My personal style coaching program, The Unfolding, is a year old today!
One year ago today was launch day, the day I gave my now-signature training webinar for the first time, and officially opened the program for enrollment.
Creating something always feels like a hot mess while you’re doing it, even when you know vaguely what you’re doing. There’s always Step 4.
Step 6 is where you see people posting self-congratulatory posts about how much money they’re making, so everyone else thinks they had it together from the beginning.
So instead of that, here’s a look back on how The Unfolding came into being.
How did you come up with the idea for The Unfolding?
I created The Unfolding the same way you create an outfit: looking at the whole, but also the individual pieces, until you create something that seems to go together.
I get asked, how did you come up with the idea for The Unfolding? by almost every client who completes the program. None of the answers I can conjure feel complete. Worse, they’re all extremely unsatisfying.
Incomplete answers include: Figuring it out as I went along. Based on my own personal experience. I joined a program that helped me set up my business model. Yawn.
What people are really asking is more like, where did you get the idea, and how did you know if it would work, and how did you go from idea to… this?
Which leads us to the unsatisfying answer: one step at a time.
Do it for yourself first.
I started where a lot of people start, when they start creating a business: by doing something for myself.
In 2017, I worked through Anuschka Rees’ Curated Closet book, which came out in 2016, a high point for self-optimization/the quantified self. This coincided with a transitional time in my life: getting married, getting promoted, realizing I felt unhealthy after years of being attached to my desk. “Figuring out my style” was the axis of my personal self-improvement project, which also included getting back to the gym and bullet journaling (were you even alive in the 2010’s if you didn’t try a bullet journal?)
In 2018, on a whim, I hosted a group with a few coworkers to read and work through the Curated Closet book. I loved helping them put words around their style… and their style frustrations. Curated Closet focuses on creating and describing your style aesthetic, but most of us didn’t have much of a problem with envisioning what we wanted to be wearing.
We were struggling with how to get there. With mindset, with patience, with body image. We were asking questions like, “but will I feel comfortable if I wear that to work?” And “will that look good on me and how can I tell without wasting tons of money?” Or “why do I feel like everyone else knows the rules already and I don’t?” And “how can I enjoy style without it being an obsession that takes over my brain?”
I wasn’t interested in fashion—I was interested in our relationships with style. There’s no point in looking ~aesthetic~ if you’re struggling with shame, over-shopping, and self-image.
By this point, I was finding my own equilibrium with style. Hearing other people talk about their struggles was illuminating; it made me aware of all the ways that Curated Closet and other personal style guides were incomplete. (In business, they call this customer research, which is just a fancy name for talking to people.) Which begs the question, or at least it did to me: how could you help people actually feel good about their style, shopping habits, and clothes?
Then teach it to others.
In the spring of 2019, I put myself out there and asked for trial clients. Yes, I seriously just posted on Instagram to find out whether or not anyone would pay me to talk to them about clothes. An absurd idea, obviously.
Did I know it was going to work? Absolutely not. Was I confident that I could help people? Uh... sort of. Did I have serious qualms about charging money? Yes—and there is a moment where you can’t know any more about a problem until you actually attempt to solve it.
Over the next year, I worked with about 8 trial clients, and I discovered a lot about where people actually get stuck.
It turns out, half the things I thought were important didn’t matter, I was wrong about half the places I thought people would struggle with, and entirely right that my methods were seriously changing the way people approached personal style.
I knew that a crucial piece of defining your style was taking outfit photos and thus having a way to look at what you were really wearing. I was convinced that this would be a hurdle for people, that they would balk at taking photos. Wrong—almost everyone accepted this as a required part of the process.
On the other hand, one of my favorite parts of the process had been brainstorming style words. It was such a “draw the fucking owl” moment that it was where people gave up and checked out of the process. This came so naturally to me that it had not occurred to me that others would struggle with it. (And this is why we iterate, because “what works for me must apply to everyone else” is absolutely not sufficient.)
By now, I was making money. Not a lot—but enough that it encouraged me to keep going. I knew I didn’t want to package up and sell yet another fluffy, useless, personal style guide. The internet is full of them, and they all sound exactly the same: Create a Pinterest board! Find your celebrity style icon! Go shopping! Voila, done! You now have style!
Instead, I wanted to make something that helped people with what I saw as the real problem: actually getting there. Figuring out where they were getting stuck, with all the bits that didn’t involve Pinterest, and solving those problems.
Then build and iterate.
This is when I went official: I was selling 1x1 personal style coaching. When a client signed up with me, they got a real contract, and a curriculum outline, defining what they’d learn and how the process would go, customized it for each client.
It’s impossible to create something like that without all the steps that went before. I had a whole folder of outlines of what a personal style curriculum might contain; I had notebooks full of my experiences; I had notes on notes on notes from my trial clients. All of those notes were referenced and used to create this next iteration.
