How to trust yourself (again)

Slowly, and then all at once.

It starts simply. Slowly.

You decide you want pizza for dinner and then notice, later, how easily you fulfilled a promise to yourself.

Your muscles fill in. You develop a subtle kind of strength.

“I do the things I say I’m going to do,” you think. “Not always, but often enough.”

Pretty soon, even you have to acknowledge that it has gotten a little bit easier.

Maybe you start by asking for help, by accepting that you can’t do it all on your own. Or maybe it’s even simpler than that: You get up and stretch when your your body tells you that it’s time.

It is time.

It does get easier.

It happens because you decide to try.

Once upon a time, I did not trust myself. I didn’t trust my judgement, I didn’t trust my self-control, I didn’t trust any of the words that came out of my mouth.

“Sure, I can have that done by later today,” I’d promise, knowing there was no shot.

“No, I haven’t talked to him,” I’d say, knowing the night before I’d sent a text so long it turned into a note.

If you’d asked me at the time, I’m sure I would’ve said that I trusted myself. The truth is I didn’t know how to tell the difference. I didn’t know that my reckless credit card spending and the countless weekdays spent crying and watching The West Wing instead of checking my email were symptoms of a larger problem. I just figured I was depressed because my Dad died.

I was 23 and a year into that grief when I had the idea to make Pretty Decent Magazine, an interactive PDF I would go on to sink hundreds of dollars I didn’t have into. I loved every second of it. I loved collaborating with my friends on articles and working with a designer to modernize the look of those 80’s computer magazines I still hoard in boxes under my bed. I loved the process of thinking like a magazine editor, of owning that as a part of my identity. I loved trying.

It is vulnerable to care a lot about something without the guarantee of outside acceptance or approval. By the time I finally released that first issue to the public, I think I knew (or perhaps had decided) that it wasn’t going to pan out. It was so much work for such little payoff. I’d put it out for free, as a “lead magnet,” but no one really knew who I was or what Pretty Decent was supposed to be. When it didn’t go viral instantly and change my life overnight, I figured it was over.

This is an example of what it looks like when I trust myself enough to try, but not quite enough to keep going.

What I find now when I search “Pretty Decent Magazine” in my Photos app.

Looking back now in my camera roll, I see nothing but evidence that I was really onto something. But in the mess of my own tangled self-image, I couldn’t see the forest for the trees. I couldn’t see what I see now: That I’d published a magazine. At 24. From my bedroom. And not just any magazine, but a completely interactive one written and designed for other artists and freelancers. There was a whole page on Desk Yoga, for goodness sake, with

Danielle Olivarez

demonstrating simple stretches in a Mac Photo Booth. It was meta and brilliant and everything I’d wanted it to be.

So why did I let it all go so easily?

www.prettydecent.org circa 2019. A boy told me this website was bad and I believed him. Now I see the vision and miss it.

I’ve always been like this with ideas, with projects. Some people say it’s because I’m a Manifesting Generator. A part of it is certainly ADHD. I’ve always wondered how much it has to do with the fact that my mom kept a copy of Linda Goodman’s Love Signs in the bathroom and every time I developed a crush I’d rush to let Linda explain what being born on November 22 meant about me. Nature vs. nurture, birth charts vs. Cosmopolitan horoscopes.

Am I who I am because I was meant to be this way, or because of all the cues?

I don’t know. I turn 30 this year, and I’m thrilled to say that I still haven’t quite figured it out. What I do know is I trust myself much more than I did before.

I had to learn how. Being self-employed will do that to you—if nothing else, entrepreneurship is an opportunity to be confronted with your own shit every day until something finally clicks.

For me, it clicked when gave myself permission to experiment. Not just in a metaphorical sense, but in real concrete terms. I started using science fair boards to plan my life. I started calling everything a “variable” and collecting “data” to support my “hypotheses.”

Just a few months after I released the first and only issue of Pretty Decent Magazine, I decided to go through The Artist’s Way. I asked my friends on Instagram if they wanted to do it with me, leaning into the idea that Pretty Decent might actually be an “Internet Café.”

We gathered throughout the Summer of 2020, a dozen or more of us meeting on Zoom from bedrooms and couches and park benches at a time when I was still sanitizing my groceries before I put them away. Together we talked about our dreams and fears and discomforts. Together we decided to try.

I credit most of everything that’s happened since to that summer. Every time I make a video that gets hundreds of thousands of views, or write a Substack essay that gets picked up as a read of the year, or get invited to speak, or see another person join The Study, I think about the joy I felt every Sunday knowing it was my job to facilitate a conversation between artists. I thank God that I still get to call that my job.

I don’t know the exact moment I learned to trust myself. I’m not sure that it happened at all, at least not in the way I would’ve expected. It’s not like I woke up one day and suddenly felt sure.

If I had to describe it, I’d probably borrow John Green’s words from The Fault In Our Stars.

“I fell in love the way you fall asleep: slowly, and then all at once.”

February 2018. A very sad and lucky girl.

The Internet Café is still thriving. Next week I’m teaching a Digital Crafts workshop about how to make a Link In Bio page for yourself on Notion. RSVP here. <3