This is Part 2 in a three part series. You can read Part 1: Honest Self-Inquiry here.
If you’ve read and followed along with Part 1 you have just spent a significant amount of time in thoughtful reflection—focused, intentional Thinking as opposed to looping thought patterns. Both Thinking and Doing are essential, but they must flow together so that each informs the other. You have thoroughly examined your life and identified what truly matters to you. With your Must-Have, Awesome-to-Have, and Can’t-Have list prepared for easy reference, it’s now time to shift from Thinking to Doing—into Courageous Experimentation.
How About Failure?
Most people fear failure when confronted with the unknown. They worry about embarrassment and not knowing how to perform a task before even trying. Experimentation alleviates much of the pressure associated with "actually" doing something because an experiment is inherently an opportunity for learning. Whatever the outcome, every result is data.
A lot of people's idea of doing something is that Doing = Success or Failure. In that model, any outcome that isn't considered success is labeled as failure. This creates a very narrow target, making the chances of achieving success quite slim, like aiming at a bullseye.
It’s an amazing feeling when you succeed after investing a ton of practice, skills, and time. However, it’s incredibly discouraging to miss even that small measure of success—especially when you’ve made progress but have no way to acknowledge it.
But what if failure were impossible?
What if every action you took contributed to your learning?
Then what would you do?
The only metric of success in Doing=> Learning is whether you learned something. In this model, failure provides as much—or even more—learning than success does. The goal of experiments isn’t to obtain the perfect answer, choose the ideal career, or land the right job; rather, it’s to uncover assumptions, offer insights, and reveal new questions.
"But how do I even know which experiments to run? There are infinite possibilities!" you might ask.
The possibilities feel endless because you haven't focused them on what matters most: you. Your preferences, desires and your actual life. They are vague ideas that stretch out into infinity, based on assumptions rather than concrete considerations. One way to focus them is to make these possibilities as real and relevant to you as possible. One method for doing this is Future Mapping.
Future Mapping
Just as a map is not the territory it represents, a future map is not a blueprint for your future. Instead, it's an imagined projection of your life over the next five years, presented in three scenarios. It serves as a tool to focus your thinking and guide your experimentation.
The three future mapping scenarios are:
Continuing your life as it is right now (with best-case thinking).
An alternate scenario where you can no longer do what you're currently doing.
A version of what your life would look like if you had all the resources in the world.
Treat this exercise as an opportunity to envision what your life would look like along each of these paths. Include details such as work, travel, projects, family, and anything else that feels fitting for that future. Give each map a title that captures its essence. The more detailed your map, the more insight you’ll be able to gather.
By converging on three possibilities through future mapping, you can gain clarity on which paths are actually similar, which ones sound appealing now but might become boring over time, and what your hidden desires truly are.
Here is the Future Mapping template you can use:
Future Mapping is based on an exercise from Designing Your Life. That book was a fantastic resource for me early in my journey, and I highly recommend checking it out.
To give you an idea of how these maps can look like, here are my three Odyssey Plans from 2019 (over 5 years ago now 🤯) :
I gained a lot from creating these maps back in 2019. At that time, I felt lost—having just quit my second job in two years, with no clear idea of what to do next. None of these maps perfectly predicted how my life would turn out, but each captured an essence of something I held dear and still value. I decided to try coaching, and now I'm writing this to you. I also published a book in 2023, moved to British Columbia, and now I regularly dance West Coast Swing. The map isn't about getting it right, it’s about opening up possibilities and directing action towards them.
From Future Mapping to Courageous Experiments
Once you have your maps, consider what you don't know and the questions you have for each scenario. Then, design and conduct experiments to answer those questions. Consider your Must Have, Awesome to Have and Can't Have List. What are some experiments you can run that test some of the Must Haves? For example, before starting my coaching business, I reached out to friends to co-host a workshop. I didn't know whether I'd enjoy working with people and enjoying my job was a must have for me. Next, I asked friends and family if I could have coaching conversations with them. I also volunteered as a coach at BGIs (formerly known as Goal Crafting Intensive). All of these experiments were daunting, but they were far less intimidating than diving headfirst and committing time, money and energy into something I knew little about.
Two important points about experiments are that they should be time-bound or constrained in some way (for example, by a set number of conversations) and focused on answering a specific question. Ensure you have both elements in place before you begin. These experiments are intended as initial samplings rather than complete solutions—the goal is to iterate and gradually expand their scope over time.
The most common experiments to run:
Talk to somebody who has done the thing you want to do
Volunteer
Take an online course in the topic
Do a small project
Go to a meetup or a conference on the topic
Commit to a 3-6 month contract rather than a full time job
Iterating on Experiments
Experiments are meant to be iterated on. Here are some questions to ask yourself once an experiment is complete:
Does this align with my values and the life I desire?
How does this experience inform my "must-have," "awesome-to-have," and "can't-have" list?
How does it feel to be doing this? Am I enjoying it?
What did I learn? What new questions have emerged?
To determine your next experiment, ask: What is the obvious next step? Sometimes the answer is clear right away, and other times it may require further self-reflection or revisiting your maps and values.
This process is iterative, becoming clearer as you move closer to the life you want to live. Although it never truly ends, it gradually settles and becomes easier with each experiment.
That being said, we as humans get stuck all the time. Getting stuck is to be expected! These moments are not a setback but an inherent part of the creative process of your life design.
Read on for Part 3: The Ways We Get Stuck.
The post is divided into three parts. You can check out Part 1: Honest Self-Inquiry here.
This is a post adapted from a Threadapalooza thread I wrote on X in Dec 2024. You can check out the thread here.
If you want to work with me check out my coaching page.
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