Learning to Write Again

Often I write a sentence and it’s so bad I wonder, “Am I actually any good at this?” I keep working, and the sentence gets a little better. Then I get up, get a snack, and sit down to work on it more. I continue like this until what was once a disjointed sentence is a sentence that is closer to saying what I meant it to say the first time.

The rabbit I drew and wrote about.

I’ve been writing most of my life. I’ve always enjoyed it and always took it seriously. As a first grader I drew little animals in my marbled notebook and wrote a few sentences describing the animals. It felt like an act of revolution. To accompany the guitar lessons I took as a 12-year-old, I tried my hand at writing poems slash song lyrics. If these still exist, they deserve to stay wherever they are (read: hidden in a box somewhere far, far from the Internet).

High school was a rewarding time for me as a writer. In English class I wrote essays about Shakespeare and Orwell and, I promise, at least a few writers who were not white British dudes. My history class essays are memorable thanks to the many hours of required research. I studied the related roots of Christianity, Islam, and Judaism for one term paper. I learned about Mahatma Gandhi’s life and the Partition of India for another. Reading history was interesting, interpreting it and expressing my opinion, exhilarating.

The summer between freshman and sophomore years of high school was pivotal in my life as a writer. Siddhartha was the summer reading assignment, and as I read it in a hammock in my family’s backyard, I had an epiphany. A person – granted, another white dude – had written this book, I realized. Books did not just appear, they did not just happen to exist. Someone set out to write them, to make a point, to tell a story. I realized I wanted to write books like that one. I realized that I could write books like it.

College humbled me as both writer and student. No longer was I a big fish in a little pond, and my grades reflected that. When it came to my writing assignments, the sophistication of my arguments, the thoroughness of my research, and the rigor of my intellect were not always what they should have been. I thought I was better than I was. Quickly I realized that the talent that had floated me through school up to that point was no longer sufficient. It was clear that I also needed some discipline. I got through it, though, and I graduated with an English literature degree, a highly marketable degree, ahem, to be sure. It was 2009, so naturally I moved back in with my parents.

In high school I’d worked for a local newspaper as a glorified paper boy, a job that I liked and still look back on fondly, and this connection helped me land a freelance writing gig with the Lake Norman Citizen. I interviewed local figures in my hometown and wrote human interest stories on Lutheran preachers, directors of soup kitchens, and religious missionaries building wells in Africa. When the Charlotte Observer put out a call for freelance writers, I responded with a short piece about how difficult it was to turn left while driving in my suburb, and wound up with another gig, covering similar local human interest territory for that paper.

While I was excited to write for these newspapers, I also found it quite difficult and terrifying. Nobody had trained me to be a journalist. I thought writing was a job done alone, in solitude, conjuring up narratives out of thin air. Getting out into the world to conduct interviews, take notes, and report fairly were not things I readily knew how to do. As frightening and strange as it was to reach out to sources, however, the drug of seeing my name in print every week was highly addictive, and I grew to enjoy the interviews. I discovered people liked being asked questions about themselves. They enjoyed seeing their names in print, too.

After working for two years as a technical writer for a large bank in Charlotte, I moved to New York at the age of 25. I held a few different jobs for a few different software companies over the course of five years, picking up client relationship and technical skills along the way. Though none of them felt quite right, I was repeatedly drawn to any opportunity to write product documentation. Usually my efforts were well-received if not outright lauded, but I failed to see the pattern.

These writing opportunities felt like distractions on the way to a serious, important job within tech. I searched for the “right fit” somewhere out there on the horizon, not realizing writing was not a distraction but rather me coming back to center. This became all too clear last summer when half of my then-company’s New York product team was laid off. I shifted into a sales engineer role, where writing was no longer part of my job. While past jobs had felt slightly off, this one felt altogether wrong. Not until it was missing did I realize how important writing is to me on a professional level.

So it became clear: all I wanted to do was write. It was that simple, and it had always been that simple. The answer had been right in front of me all along, but I had overlooked it.

