Start Experimenting
This is for anyone yearning for new experience and self-growth who nonetheless gets stuck in their own head. Who may have succeeded because of being good at planning, analyzing, and researching. And yet, is finding that this habit of needing to understand everything before taking that first step simply doesn’t work with personal growth.
Core Insight
We can’t plan our way to self-discovery. We’re planning within the bounds of what we already understand, but the stuff that actually changes us lives outside those bounds. We have to do to discover it.
This was me.
I’m someone who goes deep when faced with the new and the unfamiliar. I learn, I write, I draw. I build ideas and models. For most of my life, I thought this was the only way; that if I analyzed enough, I could feel safe approaching something new.
It does not work that way.
What I didn’t recognize was I was only ever planning within the bounds of what I already knew was possible. The real discoveries, the ones that actually changed me, came from experiences I couldn’t have planned for, because I didn’t know they existed until I was in them.
A behavioral pattern of analyzing coupled with that analysis being insufficient to understand feelings meant often landing in analysis paralysis. The more I knew, the clearer I intuitively recognized how much I didn’t actually understand. I’d know a lot, but it was still scary.
So, approaching the scary remained daunting. More analysis was so much easier and less scary. The result was never actually moving meaningfully closer to the thing I wanted.
How I approach the unknown has evolved.
Summary
Self-discovery resists planning. We can only plan within the bounds of what we already understand, but the experiences that change us live outside those bounds. The more we try to analyze our way to readiness, the less we actually learn.
The solution is phased expansion of our capacity for action:
Phase Mantra When we’re here 1 ”Don’t flinch away” Our body retreats before our mind engages 2 ”Move towards discomfort” We can stay present; now approach what’s uncomfortable 3 ”Try something new” We can name the thing; now design an experiment Phase 1: “Don’t flinch away” — Before we can approach anything, we must stop retreating. Avoidance is often instinctive; we exit before conscious thought engages. The goal is simply to stay present.
Phase 2: “Move towards discomfort” — Presence creates the option for movement. We practice approaching discomfort rather than analyzing it. We’re still learning what “it” even is by moving towards it.
Phase 3: “Try something new” — With enough experience, we can name what we’re exploring and design intentional experiments. Analysis returns, but now informed by expanded bounds.
The phases build on each other: we can’t design experiments without tolerating discomfort, and we can’t approach discomfort if we’re still flinching. We may be in different phases for different aspects of identity simultaneously.
That evolution resulted in the mental model below: three phases to move from paralysis to action, from fear to experience. Importantly, this is not a case of, “here is a singular recipe to follow and everything is now perfect.” These phases reflect the step changes I necessarily made in my approach along the way as each new experience changed me and built the foundation just a little bit higher.1
My stories below relate to my own journey of unpacking and letting go of the fear, shame, and denial I carried for decades about my sexuality and gender identity. They help to illustrate how this model can apply with any identity shift where we’re working on figuring out who we are by actually being it.
The model
| Phase | Mantra | Mode | Level | Clarity | What we’re working with |
|---|---|---|---|---|---|
| 1 | Don’t flinch away | Reactive | Instinctive | Amorphous | Automatic responses. Shame, fear, avoidance running before we’re conscious of them. |
| 2 | Move towards discomfort | Responsive | Emotional | Named | Feelings we can name but maybe can’t fully explain. We’re learning what “it” even is. |
| 3 | Try something new | Proactive | Intellectual | Nuanced | Ideas we can articulate and test. Enough clarity to form hypotheses. |
Phase 1: “Don’t flinch away”
The smallest possible goal. Not “succeed.” Not even “try.” Just don’t retreat.
Why we can’t skip this
When we’re dealing with identity, especially parts of ourselves we’ve suppressed, repressed, or actively denied, the avoidance isn’t just intellectual. It’s instinctive. Shame, fear, internalized judgment—these live in our body. They make us flinch before we even know we’re flinching.
We can’t “move towards” something (Phase 2) if our body exits the context before our mind engages. First, we have to build the self-awareness to notice the flinch, and enough capacity to stay present despite it.
