Showing Another Me

A little over a year ago, I literally walked away from a good career, to pursue a life-long ambition of making a living as a writer. Since that time, I’ve published articles on transportation technology, pursued opportunities that didn’t work out well, made significant progress on my novel, and made a commitment to my short fiction.

I have a long way to go to reach my ambition, mostly because I’m still figuring out what I should be doing. But while there’s been a great deal of uncertainty so far in this journey, I have not for one second regretted my decision to take that first step. I wasn’t happy being the person I’d been the first three decades of my professional career, and everything I’ve done since walking away a year ago, even the mistakes, has been positive.

The person I used to be knew exactly where he was, and where he was headed, while the person I’ve been the past year makes things up as he goes along. This other me isn’t content, but he’s happier than the person he replaced.

Planning Sheets

When you’re working a “real” job, you never run out of things to do. Those things may lack any inherent interest, you may have to do things which are self-evidently counter-productive to the larger mission, and all the effort you put into getting all your tasks done may lead you nowhere — but you’ll always be busy.

One challenge I’ve faced since leaving that world behind has been organizing my time. With the only person telling me what to do being myself, I soon found a need to have some planning tool, a way to record goals for my days and weeks, and review accomplishments as well as missed opportunities. I used my journal for a while, but never got comfortable using it for both my writing and planning. I tried several planning journals, but found their format too restrictive and overly focused on corporate work.

Then one day a few months ago, I was tossing out clutter from my basement when I found a roll of dry erase graph sheets, 24″ x 32″, that cling to walls like giant Post-It notes. Having no idea how this roll wound up in the pleistocene strata of our family’s belongings (though I strongly suspect my wife took it home from her own corporate job), I was about to shove it into the big black trash bag — then decided it was time for an experiment.

I went up to my home office, tore off a sheet, grabbed a few dry-erase markers and began writing dates. After several weeks of trial and error, I developed a system that’s been working pretty well for me.

The Planning Sheet at the Start of the Week

To the right is the Planning Sheet (I guess that’s what I’m calling them, now that I’ve blogged about their existence) drawn up on my office door at the start of the previous week. I put everything on there — work schedules, appointments, household tasks, recreation, and perhaps most significant of all, writing goals, which gets their own section on the lower right. Every Sunday night, Monday afternoon at the latest, I put my plans for week on the board, and due to its high visibility — there isn’t a day I’m not in my office at home, and the door is just to the left of my desk — I always know where I need to be, what I need to do, and when everything has to happen.

I leave five lines between each day, and when creating my plan at the start of the week try to list three or four activities for each day. Having less than three activities in a day inspires me to move activities from other busier days; more than four is a sign I need to offload some activities to another day. I add tasks as needs arise during the week, but try not to delete any tasks, so that at the end of the week I can see which activities were either missed or deferred.

The Planning Sheet at the End of the Week

On the left is the same Planning Sheet at the end of last week. It shows the color scheme I’ve settled on — black for days, blue for activities, green checks for completed activities, and a red X for a miss. Activities were added on some days, and I even identified an extra writing goal early in the week. When I completed an activity on its scheduled day, I gave it a green check; if I completed it on another day, or only partially completed it, I wrote a note in green. I avoided any red X until Sunday, when I got a little giddy at having reached all of my writing goals the previous day and decided to add some extra tasks on what should have been an off day. But this is how we learn, right?

Having a plan is good, but seeing it every time I sit down to my new job as a freelance writer has helped me succeed at executing that plan.

A Good Week

Been very productive these past seven days. Finished a draft of a technical document, sent my story to another publication, updated another story, and signed up for an eight-week class on short story writing. Each a small accomplishment, but being successful in this career probably has less to do with scoring major victories than it does with accumulating little triumphs over a series of good weeks.

Enjoying the Endings

Finished the updates to the first of the seven stories I’m planning to submit for publication by the end of this year. Sent that story out Friday afternoon… and by late Saturday night, I received the first of what will surely be dozens of rejections over the coming months.

Today, I sent the same story to another publication. And this week, I’m going to finalize my submission plan, so that my response to the next rejection will be just as immediate.

I’m at the start of a long journey which will feature several obstacles. Heard it said that you have to enjoy the ride; I think it’s also important to realize you’re the one at the wheel.

Some Experiments Don’t Work

A lot has happened since I walked away from a well-paying but mind-numbing career, and started working the only job I’ve ever wanted to do — writing. But aside from posting links to articles I’ve written, I haven’t said much about my new occupation. And since I’ve enjoyed reading insights into this profession, I’ve decided to provide my own limited perspective

Soon after making my leap into uncertainty, I revisited one of my former occupations — teaching composition as an adjunct instructor at a community college. I knew the pay wasn’t going to be great and I’d have to re-learn how to teach after almost two decades away from the classroom… but I remembered feeling satisfied in the last couple classes I had taught, and it was the quickest way for me to make a steady if unspectacular income. This was going to be a challenge, but it wasn’t like I was starting from scratch.

