My childhood existed in the last days before the explosion of cable television. Before 1500 channels of stuff we loathed cuddled up to the twenty channels we loved. Before the Weather Channel and CNN turned us into 24-hour news junkies looking for our next storm fix.

With only three channels available, we watched a lot of shows like Gilligan’s Island, programs already a decade old by the time the kids gathered in front of the black and white set. We’d sit right back and we’d hear a tale, a tale of a fateful trip, that started from a tropic port, and now the song is stuck in your head. You’re welcome!

The thing that strikes me now as I reflect on the show—beyond the thin characters, the slapstick and sexist comedy, the brain worm of a song—is its episodic nature. Each week was a thing unto itself, separate from the others. Often, they found some unexpected method of escape, hilarity ensued, and they failed. Roll credits, wait for next week’s show.

Here’s what I’ve come to realize: the castaways had no long-term plan to get off that damned island.

The castaways read a note once again reminding them they SUCK at being rescued.

Note: this lack of forethought is most egregious in the character Roy Hinkley, known as the Professor. Genius at making complex, Gilligan-powered devices; terrible at fixing boats.

Long-term Planning

Historically I’m not a long-term planner. I’ve lounged my way through life, bouncing from one interest to the next. But between bouts of existential drifting, there were periods of focus and planning. For example, earning my college degree. Eight years of part-time school work while holding a full-time job and helping to raise kids. I had spreadsheets detailing the classes I’d taken, the ones remaining, which semesters they’d become available. The plan changed when life intruded or the university modified the schedule, but the end goal never wavered.

As I reviewed where I am at the beginning of this year, I recognized that I approached my reconnection to writing in a similar way. Two years after my decision to try NaNoWriMo (once I’d finally shrugged off the profound angst created by the dumpster fire of a novel that resulted), I made a long-term plan. I gave myself five years of dedicated effort to see if I could transition from “man who slaps words together like a room full of monkeys bashing on typewriters” to “published author.” At the end of five years, assuming I’d had no measurable success, I’d quit. Easy peasy. I’d quit before, I could do it again. This time, though, I’d give myself time to improve.

Rejection/Depression Cycle

Many people struggle with their writing as I have. We set a high bar, and when our early work inevitably falls below that bar, we crash spectacularly. Lacking anything better, we rate our success through rejections. But as a measure of writing progress, rejections absolutely suck. They almost never provide meaningful data to work with because you rarely know why you were rejected. They each serve like an episode of Gilligan’s Island: discrete failures, disconnected from each other. Rejection leads to depression, not motivation.

If the only measure of success are sales, and there are none, then why continue? Why get up at the ass crack of dawn every day to write? My writing became a drift with no purpose. I’d washed up on an island with nothing but a broke ass boat, lacking the motivation to try and fix it (look, this article has a theme, so just go with it).

A five-year plan allowed me to overcome some of those negative feelings, though I have never completely erased the sting of rejections. But I created a different feedback loop: an end date. Nothing mattered but maximum effort until the date arrived. By shifting the measure of success to future date, I could spend time attempting repairs instead of hoping random chance provided answers.

The Five-Year Plan

The plan initially was to write as often as possible. That was the entirety of it. But as it swung into motion, I also researched how to improve my writing (those pesky boat repairs). I read craft books, blogs, twitter feeds. I picked ideas that connected with me and applied them to the work. Some were discarded; others stuck, or I modified them to fit my needs. The list grew and morphed over time.

It included items like:

    • Complete stories (because I wasn’t)
    • Yearly word counts (modified from daily because missing a day left me depressed)
    • Style advice (e.g., reduce adverbs, use stronger verbs)
    • Attend writing cons (and try to get into limited ones like Viable Paradise or Clarion)
    • Read a lot, both for fun and critically

The new feedback loop allowed me to decouple from the rejection/depression cycle. Instead of disconnected points of failure, rejections became a count of work done progressing towards the end date. I still didn’t like them, but their value proposition shifted. I even took a masochistic pride in the number of rejections accumulated.

Everything I did a way of measuring the work I performed over the five years. Number of days in a row I wrote; total words written per year; total submissions/queries. I crunched numbers instead of rejections. Made spreadsheets instead of reasons to quit. Failure became something to worry about in the future. Until that date arrived, I hadn’t failed. I just worked.


My five-year plan ended last May. I had one semi-pro sale the previous winter, several held for further considerations, an acceptance and attendance to Viable Paradise, and a list of personal rejections that had grown steadily each year. Enough evidence to continue beyond the original end goal. I’ve had three more sales since then, including two at the professional level set by SFWA. Now I’m a member of SFWA.

This year I started a new five-year plan.

Maybe a five-year plan will work for you. If you’re drifting as a writer, unsure if you want to continue, replacing rejections as a measure of success with a time period of maximum effort might help you decouple from the rejection/depression cycle. You won’t be stuck on an island, hoping for a random idiot to come along and give you a lift back to shore.

But you will still have that damned song stuck in your head. The mate was a mighty sailing man…

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