Journal prompts to connect with what your heart wants

For the past few months, I’ve been caught in an internal back-and-forth over what kind of job to take. Some roles seem “smart” to apply for (i.e.. corporate jobs that are stable, higher-paying, and traditionally indicative of status). Others feel more exciting and aligned but also much more risky (e.g. teaching yoga or strength and conditioning, roles at companies that work with personal development or psychadelics). And it’s been a constant struggle of feeling like I need to set my future self up financially with a job i’m not passionate about, and feeling like doing that would be at the expense of pursuing other things I care about.

So I’ve been trying to get in touch with what my heart wants. And in the middle of this, I sent a question to a podcast I respect: Dropping In by Charlie Houpert.

I’ve followed Charlie for over seven years now. He started Charisma on Command, a YouTube channel that teaches social skills, which I leaned on heavily in late high school and early college when I was putting a lot of conscious effort into developing that area. Over time, he’s shifted away from teaching charisma based on habits and external actions, and toward deeper emotional work. And in doing that, he’s kind of grown alongside me, just a few steps ahead. He’s become a role model—someone I trust to give honest answers, even if they’re not always polished.

So when he replied to my question—about how to figure out what I actually want, not what I think I should want—it hit home. And I wanted to share the journal prompts he recommended and why I think they work.

Why It’s Hard to Hear What You Want

Maslow’s hierarchy of needs (left) and the chakra system (right) come from different traditions—Western psychology and Eastern philosophy—but both suggest the importance of meeting certain foundational needs before higher levels of expression, connection, or insight can emerge. While not a one-to-one match, I find the parallels interesting (read more here or here).

We all have certain feelings that show up automatically, such as:

• The desire to feel safe

• The desire to be liked or loved

• The desire to feel successful or admired

These aren’t bad. They’re part of being human.

But when one of those feelings feels threatened, like when your brain says “you’ll run out of money” or “no one will respect you if you do that,” it tends to drown out everything else. Especially what your heart is asking for.

In my experience, the stuff that feels most real and meaningful only shows up when those more basic needs feel honored and quieted just enough to stop driving the bus.

That’s where journaling can help. The right question can give those fears a little space… and make room for what’s underneath.

Prompts to Help You Get Clear

Below are a few journal prompts from Charlie I’ve used to get clearer on what’s really coming from me—and what’s coming from fear or pressure. The idea isn’t to “figure it all out.” It’s to turn the volume down on the noise, just enough to notice what’s true.

What would I do if I had $100 million and no one ever found out?

This removes the pressure to impress or be admired. It helps you see what you’d actually enjoy doing if money and status weren’t driving the decision.

→ You’re quieting: fear of not having enough, pressure to prove your worth.

Some examples from my life:

• Not applying to corporate jobs (Still doing it❌)

• Hire a good piano teacher and practice every day (Scared to spend money and time on it❌)

• Quit my consulting job and travel in New Zealand and Asia with my girlfriend (did it✅)

• Backpack through Thailand and Europe with people care about (did it✅)

• Spend time at a monestary to learn about Buddhism and how monks live (did it✅)

  p.s. all of those things I did do cost about $10k combined, not $100M each

What have I created that I have an unpublished backlog of?

This shines a light on where your natural expression already exists—but hasn’t been “validated” yet. What’s been waiting in the wings?

→ You’re quieting: fear of rejection, pressure to only do what’s marketable.

Examples from my life:

• Many notes app journal entries about interesting points from podcasts I’ve heard, or experiences I’ve had that I felt compelled to write about

• Annotations in books I’ve read about how points from the book connect to my life

• 2 full journals of notes, reflections, and exercises from my time in ED recovery

  → Have led to me trying to consolidate some of those things in posts like these.

• Hours of watching YouTube videos and taking notes about piano pieces and music theory

  → Has made me confident my desire to play piano comes from the heart

What am I already spending money or time on that you couldn’t pay other people to do?

What are you drawn to invest in, even when there’s no return? That’s often a signal of what you value—whether or not it’s traditionally “productive.”

→ You’re quieting: guilt over “wasting” time or money on what lights you up.

Some examples from my life:

• Spending time reading old psychology books like The Voice of the Body (see my favorite insights in this post) or Jung’s Map of the Soul →has led to me making posts on this site from a place of excitement

• Spending on relatively expensive gym memberships and classes → has led to me pursuing my Yoga Teaching certification and Strength and Conditioning Specialist certification

• In college, it was making it a point to talk to girls I thought were cute → at the time, that meant following my heart was going out to social events most evenings when I studied and noticing how I felt proud of myself for trying even when I’d get rejected

• In contrast, I did other things that felt like pulling teeth but that I thought I should. And this prompt helps me notice that these probably weren’t aligned with what my heart wanted (e.g. trumpet lessons, Spanish classes, playing college golf, coding courses). Are there versions of this for you?

If I knew no one would disapprove of me, what would I try?

A good question when you’re worried about what people will think—parents, coworkers, friends. It helps you name what’s been shoved to the side by fear of judgment.

→ You’re quieting: the need to be liked or understood.

Examples from my life:

• Singing publicly (still working on it 🔜)

• Trading making more money for having more time (still working on it 🔜)

• Make more jokes in social settings/be goofier/do more improv comedy (still working on it 🔜)

  (Notice how this one was harder for me to think of examples of how I’ve done this. This show that I likely still have a fear of judgement in my system)

If I trusted I’d figure it out later, what would I say yes to now?

Your brain wants a step-by-step plan. But sometimes, all you need is to admit what you'd do if you weren’t required to have the next 10 moves mapped out.

→ You’re quieting: the need for guaranteed certainty and control.

Examples from my life:

• Spend a year living in another country (Not yet❌)

• Spending more time meditating, playing piano, and reading/reflecting and less time focused on making money (still working on it 🔜)

• A year ago, it was spend less energy on tracking food and workouts (did it✅)

Resistance - and potential responses

These questions can bring up immediate pushback. That’s normal. Below are a few examples of the kind of thoughts that might show up, and how you might respond.

Resistance	Potential Reframes
That’s not realistic.	What if “realistic” was a story your mind is telling you to keep you in the familiar? Could you try making a small, realistic step toward it?
I’d go broke if I followed that path.	Are you certain, or is that just a fear of uncertainty? Could you explore ways to do this responsibly? Could your passion actually bring more abundance than you think?
I’m not good enough to pull that off.	The version of you who does this isn’t perfect, but they’ve learned to trust themselves. What if “not good enough” is just a signal to get started and grow?
That works for other people, not me.	Maybe it works differently for you. What’s the version of that path that honors who you are? What if your unique approach is exactly what the world needs?
I’d lose people’s respect.	What if the people who truly respect you are the ones who admire your authenticity, not your conformity? What if the best way to grow your relationships is to be yourself?

Resources For Further Exploration

If this sparked something, here are a few people and ideas I’d recommend checking out:

• Charlie Houpert, Dropping In: podcast with conversations about topics such as authenticity and blending business and passions.

• Tim Ferriss, The 4-Hour Workweek: a book that reframes what freedom actually looks like.

• Martha Beck, Finding Your North Star: a book with more exercises to help get in touch with your genuine interests.