What Writing a Pitch a Day Did to My Brain (and My Freelancing Career)

Anne H. Putnam lives in the Pacific Northwest with her husband and their cat and writes about body image, relationships, and anything else that requires an awkward amount of vulnerability. You can follow her on Twitter for politics and random musings or Instagram for cat pics and baked goods.

I began this year with a resolution to prioritize my writing, despite having a plate so overloaded it was bending at the edges. I needed to find a way to fit it in — and also to get it out, which meant, in part, that I would have to ramp up my pitching productivity. 

I’d already made solid progress on conquering my fear of rejection (or worse, ghosting) by editors, but I was struggling to come up with ideas for essays and service pieces. How many angles could there possibly be on my two preferred subjects, relationships and mental health?

To be honest, I’ve always had a hard time coming up with ideas. While so many of my writer friends complain about having too many ideas and too little time to write them all, I silently hate myself for the crickets in my brain. 

Until I wrote my first memoir, I never thought I’d have a book in me at all; until I started my second book, I was sure I’d tap out at one. I’m always surprised when I have an idea for a story or an essay that actually feels like it can be fleshed out beyond a paragraph. But I was determined to try.

At the end of January, when a writer in one of my Facebook groups announced she was going to send a pitch a day in February and asked if anyone else wanted to join, I signed on. Not necessarily to send a pitch every day — that was a little too ambitious for me — but to at least try to write one. 

As a recovering teacher’s pet and a forever student, I love any challenge with an external structure. Show me an outline and I’ll write you a blog post about tech marketing; give me some plans and a mitre saw and I’ll build us a garden box; tell me I need to write 1667 words every day in November and I’ll draft 75 percent of a fairly terrible novel. As an established writer but a relatively recent student of the art of freelance pitching, I figured this practice could only do me good.

I quickly realized that this was much harder than those other structured challenges. I went into week one with a few ideas up my sleeve, a couple of notes-to-self with topics that had been rolling around in my head for the past few months, but by February 8 I was tapped out and panicking. I was sure I’d never have another idea — after all, I’d used up nearly a year’s worth of original thoughts in just one week!

But later that day, as I baked cinnamon rolls to soothe my anxiety about not having anything else to write about, I listened to a little Taylor Swift, and the lyrics poked at the memory center of my brain and sparked an idea. I’d made it through the day with my brief streak intact. Now if only I could keep going for another 20 days…

And I did. I started every day with the wind whistling through my brain and the fear that I’d never come up with a pitch, and every day I hit on an idea. They came from songs, from conversations, from Twitter, from my own experiences, and from the recesses of my memory, where thoughts that wouldn’t leave me alone had been huddling for months or even years. 

On February 15, I put on a pair of leggings to go outside the house and then rushed to write a pitch about what a jerk I used to be about people who wear leggings as pants. On February 23, during a conversation with a friend, I said “writing is bloodletting” — and wrote a pitch about that as soon as our Zoom ended.

I stopped feeling like I had run out of original thoughts — and (more interestingly) I began seeing the world differently. Just as I found myself framing every new experience as verse during a brief (and doomed) dalliance with poetry in college, I now found myself distilling everything around me into its pitchable core. 

I interrupted heated conversations with my husband to send myself emails, ignoring his probably-excellent next point so I could capture my previous pretty-good one in a pitch. I stared off into the middle distance while attempting to read, no longer satisfied with letting my thoughts be provoked temporarily by a book — no, I had to follow those thoughts, catch them in a butterfly net, pin them into a 300-word essay idea.

As I turned the corner to March, I realized I’d strengthened my pitching muscle dramatically. I read through the 28 pitches I’d written in February, seeing them all together for the first time now that I didn’t need to be so fixated on forward momentum. Not all of them were good — probably more than half were pretty bad, actually — but none was irredeemable. There were some pretty interesting nuggets in there, in terms of “things I could write about,” and the breadth of subject matter and focus was impressive. 

I guess I’m not such a two-trick pony after all. 

Whenever I’m stuck, I push myself to do a challenge like this: the same hard-but-manageable exercise every day, including weekends, for a definite period of time. That last part is essential, because the ability to see the light at the end of the tunnel is what keeps me pushing through the hardest days. 

Practice has yet to make perfect, but these sustained efforts never fail to make me feel like I’ve developed a new muscle in my brain, a living, aching, growing part of my mind that leaves me feeling hopeful and capable and ready to keep working. I feel stronger, and (maybe more importantly) I feel confident in my ability to learn new skills and strengthen the ones I already have.

So if you’re feeling stuck, I highly recommend pushing yourself with a structured, consistent, short-term challenge. (Jami Attenberg’s #1000wordsofsummer is another fabulous example, and is coming up in June.) You just might surprise yourself with what you can do.

Oh, and if you’re wondering: yes, this piece came out of one of my February pitches.

Dear Friend

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Tara K. Shepersky is a contemplative walker, writer, & photographer based in Oregon’s Willamette Valley. Her first book is Tell the Turning, a collection of poetry with pen-and-ink illustrations by Lucy Bellwood, on Kickstarter right now!

This is the latest installment in Tara’s monthly column about the creative practice.

If you connect with Tara’s work, consider supporting her Patreon. You can also write her a letter via The PenPalProject. 

I am just in the door from my afternoon commute. This consists of a mile’s easy walking in a circle from my house — marking the close of today’s hours at the laptop-enabled money-factory, and reminding me gently of my physical body, its welcome tether to the seasons and the earth. 

In the moment before this one, I opened the mailbox to find two letters from friends. I smiled at them — a real smile, like I was greeting the friend named in the return address. Now I fold back the top of my little correspondence desk, and lay the letters inside. 

I will wait, and shape a space to give them my full and slow attention. 


