How to Keep Trying in the Stuck Places

Writing is hard. Learning to write is hard, and the more we learn the more sensitive we get to ways we could improve. Learning and growing is magical and wonderful, but it often invites a sense of futility. Let’s explore how to navigate this!

The opening of Dante’s Inferno cuts to the root of it:

In the middle of the journey of our life I came to myself within a dark wood where the straight way was lost. Ah, how hard a thing it is to tell what a wild, and rough, and stubborn wood this was, which in my thought renews the fear!

All who aim at mastery and excellence must hit many plateaus on the way. These are the places where the low-hanging fruit has been plucked but the goal is still out of reach. At these stages we tend to make great efforts that feel futile. While the growth is agonizingly slow and subtle, the frustrations are obvious, and it feels like they are winning.

Those who achieve excellence in anything share a certain mulish stubbornness in the face of such plateaus. Natural talent and “genius” are quite secondary to this main virtue of stubbornness.

How do we live in this space? We don’t think there’s anything mystical about it. Dealing with the plateau is a learnable skill. We just have to get clear on our goals and keep trying. That’s the hard part.

Yoda and Grace

Consider Yoda’s maxim: “Do or do not. There is no try”. This is a great truth, but during the plateau stage we couldn’t disagree more! Yoda is skipping steps. His words ring true only after the plateau.

The opposite of Yoda’s great truth is another great truth: we surmount the plateau through nothing but trying.

Grace Greenleaf puts it well. Since Greenleaf is not as well-known as Star Wars, we need some context. Grace is an apostate Christian who has just arrived back to her megachurch-operating family. They’re all at a tense family dinner. Grace’s mother is grilling her about whether she believes in anything at all. Grace responds thus:

I guess I believe there’s a part of everything that tries. You know, like plants try to grow. Animals try to survive. People try to better themselves to get ahead. Everything tries to do something, and I guess I think that Christianity is just one way that the trying part of people tries to connect with the trying part of everything else.

In the dark wood, on the plateau, we need to be more like Grace and less like Yoda.

There are two things to point out here. First, notice how much more tentative Grace is than Yoda. Second, notice how tender and open this attitude is to the possibility of failure. Everything tries, but not everything succeeds. Regardless of outcome, we can connect to the truth of trying as a way of staying with the process.

Honour your Trying

It’s always tricky to give practical advice when dealing with the plateau. Whether the advice hits home or appears simplistic can shift hour-by-hour and day-by-day. That said, here are some hopefully inspiring generalities.

Inside this lavender there is something that tries.

It’s easy to get stuck in achievement or productivity mode because getting things done is easy to get a handle on, especially in difficult times. The problem is: so much of productivity-mode is busywork. Individual trying is often de-emphasized in our culture. But it matters! Find little ways of enjoying the work you do! Find tweaks, adjustments, and ways to make the work less of a slog. Much of that involves ceremonializing your own trying in ways that feel appropriate.

Separate Process and Product

There are many ways to do this. Sometimes just breaking down a goal into smaller sub-goals is enough to get us out of product-mode and into process-mode. Sometimes recognizing that the product is mainly for others, but there are pieces of the work that are individual, ineffable, and just for you will do the trick. Perhaps reminding ourselves that we are most in touch with ourselves when doing creative work will help. Nobody can walk the path for us, or replicate the path we’ve walked. And that matters.

Just keep Trying

This one is most likely to be misunderstood. It doesn’t mean stiffening up with effort or powering through tiredness and resistance. Finding ways to keep trying when stuck demands creativity, discernment, and sensitivity, not force. If force were all you needed, you’d be out of the dark wood already, since nobody wants to dwell there for long.

Finding ways to keep trying involves finding little bubbles of kindness for yourself in tough situations. While the particulars are unique and individual, finding kindness doesn’t have to be lonely. Reading about other people’s process is often useful in sparking something in us. Of course, meeting with an academic coach might help as well.

We hope some piece of this work has been helpful to you. You may be finding the work hard because the work is hard. We’ve lived this life for a long time, and want to help.