13. Dreaming Within The Messy Middle

Reflections approaching Soft Place to Land’s One Year Stack-i-versary

A year ago today, I was dreaming BIG about what I was hoping to contribute to the world through Soft Place to Land. On 6/4/24, my first newsletter was published. And we’re live Ta-da!! I had committed to showing up for myself in this new way, putting my words and my heart for all (*some*) to see.

I had lofty hopes for an alternate income stream and attracting enough followers that would prove to a future publisher of the children’s books I had been working on, that I have enough of an audience to consider for a book deal.

Simultaneously, I had found that the practice of writing was something that had been desperately missing from my life since honors English class in high school. Committing to show up for myself and then committing to show up for YOU, has given me just enough accountability over the last year, that not only have I published the (as of today) 12 newsletters you all have seen, I have also been immersed in learning the craft of writing. I’ve written about 100,000 words spanning from fiction to creative non-fiction that will one day be the basis for a memoir.

Most of that has happened with Jeannine Oullette at Writing in the Dark, who articulates best why a 20+ year absence of creative writing left a gaping hole in my existence: “Writing = Living”. It’s true. Through writing, I’ve rediscovered my essential need to dream, imagine, and better understand myself and the world. She goes on to say in the about section of the WITD Substack community,

“Writing saved my life, so I teach writing as if it might save yours.

That’s what Writing in the Dark is really about—a place where we can “write ourselves into becoming.”

A place where attention, curiosity, playfulness, and surprise provide a portal to the profound on the path to discovering ourselves, the world, and each other more vividly through writing.”

I’ve come to understand that despite the circuitous nature of my ever-shifting dreams, everything is essential and everything is connected. That through writing I can continue to dream and be open to endless possibilities, not in spite of the nightmarish hellscape that 2025 has been, but alongside the fear and rage and disappointment. So many in my circles (friends, activists, my online writerly community) have expressed they too experience the waves of heaviness and temptation to submit to defeat over the last few months.

Dreaming in this world feels delusional at times. Change ‘for the greater good’ feels unlikely. Fear of recession is impacting spending. Businesses are struggling. I’ve felt it for months. Until the paradigm shift occurs where it is culturally normalized for parents and caregivers to take on the lion’s share of responsibility for engaging in the healing, understanding, and practices to support their struggling children, parent/caregiver coaching will continue to be perceived as a luxury service.

Sometimes I feel defeated. Other times I feel hopeful. Through writing, I better understand my own struggles. Through writing, I better understand others. I look for glimmers and inspiration.

Maggie Rogers is attributed to this week’s dose of hope. At 31 years old, her wisdom is clear. In an essay published this week in the NYT (which has a flavor of the Jennae Cecelia poem inspired trend, I Met My Younger Self for Coffee), adapted from her commencement speech to the 2025 graduates of her alma mater, NYU’s Tisch School of the Arts , Maggie shares that she was TOLD what I’ve spent a lifetime living (against the cultural grain) that friends ARE the most important. That “rest is a part of the job.” She goes on to reflect:

“We wanted to document everything. Write everything down. What’s happening to us is important. We’re going to see everything. Feel everything. We are going to make art that changes the world.

And really — we were learning how to dream. A lifetime making art is in some ways about your tolerance for risk, whether it’s money or lifestyle or your own heart. But it’s equally about your ability to dream.

I’d tell her to keep the dreams bigger than the fear.”

This young dreamer who wrote a song so she would pass a class. She didn’t think it was good enough. Then she became insta-famous from a moment gone viral in 2016 playing it in class for Pharrell Williams. You know that thing I keep telling you about synchronicity, well that’s the song I discovered just this year, precisely when I needed to hear it in order to acknowledge the depth of my hurt(s), then begin to mend my broken heart. With her insta-fame came chronic fatigue and panic attacks. She thought about quitting music. Instead, she figured out what was out of alignment and chose to do something about it. That something happened to be getting a master’s degree in ‘religion and public life.’ More on how she found her why here:

The experience of being thrust into celebrity meant, ironically, that she didn’t have time to make music. “I’d never been less of an artist than when I became a professional artist,” she said. “There was a really specific moment, in 2017 or 2018, where I was at camera blocking for what must have been my fourth or fifth or sixth late-night performance singing ‘Alaska.’ I had a massive panic attack. I was just, like, ‘What the fuck is my life?’ I felt like a show pony.”

