brad dickason
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How to make time for strategic thinking

You can’t hold a gun to someone’s head and say “Be Creative.”

The best PM’s don’t come up with creative ideas and strategy all the time. They create space for creative thinking and optimize their process.

It feels like the stars have to align. The right environment, the right mood, the right spark of inspiration. Now throw a global pandemic on top of that where everyone is working from their bedrooms (or at least I am). There are constant distractions, more meetings than ever, and my typical tools like whiteboards and walking 1:1’s are out the window.

You can call it ‘in the zone’ or ‘flow state’ or ‘creative mode’ but whatever it was... I wasn’t hitting it.

Last month, I found myself sitting around for hours unable to focus and make any progress on strategy or vision.

I was really struggling.

Since then, I’ve started to crack a formula to enter creative mode. It hasn’t been a single epiphany or a magic incantation, but rather a series of behavior changes.


Creative thinking takes time. You can’t just flip your brain into creative mode instantly. On a good day, it takes about 15 minutes for me to enter creative mode. On a bad day, it can take hours. If you’re always in meetings with 30 minute chunks in between, you’ll never make any progress.

Instead, we want to optimize for large, uninterrupted focus blocks. Think of The Matrix. When Keanu is interrupted IRL, everything in his brain falls apart. Your brain works the same way. You have to boot the entire project up in your brain, hold it there, and manipulate it.

The movie Soul depicts flow as an alternate plane of existence.

Select days for creative thinking - If you aren’t intentional, meetings will crowd your time and create sprawl all over your calendar. Select at least two days where you optimize your schedule for creative thinking. This will allow you to remember (and have a rationale) to defend those days. I like to setup my calendar as follows:

If I’m working on a large strategy project, I’ll block off 4+ days per week to ensure I can make plenty of progress. If you take this approach, make sure you align your manager and have their support. Otherwise, you risk getting dinged for not collaborating.

Batch meetings - Most days end up looking like swiss cheese - Lots of sproadic meetings with 30m-1hr in between. Squeeze your schedule so that the meetings all line up one after another. Paul Graham calls this ‘manager time’. Manager time is when we review and we discuss vs. when we create.

“I find one meeting can sometimes affect a whole day. A meeting commonly blows at least half a day, by breaking up a morning or afternoon. But in addition there's sometimes a cascading effect. If I know the afternoon is going to be broken up, I'm slightly less likely to start something ambitious in the morning.” (see: Maker’s Schedule, Manager’s schedule).

Going from meeting to meeting is draining, but those tiny blocks in between are useless and you’ll never make any meaningful creative progress. Batch your meetings so you have large blocks of uninterrupted time for creative thinking.

Avoid context switching - Just like it takes time to switch into creative mode, it takes time to switch context between projects. If you’re working on multiple products or projects, designate specific days to work on each one. It takes me at least 2-3 hours to switch context from one project to another. If you want to make significant creative progress in a single day, you have to be very intentional (and typically use tactics like a long walk or lunch in between to clear your head). I typically will work on one project on Wednesday and another on Thursday to minimize switching.

Let your teammates know - Now that you’ve rearranged your schedule, you need to publicize it so others respect it. Providing this context will set clear boundaries and make sure people understand the importance of focus.

  1. Align your manager to your schedule. Your manager will need to support you and help you defend your time.
  2. Share your schedule in a team meeting or small group conversation. This will help socialize why you’re blocking off this time (which will increase the chance people will respect it) and give them a chance to give feedback or adjust your schedule.
  3. Write a post/email with your schedule. Make it clear that you’re available outside of your focus blocks and will get back to messages quickly after each block is completed. Bonus points if you set this up as an auto-responder during your focus blocks.


The right environment can make the difference between a session of fidgeting and one of deep focus. To take advantage of your focus blocks, you need to design your environment for creative mode. Eventually, your brain will start to recognize this place and will shift rapidly.

Choose a separate space for creative thinking - This should be different than your typical work space. You want to avoid your brain switching into ‘task’ or ‘execution’ mode. If you normally work standing, try sitting in a chair. If you normally work in your office, shift to another room (if you have one!)

Setup the space for creativity - You want your space to fade away. It should be calming, well lit, and comfortable. Not ‘lay down in bed and fall asleep’ comfortable, but enough that you can zone out from distractions around you and not think about adjusting your position. I like to let outside light in and add a few small touches such as a poster (here's mine 🤓) or a special lamp that inspires you. If possible, avoid spaces with other people in them as their movement will distract you.