Letters, in this last apocalyptic year-and-a-bit, have become for me a particular source of pleasure and perspective — and creative ballast.

I learned to write letters the first time as an adolescent, because writing was the only inexpensive way (remember long-distance phone charges?) to keep the friends I had to leave behind every few years, when the U.S. Navy stationed my dad somewhere new. 

I didn’t learn well, though: I had good intentions, bad follow-through. For one thing, I didn’t know how to write and read letters, in the sense of understanding what I hoped to give and get from the exchange. I had plenty of ideas, but precious little discipline to help me explore them. Thus, when my mood or mindset didn’t line up with my goal, I had zero motivation. So I stopped putting pen to paper. So I lost my penpals.

Letters are a fruit of slowness and attention and care — qualities I cultivate, though often with stunted success. I have found my way back to letter-writing by paying attention to that cultivation, false starts and failures included. (I was learning to garden at the same time. This has perhaps influenced the metaphor.)

First, I noticed how much nourishment I’d begun to derive from some very long exchanges on Twitter. 

I’d ramble for days at a time with people I didn’t know at all well, about books, walking, memory, landscape. We stacked ideas on top of questions on top of enthusiasm. Our conversations were generative and exciting and connective. We lost the thread a lot, in all the excitement. I wished often for the same conversations but slower and deeper, with everyone and every thought given more time to bloom than our present suite of communication technologies allows. 

At which point, I realized I didn’t need to reinvent the wheel. I asked for an address or two. 

Also, I noticed the ways I was missing my friends. These folks are many and various. They live across town, or a few miles downriver. Also in Montana, California, Iowa, Alaska, Pennsylvania, England, Germany. We used to meet at workshops, at church, on boats, on trails, in restaurants, in backyards. 

It’s not like we ever met a lot. But I think about my friends often, and I used to store up things to turn over when we saw each other next. Going nowhere and seeing almost no one has not injured me — a solitary — as it has most folks I know, but I have absolutely missed the opportunities for depth of conversation that arise from a life lived at least partially in physical community. 

There was never a time when I realized all of these connection opportunities in person. But with the sudden inadvisability of in-person contact, relying on texts and Zoom and Twitter began to feel more hollow than before. Instead of handily filling in the gaps, those tools have become primary platforms to maintain entire friendships. They’re not, generally speaking, equal to the long-term task.

Letters are.


Why is this? I’ll offer two understandings gleaned from a year and more of writing deeply and regularly to friends and strangers. 

Both understandings require creative exercise — that formative, necessary thing you (you, reading this) need, and with which I know many of my fellow artists have been struggling, as deaths and lockdowns and vaccine worries and economic pain wear us down. 

First: To write to a person, or to read what they have written you, is to spend real time with them. It’s asynchronous, yes, but I think of it as sacred time, time-out-of-time, in which clock-time ceases to signify.

It’s real time because you are focused on that person. There is no room (indeed, no opportunity) to check your DMs or switch to a different channel, and there is only this one person you can listen to at a time. The conversation is very slow. You can read or write only one side of it at once, which forces a particular kind of concentrated presence. You can pause your conversation to think or feel about something your friend has said. You have what feels like infinite space and time to respond internally, to process, to enjoy. 

You are also doing the work, all this while, of creating your correspondent there in your mind and heart. To recall or imagine a friend is a creative act, and also a specific pleasure. A letter places this work at the center of your being for as long as it takes to write, or to read.

Also: Creating a physical object is an act of magic, or an act of prayer. 

I like to understand things intellectually. I used to think of magic as something abstruse, and I wasn’t really surprised when I couldn’t make it “work.” Obviously, I was doing something wrong. I used to be frankly baffled by prayer. How do you even start? 

Sometimes the answer is just to do or make a thing. The act of creation is… creation. You are taking the materials around you, and shaping them, with your hands and whatever expertise you own, into a new object in the world. 

To create that object with a very specific recipient in mind is to direct the power of your magic, or your prayer, to them, and to the relationship between you. 

A letter, hand-written, maybe illustrated or decorated, is a powerful, non-replicable piece of art, constructed with your hands and given life by your care, your interest, your attention. It forges something, both inside the writer and between writer and reader, that a text message can’t. 


My art has been my anchor in this last long terrible year, and my strong companion. Though poetry, my primary art, cuts as deeply as it heals, still I am fortunate that it has journeyed with me. 

I have written here before that I need to commune with my places to write the deep poems I love. This type of communion has been in short supply for some time, and it has followed that most of the new work I’ve crafted feels adrift, amorphous, unspecific. Not so my letters.

I have said that a letter is a piece of art. I think it is one quite as beautiful and valid as poem. This is the end of the similarities. 

I feel expansive when I sit to write a letter. Free-wheeling, like I’m embarking on an essay — yet much less formal. I can ramble in a letter, and excuse myself with phrases like “wandered off-topic again.” I can spell things wrong and cross them out and muddle my thoughts and still feel unembarrassed to put a stamp on the envelope. A letter feels unfinished because it is. This is a feature of the genre. 

All art is a conversation, but usually we have to remind ourselves that’s true. A letter knows that in its very form. By choosing to create, and enjoy, this physical art form, we assert to each other and we reassure ourselves that we’re not suffering, enjoying, analyzing, and exploring this life alone.

The regular work of this creative reassurance is, I continue to discover, infinitely worth the considerable time and effort it requires. Full and slow attention to ourselves — each other, our world, and our shared and divergent experiences — is yet another healing friend. Speaking for myself, but knowing I am not alone, I can say that I need to cultivate as many of those as I can.

Creativity Thrives in Community

Danielle Taschereau Mamers is a researcher at McMaster University, where she studies politics and media. She has expertise in settler colonial history, decolonization, and environmental politics. Taschereau Mamers has written about bison conservation for The Conversation, and has also been published in the Journal of Narrative Politics and Settler Colonial Studies.

