The Plan, the Plan!

This week I decided to renew my passport, which has been sitting in a drawer crying to be attended to for six months.

It did not go well.

I should say, it didn’t go as I had envisioned.

But this isn’t quite the right way to put it either, because I had not outlined any vision of how to accomplish this task or what I wanted the end result to look like.

The idea of forming a plan to renew a passport may sound strange to some. After all, how much forethought could it take to obtain an updated 2”x2” picture on a white background with no texture, no shadows, no blur, no glasses, that is not too close and not too far away, that is not a photo of a photo, and that is not photoshopped (etc., etc.)? How much planning or effort could be required to then upload this little image, fill out a quick .gov renewal form (the photo apparently carries all the weight in this matter), then plunk a handful of gold nuggets on the digital counter?

Apparently the answer is “more than none.”

But alas, for the better part of 2026 I didn’t plan this operation, and as a result my passport has come within shouting distance of the cliffs of expiring. Then, earlier this week, my anxious avoidance was granted a reprieve by serendipity—or so it seemed.

I was driving home from a different errand; one so routine that my body knows instinctively what to do and my brain didn’t store any memories about it. What I do recall is that it was a hot, cloudless afternoon, and I had on my robin’s-egg-blue prescription Ray-Bans that make me feel supernaturally cool and capable. As I coasted down the hill in my economy car, I saw a post office snoozing in a little asphalt parking lot just off the road. And inspiration struck: today was the day to TCOB.

Dry your tears, passport, I thought to myself as I parked and stood tall, drawing enough energy from the sky and sunbaked pavement to fly. It’s time to exorcise this task demon from our to-do-list pig.

That white brick impacted molar of government indifference awaited me. As I approached, the warped-glass extrusion of bureaucratic backrooms shifted in anticipation. Then the behemoth unhinged its jaws and gazed down, unblinking, as I stepped into its maw.

“Do you do passport photos here?” I asked the pursed-lipped Buddha at the counter, who glowered vacantly, I think meditating upon how not to explode.

“Yes we do,” he said, staring into space beside me.

“Do I need to make an appointment?”

“No, the woman who does the pictures is in today.”

“Do I get an email copy of the photo?

“We do the pictures right here,” he told the countertop, then he floated across the room in a lotus pose to retrieve the wig and clown makeup for me to put on.

Here is where a person without a history of extreme deference and conflict avoidance might have piped up, “But you didn’t answer my question.” But since I do have the disease of people-pleasing I obeyed his chain of commands (“Give me your license”, “It costs $15”, “Put in your email address”). Ten minutes later I walked out the door with two print copies of a mediocre picture (wondering Why do I look like a serial killer? and Is that a shadow by my shoulder?), a receipt reminding me of the offensive amount of money I had spent to not get just one digital image, and an irrational hope that an email with jpgs would be awaiting me at home.

Of course there was no such email. And my passport continues to curdle. At least now it’s going out of date on my desk instead of in a drawer.

Now that I think about it, maybe plenty of people plan how to execute “simple” tasks like renewing passports. It is after all a rare enough event and a byzantine enough process to merit an advance strategy.

Perhaps a bit like writing a book?

As a result of this passport debacle, I’ve meditated on plans quite a lot in the last week. And I’ve begun to realize that planning is much more common and necessary in daily life than I historically appreciated.

Part of what’s strange is that in many matters I have no problem realizing I need to set goals, mapping out my plan of attack, then executing. I did this when applying to grad school; when I bought my little Honda; twice when I went on backpacking trips to Europe; when I first erected my editing business; and with any number of other tasks big and small. I also manage to competently plan when I’m editing clients’ manuscripts (although I always feel my system could improve).

But challenge me to furniture shop or complete household chores on a regular basis, or to ask someone out on a date or find a new therapist, or to locate and join a summer sports league, and you would be forgiven for thinking I was born yesterday. And if you were to suggest that I plan such things ahead of time, I’d look at you like you have two heads.