Walk or move before you start - If possible, walk or move before you start. This could be a walk around the block or walking across your house to another room. Movement enables us to think more creatively and problem solve. I knew that Steve Jobs liked walking meetings, but there’s science to back it up:

"Creative thinking improves while a person is walking and shortly thereafter ... The study found that walking indoors or outdoors similarly boosted creative inspiration. The act of walking itself, and not the environment, was the main factor." (Stanford Graduate School of Education)

I’ve started using walking as a tool to start and end sessions. If I’m stuck, taking a walk (or riding my surf skate) can help unblock me.

Create playlists with noise cancelling headphones - This has been the most impactful change to my routine. Music seem sto help me enter creative mode very quickly. I have a pair of Jabra Elite 85h in beige because I like the feel over ear headphones and they never have issues connecting to my devices. Whenever I sit down for creative time, I have a specific playlist that I put on and listen to on repeat. It’s repetitive, has few words, and the volume is pretty constant. I have a similar playlist for execution/tasks. Creative Playlist / Execution Playlist

Remove every distraction - PM’s pride themselves in being available, but even the vibration from your phone can pull you out of creative mode. Turn everything off:

These may sound silly or extreme, but every little bit helps.

Make it easy to start

Ok, you’ve got your calendar dialed and you’re in your magic rocket ship creativity chair. Great. Now you pull out a blank page and.... Crap. You’re stuck.

Never start with a blank page - A blank page can be intimidating and challenging. A good note taking system can shortcut this and make sure you always have a starting point.

“Everybody’s got an eye for something. The only difference is that I carry around a notebook in my front pocket. I write everything down, and it helps me recall.” (David Sedaris via David Perell)*.

Throughout the week, jot down notes about your topic. These could be words that come to mind, short phrases or links, or even an entire outline. The key is to take ideas as they come to you (vs when you sit down to work) and plant tiny seeds of ideas on paper (or in your note taking app). They don’t have to be fully formed, they just need to give you a starting point when you sit down so you’re not starting from scratch.

I take notes using Things on my phone or desktop. You might choose an app or pen and paper. The important part is that you write them down and remember them when the time comes.

Here’s an example of my starting point for this post.

You don’t have to start at the beginning - My best strategy work happens when I start in the middle. Creative thinking is unstructured by nature and you want to let your creative faucet flow. Trying to force yourself to follow a structure will only cause you to get stuck on a specific section. “Start writing wherever you can start. Start writing wherever you feel comfortable” (Daily Writing Tips).

Think of creative mode like a fitted sheet, you put one corner on, then the other, then go back and adjust the first corner. If words come to you, write them down. If two thoughts seem linked, write both and draw a line to connect them. Let the ideas flow in any order they come. Over time, your brain will connect them.

Leave yourself breadcrumbs - Remember, each time you enter creative mode, your brain has to boot up your whole project in your head. You can help your future self by leaving notes about what you plan to do next. “Unfortunately, most writers get right in their cars and drive away. But the great ones capture the view.” (Leave a Summary for Yourself by David Perell) This could be a short outline at the top of the document or notes peppered throughout. Keep track of what ideas you were excited about so you don’t have to analyze the entire strategy or vision. For example, for this post I left a note that said “Add section on solo vs collaborative” which allowed me to pick up and finish the last section.

Collaborative Thinkers Suffer

Once you’re dipping in and out of flow state and the ideas are flowing, you’ll start to notice moments where that flow slows to a trickle. You jump back and forth between everything you’ve already written. There are tons of ideas on the paper, but your brain can’t connect the dots. You’re blocked.

Chances are you’re a collaborative thinker (vs. solo thinker). You need to find someone to unblock you.

Finding the right person - Your ideal collaboration partner is someone who energizes you, enjoys talking to you, and sparks new ideas when you chat. If you haven’t already identified this person, book 1:1 meetings with members of your team and give them a rough pitch of what you’re working on. The right person will ask great questions and leave you thinking “Oh man, why didn’t I think of that?” Once you’ve found this person, hold on to them. You’re going to need to work with them regularly to ensure you keep making progress.

Meet with them regularly - Instead of reactively trying to book time with someone once you find yourself blocked, proactively schedule a series of meetings with them. These should be regular enough that you don’t get stuck but not so frequent that you can’t make substantial progress in between. I’ve found that twice a week is typically a good starting point. Make sure you set expectations that these are problem solving sessions (vs you trying to align them or convince them of something). Also, make sure to thank them profusely afterwards :)

What do you do to get into creative mode? Do you have a system or tips? I'd love to hear more: @bdickason

Special thanks to Jeff Holek for helping me think through this.

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Post last updated: Jan 28, 2021