Epiphanies are great. But if you want real change in your life, you have to act. Thus I began scouring the internet for writing jobs. I knew I wanted to wake up and go somewhere to write, and I figured my skill set and experience made me a fine candidate for technical writing jobs. I wanted company with a “serious” product offering – say a financial tech company – which would draw upon whatever I had retained from my bank days. I also wanted to continue to work closely with product and engineering, where I could use my technical skills. After a little searching and a lot of conversations, I found the right opportunity and started a new job in March.

Most people don’t know exactly what technical writers do. That’s completely fair and, presuming that’s you, dear reader, I’ll try to explain. In short, I write documents that help clients understand and use software. Put another way, I translate between techspeak and business lingo in order to articulate to clients how to be successful with our product.

Pick a day of the week, and my schedule will likely be a mishmash of writings tasks, meetings, and research. I meet with product managers and designers to name new features and decide on copy appearing in the application. When new features are released, I write release notes to let our clients know what’s new and articles to help them use those new features. Focusing on the technical side of things, I write guides to help clients set up our pre-built integrations as well as maintain our API docs, empowering them to build new ones.

Make no mistake, it feels great to be writing full-time. However, I’ve been humbled more than once in the past six months. Just as I’ve learned a vital lesson at each stage in my life as a writer, in the past few months I’ve again been reminded that I’m often not as good as I think I am. That I need to write deliberately, with intent and fervor. That I need to more deeply understand my audience and material. I work with the highest-caliber writers, designers, product managers, engineers, marketers, et al. They ask compelling questions, venture suggestions, and demand excellence. They push me to think more rigorously about style, structure, and voice. 

I’m learning to write all over again. But this is not altogether new: I’ve learned how to write many times over. First I learned to make the characters of the alphabet, then how to string them into sentences, then how to knit those sentences into paragraphs. Later, I learned how to write in different forms: essays, newspaper stories, technical documents, blog posts. Now I’m learning how to focus on my craft. Each and every day, I exercise the writing muscle, building upon what I’ve written before to strengthen what I’ll write in the future. When all is going well, this type of learning never ends.

The pleasure of anything is found in the doing of it. It was in college that I learned I needed discipline, but it’s been as a working adult that I’ve learned the discipline itself. I write everyday, no matter what. I get paid for some of what I write. Some of it is just for me. A lot of what I write, regardless of the audience, is really bad. Luckily I am experienced enough to know when it’s bad. And that’s when I go back and re-write it, working on it steadily, regardless of whim or the weather. When I write a bad sentence and wonder, “Am I actually any good at this?” the true answer is that I’m okay, but not as good as I can be. The sentence is okay, too, but not as good as it will be.

Better Living Through Tracking My Entire Life in a Spreadsheet – Part Two

2016 is over. Let’s all rejoice. Only Chance the Rapper had a truly fantastic year.

While I think New Year Resolutions rarely work, what can work is using 2016 data to inform the future. Now, onto the data…

What worked?

Thanks to spreadsheet tracking, I successfully completed a novel draft this year. It’s around 270 pages, as I mentioned in Part One, and while I am proud the end result, I’m more proud of the daily work I put in.

Each day I held myself accountable to write one page, feeling a sense of accomplishment as I marked it off in my sheet. I saw daily that I was making progress toward my long-term goal. Without the spreadsheet to see daily success in black and white – and without the occasional pain of seeing a red cell when I missed a day – chances are I would not have done the work to get to 270.

Below are my month-over-month fiction completion rates for 2016. Except for small dips in November and December, which can be attributed to holiday travel, my completion rates grew each month.


Similarly, I ingrained meditation into my daily schedule. It took a month to make meditation a habit – which is about average – but after the first month I never fell below 70% for the rest of the year. Now if I go more than 2 or 3 days without meditating, I feel edgy. My focus fades. I’m less able to separate my thoughts from reality. I am more irritable and less patient. By tracking meditation in my sheet, I made it a habit, carving out space each morning for quiet “me” time. Meditation has paid me huge psychological, emotional, and spiritual dividends, and I wouldn’t stop doing it even if you paid me monetary dividends. Below are my completion rates:


Going to the gym: I’ll count it as a success, with the caveat that there’s lots of room for improvement. Tracking gym visits got me into a rhythm of getting up early two days a week to lift weights. Although my gym success rates varied each month way more than writing or meditation, I went to the gym a lot more last year than in 2015. (Sometimes just showing up is over half the battle.) Now that I’m in the routine of going 2-3 days each week, I have a foundation to build on.