And then there’s writing. 

People often tell me I am a very good writer. I don’t say this to brag but to point out that you’d never know it if you were measuring my skill by what I have published (a dubious way to judge skill or fulfillment of writing potential, but let’s run with it). I have been in official print precisely three times. A sci-fi story I wrote in fifth grade won second place in a children’s lit journal. A poem I scribbled in college was put by a friend into a rebel student newspaper. And the half-finished speculative fiction novel I wrote for my master’s thesis takes up modest shelf space in a library out west.

Nor could you measure my skill by counting how many projects I have finished (perhaps a better metric than publication), which is a number not much higher than how often I have published.

Let’s mash publishing into finishing to narrow our field of attention. So why haven’t I finished much writing? There are a few reasons; many involve my historic mental state and a more positive one is that lately I’m devoting a lot more energy to helping other writers achieve their literary dreams. But today I’m going to focus on a universal root cause which I think many readers and writers can relate to:

 The reality is that a lot of people who get ants in their pants to write are so eager to dig into the writing, so seduced by sheer passion, that they unconsciously decide that serendipity will do the rest of the planning and accomplishing for them. And often they wind up bewildered and dispirited—like I was with my useless passport photo—when they one day take stock and realize their manuscript is no nearer to being done than when they started. 

As I said, I’ve been thinking about plans a lot this week in the aftermath of my failure to renew my passport. I’m also reading Blueprint for a Memoir by Jennie Nash, which has abundantly nourished this train of thought. And a recent philosophical conversation with a good friend on cognitive load and what constitutes a plan contributed as well.

As a result of all this, what I’m coming to realize is that life situations that could benefit from a plan are almost endless.

You might already be a planner by nature or training. You might find all of this a bit obvious. Kudos to those of you who do plot a course for your writing vision, by the way. You are way ahead of the curve, and I salute your wisdom. Then again, you might be more of a chronic pantser like me when it comes to life and writing. To you I offer kudos for sheer verve. In either case, I believe this matter of planning is worth a closer look.

So why am I—or if you’ll allow it, why are we—not more cognizant of opportunities to plan? And why aren’t we more inclined to make use of this fantastic tool, especially when it comes to writing?

Today let’s look at three reasons why someone might not make a plan for writing:

Some of us have a hard time conceiving of how a plan could possibly be called for in a given situation. At least I do. Many, many parts of life seem to fall into the perceptual category of “it just happens” or “I just do it.” Some situations are filed under “this is too basic to plan”; others under “I don’t have enough time to plan.” But I want to offer a radical proposition:

Physical instincts are unconscious planning: built-in bodily responses to things like touching a hot stove or having a gun pointed at us. The quality of our instinctive plans may be debated, but this doesn’t make them any less plans.

The same goes for habits good and bad. These are not far off from instincts; they are just micro-plans wired into our system by repetition. Laying out clothing at night to save time the next morning. Keeping soap and towels in the closet down the hall from the bathroom so that we can retrieve fresh supplies in a pinch without having to hunt all over the house. Eating balanced, healthy meals and/or junk food at particular times of day (or at random if we like our eating system to look like a protest against systems). Walking to the bus stop every morning at 6:45 am to catch Route 83 so we can make our transfer to the commuter train at 7:30. Grocery and back-to-school shopping.

Some of our plans mix a little of column A with a little of column B. The manner in which we write by hand in a notebook, or how we throw a football, or how we kiss, are all partly due to how we’re wired and partly due to repeated choices we have made.

Whatever word you normally label these behaviors with, each represents a repeated sequence of actions and choices. AKA, a plan. Just because something doesn’t make it into our week calendar or is not codified in a document literally titled “My Plan to Do X” doesn’t make it any less of a plan.