My story
A few years before I began to even acknowledge to myself I was not heterosexual, I was at a seminar I was really into; I was active and engaged with the content and the instructors. At the end of the last day, while in a conversation with one of the instructors, the other one came up, gently put his hand on my elbow, and asked what I was doing that night. Before he even finished the question, I flinched away, physically and visibly. I think I unconsciously knew he was gay, but it hadn’t occurred to me consciously. What stayed with me wasn’t the moment itself, but the deep visceral feeling of being so afraid that my body acted before I consciously even knew what had happened.
In October 2024, I was going on a cruise for a best friend’s wedding. I had by then come out as bisexual to my partner and best friends, but had not acted on anything. I found myself in a place with many doubts and remaining fear and uncertainty, still questioning myself. I knew I wanted to have my first sexual experience with men on that trip.
As I thought about how to set a goal for the trip, the memory of the seminar burbled out of my mind. In the past, I would have set a goal like “have sex,” which is big, scary, and easy to fail. Instead, I set the smallest goal I could: Don’t flinch away. 2
If I came home having put myself in a situation where something like the seminar moment happened, and I didn’t flinch? That would be enough. That would be success. That would be progress. And that would be a new experience I could build upon.
And it worked. Having such a small target gave me a much smaller experience to seek. I didn’t have to find sex. I just had to stay present when something unexpected happened. I went to the LGBTQIA+ meetup on the trip the first night, not knowing what to expect, but knowing that situation might occur. When it did, I did not flinch away.
The next step was easier. And the one after that. By the second night of the cruise, a gay married couple took me under their wing … and eventually back to their room. That night, I wrote in my journal: “I am bisexual.” No modifiers. No qualifiers.
What Phase 1 is about
| Dimension | Status | Description |
|---|---|---|
| Mode | Reactive | We’re not seeking anything, just practicing not retreating. |
| Level | Instinctive | We’re working with automatic responses. |
| Clarity | Amorphous | The thing we’re exploring is still amorphous; we might not even be able to name it yet. |
How we know we might be ready for Phase 2
We notice when we’re about to flinch. We can sometimes choose to stay present instead of retreating. The thing that used to be purely instinctive is becoming something we can observe.
Phase 2: “Move towards discomfort”
Once I could stay present, I needed something more. I had become aware of the situations where I would have flinched and realized I could stay in that moment; I also began to see new possibilities for what I might experience. While thinking about those new possibilities no longer felt overwhelmingly scary, they remained very uncomfortable.
If at first I was focused on what happens to me, now it was time to focus on what I choose to feel.
The mantra became: When something feels uncomfortable, move towards discomfort.
Why we can’t skip this
Phase 2 requires us to tolerate emotional discomfort; not just notice it, but approach it. If we haven’t done the work of Phase 1, we won’t be able to hold the discomfort long enough to move towards discomfort. We’ll flinch away before we can choose.
And we can’t jump to Phase 3 (designing experiments) from here because the thing we’re moving towards is still vague. We can feel it, but we can’t fully articulate it. We’re learning what “it” even is by approaching it.
What this looks like
This is different from “don’t flinch.” Flinching is unconscious; it’s our body reacting before we can think. “Move towards discomfort” is a conscious override. It’s what we say to ourselves when our brain starts generating reasons to avoid something.
“Is this outfit too exposing?” Move towards the discomfort. “I don’t know what to expect at a gay bathhouse.” Move towards the discomfort. “What if people stare? What if they assume I’m queer?” Move towards the discomfort.
This mantra offered an alternative to the instinct to analyze whether I should do something.
My story
One of my first times really leaning on this mantra was coming home from my first time at Pride as myself. I was dressed happy in (very!) short shorts, a femme top I loved, and rainbow butterfly wings. I’d seen people with bisexual pride gear and learned they got it from Spencer’s. Not wanting the spell of Pride to end, I thought, “I’ll stop at the mall on the way home and check it out.”
