Musings + Essays

How to Get Started with Writing.

By: Jen Shoop

I recently received the loveliest note from a Magpie.

“I’m a noticer/feeler with words constantly swirling in my head,” she wrote. “I so want to be able to put those thoughts and feelings on paper as you do. I know I need to just begin somewhere, but I stall out.” She ended with a solicitation for my advice.

I wrote back volubly, compulsively — I have so much to say on this matter.

First: this seems to be in part an issue of creative confidence. I used to have my team members watch this video on building creative confidence by David Kelley, the founder of celebrated design firm IDEO. The TL;DR is that we are all inherently creative. It is part of the human condition. Somewhere in childhood, we begin to think that doodling and coloring are juvenile, and often, our creative appetites curb, or stall, or otherwise retreat. I think that being “creative” can make us feel vulnerable, or silly, or frivolous. But we were born to tell stories, and I use that phrase loosely — we can tell stories in the way we design our days, the way we style our hair, the way we knit our scarves. Cavemen etched on walls for a reason. The creative impulse is there — tap into it.

In his video, Kelley acknowledges that some of us fear failure when we undertake a creative endeavor. He proposes continuous exposure as a prophylactic. I completely agree, and this is where I really hit the gas pedal in my response to the Magpie note:

Start with something low-stakes. The thought of sitting down to “write a novel” or even “write an essay” scares me, and I write for a living. I find that medium matters here. I am most at home typing into the WordPress visual editor. It gives me the impression of impermanence, fungibility. If I don’t like what I write — eh, well. It can sit in drafts into eternity, or I can delete it. For some reason, writing in Microsoft Word is far more daunting to me. It feels overly formal. It’s like the tuxedo of writing tools — at least for me. The point is to find some medium that feels comfortable, draft-like, low-stakes to you. That could be a plain sheet of computer paper. A gridded notebook. A leather-bound journal. It might in fact be Microsoft Word. I do some drafting by hand — especially when I am massaging a particular passage or phrase — but I tend to find writing on a computer keeps better pace with the flow of my thoughts.

Once you’ve found a non-threatening medium, remind yourself that you do not owe this moment of self-expression to anyone but yourself. You are not writing for audience or acclaim. You are writing to let feelings run dry on paper. This is a no judgment zone. I know next to nothing about the quality of my own writing, but I can tell you that by writing voluminously, daily, I have found it increasingly easy to express myself in language that I believe is accurate to my own experience. Any “success” in writing — by which I mean any instance in which my phrasing has resonated meaningfully with a reader — has only happened by virtue of continuous exposure to the practice. It is a process thing. I focus on the feeling of language in my hands, cultivate my own idiosyncratic revision strategies, examined what I enjoy writing versus do not. (Dialogue is so, so hard. I dread it.)

And — keep at it! Every day. A little bit more. I’ve written elsewhere that you will not always be inspired, so you must learn to be disciplined. Write when you feel like it, and write when you don’t.

If you are writing with the goal of self-discovery (“I write to know what I think!”), a few solid journaling prompts:

“What is the most important thing?” This is a moveable feast. I find my answer to this question can change by hour, or, sometimes, stay the same.

“A thought pattern I would like to release is…”

“When I am most joyous, I look like…”

A key for me is getting gritty with the details. One of my favorite creative writing “jump starts”: capture a specific memory in exacting detail. I will strain to remember the colors of cushions, the sound of feet on pavement. This relates in part to a widely-known tenet of good creative writing (one of the few sagacities I took with me from that weird creative writing class I took in college): “show, don’t tell.” Good writing observes. Details are the aperture.

Finally, once you are in a rhythm, take some time to notice the conditions in which you feel most generative. I’ve shared some thoughts on finding fruitful times, habits, and spaces here and here.

I am reminded, as I draw this prolix disquisition to a close, of two of my favorite quotes: “The harder I work, the more luck I seem to have” and “Begin as you mean to continue.” I hope you feel the same driving energy I do when I read those words. I know it is easier said than done, but — Go! Start! Onward! You are creative, you have everything you need to succeed, and — off we go!