For the past three years, I have been writing with others — not collaboratively, but in community. As a writer and researcher, my work is often solitary. By joining together with a small group of fellow writers and scholars, our writing practices have thrived. Working in community is the single best thing I have done for my creative practice.

In the fall of 2018, I was passing days alone in my office, surrounded by stacks of books, overflowing notebooks, and half-empty coffee cups. It was far from romantic. Adrift and mostly miserable, I needed creative companionship. I reached out to other women working out of the same research centre, who were also in solitary office spaces and similarly struggling with overwhelming writing projects. Perhaps, I ventured, we could write together, at the same time and in the same space? 

We started as a small group of four, meeting for two hours every Thursday morning. For the better part of a year, we soaked up the small luxury of having access to a well-lit conference room and fancy espresso machine at the centre. Each week, we assembled our laptops, reference materials, and drafts around the small table and declared our intentions to one another. Small statements of tasks that we could reasonably complete during our two-hour session. These tasks often felt trivial in the face of a book or dissertation manuscript: drafting a paragraph, summarizing an article, inputting revisions. Yet, as the year stretched on, the work we did together accumulated. Our projects inched closer to completion. 

That big projects are the accumulation of smaller components is hardly a revelation. The magic of our writing group is the articulation and celebration of those minor tasks as goals in and of themselves. Speaking aloud to one another what we would do and then checking in at the end of our two-hour work session, we were not just writing. We were also giving  narrative accounts of how our writing processes unfolded, and learning from one another the many ways in which writing can unfold. 

Working in these focused blocks helped me reckon with one of my biggest challenges: my sense of just how long writing takes. As a graduate student, I was forever dispirited by the bold lists of projects and deadlines I would set out for myself. Each day there would be much left undone, endlessly pushed forward to the next day. From week to week, semester to semester, my sense of what I wanted to accomplish was increasingly distant from what I was able to get done. I promised myself over and over again to work faster and more efficiently and for longer stretches. 

In writing and other creative work, the line between promising to work harder and haranguing oneself for not being enough is very fine. Over these years of not feeling smart enough, fast enough, or accomplished enough, it never occurred to me that my expectations were the problem. Writing in community, I’ve witnessed how common struggles with time and expectations are, while also coming to understand how different writers approach these issues. Together, we have found ways to be enough.

By working in community with other writers, I saw how others worked. Through our meetings, I listened to their descriptions of trouble with a particular paragraph or attempts to braid different narratives together or approaches to thorny peer-reviews. But alongside hearing different approaches to the writing process, I also came to better understand just how incrementally a manuscript comes together. More importantly, I saw that it wasn’t just me that wasn’t enough, but that the process is long for everyone. Settling into our consistent two-hour blocks, I set more modest goals and saw them through. While working in community hasn’t made me smarter or more efficient, it has taught me what I can do in two hours. Most importantly, our group has showed me how to consistently show up for modest writing goals. 

The onset of the pandemic coincided with moves across the country and new jobs. Our group moved online like the rest of the world. In a period that has brought isolation and distraction from creative practice for many, we have grown. An accumulation of modest goals and their celebration that began on Thursday mornings in a sunny conference room now unfolds two afternoons a week over zoom. 

When I hear writers and researchers express frustration over stalled projects or the loneliness of our vocation, I always suggest finding a writing group. Or making one. Finding just one other person makes a group. Drawing from the three years that our group has been writing together, I have four suggestions for building a writing community:

Be consistent. Set up a time and place where you will come together. We started with weekly morning meetings in a physical location that was comfortable and already a part of our working lives. Consistency needs flexibility. We check in seasonally to decide our meeting schedule. When we met in person, there was a season of shifting from Thursday to Friday mornings. When we no longer had access to the research centre conference room (and the pandemic meant we could no longer meet in person), we moved online and increased the frequency of our meetings. But as an online group, we are still together for two hours of co-writing where we hold space for modest goals and for celebrating their achievement.

Size matters. The size of our group is part of our success and key to being consistent. Our group has grown from four to eight over the years. It is small enough that we know each other and have come to know one another’s projects well. But it is big enough to withstand a couple of absences on a given week or season. In busy times when there have been just two members available, the consistency of community continues.

Prompt each other. After a few minutes of chatting at the start of each session, we write. Each session begins with a prompt: “In the next two hours, I will…” We finish this sentence aloud and then build on it with a few minutes of free writing. Sometimes we offer one another prompts to move the writing along. These include listing the key points we care about, writing out the things we do and do not know about a topic, or putting the feelings we have toward our work into words. Setting a timer and scribbling by hand together brings a special energy to getting started and to keeping going.

Create special sessions. Once a season, usually aligned with the beginning or end of an academic semester, our group holds longer retreats. We pick two or three days where we meet for full days and set larger, but still achievable goals. Along with focused writing sessions, we take lunch breaks together and build in brief yoga sessions to keep up morale. Whether in person or online, we conclude retreats with a celebratory happy hour. 

The impact of this community practice has been profound. Between us, we have completed book manuscripts, submitted articles, begun creative writing pursuits, and made headway on stalled dissertations. By working side-by-side (and now, screen-by-screen), we have learned the productive limits of two hours. When shared, these two-hour increments expand in ways that have made us better writers, committed to our craft and to each other.

How a Teacher Turned a Comms Habit into a Full-Time Gig

After spending 16 years in public education as a special education classroom teacher and district support specialist, Tim Villegas turned his communications habit into a full-time career. He is the Director of Communications for MCIE, Editor-in-chief of Think Inclusive, and hosts the Think Inclusive Podcast. He also freelances while working on a book about his journey from being an inclusive education skeptic to becoming a self-proclaimed inclusionist.

My first PR job was for an indie record label nestled in a second-floor office above the main drag of a sleepy suburb close to Los Angeles.