The semester began in late August, and by Halloween I had come to three key realizations:

  1. Re-learning how to teach wasn’t going to work, because I had never really learned how to teach in the first place. My pedagogical strategy back in the day had been based entirely on improvisation, and that’s not a healthy approach for someone who’d been away from the classroom for so long.
  2. Students respond well to teachers who address their needs. But as I had completely misjudged those needs at the start of the semester, I was not getting the response I was looking for.
  3. I wasn’t writing. Preparing for classes and grading papers was taking too much time and mental energy. A part-time job had become a full-time occupation.

By Thanksgiving, as the English Department at my school asked for my teaching preferences in the coming semester, I knew there was only one good decision. I had to stop teaching. I had embarked on this journey in order to write, and after a few months of failing to write much of anything, I knew changes needed to be made.

And yet, I don’t see my teaching last fall as a mistake, but more like an experiment that didn’t work. There will be plenty more experiments as I continue on this path, and some have yielded more positive results lately — I’m writing, lots, which has always been the priority. But in the coming months and years, there will be many more projects which will blow up, and I’ll by wiping soot off my face plenty of times. Sometimes the only way to figure out what works, is to discover what doesn’t.

A New Opportunity

Over the holidays, a colleague from a couple jobs ago asked me about about writing for their company blog. Marketing, basically — not the most engaging subject matter, but the pay is decent and there’s no threat of compromising my self-importance. Just submitted my first article; the research required made it out to be a pretty fun experience, actually. Assuing they like what I wrote, they’ll help keep me busy in the coming months. Might just be the type of opportunity I need to move forward in my new career.

Trust Imagination

It was some time in November 1990 — I don’t know the actual date, or even the day of the week — when I walked into an office on the northwest side of Chicago and worked my first day in a “real” job. I had just finished the coursework for my doctorate in literature, and my attempts to earn enough money to feed myself through teaching and grants were proving to be frustrating and futile. When the offer of a steady paycheck came up, I was too desperate to say no. My idea at the time was to test the waters for a few months, and if I seemed to be swimming all right, I’d stick with it until I finished my dissertation. Six years later, diploma in hand, I finally left that job — and immediately took on another, which eventually lead to another, and another, until eventually I had close to three decades of experience working with many wonderful and some truly awful people, in addition to a heavy dose of corporate systemic incompetence.

Yesterday, that ended.

After turning in my laptop and identification badge to my manager, I walked out of my most recent office building for the last time. Twenty-seven years and eight months of steady employment, interrupted by a few brief voluntary transition periods, has been left behind in order to pursue making a living as a writer. It’s an ambitious goal, one I had considered as far back as 1990 when it became apparent my academic career was going nowhere. I had known many professional writers during my university years, and they spoke regularly of the occupation’s difficulty, going so far as to actively discourage students like myself from its pursuit. I was easily persuaded (a fault that carries with me to this day), and took the advice to pursue a more practical career.

Yet the desire to write, not as a hobby but as a career — to write as if my life (or at least its creature comforts) depended on it — never left. During those brief periods of unemployment, as well as those times when the mundanity of working life seemed unendurable, I was tempted to finally act on my ambition, only to have those dire warnings from the past urge me to play it safe once more.

So why make the move now? Years of good financial planning, and (let’s be honest) incredibly good fortune, have put my wife and I in a good position. We’re not independently wealthy, but we can afford to take on a little risk in both our careers. My wife runs a cake decorating business out of our home — check it out. We’ll need to earn a living for at least another decade, but if I need to be working, I want to finally do the job, the only job, I’ve always wanted to do.

When I walked out that door yesterday, I started on a new path. journey ahead is full of more uncertainty than I can ever recall. But I’ve never been so certain that I’m on the right path.

On occasion, I use this blog to comment on music. After turning in my notice at work a few weeks back, I was listening to random songs on my phone when a gem from Peter Gabriel started playing. He wrote the song immediately after leaving Genesis, and the decision to pursue his own career left him feeling anxiously excited. I’ve enjoyed the frenetic energy of this song, with its unusual yet uplifting rhythm, for decades, but hearing it now, as I felt my own heart going boom-boom-boom in response to my career move, made me appreciate its power in a way I couldn’t comprehend before. To get what you want, you have to let go of what you have; to stop playing it safe, you have to trust imagination.