizes you.

    • Core traits and values (things you are naturally good at).

    • Career paths and social dynamics that actually fit you.

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Level 2. - Optimization (Career + Biz)

  • Time needed: 6 - 8 hours

    • Answering the initial questions: 30 min

    • Assessment (5 of them): 3 - 5 hours

    • AI Prompting: 1.5 hours

    • Analyzing + reflecting + Implementation advice: 1 hour

  • Cost: $50 - $120

  • Who should do this?

    • Those who are looking deeper into the motivations and relationship approaches (from a romantic perspective, all the way to running a business)

  • What you will be able to answer:

    • Why do you do certain things in relationships

    • What business models and structures fit you

    • Why do you clash with certain personality types

Level 3. - Complete Overview

  • Time needed: 10 - 12 hours

    • Answering the initial questions: 30 min

    • Assessment (7 of them): 5 - 7 hours

    • AI Prompting: 2.5 hours

    • Reflecting + Implementation advice: 2 hours

  • Cost: $160 - $250

  • Who should do this?

    • Those who are hiring people, working in complex environments, or want to be fully in line with who they are.

  • What you will be able to answer:

    • How to build a team (it is not as easy as everyone claims)

    • Your leadership style (better said, how others perceive you)

    • Business models and structures that align with your type

Don’t skip the levels: If you want to do all three levels, that is fine. But understand that to get the most out of it, you want to do levels 1 and 2 first. If you have already done them and have results. Perfect. Feel free to skip those levels if that is the case, and start with the others.


The Tests This System Is Built Around (+ Where To Take Them)

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