The president of the label handed me a phone book and a sheet of paper with dates and locations. “Here you go, book us a tour.”

I spent the next few weeks during off times from my studies at the university, cold-calling venues up the Pacific Coast to book our indie rock band tour.

It was a tough gig. But you know what? I loved every minute of it. There was something magical about using my conversational skills to convince other people to take a chance with booking our band.

Little did I know that my next official communications job would be as Director of Communications for a nonprofit — or that it would take 20 years of experience and education to get me there.

Initially, I went to school to become a counselor — but there weren’t too many jobs right out of college for Psychology majors. As a stopgap, I took a position at an organization that worked with young autistic children and realized that I had a knack for teaching kids. That’s when fate took over. 

When my job led me into a public school to support one of our clients, I surveyed the educators around me, and thought “I could do that!” The advice given to me was to become a substitute teacher and see if it was something I wanted to do. And I did! That year, I applied to a local teaching credential program. Within 18 months, I obtained a provisional teaching certificate so I could get a job as a teacher.

When interviewing for my first job as a special education teacher, I remember saying “I think special education has a PR problem.” Before taking my first courses in my teacher education program, I had no idea what it took to be a teacher — and working with students with disabilities was still a mystery to me and everyone else I knew. 

Not only did most people not know what teachers do, but it also seemed to me that there was a significant disconnect between what my teaching credential program taught me and the reality of public schools. My program was supposed to prepare me to work in schools, but the inclusive values instilled in me — that students (with and without disabilities) should be educated together, not in separate classrooms — were not evident with my first employer.

As it turns out, segregating too many students with disabilities into separate classrooms has been a big problem since the federal government passed the Individuals with Disabilities Education Act in 1990. The United States has definitely made progress since then, but not enough. 

Although I had some allies, many people did not understand my passion for inclusion. It wasn’t until I moved from California to Georgia that I found the problems present in my first teaching job were very similar in my new job. I had the idea of creating a blog to share my thoughts about how educators could do a better job of including students with disabilities in general education.

I started a Twitter and Tumblr account as I was preparing to present at a disability rights conference near Atlanta, GA. Once I began writing and sharing, I realized how powerful social media could be — and how my writing could help connect me to like-minded individuals. 

A friend helped me set up my first domain, ThinkInclusive.us, and I was off and running, reading everything I could about blogging and website design. I asked friends that I met through social media to write blog posts centered around inclusive education. Shortly after that, I started a podcast to interview people who are actively working to change educational and societal systems to be more inclusive.

Promoting the blog and podcast felt very similar to the days when I worked for the record label — except this time, I was armed with the internet.

I kept up my side hustle for eight years; teaching during the day, and blogging, editing, and podcasting by night. I’m not going to lie. It was exhausting, and there were many times I took long breaks. A few times, I even said I would quit. But every time I was tempted to hang up my keyboard, I would listen to the whisper inside of me to keep going — and I am so glad I did.

Today, my comms habit has turned into a full-blown gig as the Director of Communications for a nonprofit dedicated to promoting and sustaining inclusive education. I’m writing, editing, and podcasting every day, and I wonder what my younger self would think if I told him what I was doing now. 

I’m grateful for everyone who ever told me not to give up. If there is one takeaway from this, it’s that you should always make your passions part of your journey. If writing is what gets you up in the morning, don’t let go of it. You might just find yourself back where you started, home.

How I Balance Freelance Writing and Teaching Piano

Kate Oczypok is a 30-something freelance writer and piano teacher. She has been published in The New York Times, Real Simple, Brides, and various local publications in DC and Pittsburgh, where she grew up. Kate currently lives in the DC area with her fiancé Brad and dog Tito.

I thought I’d be working full-time for a newspaper, or perhaps teaching upper elementary or middle school, the usual 9-5 or 8-4 job. Instead, my day-to-day routine is certainly something I never imagined.

The first story I ever wrote was called “Starlight the Magical Horse” about — you guessed it — a magical pony. I became hooked on storytelling, writing more pieces about families with lots of children and protagonists that sounded a lot like me. As my parents continued to have kids after me (I am the oldest of five), I discovered how much I loved being with kids — and later, working with them (not just writing about them).

Through lots of hard work and determination, I have managed to become a successful freelance writer and piano teacher. I also have a “side hustle” (as the kids say these days) as a family and portrait photographer.

Teaching 25 children ages 6-16 requires lots of organization. Writing for multiple publications at once needs plenty of calendars and to-do lists to make sure I don’t miss a deadline. Here are some ways I manage my teaching and writing careers — at the same time.

Organization

If I wasn’t organized, I would not be able to manage what I do — especially as someone with diagnosed generalized anxiety disorder. Every Sunday, I sit down with my paper planner (this year I went for a Kate Spade one) and write out who I have for lessons that week. Most of the time my lesson schedule stays the same, but there’s inevitably someone out of town on vacation or taking a make-up lesson on a different day not typically their own.

Then I write down any due dates, meetings or appointments that week. I even write a reminder for ordering groceries, which my fiancé and I do through Instacart since we don’t have a car. I pick a day that’s the least busy to do laundry or clean the apartment (I alternate weeks with those).

For piano, I stay organized by scheduling a lot of emails in advance. I send a reminder every Sunday at noon to my piano students’ parents. I also send a monthly progress report and estimate for the upcoming month on the third Friday of each month. 

Initiative

I find it very hard sometimes to test my creativity with a pitch, but I know that if I don’t put myself out there I’ll never get anywhere as a freelancer. I’ve learned that at least 80 percent of freelancing is looking for pitches — and being creative enough to understand what your experience could bring to the pitches. 

I subscribe to multiple freelance newsletters, both free and for pay. The investment I make into these newsletters allows me to pitch publications I never knew existed (or never knew were accepting pitches).