Keeping a nightly journal and a daily gratitude board were dynamite successes. My completion rates were high for both – so high that I won’t bore you with them – but the real benefits are less tangible. The true benefits of writing down things I’m thankful for, of less than 5 minutes of daily reflection, can’t be seen in a spreadsheet. The spreadsheet helped me make these practices into habits, but the habits themselves have more qualified rather than quantified results. I’ve mellowed out and am more able to concentrate on the good in my life. I’m more aware and appreciative of my loving family, great friends, and an overarching sense of purpose. My life is chock-full of privilege that so many people may never experience. Appreciating what I have, and not worrying about what I don’t, helps me focus on how I can help others.

What didn’t work?

I fell short on blogging every day. My goal was to write for my blog 15 minutes each day, but it was easy to not do the work, perhaps in part because of the several ideas I had going at any given time. With too many early drafts floating around, it was easy to work on nothing due to lack of focus. A timed approached – as opposed to a daily page allotment like I instituted with fiction writing – could have also been partially responsible for my failure.

I also never got into a regular running routine. I only tracked running on an ad hoc basis, with no established specific race or distance goal. I’ll be gunning for a spot in the Brooklyn Half this year, and if I get in, I’ll use the May 20 race date as the obvious achievement to inform a weekly running schedule.

Last, I failed at taking my lunch to work. I’d like to implement this to increase cost effectiveness of Blue Apron and other meals I cook at home, but I know why I didn’t make it a habit. The thing is, I love the daily novelty of leaving my office with coworkers to buy lunch. I enjoy the camaraderie that comes from debating Shake Shack versus Sweetgreen each day.

To keep myself honest, and in case you are interested, here’s the data for these “failures”:


Why did the spreadsheet help – or not?

I’m fascinated by the psychology behind tracking all these items in a spreadsheet.I touched upon this in Part One. Why did a spreadsheet help me implement activities that help me live a more fulfilling life? By accounting each day for each activity with a “Yes” or “No” reinforced whether I was actually doing the activity or not. This is what Tony Robbins has written about linking specific behaviors to Pleasure or to Pain.

Robbins states, and I agree, that all of life boils down to two things: Pleasure and Pain. We do things to either gain pleasure or avoid pain. Prior to tracking daily fiction, I wanted to write, but I wasn’t actually doing it every single day. Facing the blank page and the blinking cursor each morning was unpleasant, so I linked pain to writing fiction. My anticipation of that pain made it easy to put the work off. Days of putting the work off added up, and soon months had gone by and I hadn’t written a word of fiction.

In contrast, after I started tracking daily fiction progress in my sheet, I made it a habit by changing the emotion linked to the action. Was it difficult? At first, yes, it was very difficult. But after several weeks of marking “X” in my sheet on the Daily Fiction row, I felt rewarded. It was pleasing to see all the Xs all neat in a row, pretty as ducks. My brain sought the pleasure of the daily X, and it was no longer a question whether I would write a page each day. It started to feel too good to not do it.

Similarly, when I skipped a day at the gym I had to mark that day’s cell red. Marking these cells red felt bad. Say I skipped working out because I wanted another hour of sleep. At first sleeping longer was linked to pleasure, but later, when I forced myself to look at my sheet and fill in the cell with red, I regretted it. Sleeping later and skipping the gym made me feel like I was undercutting my goals. Hitting snooze = giving up on myself.

Soon, when the alarm went off at 6:00 am on a cold, dark morning, I thought less about how good it would feel to stay in bed and more about how bad it would feel to mark that day’s cell red. (I skipped the gym the morning of this writing, by the way, and typing this section feels makes me prickle with disappointment.)

Someone once told me that “even false motivation is motivation.” (This someone went on to become an Army Ranger, so I give him credence.) Tracking activities I want to implement in my life has been the most effective way of forming new habits, changing behaviors through the Pleasure-or-Pain principle, and making myself happier because of these new behaviors.

What will I change in 2017?