+Begin as you mean to continue.

+On finding a calling in writing.

+The best books I’ve read in the past few years.

Shopping Break.

+Lake Pajamas’ holiday collection just launched! I picked this star print set and this poplin set for myself and am IN LOVE. Gradually, over the past few years, I’ve replaced all my pajamas with Lake and have gifted them to every woman in my life. A note on sizing: I find this brand generally runs roomy. While I’m typically an XS/0 in most brands, I usually order an XXS here — and that even accounts for the shrinking that will happen when running these through the dryer. However. In the long-long set I ordered, I did size up to an XS, as I just like the fit of the pant when it’s a tiny bit roomier. But for poplin and all other styles, I take an XXS.

+Their launch also includes these adorable holiday jammies for littles — high sell out risk. These patterns for children always sell out quickly.

+Pink City Prints just released a bunch of beautiful fall pieces — love this dress and this top/skirt combo.

+I can’t get over how good Banana has become recently. I absolutely love this suede bag. It looks like it could be RL, or Khaite? And this corduroy blazer! Ahh! So good!

+Fun little fall blouse.

+This mirror is under $250 and so chic!

+Just bought this as a gift for my MIL!

+These mules are under $20 and give me Mansur Gavriel-meets-Manolo vibes.

+Loved Little English’s latest launch — this sweater would look so cute with duck boots! (Note: Sperry toddler boots run really small – size up at least one, maybe two, sizes.). And this little gingham top for girls! I have been leaning into the cute top with Old Navy leggings formula for my daughter this fall.

+Can’t stop thinking about this funky mushroom sweater.

+Great boots for under $250.

+Fun, dramatic dress for a cocktail party.

+Have heard these Mother cords are very flattering.

+Great raincoat for a little — this brand is legit; the Scandis know inclement weather. Consistently ranks highly on quality. If you want something less expensive, I’m still impressed with the quality and style of this $31 style, which comes in several great colors. My son has the blue.

+AMAZING sequin gown.

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6 thoughts on “How to Get Started with Writing.

  1. I loved reading about your process for writing and the discipline involved. Sometimes when I see how talented other people are, my mind can tell me that they’re gifted and I’m not. Reading this reminded me that, save for the savants and prodigies, most of us must practice and hone our skills. Thank you for that.

    As far as your shopping picks – amazing as usual! For the Lake Pajamas, do you get yours hemmed? I have hesitated to purchase them because I am 5’2″ and I don’t want to trip on the length. I am assuming you must get a lot of your pieces tailored because when I click to buy I don’t see them available in petite or shorter lengths. I may have to source a good tailor and do the same thing.

    1. Oh yes, Marthalynn! “Great anglers are made, not born.” I don’t know where I heard that quote — probably saw it in a tackle shop with my flyfishing Dad when I was younger — but I think of that so often when I am approaching anything creative. Repetition, discipline, practice, enthusiasm, *just showing up* get you so far in so many pursuits. Glad this post was galvanizing for you!

      I do not get the PJs hemmed! The poplin ones are noticeably too long, but the star print/cotton ones aren’t too bad — honestly, a little extra length has never bothered me with jams? I usually wear with slippers around the house and just don’t notice at all. Maybe this is also because I don’t change into PJs until just before bed, and then I’m usually out of them before breakfast, so they really are just for sleeping for me. But even when I do wear them around on a lazy Saturday, I have never felt like I am tripping over them at all — with the exception of the poplin style, I’ve never even thought about it. I’m 5’0 for reference.

      BUT if you are bothered by the feeling of too much fabric or skewed proportions, try this specific pair in any of the prints:

      These are definitely not too short. They hit at the top of my foot / when shrunk, around the ankle.

      I do have most daytime pants tailored if they aren’t available in a petite length!

      From one shortie to another, hope this helps —


  2. I appreciate the tip about finding a low-stakes *medium.* I’m familiar with the idea of “lowering the bar” to get over perceived writer’s block, but this seems like an especially practical, concrete way to build that into your approach.

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