To be a successful freelance writer, I’ve found that you must be willing to pitch anything that looks intriguing to you — of course, you’ll also want to make sure you fit the description of what a publication is looking for! I love education and children, entertainment, lifestyle stories, and pets, so I look for publications seeking that kind of work. Another part of the pitch equation is thinking about what’s going on in your life at the moment. Right now, I’m engaged to be married, am a dog owner and work in freelancing and teaching. Using your strengths and experiences make the occasionally tedious task of coming up with pitches a lot easier.

Balance

Having two very different careers that both demand 100 percent of my attention requires a lot of balance. I can’t leave a writing deadline until the evening it’s due — not if I have an afternoon of piano lessons ahead of me. I have found that writing in the morning is the best for me. Not only do I work better in the mornings in front of a computer, I also tend to write my best in the earlier hours.

Since the children and teens that I teach attend school, I teach piano lessons in the after-school hours, approximately 3-7 p.m. Monday through Thursday. Reserving Friday for make-up lessons and/or writing work I haven’t finished was a crucial addition to my schedule. If I taught Friday 3-7 p.m. too, I would not have time for any last-minute deadlines.

As I mentioned earlier, I have generalized anxiety disorder. Without taking time out for self-care, my work suffers. I have the Calm App on my phone, love to spend time walking my dog and my youngest sister just got me into Peloton (I just use the app and our apartment’s gym equipment). I also see a therapist bi-weekly to help me manage my anxiety. Doing those things helps me with my work-life balance.

Relationships

Even though my monthly earnings can be variable — with some months bringing in a lot less than the previous month — to me, freelancing is worth it. So are the piano lessons I give. I love being able to work from home and in the after-school hours, work with children on a one-on-one basis. I’ve been able to establish long-term relationships with lots of publications and I’ve been teaching some of my students for seven years now. It’s fun to watch them grow up. 

Sharing music with my students is very rewarding to me — I am so proud of them when they play a scale correctly or pass a difficult song in the lesson book series that I work in. Recitals are particularly happy times for me. Even though we’ve had to move them to Zoom these last two years, it’s so wonderful to see everyone in one place playing pieces they worked on for months. It is so incredibly rewarding to see a child understand a concept or play a song perfectly for the first time. It’s equally rewarding to see my byline at the top of a story I’ve worked hard on. 

Now that I’ve been freelancing and teaching for almost a decade, it’s been interesting to reflect on my career choices. Yes, sometimes I worry about my finances on certain months. I sometimes feel frazzled when I am working on multiple projects at once. I wouldn’t change anything though. I feel proud of the fact that I can honestly say I love my job — or, in this case, jobs!

On Opportunities and Opportunity Cost

Photo by Ryan Baker from Pexels.

Michelle Song is tired, happy, and figuring it out.

The opportunity cost concept is intrinsically capitalistic, but in that unique intensity that is American in flavor. What other thought exercise implores one to consider the relationship between money, time, risk, return, and optimization so literally? Opportunity cost is all about bootstrap-strapping-up and making hay while the sun is shining because — here’s the kicker — there’s an imaginary cost to every resource you expend and that cost is an abstract and unconceived opportunity that could be.

I worked in Corporate America for years because I believed in opportunity cost. As a young adult, I understood that I would have to be my own safety net; that money would be a problem for me to solve before I could earn the privilege to design the life I wanted. So I focused on the urgent problem of keeping body and soul together and punted the more challenging and existential questions of “what kind of work would I ultimately like to do?” and “what qualities make my life enjoyable?” It’s much easier to focus on numbers and the quantifiable than it is to measure quality of life and progress made towards creative endeavors. This is true for me partly because I haven’t had the time and space to explore in earnest what this alternate life would look like — or how I could make it happen in a real, practical sense.

In the meanwhile, I worked on the practical things. The term “golden handcuffs” is trite, but accurate; the deeper one gets into their chosen field of focus, the better you become at solving problems and working under pressure. As you develop experience, skill sets, and hard-earned wisdom, both the work and the money come more easily. With intentional and consistent investing, the fruits of your labor compound throughout the years. (Years later, you recall reading somewhere that “a dollar saved and invested today is worth $16 in 40 years” and you realize that your investment portfolio might actually follow that anticipated growth trajectory)

While I kept working my W2 job, I dreamed. I dreamed of writing, woodworking, designing, making art, and maybe running my own business.

I view creative endeavors and starting new businesses in similar ways — or at least, I could draw a Venn diagram proving a considerable overlap between the two paths. There are upfront costs in both time and money and no guarantee of a successful outcome. With time and money spent on uncertain pursuits, the opportunity cost for both paths could be directed towards a sure thing like a full-time job with a payroll department that cuts your check on an agreed-upon schedule. And, again, I still didn’t know what I wanted to do in my next, and more importantly, intentionally chosen career.

But what if I knew exactly what creative output I wanted to devote my life energy towards? What happens when you do the thing that is in perfect alignment with your values, ideals, motivations, and best qualities? What could come after that? These missed opportunities are even more abstract and unconceived; after all, imagining the qualifiable is nebulous, whereas numbers are straightforward.

So I imagined all the things that could-have-been if I had pursued other passions, and asked myself what still-could-be if I started now. What are the opportunity costs that cannot be measured by numbers and financial statements? What about the people I could meet while carrying out my most valued priorities? The communities to which I might contribute? The ways in which my life would be enriched and maybe even bring value to those around me? The businesses I could grow and — and practically speaking — the money I could make pursuing a different path?