So the reality is, when it comes to the parts of life we struggle with—which might include starting or finishing a writing project—we could be facing an amazing opportunity that starts with simply noticing, “Hey, maybe I could make a plan.” Then we might gather some resources to and start to do so.

But then there’s the problem of willingness. 

This is as much a point about learning as it is about planning.

Here’s the reality of human existence: We might be great at engineering, but need to watch a tutor to play a C chord on a musical instrument. An amazing driver, but require the guidance of a friend to navigate a phone tree. A fantastic surgeon; but must consult a cookbook to make ramen.

When I think about this sort of thing, it’s like looking at one of those 3D pictures. I see something, then I don’t, then I see it, then I don’t. It seems both perfectly natural and utterly bizarre when I reflect that each of us can be highly competent at some things and a babe in the woods when it comes to others.

But I suppose that’s just how it is. Humans are complex. Finite. Eager. Flawed. Able to grow!

Yet how many of us, when we run into a challenge, see it for what it is: that we are simply out of our depth (no judgment in that—it’s just a material fact), and that we have options to either intelligently climb to a higher place or pretend we are a bird and take a swan dive.

If we accomplish this feat of recognition, how many of us proceed to the next heroic insight: that further research, maybe some counsel, and at last making a plan would do us wonders?

When it comes to writing and editing, I sometimes witness people mistaking their keen memory of events as transferring naturally and effortlessly into the power of telling a good story. Or they know they are good at telling a story—in person, to family—and they assume it is the same thing as writing dozens of hours’ worth of such stories to entertain strangers. Or they believe that having internalized a life lesson will translate seamlessly into teaching it to others in book form.

There is no shame at first in any of these assumptions. We can’t know what we don’t know until we learn it. What’s important is what we do with the knowledge once we have gained it.

Some people seem unwilling to acknowledge the divide between what they can and cannot handle adeptly. Others are painfully aware of the gaps in their skillset and they avoid weak areas like the plague. As much as I can be an eager student, too often I’m an avoider instead. I can become frustrated and dispirited in the face of my limits (see Exhibit Passport Photo). It seems somehow shameful not to have already mastered something—when that’s one of the last things we ought to feel bad about (if you haven’t yet, check out my last newsletter, where I sang the virtues of being a lifelong learning). 

When the distance between ambition and execution in a writing project is pointed out by an editor (who is half educator, half creative executive assistant) plenty of writers respond amiably and redouble their efforts, using the editor’s constructive suggestions as light on the path and a draft strategy which they are free to tweak as needed.

But sometimes an aspiring writer becomes stubbornly defensive or inconsolably depressed. This can happen for a variety of reasons (including poorly worded feedback from an editor). It is within a writer’s rights to respond in this way. But it is tragic, too.

Because here’s the thing: many chasms in our current knowledge and skill—in writing and many other realms—can absolutely be crossed, especially when one already has a full tank of that vital fuel, passion. It is just that one needs more than ego and good vibes to traverse the gap. One needs knowledge and a blueprint before they can build a bridge.

Another thing I pointed out in the last newsletter is that none of us knows anything as well as we think we do. So for the writers among us, the good/bad news is that no matter what we write about we will run into the boundaries of our current aptitude.

When, not if, this happens, I believe most of us would benefit from pausing, breathing, and calmly acknowledging that forming or revising a plan—perhaps with help—could be just what is needed to help us move forward.

The final mental block to planning to write that I want to look at today is a categorical objection. 

Do any of the below statements feel familiar?

If any of these rings a bell, you’re not alone. I pulled all three of these from my mental archives. I confess that once upon a time, the notion of planning before writing appalled me.

In my romantic writerly youth (which dates to about five years ago, when I became a full-time editor), I clung to the fantasy that art was all accident and inspiration. If I was not writing for a term paper or a work project or some other externally imposed assignment, I wrote the way I tried to get my passport photo: coasting on vibes and accidents of circumstance and derailed by, well, everything.

