Ultimate Guide to BIG Goals

Dreams → Action Plans

Welcome back to THE JAILBREAK.
(along with 650+ readers 🤯)

I’m going to cover 3 goal-setting exercises that have helped me go from completely lost in life, to having absolute clarity over the things I want and with an actual path to get them.

By the end of this email, you won’t just have goals …

You’ll have a roadmap to your dream life.

The tragedy of life doesn’t lie in not reaching your goal.
The tragedy lies in having no goals to reach.
It isn’t a calamity to die with dreams unfulfilled,
but it is a calamity not to dream.
Not failure, but low aim — is sin.

 — Benjamin E. Mays

Not failure, but low aim—is sin.

Before we get started I want to give a bit of a disclaimer:

When setting truly large goals, for the love of God…

Aim high.

If your goal is to “get absolutely shredded”, you’re probably going to make it further than someone whose goal would be to just “get in better shape”. You’ll rarely find someone who sets a goal and then blows right past it, but people who aim high usually make more progress than those who don’t even if they don’t end up hitting their goal. If I want to run a marathon and I crap out at mile 10, I still absolutely crushed the guy who only ran a 5k.

This is also not the time to succumb to societal expectations. Your parents, your friends, and everyone you’ve ever met have preconceived notions about who you are and what you should be. If you adopt the identity that is forced upon you by society, you’re likely going to adopt the goals society thinks are good for you — the problem is that these goals ARE NOT YOURS and they will not lead you to fulfillment and true self-actualization.

  • What do you want to experience?

  • What would you do with your life if nobody knew you?

  • What would you regret not having done with your life?

Be selfish, be honest with yourself, and aim high.

Okay — enough motivation. Get out a pen and paper.
Let’s get down to business.


This is a technique designed to help you find what you want in life.

Learn more at RIGSMethod.com

Without having a clear idea of the things you want to happen in your life, it’s almost impossible to set goals that feel truly meaningful. Without meaningful goals, it's almost impossible to do the hard work required to get to the other side of success.

Exercise 1: DO

Step 1 is to Write 3–5 things that you want to DO before you die.

What experiences do you want to have in your lifetime?

Life is finite and so is the list of peak experiences that you can have and often if these experiences aren’t explicitly defined they don’t happen. Most people don’t accidentally run an Ironman or visit every continent by happenstance. You need to define your dreams.

  • Examples: Traveling the world, starting a business, learning filmmaking, or performing original music to an audience

If you were 90 years old and on your deathbed, what would you regret not having experienced?

Exercise 2: BE

After writing what you want to DO in your life…

Write 3–5 things that you want to BE in your lifetime.

Channel your inner child when being asked:
What do you want to be when you grow up?

You can think about this in terms of titles and identities and you don’t just have to pick one. We take on many of these titles over our lives but without defining what we want our title to be, the world has a way of forcing one upon you. We want to avoid this.

The goals around what you want to DO are vital, but they are only part of the equation. Understanding what you want to BE taps into your character, your values, and the version of yourself that you want to become.

A musician doesn’t merely play music; they live, breathe, and exist in a world defined by melodies and harmonies. A good person doesn’t just do good things on occasion, being a good person is the bedrock of their identity and from that foundation is where they make their decisions.

You channel the world you experience through the identity you assume.

Who you think you are will affect what you do, so having an identity that matches your goals is just as important as the goals themself.

  • Examples: Musician, Pro Snowboarder, CEO, Parent, World Record Holder.

After you’ve found what you want to DO and who you want to BE, it’s time to figure out what you want to HAVE.

Exercise 3: HAVE

While I do try to practice minimalism, it’s essential to know what possessions (material or not) you want to attain.

Write 3–5 things about what you want to HAVE.

  • Examples: Financial Independence, A Sports Car, a Supportive Group of Friends, Nobel Prize.

From tangible items like Lamborghinis to abstract things like personal freedom (which I recommend more than sports cars), knowing what you want to have will give you insights into what you should do.

Exercise 4: Sacrifice

After writing down the things you’d like to DO, BE, and HAVE in your lifetime, you might feel a sense of boundless possibility. But remember that we’re only here for a short time.

Part of the beauty of life is the fact that we can’t do everything. And big goals take sacrifice.

This brings us to the most critical (and probably the most difficult) part of this entire process.

From your list, circle ONLY the top 3 most important items.

These are your non-negotiables, the goals that you’re willing to devote your time, energy, and resources toward achieving — the dreams that you’d most regret not achieving.

You’re probably not going to be the first astronaut to walk on Mars and become the best violin player in the world. You can’t spend 100 hours a week running a successful business and expect to have enough time to write romance novels and spend time with your family.

This isn’t to say you need to abandon all but 3 of your dreams, but if you want to achieve something truly great — you need to know which dreams matter the most.

The Problem

After sacrificing the goals that aren’t truly important, you now have a focused and honest list of the things you truly want to achieve — this exercise will provide a starting point for creating the life you want but it doesn’t answer one fundamental question that stops 99% of people from achieving their goals:

I know what I want to achieve…
But how do I actually get there?


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Reverse Iterative Goal Setting (RIGS)

Learn more at RIGSMethod.com

Achieve Your Goals with Reverse Iterative Goal Setting

The RIGS Method, which stands for Reverse Iterative Goal Setting, is a powerful technique I designed to help you reach your goals. Unlike traditional goal-setting methods, the RIGS Method works in reverse by starting with your end goal and building a clear path to success.

RIGS Method also separates input and output goals, allowing you to work strategically towards your desired outcome without having to stop at roadblocks caused by things outside of your control.