The story I’ve identified with for so many years — that I have to be my own safety net, that I have to prioritize the money problem and that lifestyle design is a true luxury — no longer reflects my current position. I grew up. I worked hard, saved and invested consistently, and am a capable person with valued skills. I know how to make and do money. After I answered the basic needs of survival, different but also challenging queries demanded my attention. How do you like to spend your working hours? What do you want to trade your life energy for? This thinking becomes more and more existential as time passes — and although “time is money” is another common (and very American) expression, the hours we have really aren’t equivalent to the cash we could be earning.

Instead, time is just life.

I still wonder if I’m brave enough. How does a person leave money on the table? Wrong question, again. I could instead consider, How much might my dream cost to realize, and is that a cost I’m willing to pay?

I’ve not yet reached financial independence, but I’ve got “fuck-you money,” so I’m taking a self-funded sabbatical — transitioning, finally, from the money season to the writing season. I’m very fortunate to have learned how money works at a young age and to be positioned to purchase this time to be intentional about how I want to live and work. Now that I have the time to chase whatever curiosities stoke my interest, I think of my younger, more idealistic self and long to connect with her and make her proud.

As for the opportunity cost of this sabbatical? It’s an enormous financial cost, I’m sure. But I haven’t run the calculations and I don’t care. The point of my life isn’t to optimize my earning potential. Instead, I’m learning that life is about something much more… unquantifiable.

Three Healing Friends

Tara K. Shepersky is a contemplative walker, writer, & photographer based in Oregon’s Willamette Valley. Her first book is Tell the Turning, a collection of poetry with pen-and-ink illustrations by Lucy Bellwood, which will be available for pre-order in May 2021.

This is the latest installment in Tara’s monthly column about the creative practice.

If you connect with Tara’s work, consider supporting her Patreon.

About a month ago, I had one of those days where everything feels hard. Without belaboring the intensity — perhaps you already know what I mean — I will say that the feeling is like a long and unexpected eclipse. A dark day of the soul. 

These eclipses come upon me periodically. No precipitating event is needed. No particular activity, no success, and no special treat will solve them. But I have accumulated a number of useful prescriptions for getting through them.

I recite poems. I remind myself that no feeling is final. I try deliberately to react to the day’s specific difficulties with patience, kindness, and courage. These help, over time, by building my experience of resilience. (“I knew I could do it…because I’d already done it,” as Harry says to Hermione.) It’s true they don’t make me feel better right away. This particular day, I found, to complement them, something that did. 

Three somethings, in fact. I want to think about these three for a little while; about how they serve as healers and friends — not just on dark days, but also everydays. About how, if I invite them, they also heal and companion my practice of writing poems. About how I suspect that they, or somethings like them, are universal friends — not just to me, but to you as well.  

The first healing friend is silence.

Silence comes in many forms. I happen to have a deep need for the one form over which I have no control: silence external to me, all around me. On the particular day I am remembering, I didn’t have it. What I did have: the ability to still my own hands, and close my own mouth on sighs of frustration, explanations, and that talking-it-through-out-loud thing I often do when I feel stressed.

There’s a particular serenity that attends the arrival and settling of inner silence. I cannot compel it. But I’ve discovered that I can invite it by the practice of outer silence. The outer sort and the inner are not equivalent; one does not necessarily even lead to the other. But their substances are similar enough that it’s worth learning how to do the one you really can affect. It’s also more difficult than it sounds. Try it — for more than a minute, or an hour, or a day, whatever your threshold is — and you’ll see.

For awhile, I had a regular practice of deliberate outer silence. I moved house, the pandemic moved in everywhere, and my practice fell away. On this particular dark day, I remembered to turn back toward it, and it felt like turning toward home. 

The second healing friend is sunshine.

If the first friend was familiar, this one surprised me utterly. I have always been a shade-seeker. But this day, I sat at the kitchen table, where the sun is strongest in my house, and I shut my eyes and spread out my hands and just fully soaked in the strengthening light. 

I never do this. My skin marks, for one thing. So I was startled to find, after only a couple of minutes, that my pain had shifted, enough that I didn’t feel constantly like screaming.

I moved to the front porch, so the sun could bathe my whole self. Out of the silence I’d been holding, I sang the sun a song of praise. And then I sang another, and then some totally unrelated songs, just because it felt so good to keep singing, and to keep feeling grateful. 

Singing is the third healing friend.

“Of course,” said a human friend I told about it later. “Singing forces you to breathe.” 


Since that day, I have sought out my new friend sunshine for short soaks. This is the right descriptor — the action is like a warm bath, in its pure pleasure and slowness and physicality. 

And I’ve started a weekly practice of silence and singing. Leave me alone long enough and I’ll sing, but I forget this friend when I’m emotionally tired, or near other humans who aren’t also singing, or keeping company with too many responsibilities. So my practice is sited mid-week, in the afternoon, when I’m most likely to forget without the ritual to prompt me. I sit somewhere by myself, and after holding some silence I let a song rise up, and then another and another, until I feel even. 

Pretty often lately, I’ve been sitting outside, combining my healing pleasures. And pretty often — not always right away, sometimes the next morning, as I walk outside — a new poem leaps from the nest and tries its wings. 

My working theory is that the silence and the sunshine and the singing are key materials of the nest I am always building, to hold whatever thoughts, feelings, rhythms, and ideas become my poems. The more attentively constructed the nest, the more nourished the wordlings it incubates. 

In themselves, silence, sunbathing, and singing are just play. They have neither obvious use nor monetary value. They therefore cannot get in the way of creativity. Once you embrace “wasting” time, and not getting paid, whatever you really need to do or says starts opening up.* 

This maybe sounds counter-intuitive, but it’s not at all. It’s counter-capitalist for sure: it rubs the wrong direction across all the ways we’re trained to think about “producing” — a type of knowledge so ingrained we sometimes mistake it for instinctive or intuitive. But intuition is just experience added to paying attention. And that leads me right to silence and sunbaths and singing, and says to my poem-grasping brain: Stop talking. Start right here. 

