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

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:

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.

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.

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.

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.

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.