Two Month Update: The Money & Doubt Rollercoaster

Psst.. you can listen to a podcast version of this post right here

This past month has been HARD, HARd, HARD.

What triggered the hard-ness?

My old frenemy: MONEY (or more accurately, my THOUGHTS about MONEY).

When I decided to do this Radical Experiment with my business in February 2023, I took a glimpse at my bank accounts and concluded: “It would be ok if I didn’t make ANY money this whole year.

And that comforting belief carried me for a little while, like I was clicking up, up, up a hill of possibility. The higher I went, the more potential I could see all around me…

…I could play, and post whatever I wanted and not sell anything and lose Instagram followers, and it was all in the name of experimentation and spiritual growth.

Until some uncomfortable money facts came to light and it felt like, for the first time, I saw a terrifying drop in my future:

  1. My husband let me know that he was having a hard time covering certain expenses, now that he was putting more in his 401K

  2. Which led us to look at how much we were actually spending each month

  3. Which led me to realize that I was eating into my savings a lot more than I thought

Which led to very PANICKY, ICKY feelings.

And panicky money feelings can lead me quickly down a doomsday spiral:

  • What if I’m never able to bring in as much money with my business as I did before?

  • What if no one’s interested in learning calligraphy anymore?

  • What if my previous business success was just a big, old fluke?

  • What if I drive everyone in my audience away with my weird-ass experiment and vulnerable personal talk?

  • What if my husband suddenly loses his job?

  • What if we lose the house?

  • And on and on and on…

I’m gonna be frank with you, I’ve been completely lost lately in those fearful thoughts.

Suddenly, it feels like I’m free-falling down into the unknown, hurtling toward the earth with nothing to catch me.


Last night, my brain kept me up until 3am, examining each of my worries from all angles…

…my business, my new coaching practice, my failure, how I might lose everything.

I lay in bed for a solid four hours, trying to sleep. Reading old, familiar books until I felt drowsy, but as soon as I closed my eyes, the wave of chittering anxious thoughts rolled right back in.

The worst part about insomnia is the fighting of it. The frustration, the “why is this happening?”, the building fear that the next day would now be ruined…

I felt that struggle for a short while. But, here’s where all the internal work I’ve done over the years showed up to save me. If I wasn’t going to be able to sleep, maybe I could look at the dark hours as a wonderful opportunity to meditate. I always told myself I should meditate more, and I never gave myself the quiet spaciousness to actually do it. So, I started to breathe in and out longer, with intention, focusing on my thoughts.

= It didn’t work =

My mind kept drifting back to the anxieties. I forgot I was meditating and I would latch on to one of the little big troubles and start observing it intently.

I tried tapping. Slowing my thoughts down to a sleepy crawl.

At some point in the night, between brief moments of semi-unconsciousness and wide-awakeness, an image floated into view. A familiar one.

My little girl self. The seven year old inside me who just wanted to play.

I had forgotten about her, as I often do.

She’s a good, helpful little girl and was used to scrooging down small when the adult-sized anxieties entered the room and filled it with their unhelpful thumping.

“Of course I can’t play now. There are real problems that can’t be solved with fun and laughter. The adults know better. This is a time for serious worry.”

But is it?

Because my very “real” problems look a little ridiculous in the gray light of the morning:

  • We’re going to run out of money… even though we have almost $400K in the bank.

  • No one wants to learn calligraphy anymore… even though I have over 100K Instagram followers and one of my calligraphy posts just went viral.

  • No one will want to buy anything from me if I fail at selling calligraphy… as if calligraphy is the one lucky thing I can do well. As if I didn’t pick up calligraphy and then five years later, become one of the most well-known names in the industry. As if I hadn’t gotten myself into the best university in the nation, and one of the best law schools (despite not really wanting to go). As if I hadn’t succeeded at nearly everything in life that I had put my mind to…

And maybe that was the problem. I’ve never truly failed before. I’ve been so blessed and gifted with life skills that I’ve avoided any major failure. Which makes me TERRIFIED of doing it for the first time.

These weeks of anxious agony, every day wondering, “what the hell am I doing here?”, every day assuming nothing would work again… I think it was an inevitable low on this life roller coaster that I’ve chosen to ride.


When you really LIVE… when you go after a life that’s big and unusual and scary… there will be higher highs and lower lows. And this time, I had to get really low before the absurdity of it all really sank in.

Which is why I’m crying as I type this. Crying and laughing, both at the same time. In relief and gratitude and wonder at how ridiculous this life is. How much there is at stake and how very little. How small we are, each clutching our tiny collection of worries, as we cling to the surface of a watery ball spinning in a galaxy among infinite stars in a sea of dark matter.

How, when we finally come to face death, none of the worries really matter. How our brains do their best to fixate on and solve our problems, and only take us away from what’s really important.

I can’t believe I get to be so alive. I love it, all of it. For now, at least.

I’ve hit the bottom of another trough and feel myself rising again. I think life was always this way except now I have a deep, fundamental belief that it’s OK that it’s this way.

  1. Imagine riding a rollercoaster, except you don’t know what a rollercoaster is, you don’t know that it’s safe. Every twist and drop would feel deathly scary and every climb up would feel like a temporary relief, plagued with anxiety about what was coming next.

  2. Now, imagine you understand what a rollercoaster is, and trust that it’s been welded solidly and safely and its very purpose is to lift and drop you, to make you feel the thrill of being alive.

Those two experiences would be completely different, even if the rollercoaster itself was the same.

I’m learning to trust that this entire rollercoaster of life is ok and safe… no matter how scary the drops feel.


The difference is my UNDERLYING FAITH. It’s my CORE BELIEF that I am worthy and lovable and capable and that I CHOOSE THIS LIFE.

Here’s what that looks like in concrete tools:

  1. Anti-anxiety techniques - like tapping, deep breathing, taking a short walk, petting my dogs. When I remember to use them, I remember that I do have some CONTROL over the way I feel.

  2. Perspective-shifting thoughts - like imagining, vividly, how I would feel if I KNEW I had three years left to live. Like remembering my best friend who died at 38 and would be so proud of me and would encourage me to KEEP TRYING and experience everything (even the uncomfortable parts), because that’s why life is so precious.

  3. A deep sense of acceptance - my current belief is that my infinite soul chose to experience this current human life that I’m living. My soul doesn’t just want the easy and comfortable parts. It wants the hard parts, too. It wants it all… what it means to be ALIVE.

All of this helps me to embrace the roller coaster and trust that, whatever happens, I’ll be alright in the end.

That faith waivers sometimes.. but I always come back to it.

And I think that’s the “goal” of all the internal work I’ve been doing. This is what it means to be a resilient, badass, vulnerable and messy human being.

The goal is Not to get to a place where everything is golden zen. But, to reach acceptance that life will always be hard and that is beautifully ok.

It’s the ability to ride this roller coaster, with a little more love and grace for myself and for everyone else riding their own insane coasters of life.