What I am doing when I compose is breathing, praying, attending. This is the key, I think, to why my three particular healers encourage my specific work. Each of them teaches these things in the body.

To sit simply in the sun is prayer, is attention, is gratitude. 

To be silent is to attend, without trying to mediate, to the world that breathes inside you and around you. 

To sing is to breathe with, and to make an offering in return. 

Which reminds me that I recently named a particular phase of writing “The Singing.” I gave this name to the time after I’ve finished a complex work, and it’s still inhabiting me, still actively a part of my daily being. What I end up doing in that phase is offering those poems—out loud and with gratitude—to the places, and the states of mind and heart, that helped me compose them. 

I like the symmetry of this: sun and silence and singing lead to attention, leads to Shaping, leads to Singing. Which leads, when the voice is ready, back to silence. Back to sitting (in the sun, perhaps), and accepting this moment’s gift.

What is the moment’s gift, on a day such as I described above, a dark day of the soul? The spiral here is so tight it’s nearly a tautology. The moment’s gift is the sun (or the rain, or the thunder, or the warm breeze.) It’s your body’s ability to quiet, and your throat’s — or just your soul’s — willingness to sing.


*This is the part where some of you say “what a privilege, to accept not getting paid!” And yes, you’re right. The acceptance applies without the privilege, too, but it’s harder to literally live with. Give away money, join a community organization, get involved in local politics. Replace profit-worship capitalism with a system that’s based on people instead of money. Yes, yes, yes, yes this is very hard, and also we can do this.

How a Daily Warm-Up Lit a Fire Under My Writing Practice

Valerie Reed Hickman is the recipient of a Writing By Writers Wolf House Residency and the winner of the 2019 Sewanee Review Fiction Contest. She lives and writes in Madison, Wisconsin.

I’m a fiction writer with a day job. This means that on a good morning, I get maybe an hour of writing time before my workday begins. So I’m tempted to leap right into it — the house still cold, coffee barely poured — trying to get as much done as I can before it’s time to open up my email. But I’ve found that, however strong the impulse is to just start writing, both the quality and the quantity of my writing are improved when I set aside a few minutes at the outset for a warm-up.

Here’s how I got to this point. I would get up every morning with the best of intentions. But often, when I sat down at my desk, I felt unable to begin. I was sleepy; I was preoccupied; whatever writing I’d done the day before seemed like it had happened in some other lifetime, on the far side of twenty-four subsequent hours of tasks and to-do lists. How much easier it was to think about what I was going to cook for dinner that night, or make myself a note to pay the electric bill, than to put pen to paper and try to create a world out of thin air.

Then, a couple of months ago, I saw a post in an online writing community asking if anyone had tried doing “morning pages” — one of the practices recommended in Julia Cameron’s book The Artist’s Way. I’d been through the whole book a few years ago, finding some of the ideas more helpful than others, but the morning pages, in particular, had turned out to be surprisingly beneficial. So one morning, feeling especially stuck, I decided to bring them back into my routine.

Cameron’s recommendation is to write three pages, longhand, every morning. The pages can contain whatever you need them to contain, but think “brain dump” rather than “detailed chapter outline”: the point, as Cameron presents it, is primarily to clear your mind of whatever clutter has accumulated there overnight so you can get down to business.

For me, at least, the morning pages are also part of a process of shifting into a different mindset altogether, one more conducive to creative work. For this, a certain lightness is required, a willingness not just to press pen to page but to lift it up again, to skip ahead to the next thought and then the next. We’re not looking for well-articulated connections or transitions here, logic or narrative flow. If I fill half a page with meandering thoughts about whether to buy a new coffeemaker, and then the next sentence is a half-remembered song lyric (the coffee cup, I think about you), and then I’m suddenly describing the bookstore I worked in when I first came across those lines — then I know I’m doing things right. 

I’ll admit that I don’t do the full three pages; I fill a single sheet of paper, front and back, in a smallish notebook, more or less 8×7. But yes, the longhand part is important: I can type a lot faster than I can write by hand, and it’s easy, maybe too easy, to spew words out onto the screen. Writing by hand, I find that I’m less likely to edit as I go, less likely to try to sound polished or respectable, less likely to second-guess myself.

So this is Step 1.

Step 2 was Step 1 until I figured out it needed to be Step 2.

Step 2 is poetry.

More than one novelist I admire has recommended that fiction writers make reading poetry a regular habit. In an interview published in The Atlantic a couple of years ago, Jami Attenberg talks specifically about beginning her writing day with poetry whenever she can. Since reading the interview, I had been trying to make this a habit of my own, but I couldn’t get it to stick. When I made poetry the bridge between my morning pages and my fiction writing, everything changed.

Reading poetry is crucial for any writer for a hundred different reasons. First and foremost, it helps attune your ear and open you up to all the beautiful, surprising things language is capable of. 

But poetry is also interesting for a writer of narrative prose simply because poetic logic is often very different from narrative logic. A poem might connect two ideas or images through rhyme or figuration, or simply by setting them next to each other. If my morning pages — with their leaps and runs — prime my mind for this kind of thinking, reading poetry shows me what these kinds of thoughts can achieve.

Each day I spend about fifteen minutes on this, all told — morning pages and poetry — and it has benefited my creative work enormously. When I finally turn to whatever project I’m working on, I find myself more able to focus, more ready to think in the way that fiction demands. I feel, well, warmed up. It turns out that what I needed was a buffer between the swirl of thoughts I wake up with and the stiller, slower, stranger eddies of my writing mind.

