Everything I need to know about planning my life I learned from ‘The September Issue.’

Everything I need to know about planning my life I learned from ‘The September Issue.’

This month I took the time to re-watch R. J. Cutler’s fantastic documentary The September Issue, Cutler spent eight months embedded at Vogue, beginning with the January fashion shows and ending with the finished magazine rolling off the presses.

I don’t read a lot of glossy magazines, and I don’t closely follow the world of fashion, but I love this documentary for its portrayal of the creative process.

Vogue is about fashion, and The September Issue features plenty, but the real heart of this film is the relationship between Editor in Chief Anna Wintour and her longtime creative director Grace Coddington. The women started at American Vogue on the same day in 1988, and have been working together ever since. Their unusual relationship is key to the magazine’s success, but whenever the two appear in the same scene, sparks fly.

(Interestingly, Coddington at first refused to be filmed for the documentary, but Cutler eventually won her over, to his great relief—he said he had to have someone who wasn’t afraid of Anna.)

The September Issue shows how a dedicated team of people pull together the year’s most important issue, over many months, with lots of collaboration, a good bit of conflict, and continual trial and error.

As I watched the film, I was struck by how applicable the film’s insights were to putting together not just a magazine, but a life:

The September Issue poster

1. YOU HAVE TO HAVE A STORY.
A bunch of pretty things thrown together is still a jumbled mess. Whether in a magazine layout or your own calendar, unifying themes are crucial, and should be obvious to the reader.

2. LOOK AT THE PARTS AND THE WHOLE.
The individual pieces must stand on their own and work together.

3. PUT IT ON THE BOARD.
At Vogue they use a giant display board to storyboard each issue. This makes it easy for the viewer to see how the issue flows, to evaluate what fits and what doesn’t, to judge what belongs, but would be better in a different position.

As the issue comes together, the changes that need making, the gaps that need filling, and the missing pieces become obvious—once they’re on the board.

4. CONTRAST BRINGS IT TO LIFE.
Unifying themes are important, but a magazine (or a life) filled with things that are too similar—even if they’re quite wonderful on their own—becomes tedious.

5. SCALE MATTERS.
Some things look best when they’re huge. Some topics should get lots of coverage. Some topics are best done on a small scale. It’s important to know the difference.

6. EDIT, EDIT, EDIT.
Slash the unnecessary stuff. Be relentless.

Vogue display board the september issue

7. THERE’S USUALLY ONE BIG DISASTER IN EVERY ISSUE.
Especially in September—it’s a big issue. It happens to everyone working on something big, or in a busy season. Accept it. Plan for it.

8. SET GOOD BOUNDARIES.
Choose whose feedback matters, and whose opinions don’t. Protect your personal time and your personal space. Don’t make yourself accessible to people you don’t need to be accessible to.

9. HAVE PEOPLE IN YOUR LIFE WHO WILL GIVE YOU PUSHBACK.
The combustible relationship between Wintour and Coddington is at the heart of this documentary. They obviously respect each other, though they’re not always particularly cordial: they push each other, hard, and share their unflinching opinions about the work. The magazine is better for it.

10. FIGHT YOUR WAY THROUGH.
If you really want something, fight for it. It won’t be easy: in the words of Coddington, “You have to be fairly tough to withstand it.”

11. KNOW WHEN TO STOP PUSHING.
To protect those personal relationships, learn when to ease up.

Vogue collage September 2007

12. YOU HAVE TO WORK YOUR WAY UP.
In fashion, everyone starts at the bottom with the grunt jobs that aren’t much fun. The same goes for schedulers: skill comes with experience. You won’t be very good at planning your life when you first begin. As you work at approaching your life—and your calendar—with intention, you’ll continue to improve.

13. IMPOSTER SYNDROME IS REAL.
There will be a day—at least one-when you feel like you don’t know what you’re doing. It happens to everyone.

