The Most Important Thing About Creative Work

One of the things I’ve had to learn about transitioning into a more creative and visionary role with my new job is to change the way I think about when and where work gets done.

The most important thing about creative work is that it gets completed by your deadline. Everything else is secondary.

I’ve always worked remotely, but in my past two jobs, my remote work required me to be at my desk to handle incoming requests. Even going out to lunch was stressful because I didn’t want to have to take a Skype call from a client at the local sandwich place. When 5 years of working means 5 years of being at your desk from 9am to 5pm, this is a difficult mentality to break.

I started out the day being unable to focus. By lunchtime I was getting worried and feeling bad about not getting enough done. Then after lunch I asked myself a question: “Do I need to be at my desk to get this planning done?”

No. There was nothing keeping me at my desk but my own mind. So, I turned off my laptop, grabbed my notebook, pen, phone, headphones, sunglasses, and keys, then walked out the door.

I’ve gotten more outlining done and more clarity about what I need to do for the next few weeks in the past hour and a half at a dirty picnic table in the park down the street from my apartment than I have in the last two days at my desk.

Giving myself permission to step away from my desk over the past two months has been wonderful. My fears of missing something were unfounded. I’m able to take a phone calls with minimal distractions and I’m still able to answer questions on Slack from my coworkers. The biggest step I took in that direction was setting the expectation of not being constantly online, but checking in every few hours instead. I’m still reachable if something is urgent, otherwise I get up to speed and weigh in every few hours.


Realizing that work doesn’t have to be done solely during the traditional 9-5 schedule has been crucial for me, too. This statement actually has two parts:

  1. Working outside of traditional hours is okay.
  2. Not working during traditional business hours is okay, too.

Before this job, I understood #1, but I never gave myself permission to not work during business hours.

The most important thing is that a task gets done by its deadline, not that it gets done between 9-5.

If getting up early, working for an hour or two, then making breakfast and reading or walking for an hour allows you to stay focused for the rest of the day, do it.

If going home at 4pm and doing those invoices after dinner will reduce your stress levels, do it.

If staying offline for a few hours reduces distractions and allows you to get important work done, do it.

If researching new tech platforms is easier with a cocktail after 10pm, pour a drink and do it after 10pm.

If taking off Friday to spend the day with visiting friends and completing your tasks on Sunday after they leave works best for you this week, great!

Do what you need to do in order to get your work done in the best way possible. Everything else is secondary.

What assumptions are you making about how your work must be done? Question them. Try breaking those assumptions and see what happens. The downside might be smaller than you think. The upside is a better life.

Integrating Care into the Customer Experience

I was at an Intelligentsia coffee shop in Venice, CA, a few weeks ago. I ordered an espresso. As my order came up, I watched the barista. He pulled the shot, and as I was ready to take and enjoy it with the side of sparkling water they include, he paused before he gave it to me. He took the towel tucked into his apron and carefully wiped off the few tiny splashes of espresso that ended up on the rim of the cup and around the saucer.

He could have easily given it to me as-is and I would have been happy. But he took that extra step. And I noticed.

This is one of the reasons Intelligentsia is so successful: They’ve integrated care into every part of their customer experience.  That isn’t necessarily the kind of thing that gets people in the door for the first time, but it is what keeps them coming back again and again.

You aren’t the first to romanticize failure. Keats was way ahead of you:

Failure is, in a sense, the highway to success, inasmuch as every discovery of what is false leads us to seek earnestly after what is true, and every fresh experience points out some form of error which we shall afterward carefully avoid. – John Keats

There is no right time to quit a job, have kids, or start something new. If you want something, you have to take the first step immediately and figure things out along the way. The right time will never come. Jump now.

Takeaways from this week’s Breaking Smart newsletter, Betting the Spread on Inexorables:

  • Try multiple ultra short-term bets around a shared assumption. 
  • Don’t stick with something you don’t find valuable just so you “aren’t a quitter.”
  • Constantly question whether or not the next step is what will produce the best results. 
  • Bet the spread, then switch between parallel bets as data changes. Work isn’t the horse races. You can change bets whenever you want. 
  • There is a difference between unfocused dabbling and betting the spread around a central inexorable trend. That difference is that learning and outcomes around that single trend compound. Unfocused dabbling doesn’t. 

Great stuff on marketing from my coworker Derek Magill:

“Hold off on new marketing efforts and let’s fix your funnel first.” Oftentimes the most promising “marketing” strategy is not to focus on growing awareness and traffic, but in making the most of the existing awareness and traffic you already have.

Read his full post here. Scroll down to May 5: Awareness vs Activation.

Ignore the Rules and Be True to Yourself

“Writers write every single day.” “If you aren’t writing code every day, you can’t call yourself a developer.” “The best in every field get up at 4am and start working by 6am after a workout and an hour of reading.”

Rules are so fun to state. They make you look hardcore, driven, and disciplined. But if you are on the other side of that exchange and are the one hearing those rules, ignore them.

Seriously, fuck those rules.

Don’t get me wrong, I love hearing about people’s processes. I love reading books like Daily Rituals. But you won’t get anywhere by worrying about following someone else’s process. You have to figure out with works for you and be ruthless in following it.

I personally see a lot of benefits of showing up and doing things daily. I don’t wait for inspiration to find me, I spend time consuming great stuff and thinking about it. I’ve recognized that I need space to think, walk, read, and listen. Inspiration always comes, and when it does, I’m ready.

That said, I don’t stress out too much over it. While I do get stuff done every day, that isn’t necessarily when my best work hits me. Sometimes I’ll have weeks where I get tons of ideas and am excited to work on some cool stuff. For example, I had the idea to build this WordPress theme this week. This is the first full WordPress theme I’ve done all on my own. I couldn’t get it out of my head until I got the templates done and shipped it. My Jekyll blog template was the same way last year. So was the Sol LeWitt project, the Slack Toggl slash command, the Apple Photos analysis project, and the Cocktail library.

Other times I’ll go a few weeks without being moved to do anything beyond the daily tasks I’ve set for myself. I’ve learned to be okay with that. Fuck what works for other people. These are my projects.

What I can never forgive myself for, though, is not doing the work when I feel the call.

Not following the traditional rules is totally fine. What is inexcusable is not staying true to your own terms and getting your work done.

I got a tip today from a Persian chef about cooking rice the Persian way: After it boils for a few minutes, drain and rinse it. Then put it back in the pot for 25 minutes. You get a nice crispy layer at the bottom and rice that is completely separated, not gummy.