This is Part 3 in a three part series. Read Part 1: Honest Self Inquiry here and Part 2: Courageous Experimentation here. This post will make a lot more sense that way but you can do what you want.
So, you've completed your honest self-inquiry and created your Future Maps with plans for your courageous experiments, yet you're stuck and those experiments just aren't happening. Do not despair or beat yourself up! This is an expected part of the process. We as humans get stuck all the time. The next step is to acknowledge these blocks, label them, and approach them with curiosity. Remember, you cannot fall out of the Universe—everything happening within it can be worked with and might have more of a creative solution than you can imagine right now.
Here are the most common reasons people get stuck that I've seen, and what to do about them:
Making Friends with Fears
People often view their fears as reasons not to act—seeing them as blocks instead of essential parts of the experience that carry valuable information. Rather than trying to suppress or confine these ideas, try to understand why these fears exist, what they are protecting, and how you might address their concerns. Imagine each fear as a little advisor on your shoulder; it's there to protect you from something, even if that fear is outdated or out of context.
One way to engage with fears is to have a conversation with it. Think of it like inviting it over for tea instead of letting it bang on the door endlessly. Imagine that you are sitting across from the fear and open up with curiosity asking it questions such as, "What do you really want?" and "What do you need?" Try to see things from its perspective—you might be surprised at what you discover.
If you're more of a visual person, consider drawing figures to represent your fears, turning them into monsters or objects—whatever best symbolizes them for you. Humor can disarm fears, even if the subject matter initially seems far from funny. Part of this process is also expanding our own ability to hold intense emotions by not distracting or numbing them but opening ourselves up softly to what might lie below a prickly and scary exterior of the fear.
(If this approach sounds familiar, it's a blend of techniques from the Feeding Your Demons meditation by Lama Tsultrim Allione,Parts Work/Internal Family Systems by Dick Schwartz, and Coherence Therapy. I highly recommend exploring these resources for a deeper dive.)
Making Fears Specific
Fears are most powerful when they are vague and uncontrollable. The more specifically you can define your fears, the more power you have to address them. Tim Ferriss' fear-setting exercise is one method for naming and tackling these fears one by one. Here’s a template for it.
Whether or not you use this template, examine your fears for validity. For every fear related to, say, quitting your job—such as “I will run out of money within one year,” “Everyone will think I’m a failure for quitting my job,” or “My partner will be angry”—write down how you might prevent it from happening and what you will do if it does. Remember, you are more adaptable than you give yourself credit for. You've overcome at least one significant challenge in your life and learned from it, you can do it again!
Finally, ask yourself whether the cost of inaction is worth it. What will it cost you—financially, emotionally, and otherwise—to not pursue what you want to do? Sometimes, doing nothing might seem like the best option, but that is rarely the case. With all this information, you’ll be better equipped to make your decision.
Where do I even start? There is too much
Another common obstacle is feeling overwhelmed—believing that you must change everything in your life and start over when you realize your current path is making you unhappy. Changing everything at once is not only overwhelming but also unsustainable. Continuous iteration is the most sustainable approach, and this is where experiments and viewing every experience as a learning opportunity come into play.
Remember, this is an iterative process—let me repeat, it is iterative! Not everything will be resolved in a week, a month, or even a year, but with consistent attention and care, change will come. Keep faith in yourself, reflect often, and make small changes that add up over time.
In terms of a strategy of how to start on something that seems overwhelming, start with the three smallest steps you can take. For example, if you need to edit a video but can’t seem to get started, break it down into simple steps:
Sit down at your desk.
Open your editing program.
Upload the video to begin editing.
If you’re still stuck, figure out the next three actions and take those. It might seem trivial, but even the smallest action generates energy and ideas for future actions. Recognizing that you do have an impact builds confidence and encourages you to keep going. You don’t have to do everything at once—just take the next obvious step.
But is this the Right Job/Path for me?
One of the most challenging aspects of designing a life you love is dealing with uncertainty. Most people who reach out to me feel stuck because they are afraid of the unknown that lies ahead when trying something new. They want assurance that the path they choose will be the perfect career, dream job, or ideal life that makes them completely happy. Almost everyone I speak with would eagerly take the leap if they were sure it would turn out well—I would too!
But we can never be 100% certain. All we can do is make our best bets, try new things, and live courageously—courageously making mistakes, experimenting, looking foolish, and learning from it all. There is no one job, career, or life that will fit you perfectly forever. Expecting perfection might cause you to overlook opportunities that could lead to a life you love.
We are all evolving, and our needs and desires change as we grow. Rather than searching for the perfect option, focus on trusting yourself to recognize when something isn’t working and have the courage to change it.
Life Worth Loving
Loving your work doesn't guarantee that you'll love your life, but it goes a long way—especially when your work supports and makes possible the life you love. This is an endeavor we must undertake on our own, but it doesn't have to be a lonely one.
Involve others, ask for help, and share your learning; these actions can inspire those who are also seeking the courage to ask their own questions. You've got this.
Start internally by getting to know yourself, then engage with the world through experiments, and give yourself grace throughout the process. There are no mistakes—only learning—and this life is one wild journey.
The post is divided into three parts. You can check out Part 1: Honest Self-Inquiry here and Part 2: Courageous Experimentation 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. I offer 1:1 coaching and group programs.
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