14. LIFE ISN’T FAIR.
Sometimes you do everything right and you still crash.

15. STICK TO YOUR GUNS.
Even if it’s not in style, or what everyone else is doing, or what you’re “supposed” to like.

The September Issue fashion show still

16. IF YOU HATE SOMETHING, ADMIT IT.
Be ruthlessly honest with yourself. And if you really hate something, just say, like Wintour, “I never want to see that in the magazine.” (Or, in your case, on your calendar.)

17. EXPECT SERENDIPITY.
Disasters are inevitable, but thankfully there’s a happy counterpart. In the words of Coddington, “Somehow everything I did I kind of fell into.”

18. GO WITH THE SEASONS.
September isn’t the only issue. If something isn’t well suited to one season, it might be an amazing fit for another. If there’s not room in September, maybe you can make room in October. Or January.

19. TAKE GOOD CARE OF YOURSELF.
In The September Issue, there were bottles everywhere, and even the models were shown eating. (Cherry tarts, no less!)

None of this is easy. Set yourself up for success by minding your foundation.

20. ALWAYS KEEP YOUR EYES OPEN.
Inspiration is everywhere.

21. IT’S AN EVOLVING PICTURE.
Intentional planning is an evolving process that never ends.

 

The September Issues sheds insights on putting together not just a magazine, but a life.

I’d love to hear your unexpected sources for life-planning inspiration and any favorite planning tips or tricks in comments. 

For further watching: Bill Cunningham New York. For further reading: Grace: A Memoir. More on the blog: planning for visual types.

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30 comments

  1. I loved the one about the imposter syndrome! I feel that way quite frequently as a teacher. I also remember having that feeling before writing each paper in undergrad and grad school–“Maybe this will be the paper where they find out I really can’t write.”

    • Jennifer says:

      Imposter Syndrome is way more present in my daily life than I would care to admit. Like Sarah, when I’m in the classroom as an instructor – or playing the part of student, researcher, presenter, etc (currently working on my phd) – I consistently battle this situation (making me pretty much a grad school cliche!). On another note, I loved this post & I really appreciate how you were able to pull these immensely applicable points out from the content of the documentary. I was also so intrigued by the documentary that I reserved it at my local library. Perhaps it will offer a nice respite from my candidacy exams prep…!

  2. Bekki says:

    Wicked good article!!! Thank you, thank you. Your synopsis of the planning process came the same week we’re switching our business, family, and church over to Trello. Sweet timing.

  3. Sounds like a fun documentary. I’ll have to check it out – and maybe pick up the September Vogue. I used to subscribe, then I stopped, but I’ve been missing it (well, parts of it).

    • Anne says:

      My pattern over the years has been to subscribe, then let my subscription lapse when the unread issues start piling up. But then I start to miss it—or parts of it.

  4. I’m not a fashion person either, but I love documentaries. I’m going to make watching this one a priority. I love the life lessons you pulled from it, especially #1. I’ve never thought about my calendar (and my life) having a story. Thanks for this great post. I’m going to link to it for my readers tomorrow.

  5. I loved The September Issue, but I loved this post about it even more.

    I really resonated with two items: first, needing to expect there will be disasters. When we do that, then when they come up, we don’t have to wonder what we did wrong. Expect and prepare is the mantra.

    And secondly, have people in your work (and life) who will push back. I run my company and absolutely need my staff to be willing to push back on me. I don’t always get things right, they have to be willing to push back, to make our product better.