I realize that especially now, when so many of us are juggling artistic practice with work and worry and kids doing Zoom school in the kitchen and a hundred other things, this might all seem like a pipe dream. If you’re lucky to get even fifteen minutes to spare for your writing, and you use them up just clearing your head, you’re never going to get any actual writing done. But the warm-up is scalable. If you only have fifteen minutes, free-write for sixty seconds. Read one poem. Take one minute to close your eyes and pay attention to your breath. The amount of time you spend isn’t the point; the point is to create a habit, a reliable boundary, that helps you move from one mindset, one version of yourself, into another.

There is a space of ease and possibility where creative work thrives. I think these habits have been so crucial for me because they help me enter that space. They help jar my brain out of its usual cacophony of tasks and preoccupations and allow it to become more expansive, more fertile, more surprising. When this is the frame of mind I bring to my fiction, it’s also more possible for a story to take a surprising turn, or simply to leap ahead without worrying about how to explain the leap. (If it turns out to need explaining — that’s what revisions are for.)

The poet Jane Hirshfield has a pair of essays, collected in her book Nine Gates, arguing for the necessity of having both “a mind of indirection” and “a mind of concentration” in order to make poetry. Concentration, she says, must be understood as “a particular state of awareness: penetrating, unified, and focused, yet also permeable and open.” It’s this state of awareness that I’m seeking during that bright hour every morning when I sit down to write. By taking a few minutes to warm up first, I make it more likely that I’ll find it.

Planners, Colored Pens, and the Creative Process

Tatiana Moreno-George is a lifestyle writer who has written for Celeb Magazine, Society 19, and The C Word Mag.

In August of last year, I was laid off due to the pandemic. I received a severance package that included a free, three-month outplacement program where I was paired up with a development coach and would have bi-weekly, goal-setting phone meetings, all to help me find a new job.

In our last session, I shared with my coach my fear that going back to work full-time would mean little time left to pursue freelancing. She simply asked me, “Do you have a planner?”

After I got off the phone with her, I went out and bought my first planner in over ten years.

In high school, I was never the person who forgot to write their assignment down — because I always made sure I had my planner with me. Since graduating high school, I hadn’t given much thought to the necessity of owning a planner. But when you’re breaking into freelance writing, trying to keep up with friends and family while juggling a full-time day job, it’s easy to get overwhelmed. In the first month of learning about freelancing, I developed such anxiety about this potential career path that I began to shut down and almost decided to quit. I tried to do everything at once and was failing. I had to figure out a way to stay organized, and I have my job coach to thank for reminding me about the benefits of owning a planner and creating a color-coordinated schedule.


Here are the ways in which following a colorful daily schedule have helped me manage my to-do list, boost my writing productivity and achieve my personal goals:

Time Management

Using colored pens makes me look forward to scheduling out my week —because I can visually see exactly where I’m spending the most of my time, and, if need be, adjust for balance. Each task is written in my day planner in a particular color. I even assigned specific colors to my leisurely (but equally essential) activities, such as going for walks, grocery shopping trips, and catching up with family and friends.

In the beginning, I spent most of my week just pitching to editors. I did not leave much time to work on my blog, building connections with other freelancers, contributing to publications to build my portfolio, and learning the craft. Without a planner, I usually found I was wasting time rather than using it wisely.

Even though it takes a bit of time to create my color-coordinated schedule, it has alleviated a lot of stress, and I have found it to be one of the more enjoyable tasks I look forward to each Sunday evening.

Goal Progress

I have this fear that I’ll never get around to completing all the goals I have because I have so many. But breaking my big goals down into small ones has allowed me to see that I am making progress. Keeping a planner and taking a moment to carve chunks of time during the week that are strictly devoted to a specific goal makes the idea of becoming a self-employed writer in the future not too grand a dream anymore.

Task Completion

Starting out as I am freelancing, you quickly feel inadequate — but checking off completed tasks in my planner gives me a small sense of accomplishment.

I believe it’s crucial in the earlier stages of freelancing to believe in yourself and believe that your work will eventually pay off. Checking off a completed task in my planner does that for me. I find comfort knowing I have one less job to do, and I am one step closer to getting an article published.


If you are interested in building your own color-coordinated schedule, here are a few tips that helped me boost my productivity and stay better organized.

Find a planner that is right for you and meets your needs.

If you need a bright, loud, or flowery planner to keep you motivated every time you look at it, get one with a fun cover. Some people can do all of their planning in a simple notebook or bullet journal; if you are like me and need a lot of structure, a planner with an hour-by-hour timetable is a great option.

Set aside a consistent time each week to plan out your schedule.

I usually plan out my week every Sunday so that I’m ready to start on my first task when Monday comes. Whatever day you choose, make sure to keep it consistent.

Create a schedule that works for you.

Before writing your tasks into your planner, brainstorm a bit about how you’d like to break up your days. Do you work better if you dedicate one day to just writing and another to just pitching? Or do you need a bit of variety and can manage writing for a couple of hours in the morning or the evenings after your full-time job ends for the day and then tackle smaller tasks? The goal is to work with your already busy schedule, not against it.

Choose a consistent color scheme.

When you are putting your daily objectives into your planner, choose a specific colored pen for each specific category. For example, all of my writing tasks are blue, pitching to editors is in red, and reading related content is in green.  

Do your most challenging task first.

If you tackle the more difficult task first, you’ll start your day off with a sense of accomplishment — and the other tasks on your list will feel that much more doable.

Create a rewards system.

Any time you try to create a new habit, you need some motivation to stick with it. Whether you celebrate at the end of each day for completing your tasks or save up your celebration for the end of the week, come up with a tailored rewards system that keeps you on track. 

Life does happen, and some things will go left undone — and that’s okay. Just make sure you reward yourself for the work you’ve put in.  

It’s only been six months since I’ve actively pursued freelancing, and I know that if I hadn’t found a way to stay organized, I would have burned out and quit. But I didn’t, and I’m here now and just wrapping up my first guest post for this blog — and I can’t tell you how excited I am to see what is to come in the next six months.