This year I’ll have to change my daily fiction work. Since the novel draft is done, I now need to let it sit for a while before editing it. My daily work won’t be writing but rather redlining, reconfiguring the narrative arc, and other ancillary necessities to move the project forward. I’ll still mark my sheet “Yes” or No,” but I’ll need to better plan ahead to know exactly what I need to accomplish each day.

I’ve changed my exercise schedule to allow for more running days. Providing I get a spot in the Brooklyn Half, I’ll run three days each week, balancing it with a couple gym visits. Now that I’ve proven I can get out of bed for the gym two days a week, changing my regular gym days won’t be as difficult as going from zero to two last January.

I’m proud of the work I did last year to take charge of my schedule as a means to a more fulfilling life. I realized that I’m responsible for my life – my happiness, my health and fitness, my contentment with my career, relationships, and finances. No one is going to make these changes for me. Ownership was a key theme for me last year, and as 2017 starts, I feel more grounded, more sure, more equipped than I was a year ago. 

Which is all to say I think the spreadsheet works. 

Better Living Through Tracking My Entire Life in a Spreadsheet – Part One

“You can’t get clean by continuing to wallow in the mud.”


I may have coined this phrase…or I may have purloined it from another writer – potentially Orwell or E.B. White. I’m not certain. A quick Google search didn’t result in any clear signs of theft, so perhaps only porcine associations I have with each writer makes me think I stole it.

At any rate, I repeat this saying to myself frequently. Too often I forget the necessity of removing myself from a situation in order to see it clearly. It’s vital to admit to and examine a problem before I can ever be equipped to solve it.

This February I flew to the other side of the world with one of my best friends. We spent a week in Vietnam, a week in Myanmar, and a couple days in Bangkok, Thailand, before returning to New York. It was a great adventure, my first visit to Asia, and a chance to get away from the routine of my everyday life. Being thousands of miles away from home, I had time away to step out of the mud and see where I needed to get clean.

How happy was I with my life? In which areas was I doing well? Which areas did I want to improve? Like the many Buddha statues we saw in Bagan, I reflected. I sought enlightenment.

buddhaAnd what “enlightenment” did I come away with? The overarching takeaway was that I wanted to take control of my emotions through action, thereby improving the quality of my life. I felt too often preoccupied with things outside my control, which caused unnecessary distress. I wanted instead to do things that made me happy and helped me focus on what I could control. Doing so would free my mind of worry and anxiety and empower me to be more creative, more focused, more present. 

Which actions did I decide to focus on? For one, also much like the Buddha, I wanted to start meditating. Seems like I see dozens of tweets and articles about its benefits every single day. And I wanted to get back into shape. Following a shoulder dislocation in July 2015, I was finally recovered enough to hit the weights again. And I wanted to practice daily gratitude, something I flirted with late in 2015. And most importantly, I wanted to write a page of fiction everyday.

The writing was priority. I’ve always had talent. What I’ve never had, however, was discipline. Writing papers in high school about Shakespeare and the Renaissance didn’t require much discipline. I knocked them out with only a few minor revisions. My talent carried me. However, I had no stamina. How could I ever realize my dream of writing books without the discipline to work on a story from page one to page n? Wasn’t going to happen.

Discipline is key. I need to write every single day, no matter what. It doesn’t matter whether what I write is good, whether I feel like it, whether it’s sunny or raining outside. All that matters is that I get the page done. The page can be, and probably will be, absolutely terrible, but I can fix it later.

(I attempted to learn discipline specific to fiction in 2014, when I wrote a novel draft in a calendar year. [A draft, by the way, which shall never see the light of day.] This time, though, I needed a system to ensure I wrote that daily page. Given the other things I wanted to implement and track, a spreadsheet would do the trick. After all, “what gets measured, gets managed.”)

I started my spreadsheet after returning from Asia, logging these items on a daily basis:

  • Meditation
  • Gratitude board
  • Daily fiction
  • Nightly journal
  • Run
  • Gym

This is what it looked like:


I started with these seven things and over the course of this year added a few more activities. Additions included:

  • Bike rides
  • Daily blogging for 15 minutes
  • What I eat for each meal
  • Taking my lunch to work

Why focus on these activities as opposed to the multitude of others?

Daily fiction

I’m a writer. It’s integral to my identity. I’ve written my whole life, and it’s key to how I understand the world. Only in the past year or two, however, have I started earnestly pursuing fiction writing. It’s my dream to write and publish books, specifically novels.