How Does the RIGS Method Work?

I’ll use myself as an example. One of my current goals is to join the YouTube Partner Program so I can monetize my YouTube channel.

To be eligible, I need to achieve specific milestones:

  • Upload 3 videos in 90 days (input goal)

  • Gain 500 subscribers (output goal)

  • Accumulate 3000 hours of watch time (output goal)

In the RIGS Method, these milestones (or criteria) for hitting my goal are considered separate projects. Each project represents a significant step towards the end goal and completion of all projects results in 100% completion of the goal.

If your goal is to get jacked, your projects might be:

  • Put on 15lbs of muscle (output goal)

  • Get to 10% body fat (output goal)

  • Workout 5x per week (input goal)

  • Learn about nutrition (input goal)

Keystone Actions and Iteration

What sets the RIGS Method apart from traditional goal setting is the emphasis on the importance of “Keystone Actions” and “Iteration” to keep progressing toward your goals when you’ve run out of actionable input goals.

Keystone Actions

Simply uploading 3 videos won’t guarantee 500 subscribers or 3000 hours of watch time. However, uploading videos is a fundamental input goal that I can control. This is my “keystone action” for achieving my goal.

Same with working out — going to the gym 5x a week won’t guarantee you get the results you want. But you’re not going to put on muscle if you’re not consistently making an effort in the gym. 


After completing the initial goal of uploading 3 videos or consistently going to the gym, you need to pair the keystone action of uploading a video or working out with an iteration that benefits another project

For example, I can complete my keystone action of uploading a video but iterate for better subscription rates or higher watch time.

I can complete my keystone action of working out but iterate for lower body fat % by adding cardio into my routine.

By iterating on your keystone actions, you will also get better at the action itself. This will help you start to tackle larger and larger input goals in the future.

To learn more about the RIGS Method for goal setting check out rigsmethod.com.

Now there’s only one thing standing in your way from achieving everything you’ve defined. Fear.

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Fear Setting

Achieving goals isn’t just about knowing what you want. It’s also about understanding and navigating the fears that could potentially hold you back. Fear is natural — it’s built into us to help with our survival, but often, it’s not based on reality, or it’s an exaggerated perception of it.

Learn more at RIGSMethod.com

Fear Setting is a method I learned about from Tim Ferris that helps you deconstruct those fears, making them tangible, and creating strategies to overcome or mitigate them. You can do this exercise yourself by getting a piece of paper and drawing 3 columns.

1. Define

In this column, write down in detail every fear you have related to your goal.

Fear is like a shadow in your bedroom. In the dark, in the middle of the night, there’s a silhouette of something terrible lurking just out of sight — this is your fear. Pulling the covers over your eyes and refusing to see what that fear actually is will make it all the more terrifying. But if you get out of bed and flip on the lights, you can see that the monster in the corner is just a jacket hanging on a lamp. Not so scary.

If you want to conquer your fears, name them. For instance, if your goal is to start a new business, you might fear losing your savings, facing criticism from people you respect, the possibility of the venture failing, or even the fear of it succeeding. In as much detail as you can, write down everything you’re afraid of encountering on the road to your end goal.

2. Prevent

In the second column, write down everything you can do to prevent those fears from coming true.

If you’re afraid of losing your savings when starting a business, you can take courses on financial management or budgeting, or even consider getting a financial consultant to guide you. These things would at the least create a buffer between you and your fear.

3. Repair

The final column is for you to write down everything that you can do to repair the situation if those fears were to come true.

Often, we overestimate the lasting impact of our fears, thinking they can cause irreparable damage. But in most cases, there are steps we can take to remedy or, at least, lessen their negative impacts.

Think of this as your contingency plan. For instance, if one of your fears about starting a business is the potential loss of savings, your repair actions might include moving back in with your parents, getting a loan, or even considering a part-time job to help cushion the financial blow.

Another strategy is to seek mentorship or guidance. If your fear is around the business failing, then maybe connecting with a seasoned entrepreneur or joining a business incubator could provide you with the guidance needed to navigate challenges.

It’s also important to note that “repair” doesn’t necessarily mean “fix entirely.” It’s about managing the aftermath in a way that helps you regain control and move forward. Things will go wrong, but people who succeed are people who can reassess and keep moving.

By the end of this Fear Setting exercise, you’ll likely realize two things:

  1. Many of your fears aren’t as daunting when placed under scrutiny. Often, they are products of our imagination, magnified by anxiety and uncertainty.

  2. Even if some fears do come true, there are often actionable steps you can take to repair and move forward. Understanding this provides a sense of empowerment and reduces the paralyzing effect fear often has.

Fear Setting doesn’t eliminate the presence of fear. Instead, it transforms it. By identifying, understanding, and preparing for our fears, we turn them from looming threats into challenges we’re equipped to handle. Remember, fear is just an emotion. What defines us is not the fears we have but how we choose to confront them.

Now, with a clear roadmap of your dreams, actionable steps to achieve them, and strategies to handle potential fears, you’re set to embark on a journey to your dream life. Don’t let fear hold you back; let it fuel your drive. Because on the other side of fear is everything you ever wanted.

Thanks so much for reading another issue of The Jailbreak!

Til next time, Nomads. ✌️

- Jack Ross

Jack Ross (Data Engineer, Writer, Nomad)

Chat with me directly by replying to this email, follow me on Twitter for regular updates, and subscribe to my YouTube channel for travel vlogs, tips, and insights on unlocking freedom in the digital age. ❤️