I had no clue where I was going, why, or how I intended to get there (wherever “there” was). And as a result I have an entire small bookcase dedicated to the fruits of my aversion to creative planning. So. Many. Unfinished. Projects! I wonder if I can patent my process for breeding dust mites and silverfish in piles of half-done manuscripts?

How ironic that I avoided planning because I thought it would stifle my creativity, when as it turns out the reality might be the opposite: my creative flames have been choked by an unlimited supply of open, highly oxygenated roads. I’ve suffered from having no guiding, motivating waymarkers.

What about you?

I mentioned earlier that I’ve been reading Blueprint for a Memoir by Jennie Nash. She has made short work of my historic attitude toward planning a writing project. Check this book out if you write memoir or personal narrative of any sort. Even if you don’t write in those genres, but you are historically a pantster, you might still have a plan-your-writing conversion experience.

Here are just a few benefits of planning a writing project—and maybe of planning anything—that Nash is helping me to identify:

Questions and answers can of course change, but when you plan—consciously plan, I mean; not leaving nothing to fate but also not neglecting 90% of the course by crossing your fingers and hoping for the best—you’ve given yourself an amazing gift of clarity, direction, and drive. Plus you may have more energy to spare for the actual writing.

I don’t have space in this newsletter to do a deep dive on what constitutes a quality plan, but that was not my objective.

My intent today has been to supply you with awareness and appreciation that plans are everywhere, and it couldn’t hurt us to add a few more to our working and living environment.

Last time around, my central exhortation to readers was to go long. This week it’s even simpler: plan. Plan, because as it turns out, that’s probably the best way to go long. 

One last thought on plans, for those still chafing at the thought that plans are restrictive.

I’ll never forget something my college Shakespeare professor said while we were studying the sonnets. He observed that many of his students curdled at the thought of being “forced” to write within a particular poetic form.

Something I notice a lot with first-time writers is that they try to write about everything at once. A plan helps restrain our impulse to fill a story with kitchen sinks. Additionally, functional constraints on a writing project quite possibly increase the writer’s odds of finishing at all.

Truly infinite possibility is such an odd romantic fixation, because in reality it is just a paralyzing abstraction. Like walking through Venice without a map, or trying to find your way out of Borges’s boundless, featureless, desert prison, it’s impossible to pick a direction because you can go everywhere (or you do pick a direction but then you have to pick and pick and pick and soon you’re exhausted, dizzy, and dehydrated).

Just think: planning to write a sonnet, haiku, or sestina—or planning to scribe a memoir about a finite period in your life in order to deliver a particular point to a well-defined audience—this does not lock you in a cage. Perhaps quite the opposite.

Especially if you are the sort who struggles to start writing (or to finish), planning your story could be like stepping out of a hedgeless maze of infinite distance, directions, and decisions. A plan may be just what the doctor ordered to plunk you in a proper creative labyrinth that, while still winding, draws you forward and leads you somewhere meaningful. 

I’m not claiming that every writer must plan lest their writing crash and burn. But I respect now why so many writers do plan, and I humbly suggest to my fellow pantsers that if you, like me, have historically been a terminal non-finisher, take a second look at planning your writing.

And once again, check out Jennie Nash’s Blueprint for a Memoir. Even if it doesn’t wind up being exactly what you need, it’s a good place to start.

Dear reader, as we part today, I’m curious what you need to accomplish that’s giving you anxiety this week, creatively or otherwise. What is the ground on which you fear to tread? Might a little plan help you get started? What resources or people might help you make that plan?

I invite you to write back and share with me—I would be delighted to be a quiet witness and cheerleader for you as you discover, with the help of planning, that you can step out thoughtfully and grow beyond your current boundaries.

As you make small, brave plans for small, life-affirming steps,

P.S. – Don’t worry, I’ll get the passport photo sorted out.

P.P.S. - I enjoy genuine connection, so if a thought or question came up for you, hit reply and tell me about it.

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