The only way to get better at writing is to do it daily. Tracking my fiction writing in my sheet helped me link pleasure to the getting-done of the daily fiction. When I miss a day and have to mark the cell red, I feel bad. I feel like I let myself down. I feel as though I have to make up for it the next day, and indeed I do. By end of year, I will have approximately 270 pages of a novel draft complete. It may not be good, but it’s done. 2017 will be for making it better.

Gratitude Board

I started my Gratitude Trello Board in December 2015 and continued it this year. Here’s a template that you can copy and use. At the start of each month, I have three lists for that month. The main month list has a card for each day of the month. Here’s what it looks like:

trello board 1.png

Each day, I write three things I am grateful for, then move the card to the “Done” list, after which I mark my spreadsheet with an “X.” If I miss a day, I move the card to “Missed” and mark that day’s cell on my sheet red. (Again, red = no fun.)

I linked to the Trello board from my sheet, so I could more easily remember and navigate to that day’s card. At first I missed a lot of days (as you can see above, I only hit 61% in January, whereas I completed 83% in November), but now this is an ingrained part of my morning routine. By focusing on what I had instead of what I didn’t have, I learned to be more cognizant of just how many great people are in my life and how many wonderful experiences I’ve had. I live a privileged life, and practicing gratitude reminded me of that and helped me be less of a miserable son-of-a-bitch.

Running/Gym/Bike Rides

armAfter dislocating my shoulder in the Catskills in what I like to call the Great River Tubing Debacle of 2016 (the aftermath of which is at left), I couldn’t lift weights. My left shoulder and chest muscles atrophied. My belly ballooned. I couldn’t run, either, so I felt both lethargic and anxious to get outside and do something. During this time I realized that exercise is a keystone habit for me. I have to exercise in order to be happy with other parts of my life. For me, it’s non-negotiable. Going to the gym twice a week (early Tuesday and Friday mornings) was an achievable schedule, and paired with running 1-2 days per week, I got back into presentable shape. Bike rides were and are mostly for fun and not tracked too seriously. I log them whenever I get out and cruise around Brooklyn with friends.

Nightly Journal

Similar to my gratitude board and times of large self-reflection, I wanted to institute nightly journaling to reflect at the end of each day. Each night I write three things that were positive about the day, three things that could have been better, and three things I need to do or am looking forward to the next day. The three positives help me focus on what I have and what I am grateful for. The three negatives force me to think about why they happened and to focus on what is within my control and my response to things outside of my control. The three next-day things help me focus on the “to-accomplish” list for the next day, giving me something to work towards as a means of progressing towards larger, long-term goals.

I track each as it makes sense. For example, shooting for one page of fiction a day, I use a percentage of pages completed against number of days in the month. But for bike rides I am only going to get a few in each month, so a raw total is sufficient.

At the end of each month, I calculate how many times I did each activity, providing a snapshot of what’s working and what’s not. Adding new activities is often painful, but I have found that after tracking the activity for a month or two results in high percentage-complete stats and a successfully adopted new habit. There are only so many days I can mark cells red in my spreadsheet without feeling so badly about it that I re-double my efforts to implement the activity in my daily life – or else cut it out altogether.

This is a glimpse into why I started tracking my life in a spreadsheet (a practice that at least one friend and one former lover characterized as “pretty OCD”) and what I decided to track and why. In part two, I’ll dig into what worked – and what didn’t – over the course of 2016, as well as what I’ll keep doing in 2017 and how I’ll tweak my tracking, schedule, and activities to improve the quality of my life.

Turn and Face the Strange

This post has been difficult to write. I’ve been thinking about it for a while and have scrapped at least three drafts. I’ve known I want to write about change, but I’ve sidelined the post because I wasn’t sure what specifically about change that I wanted to say. Months have passed since I first made the Evernote “write post about change”; weeks have passed since I started the first draft. In that time, so much has changed. Go figure.

(I’d like to note that this isn’t meant to be – and won’t be – an elegy for David Bowie. However, seeing as I was going to utilize “Changes” anyway, it’s only fitting to talk about the Starman himself, too, in light of his death.)