Nothing is conjured out of thin air, and nothing is wasted.
I remember the next big turning point clear as day: the first moment I dreaded getting on a 1x1 client call. (Not because of the client, either.) I was going to spend half the call teaching a lesson I had taught to three other people that month, repeating myself yet again. Why not do that once, and spend the time with my client on what was actually personal to them?
That’s how The Unfolding was born. It made instant sense to move from 1x1 calls—scheduling and rescheduling calls, repeating myself, emailing curriculum to each client individually—to a group format. I had found myself telling one client what another was doing, because they shared similar experiences, and wishing they could talk to each other. I had found that instead of a completely customizable curriculum, 90% of the process was the same for all my clients.
I turned all my notes—yet again, back to the old outlines and notes!—into a single curriculum.
First, I talked to past clients, and asked about their aha moments, their frustrations, their motivations. That helped me map the ups and downs of the journey, so future clients would have a path to follow.
I asked people about wording—did you reinvent yourself, or evolve? what resonates more, authentic self or best self?
When you’re defining your personal style, you want the outcome—stylishness—but what you’re doing doesn’t always seem productive. Great, you bought a shirt, took an outfit photo, so what?
This whole period of my business felt extremely meta, because I had been doing all these small things that didn’t feel like they were getting me anywhere. A curriculum outline here, an Instagram post there, a brain dump of notes, a frustrated client, a happy client.
On the days I was convinced this whole endeavor was pointless—and there were lots of those days, lots of tears—I went back to my clients. They were turning small actions into transformations, and that gave me hope.
Yet suddenly, with surprising clarity, it coalesced. All those notes and conversations turned into my framework: style clarity, strategy, mindset. Visually showing a process is magical, but I could never have made this without knowing my customer and my process as deeply as I did at this stage.
I launched The Unfolding in October of 2021, and despite how polished it might seem, it still felt absolutely terrifying in exactly the same ways taking trial clients did. Would it work? Could I charge this kind of money for this program? I was simultaneously so proud of what I had made and absolutely unsure of myself.
I had a sales page, a great webinar, a framework, tons of selling copy, a bunch of tech, and a curriculum online—and barely any actual program content. I was effectively pre-selling a program I hadn’t created yet. (This is great business advice and/or hubris.) I shudder to think about spending the time creating six months of program content before I ever even knew if anyone wanted it.
Thankfully, that initial validation launch was a success—five clients for a total of $16k—enough of one that I was willing to keep going.
It didn’t feel like I had anything, until I looked back and realized what I actually had created. I wasn’t sure if I had “made it” until I had some clients and realized that I could make it.
“A sequence of momentary, self-contained, eminently doable actions”
A client once told me that she “doesn’t get any value out of logging my outfits daily, or taking a photo daily, but I get a ton of value out of having an outfit log, over time.”
In The Unfolding, outfit logging is where we start defining our style. We start here—not with #inspo or anything so heady—but with reality, because it shows us where we are, our progress over time, providing data that we can’t easily recall or access after the fact, and most importantly, it’s actually doable, one little bit at a time.
I’m not sure that I could have started with “I want to make a personal style coaching business.” That mountain felt impossible to climb on day one.
We look at other people’s finished results—the outfit, the business, the 100k followers, the book—and go, wow how did they get there, they must be born that way, just effortless, they just know how. As if it was done in one moment, or they were born good at style, or good at making Instagram influencer content, or there’s One Secret Trick You Won’t Believe (but you can definitely buy it in this online course!)
It’s extremely unsatisfying to know that the answer is simply that you have to just do small things until something big comes out the other end. How annoying!—that doesn’t let us off the hook at all. It’d actually be a relief to hear, I have a magic skill you don’t have that made it easy for me but impossible for you.
Instead, we are faced with the truth: we have to try, without knowing if it will work, one little pointless action at a time.
In Oliver Burkeman’s wise words:
If you can approach your daily life in this way for a while – as a sequence of momentary, self-contained, eminently doable actions, rather than as an arduous matter of chipping away at enormous challenges – you might notice something profound, which is that, in fact, this is all you ever need to do.
Now, whenever an Unfolding client asks me this question, I turn it around on them: how did you get better at making outfits and personal style?
Of course, the answer is something like, well, I kept track of what I was wearing, and most of it was terrible, so with your help I took notes on what was and wasn’t working, and had some small wins, and slowly realized that my everyday baseline was getting better, and shopping was easier, and then I wrote down what I knew, and used that as a reference, and that took me in an unexpected direction, so I made more outfits and took more notes, and at some point I realized, hey, I know how to do this now.
Well, that’s exactly how I did it, too.