  6. The magazine industry absolutely fascinates me! Such a cool post . . . I’ll have to watch that documentary when the hubby’s not around. The words fashion and documentary together will definitely make him run for the hills. Especially if it causes me to examine our whole life plan. lol

  7. Rayni Peavy says:

    Great commentary and take-aways, Anne! I watched The September Issue recently because I love fashion and have heard so many negatives about Anna Wintour, I thought it would be interesting to see her in action. My take-aways were more about her, like how she seemed a bit sad underneath it all. And that her daughter thinks having such an intense focus on fashion is rather silly. Anna did say one of her strengths is decisiveness, which is a great strength to have when making as many daily decisions as she has to make. It crossed my mind that if she were a man, people probably wouldn’t think of her as such a harsh person. She’s simply running a magazine and needs to be straightforward and make decisions. I loved watching Grace in action as she styled all of her photo shoots. What a creative person! And a number of the interactions definitely reminded me of The Devil Wears Prada. The designers really do listen to what Anna has to say and she’s even making suggestions to fashion icons such as Oscar de la Renta! A random take away was that many of the older, established employees didn’t seem to make much of an effort to look fashionable. Thought that was a little strange. Another fun and interesting fashion documentary on Netflix is Mademoiselle C. It’s about the former French Vogue editor Carine Roitfeld starting her own fashion magazine.

    • Anne says:

      Those are such interesting points. Yes to everything about Anna Wintour (although I can completely understand not wanting to bare my soul to a filmmaker). I loved watching Grace in action. The September Issue has been called the “real” Devil Wears Prada. And I did notice that the established fashion people often had very plain looks, and no makeup.

      I haven’t seen Mademoiselle C. Thanks for the recommendation!

  8. PamDDO says:

    I found it interesting that only in the third paragraph do we find out which magazine the film was about. Would everyone but me realize that it is Vogue?
    I love the way you distilled valuable insights for life from the fashion industry.

  9. Marne says:

    Oh #8 is my downfall. “SET GOOD BOUNDARIES..Don’t make yourself accessible to people you don’t need to be accessible to.” I couldn’t do it in my last job…so I quit. After 22 years.

  10. I love it when you write pieces like this one. When I watch this now (it was already on my watchlist – I think we have really similar taste!) I’ll be thinking about your connections which will lead to more connections of my own. It’s just wonderful – thanks!

  11. Beth Anne says:

    This post is so insightful! I love how you pull insight from every place your eyes gaze upon in this world. It’s a gift.

    Now I have to check this documentary out.

    My most recent insight: Do the thing. Edit later. Getting started is just so hard sometimes. We want things to be epic. But epic comes after lots of editing, as you’ve mentioned. And, a recent episode of Seinfeld reminded me of that. Jerry and George sit for hours trying to write the script for the pilot but instead procrastinate with phone calls, the TV, naps, visitors… there’s always a reason not to do the scary, big thing. Do it anyway. Push through. Pen to paper. Brain to computer. Go!

    Can I just say, Anne, that I love that you love great books and great fashion? I find that’s quite rare.

    • Anne says:

      I love YOUR insights. Do the thing, edit later, pen to paper, brain to computer—those are all huge for me.

      Also, I should find that episode of Seinfeld.

  12. Dawnie says:

    Fantastic take-away from the movie. I watched it … last year i think, i think i had about five or six of those thoughts that you listed -the don’t say you like it if you don’t, be honest!, edit, set boundaries and who cares what people think that have nothing to do with your life- are the ones that i noticed right away where the same. It takes a while to actually put them into action, i am still working on not caring what others think of me, especially on specific topics.
    I recently read the quote “Pretty good is not good enough, i wanna be great!” somewhere i for some reason that really inspired me to actually start doing things that i never actually done before and always wanted to do. Its not necessary an actual inspiration, but for me it worked, so i wanted to share it 🙂
    Fantastic post, i definitely took quite a bit away from it, so thank you.

    • Anne says:

      “Pretty good is not good enough, i wanna be great!”

      Love this. I definitely think there’s a time when pretty good is absolutely good enough … but there are times to be great. (I’m hearing Anna Winter in my head from the movie, when she thought a certain layout was only “pretty good”: “It’s Vogue. Let’s lift it!”

  13. Brilliant! Your insights are wonderful, especially in regard to disasters and serendipity but I think the big one for me is “#1 You have to have a story”.

    I’ve always believed that if you don’t write your own story, someone else will. So, take charge and start plotting. Today!

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