Change. There is no more fundamental aspect of life – yet we are terrified of it. Change is a hard pill to swallow. Every second that goes by, something is different than the moment just before, than the moment following. These seconds add up to minutes, minutes to hours, and so on, and we wake up one day to realize that life is unrecognizable from what it used to be. It’s unrecognizable from what we thought it would be. Each life – yours, mine – is one big constant change. Scary as it is, Pink Floyd summed it up perfectly: “The sun is the same in a relative way, but you’re older / Shorter of breath and one day closer to death”

Looking back at 2015, much has changed. I’ve had good friends leave New York. They moved to New Zealand, relocating to the other side of the world for a few years, undertaking a three-continent adventure en route. All through the summer, we had periodic group outings in a long lead-up to the goodbye – itself a wonderful all-night event full of emotion. I could feel the change happening, slowly then in a rush. It reaffirms that wonderful people move in and out of our lives, and that it’s worth the effort to keep up with those we truly care about.

Another change was moving boroughs, from Manhattan to Brooklyn. Switched zip codes, switched apartments, switched roommates. It was the right move, but the change was scary. I had questions and concerns, even though I felt good about the move in my gut. Every change we make, as well as every change that is foisted upon us, raises concerns. The vast majority of things are out of our control; the best we can do is look at the information in front of us and make the best decision. Things tend to sort out.

On the work front, my job changed continually (something I thoroughly enjoy). We began building out a product and engineering presence in New York, going from a product team of 1 (me) to 13 between January ‘15 and January ‘16. We changed floors two times, desks four times, and OKRs a couple times, too. People have left the company and people have joined the company. A few years ago, this would have scared me; I would have gone to get coffee with coworkers to bemoan the changes. Now, I know turnover is natural and inevitable, and in fact it can often be good for everyone. Change, if not ostensibly positive, is at least different, and that state of different-ness challenges us to grow.

Still, change is scary. It’s strange. It’s new. It’s the unknown coming to sit in front of your face.

Why are we often so afraid of change? Increasingly, I see this as a control issue. We fear what we cannot, or feel we cannot, control. The world turns, things happen, states of comfort and understanding are broken and shaken. This lack of control causes us to feel that we don’t understand, and we often fear what we don’t understand. It’s a base human instinct to which even the most evolved of us are susceptible. How to overcome the fear? Change our approach to change and improve our ability to deal with it.

Sometimes you just have to suck it up and turn and face the strange. How do you do this? Accept and Adapt.

Accept that change is inevitable, that it’s going to happen whether you want it to or not. Accept that when you’re riding high, the circumstances behind your elation will change. You’re going to have your bubble burst. Accept that nothing is static, so when you feel in command of your domain, it’s only an illusion. You may be doing well at any given moment, but a moment is only that, and the next moment will be different. (Potentially better, better, worse, or the same, but always different.)

Then Adapt. After you’ve accepted that change is constant – that things may have changed between the time you started reading this and the time you finished reading this – you must adapt to this understanding. Learn how to be flexible, nimble, to make decisions given the reality in front of you. Adapt to the new environment in order to not be left in the dust. (Humans have survived for a long time by being adaptable, whether we consciously tried to adapt or not. It’s the height of consciousness to adapt at will, and that’s something we should strive for.)

Now, what about David Bowie?

The man was constantly evolving. When he started out he was clean cut, late ‘60s mod, then morphed into Ziggy Stardust, then Aladdin Sane, then back to himself in ’90s style. He adapted and changed with each decade, loyal to no single haircut, no single facial hair style, no single musical sound. Bowie sang, played, acted, hosted, appeared in places you never expected. He consistently tried new things, exploring himself, the world, and his place in it. As Sarah Larson wrote in the New Yorker, Bowie “was finding himself, trying everything out.” He lived in permanent beta, to use the zeitgeisty nomenclature. And most importantly, he seemed to be afraid of nothing. He accepted the changes and never failed to adapt. If nothing else, Bowie is a testament to how successful a person can be by embracing change.

How do you approach and navigate change? What are your thoughts on David Bowie’s death and legacy? Tweet at me and let me know!

(Note: A big thank-you to a couple early readers who provide early feedback on my writing. These posts wouldn’t be the same without you.)