Enduring the Messy Middle

One of my favorite books about the creative process is Carol Bly’s Beyond the Writers’ Workshop. I’ve bought and given away several copies, and many people who’ve read the book upon my urging some months later email me to communicate some level of wonder and annoyance. Bly’s book is prickly. She comes across as principled and cranky, enraged by moral and ethical laziness and greed, and determined to make the reader despise what she despised — which, to her credit, are mostly hateful things. But she was also, in her teaching of writing in social work and therapeutic circles, seemingly a person of great compassion for those in the process of becoming — more integrated, more comfortable with living with ambiguity, more devoted to doing justly.
Beyond the Writers’ Workshop also introduced me to the concept of the “long middle stage,” which Bly brings up to address the implied question of why so many books just aren’t that great. “The conventional wisdom has it that to write a piece of literature, first you have the inspiration, and then you do literary fixes on it. But that skips a long middle stage in which the expertise needed involves psychological, not artistic tools,” she writes.
The long middle stage: All complex projects, requiring many and varied inputs and coordination among those elements, go through it. It is indeed long, but feels longer. It is messy.
Authors experience it when they’re well past the first blushes of excitement that is starting a new project, yet nowhere near being done. Nonfiction writers whose books involve layers of research experience the worst of it. They may have dozens of pages of material but no strong through-line. The outline they’d drafted no longer fits their aspirations, or the manuscript they’ve since developed. Often the whole project feels hopeless.
For startup founders or product developers, the long middle stage can strike anytime. It’s when every item crossed off the to-do list invites three more. Some claim to experience it after they’ve launched a product but customers have yet to appear, but from my experience, that’s really not it. That might be just the pain of uncertainty, of “will they like me?” moments of doubt.
The messy middle has nothing to do with popularity, as I see it. Its central question is not whether all your hard work will be appreciated by others. It’s whether all your hard work will be appreciated by you.
Regardless of what realm of human endeavor you’re working in, the middle stage has three characteristics. First, it is lonely. Second, it is marked by inadequate feedback. (That is, the person in the messy middle might be receiving some feedback, but never enough, and what they do get is not immediately useful.) Third, a significant share of one’s mental energy goes toward prioritizing. Prioritizing during the messy middle is immensely difficult, because if nothing appears to be gelling — and again, tough to say, given the inadequate feedback — then mulling over which potentially fruitless task to focus on next starts to feel quixotic in itself.
One thing that propels one through the messy middle is “hold-my-breath pigheadedness,” according to Anne Trubek, founder of the indie press Belt Publishing, speaking of the press’s early years. “I was terribly stubborn: I was not going to let it fail.”
But there’s no universal remedy for the messy middle, and anyone who professes to know one isn’t taking into account different psychological makeups that, beyond stubbornness, could make it easier or harder for people to endure it. (Not to mention differences in access to project-sustaining capital.)
Here, however, are some mindsets and mental habits that have helped me and the dozens of creators and founders I’ve collaborated with over the years:
Imagine a formidable opponent
“All good writing in the end is the writer’s argument with God,” the Irish writer Sean O’Faolain is reported to have said. One doesn’t have to be a deist to appreciate that wrestling with a larger force has its uses purely from a productivity sense. You could say that all startups reflect the founder’s argument with fate, essentially. Can’t find the motivation? Try “I’ll show them! Just you wait!” Even spite works.
Peer further into the future
Everything good takes longer than one thinks it’s going to take. Even when I make my informed, experienced calculation of how long a project will take, and pad my schedule estimates accordingly, I can be surprised. So it may seem paradoxical, when feeling mired in the middle, to motivate yourself by imagining yourself still at the start. But it works. If you tell yourself something will take five years instead of being wrapped up by Christmas, as you’d hoped at the beginning, you’ll waste less emotional energy being disappointed with yourself or with time itself.
Or, as David Moldawar, publisher of the Maven Game newsletter suggests: “Push the finish line so far out of sight that there’s no conceivable way you’ll ever get there.” At the House we’ve quoted the investigative journalist I. F. Stone’s remark that “if you expect to see the final results of your work, you simply have not asked a big enough question.” But you don’t have to be all grandiose about it. Years ago a friend of mine was forced to attend a pep rally in celebration of his college’s football team winning the national championship; it’s a memory he doesn’t hold dear but for being present to hear tight end Andy Heck say to the adrenaline-jacked crowd: “If you shoot for the stars, the worst you can do is land on the roof. If you shoot for the roof, the worst you can do is land on your ass.” That ass-y image somehow buoyed his resolve through a rough career change.
Limit your conversations about it
Yes you’re lonely, but inviting more friends and conversation into your messy middle is not a foolproof solution. It’s simply a fact that certain people will be glad to discourage you from pursuing certain goals. They’ll gently, kindly suggest that you’re too optimistic, or that someone before you did succeed in generally the same area you’re toiling in, and so your ultimate success is theoretically conceivable — but then again, that those people succeeded under vastly different circumstances than you have, circumstances which are beyond your control. In my time I’ve heard the following: I’d have a better shot at success if I’d started this project during an economic recession; if I’d started it during an economic boom; if I’d gone to business school; if I were not female; if I’d had an entirely different career to date.
Limit your conversations with people who will say things like this. Also, I find that at a certain point, questions like, “Did you get done what you needed to get done today?” or “Did you have a productive day?” from even the most encouraging and sympathetic supporters can spike my anxiety. The internal pressure during the messy middle is intense enough without feeling like one has to report to external parties how well, or not well, things are progressing. Many writers will decline invitations to great parties, for months, even years, just to avoid being asked, “How’s the book coming?”
Reduce everything
Don’t just limit conversations, but develop a kind of tunnel vision. Stop doing something you habitually do, if it’s something you can stop doing without the ecosystem that is your life collapsing. Do not Google yourself. The kind of self-consciousness self-Googling engenders is the enemy during the middle stage. (And per Bly, you’ll need all the psychological strength and subtlety you’re able to muster now.)
Accept your fiscal or temporal limitations as helpful creative constraints. Reduce until something clicks, and you actually feel physically lighter. Having a list of small tasks one can tick off while more substantive creative thinking eludes you, or you’re simply too tired, also helps. Compile receipts. Choose accent colors. Declutter your digital workspace.
Love
Stubbornness absent love is cruel. Stubbornness born from love looks like devotion, and it’s the devotional posture that will ultimately carry you through the messy middle. Not because you’re working on a “passion project” but because when in your head you have shushed the skeptics and the sophisticates who question your abilities and good sense, you know. You know. You’re not passionate, with all the flush and drama the word implies. You are dedicated.
On page 58 of Beyond the Writers’ Workshop, Bly proposed a “final check” for writers leaving the long middle stage and going on to the “literary fixes” of line-edits, and that’s to ask: “Have you served or have you betrayed your innermost self” in what you’ve accomplished here? My hope for everyone undertaking a complex project, be it writing or founding a company, is that love helps them answer this question.