Rogers’s second album, “Surrender,” from 2022—a hungry, carnal pop record about yearning for transcendence—shares a title with her master’s thesis; her appearance at Coachella in April of that year fulfilled the degree’s public-presentation component. Rogers is now in the midst of a postgraduate fellowship, which will end in May. She’s using the time to adapt her thesis into a book, a process she has found similar, in one way, to songwriting. “You have to be specific about experience,” she said. The manuscript focusses on the idea of creativity as a form of religion, and stardom as a kind of default modern pulpit. “Early in my career, people were using religious language to describe my shows,” she said. “Rolling Stone published a piece in 2019 with the headline ‘Maggie Rogers: Festival Healer.’ The BBC published one that said ‘Billie Eilish is my cult leader. . . . Maggie is my God.’”

Headlines are overblown by design, but her audience’s devotion—something akin to worship—was real. The tumult of the Trump Administration and the pandemic meant that Rogers’s fans, like everyone, were increasingly desperate for moral guidance. But Rogers was, too. “I was looking for answers, just the same as everybody else,” she said. “It was really jarring—people asking me for advice on suicide, or to perform marriages. I started to realize that there was this functional misalignment with the work that I had trained to do and the work that I was being asked to perform. I was put in this unconventional ministerial position without having undergone any of the training. Anyway, that’s how I made it to divinity school. What I ended up doing was developing a system for myself to hold these things. And then I went out and tested it.”

A few weeks ago, she told those graduates the most true things about dreaming:

“But no one saw the hard work. Or all the times I almost quit. No one heard the songs that didn’t work or the shows that were just bad… There were all these almost exits. Things that people will never see. Moments when it almost didn’t happen or I missed the window… What matters is how you make people feel.” The end of the essay floored me. Articulating something I’ve written about and talked about and remind myself of as often as possible, since it took me ~38 years to grasp.

“I’ve been thinking a lot lately about Radio City Music Hall. It’s where my New York University graduation was held, where I’ve been lucky enough to play many sold-out nights and where I was honored to be the commencement speaker two weeks ago.

The thing I always remember about that stage is that when the spotlight hits you and the crowd goes dark, the only things you can see are the exit signs. There are 47 of them, the last I counted.

Maybe, just maybe, all exits can be entrances, too. Maybe it’s about embracing the time in between — the minutes we have left. And all that will always be left unsaid.”

The kids are gonna be alright.

If we keep showing up when and how we can. Individually, collectively, in the ways that truly align with our values. If we do what we can to do our best to support these generations who are being raised to dream us into a more just world.

I’ll leave you with the flash piece I wrote during a Writing in the Dark write-in on February 17^th along with the reflections I wrote on the process of engaging with the prompt. All of which was very likely within days of discovering Alaska. When 100 moments a day reminded me of an exit I knew I’d eventually recognize as an entrance.

2/17/25 WITD Write-In, Process and Reflections:

Sometimes a writing prompt immediately responds to my reach and words flow. Others, particularly recently, have led to a forceful excavation, reaching for something distant and often unseen, a ghost bumping against the two way mirror. It is those times that I can close my eyes and trust that something will come, whether for practice or otherwise. Sometimes the reaching is into an abyss, my hands coming back empty. Occasionally though, reaching for a writing prompt feels like stepping into the Fire Swamp in The Princess Bride. A reach for words or memories or inspiration to draw upon requires a dangerous walk through a dark forest full of spurts of flame (spontaneously combusting sulfur), R.O.U.S’s (rodents of unusual size, aka giant flesh eating rats), and snow sand pits (quick sand, but way worse). The giant teeth gnashing, vying for purchase in tender flesh, reminding me that I’m not quick enough. Flame erupting under my feet reminding me that I am not listening hard enough. Getting swallowed by the sand, a suffocating reminder that there is no Westley to save me, and since when has there been anyone but myself to save me?

Logging in for this write-in, I could feel the door to emotion open when the title was read of the opening poem, The Healing Time (included below). Tears were flowing by line 6 and I wondered if I should turn my camera off to cry. I committed to feeling everything, which I’ve been doing plenty of in private. Does sobbing on zoom cross the line beyond socially acceptable emotional expression? I saw a few familiar faces in zoom squares who would understand- the others though, I do not know whether they’d consent to witnessing the expressions of this tender heart. I left the camera on and the poem was complete.

I had stayed.

The Healing Time

Pesha Gertler

Finally on my way to yes

I bump into

all the places

where I said no

to my life

all the untended wounds

the red and purple scars

those hieroglyphs of pain

carved into my skin, my bones,

those coded messages

that send me down

the wrong street

again and again

where I find them

the old wounds

the old misdirections

and I lift them

one by one

close to my heart

and I say holy

holy.

