

Tuesday, August 05, 2025
How do you build confidence in something you’ve never done before? You don’t. You just show up and start.
I’m trying something new here.
A coach friend of mine publishes a newsletter every week, consistently. When I told him I admire his ability to do that, and that I’d like to build the skill myself but didn’t know where to start, he told me very simply:
"I just started with sitting down to free-write."
I think pretty often, we admire someone’s skills… over there.
We sort of wish we could be like that. But then we find ourselves afraid to take the first step.
What if I look like an idiot?
What if I disappoint myself with how terrible I am at it?
What if I spend a lot of time trying to do it… but fail anyway?
And that’s sort of the problem, isn’t it?
“Trying.”
But what if it isn’t really about being good at something, but just sitting down to “free-write”?
That’s how this thing you’re reading right now started. And anyway, to quote Jake the Dog from Adventure Time:
"Sucking at something is the first step towards being sorta good at something."
So, here I am, sucking at free-writing something that I'm going to share with you.
But also, here I am, doing it anyway.
And I'll learn as I get my hands dirty anyway. Experience is a great teacher, after all, if we're willing to listen without judgment to the results we get, and make adjustments as we keep going.
There was a first time I ever hypnotized someone.
At a certain point, I had to get over the "learning" phase and into the "doing" phase. It wasn't a perfect execution, but it was quite the thrill to realize I had finally done the thing.
And you know what? I was proud of myself for having done it.
Now doing hypnosis with people feels so second nature that I don't need scripts, and usually go in without any rigid plans or structures and just listen and compose the session with the real person with their real challenge right in front of me.
There was the first time I built a website for my business. It sucked. But I was proud of it anyway, because I just finally decided “f*ck it” and put it out there.
I just finished rebuilding the whole thing all over again.
It’s probably my fifth iteration of it since I became a hypnotist in 2021. The last one was clunky and confusing and wasn’t working very well to build trust with people who might want my help.
And I’m just as proud of this new version of it as I was the first one I built. Really, it’s the same feeling. And I’ll save my old pages, just so I can realize how far along my design skills have come.
Will I rebuild it again at some point? Yeah, I probably will.
I still don’t think I’m a “great businesswoman” or “skilled entrepreneur”, but I am really good at realizing when I could be doing something differently to get better results or a smoother experience for the people who work with me.
I used to suck at singing, but then I just decided to get really good at songs I love singing and expand over time. To hit the wrong notes and rewind and try again.
Now people tell me all the time: “You have a lovely singing voice. Have you thought about doing it on a stage?”
And I’m working up the courage to do that.
Pretty soon, I will suck at being on stage until I get the hang of bringing my “real self” up there with me.
Whenever I catch that inner critic saying, “I suck at this,” (which may or may not actually be the truth)...
I say, “Yeah, maybe I do, but I want to get better at it, so what specifically can I focus on the next time I do it?”
Because I don’t think it’s even really about “trying” something new…
But “doing” something new, sucking at it… and feeling proud of yourself for having even done the thing at all...
And then proud of yourself for making adjustments and doing again, but slightly better this time...
And doing it again and again until you’ve mastered the thing you once sucked at.
Anyway, here you go. Ta-da. I’ve done the thing.
What’s the new thing you’re going to sit down and suck at today?
Much love,
Jessi

I teach you how to work WITH your mind, not against it.
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