As I pulled into the parking lot and saw the everyday people walking in, I realized: Oh. This is not Pride. This is the normie world.
I had the immediate and clear thought that I should turn around and drive away. I very nearly listened. Every analytical instinct said: assess the risk, consider the outcomes, just go home. This is scary and unknown and uncomfortable.
“Move towards discomfort” gave me an alternative. I changed my shirt to a Free People tank I loved (the other shirt and my wings were soaked from rain, anyways!) and walked in.
The first thing that happened was exactly something my past self had feared. Three high school boys walked past me. A few paces later I heard sniggering and giggling and whispered comments. I braced for the emotions to hit; they didn’t. I realized that I didn’t care. Why should I care what some random teenagers thought? I knew a past version of me would have, and yet, I only now recognized that the me of that day had moved beyond that insecurity.
When I walked into Spencer’s, the first thing that happened was an employee gave me a gushing compliment over my outfit! That was a novel experience for someone who historically hid themselves and had lots of shame and body image issues. I also stopped at Hot Topic on the way out, and only later realized the cute clerk was flirting with me the whole time.
If I had analyzed that situation, I would have talked myself out of walking in the front door. “Move towards discomfort” offered me an alternative choice, which resulted in having an array of new, positive experiences.
What Phase 2 is about
| Dimension | Status | Description |
|---|---|---|
| Mode | Responsive | We feel the discomfort and choose to approach it. |
| Level | Emotional | We’re working with feelings we can name but maybe can’t fully explain. |
| Clarity | Named | The thing is becoming named; we’re starting to understand what we’re moving towards, though we still don’t know what will happen or how we’ll feel. |
How we know we might be ready for Phase 3
We can name what we’re moving toward, even if imperfectly, and we actually move towards it. The discomfort now has a shape. We’re starting to have enough clarity to form a hypothesis: “I think X might feel like Y.”
Phase 3: “Try something new”
As I built a habit of moving towards the things that feel uncomfortable, I also learned to trust myself to recognize “safe discomfort.” And the reality of what actually was “safe discomfort” continuously shifted further afield.
By reflecting on the experiences, I was learning exponentially more about myself: What are the experiences I enjoyed? How does that reflect back on the prior self-images I maintained? How does it feel to continuously put myself into scenarios that I thought would be scary or negative?
As the learnings built up, I began to be able to name and articulate—at least in my mind or in my journal—nuances that were previously invisible to me. And with that, I could think further ahead about new experiences I wanted.
Focusing with intention on what I choose to feel was powerful while still being reactive; I was responding to the discomfort as it arose. I was now feeling confident enough in areas to shift towards being proactive, i.e., to design the experience with intention.
Why we can’t skip this
We can’t design an experiment if we don’t know what we’re testing. And that clarity only comes from having sat with the discomfort (Phase 2) long enough to understand its shape.
If we try to start here, designing experiments from pure analysis, we’re back to planning within the bounds of what we already know. Our experiments will be too safe, too predictable. They won’t teach us anything new because we’re not actually pushing into unknown territory.
What this looks like
My therapist gave me language for this: micro exposures.3 We define something specific, intentionally set up a safe version of the experience, and then reflect on how it feels relative to our expectations.
This closed a circle for me. I started as an overly-analytical person who needed to understand everything before acting, in part because that made me feel safe. I couldn’t have started with “design experiments”; that would have felt too big, too scary. But after re-learning through Phases 1 and 2 how much experiences teach us things analysis can’t, I could bring my analytical nature back while being more well-balanced with ongoing real-world experimentation and leaning in to discomfort in new areas.
The key distinction from Phase 2 is that “Move towards discomfort” is vague (that’s okay!). We feel discomfort while not yet being able to name what is causing the discomfort. Whereas to “Try something new” requires us to define what “something” is. We’re not just responding to feelings; we’re creating hypotheses.
My story
As I continued to become more comfortable with different ways of gender expression, I eventually felt little discomfort in queer-safe spaces with even the most femme outfits, e.g., queer bar for dancing or a private party.