77 words speaking directly to the complexity of ‘healing’ that I have been reckoning and rumbling with through writing, in dreams, in conversation, and most often in the rodent wheel of my mind. Familiar with the untended and old wounds, the visible scars, coded messages I thought I had the cipher for and later learned my certainty at the decoded messages was an illusion. In part created by wishful thinking. Familiar too with the desperate prayer and newer practice to hold each wound and misdirection tenderly and in reverence. To see a heat map of my body walking down the same wrong streets and clinging to the belief that one day I will look up and notice the familiar doors with their welcome signs and flower boxes, and turn around before reaching the inevitable dead end. Without the prayer and and without the belief, it is too easy to conclude I will never be on my way to yes.

To my surprise, when Jeannine’s invitation to write was to start with the opening line of the poem, ‘Finally on my way to yes,’ the words I reached for were hovering right there, waiting to be harvested. Brought close while working through a prompt the evening before that had felt more like the ghost and the two way mirror. There had not been flow, nor were there R.O.U.S.’s the evening before. There had been a practice and a curiosity held together by trust, that each old and fresh wound brought to the page was in service of healing or craft or both. Nothing wasted. No time is wasted (a tiny mantra/reminder inspired by Jeannine’s teachings).

As I wrote, I was reminded that I’ll never truly know when I’m finally on my way to yes. It is then, my responsibility to proceed as if I am on my way to yes until unless I recognize the familiar welcome mats. Then while whispering sweet nothings to the old wounds who grumble at the loss of momentum like a sleeping child in the car who wakes at the stop light, I change direction by one degree at a time as I find my way. My own way, to my own yeses.

Dancing to the Rhythm of Light’s Song

After The Healing Time, by Pesha Gertler

Finally on my way to yes, at first all that I am conscious of is the ‘no’ and ‘not this.’ Not this person. Not this place. Not this time. Not this career. Not this story. Not this ask. Not this idea. Not this way. Not available. Not for you. Not with you. Not from you. Not this. No.

Yes pushes through every so often, a whisper of blue sky or a giggle pushing its way out of my chest for no reason at all. The yes is an invitation to stay. The yes is a little break into dance while walking the dog along the 205 footpath, in full view of passing traffic.

Yes is remembering that every no feels like rejection, when maybe it is sometimes an invitation to see beyond. That feeling that asks to be seen and held without being pushed away. Not quite yet. “No pushing in line” the teachers say. Why then, are we taught to push feelings? Away and down. On the way to yes there are disappointments and diversions and the human condition is to feel.

Moments when no sends a wrecking ball through the first floor of the carefully built structure. The vision and grasp on the dream as lost as the crumpled walls until the dust settles. Yes is there waiting to see if you have stayed to witness the clearing. Yes asks if you’ll honor the truth of destruction. If you have, yes asks whether you would like to rebuild or if it’s time to gather your precious items, like the now broken stained glass heart that hung on the wall and find a truer, gentler home for it all. A home that gently nods when the wind of emotion knocks on the door, allowing you to open and close that door as you please.

Yes then asks how soft you are willing to be with the broken heart. Are you willing to display it with its fissures for all who enter to assess? Not its worthiness, but their own truth and capacity to hold something so fragile. Not all are able to accept the responsibility of proximity to a heart like this.

Some will gently decline- no thank you, not now, not like this.

Some will jump to solutions- we can repair the heart, fill in the cracks or carefully break apart the pieces and make a brand new mosaic.

Some will move closer- yes this, let’s hang it in the window so the light shines through, just like it is.

Yes is the dancing light catching in the crevices and the body that moves to the silent rhythm of the light’s song.

Video description: A crowded patio filled with people and dogs, panning across dancing light and mist to a jam band.

Reader Invitations 💌:

👩🏻‍🎤 When you are on the stage and all you see is 47 exit signs, how do YOU choose to sing your song anyway?

✨ What gives you hope? Where have the glimmers been recently?

🌎 What are your hopes and dreams for your children and/or sibkids, as the generation(s) that will inhabit the earth and society we leave for them?

TLDR: It’s rough out there. Lots of folks are struggling in lots of ways. It’s me. I’m struggling too. I share how musician Maggie Rogers and her wisdom and ability to find HER alignment has inspired me to keep dreaming. I also include some relevant creative non-fiction I wrote this February along with the process notes I wrote along with it. Because nothing is wasted.

Land Acknowledgement: This newsletter was written and inspired by multiple geographical locations. I am publishing today from lands sharing geography with the following Indigenous Nations: Clackamas; Umatilla & Walla Walla; Confederated Tribes of Siletz Indians; the Confederated Tribes of Grand Ronde; and Cayuse.

Harm and violence occurred for me to have the privilege to write about and visit the lands that inspire much of what you read here. I thank those who originally and continue to steward these land in resistance to the continued damage to the lands and and nearby waters via practices and laws maintained by colonizers.

Proof of life. And joy. Within the messy middle.