I’d never worn a skirt or clearly-femme or even fully androgynous outfits in a “normal” public setting. I found I was increasingly curious about what it would feel like, and yet the idea of doing so on my home turf felt incredibly scary. I could even name reasons behind that fear, e.g., it was something I could not unwind if I saw someone I knew.
So I designed an exposure that sidestepped those reasons. On my next trip to Providence, I brought some outfits I’d only ever worn to queer-safe spaces, including a few longer skirts. I had been going to a great coffee shop across from my hotel. One morning, I got up, dressed femme with makeup and a skirt that made me happy, and walked over to get coffee.4
I planned to sit there, in public, and see how it felt. I knew I could leave at any time, yet once I was in the moment—
I felt good. I felt comfortable.
The key variable turned out to be being away from home. As I didn’t know anyone, I could conceive it as an experiment, not the first step of a permanent change. I could more deeply reflect on the experience. Would I want to do this more? What did I learn about myself?
After this trip, in fact, I began to shift in my everyday wear. At least for now, I don’t feel the desire or need to be fully femme in everyday life. However, opening up that possibility space led me to recognize and embrace that I do feel good and happy landing in a more consistently androgynous5 expression.
What Phase 3 is about
| Dimension | Status | Description |
|---|---|---|
| Mode | Proactive | We define the experiment and run it. |
| Level | Intellectual | We’re working with ideas we can articulate and test. |
| Clarity | Nuanced | We understand the thing well enough to hypothesize about it. |
The progression
We don’t have to do these in strict order or master one before touching the next. But there’s a natural progression: it’s hard to design experiments (Phase 3) if we can’t tolerate discomfort (Phase 2), and it’s hard to approach discomfort if we’re still flinching away from everything (Phase 1).
Additionally, we will be in different phases for different parts of our identity. I might be in Phase 3 for how I dress, but Phase 1 for something else entirely. That’s okay. The framework isn’t a ladder we climb once; it’s a tool we use wherever we are.
What’s beyond this
One day, we realize we aren’t the same person who first feared a big scary new idea. What used to take intention and energy just becomes … how we live.
We’re no longer flinching; “Don’t flinch away” is superfluous. We’re hanging out where we want; “Move towards discomfort” is not needed. What was “try something new” is now just us.
Someday, we won’t need the mantras. We’ll just be.
I’m not there yet for everything. But I’m there for some. Things that used to seem overwhelming and scary. There have been numerous moments in recent months where I was walking into a situation where past me would have been freaking out or gotten stuck in a loop of avoidance behaviors. And yet, I was calm and excited, without anxiety or shame or fear. I have literally said out loud, “Who am I right now?”
And then smiled, shrugged, and took that next step forward.
One small step
We don’t need all the steps mapped out. We don’t need to understand everything before we start. We don’t need to prevent every possible scary scenario we can imagine.
We can just take the next small step. Towards awareness, towards discomfort, towards exposure.
What will your new experience tell you?
I don’t know. Neither do you. That’s the whole point.
Trust yourself to find out.
Footnotes
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An additional element that has been key for me is consistent daily journaling. Even something as simple as using voice-to-text dictation to talk while driving creates a focus and intention to reflect on the recent new experiences and acts as an accelerant for what we are learning about ourselves. ↩
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I actually set multiple goals, more of a “good - better - best” progression. It was actually looking at my first version of that progression where I realized even “good” was instinctively scary, and led to me remembering the seminar experience, and for the first time setting that goal of “Don’t flinch away.” ↩
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I also like to use the term mini experiments sometimes as it can help me remind myself to think about it slightly more rigorously as well as validate that I have enough clarity to actually do so. ↩
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I sent a selfie to my therapist before heading inside. Their reply was simply, “you look so relaxed and comfortable with yourself - that is great!” ↩
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I used to think of androgynous as “a lack of any clear gender expression,” think of the Pat character from SNL (Saturday Night Live). Instead, I now think of it as a blending of masculine and feminine. ↩