3 planning tips to help you do more of what you love

Day Planning

Meet Mark, a fictional entrepreneur and amalgam of several Open Door Teams members, two former bosses, and one movie character (Jon Favreau’s passion-driven Carl Caspar in 2014's Chef, if you’re curious). Two years ago, Mark left his marketing gig at a Northwestern brewery and pub house so he could focus exclusively on graphic design, the part of his job he liked best. So far, so good. He’s got a healthy roster of clients and the freedom to spend his days designing logos and custom fonts, menus and mobile interfaces, brochures and presentations. But as his business has grown, so has the amount of non-design work required to keep up with it. More and more, Mark feels as if he must hack his way through creeping, bureaucratic vines just to get to the place he most wants to be: at his drafting table or in front of his computer monitor, sketching, drawing, coloring, shaping.

Mark’s a maker-manager hybrid, and as such he has unique scheduling challenges. Challenges that seem suspiciously more daunting the harder he tries to overcome them.

Mornings with Mark…

It begins, innocuously enough, with breakfast. That’s when the pings generally start, which means the Do Not Disturb setting on Mark’s phone has reached the shut-off hour and the emails and texts are rolling in.

“Can you move the header copy to the right and flip the image behind it?”
“We can print 3k of that brochure by the 18th but I’d need to get you on the books today. Let me know.”
“Question about the contract. I’m in the office until 10:30 then after 2. Give me a ring?”

The influx of notifications still catches him a little off guard. He’s renovating a mother-in-law apartment on his property, working for an hour or so each day before breakfast—the only time he’s certain he can carve out—and he gets so focused that it’s usually the pings, not the 8am deadline, that spur him toward work. From there, it’s two hours plus of catching up on requests, responding to emails, returning calls, and planning his day. Then there’s usually at least one meeting. Finally, after a quick bite for lunch, he puts his head down on some real design work. By late afternoon, he’s fielded more calls and emails and is loathe to stop working now that he’s got some uninterrupted time to dedicate to it. But evening with the family calls, so he puts a pin in things, hoping he’ll be able to get back into the groove more easily tomorrow.

We’ve got news for Mark. And, if you recognize any of your own story in his, for you too: It doesn’t have to be this hard. With a just a few simple planning tweaks, you can do more of what you love and less hacking away a path to it.

1. Plan the making—all of it.

Mark’s first mistake is an understandable one for any beleaguered maker: shoehorning personal projects into early morning hours to get that coveted stretch of uninterrupted, no-strings-attached creative flow. He needs to be able to make things—a renovated apartment, a tiny house in the back field he’s been dreaming about, wooden toys for his kids—purely for the joy of making them, and not also because there’s a contract to fulfill and a client to impress. Doing so helps sate his creative hunger and allows him to navigate the inevitable interruptions, managerial duties, and customer preferences (if he had a dime for every request to ruin white space…) with greater resiliency. The trouble lies in how he’s going about it, i.e. in a mad early morning push to get an unreasonable amount done before work intrudes.

A more fruitful approach would be to integrate work and play, letting them coexist and feed off of one another rather than pitting them against each other. How? By planning. Incorporate those personal projects into your day through unapologetic non-work blocks. Take a two-hour lunch and dive in, or schedule an hour in the afternoon. There’s a valid argument for starting your day with work, namely that it gets your mental momentum flowing in the direction you want it to, but there’s no reason at all not to tackle personal projects during your workday. It requires learning to accept time limits—a difficult thing for makers—but the upside is you’ll become a better planner.

"Here's something I only learned recently: I need to be able to accept incremental steps on my ‘making’ projects. Sometimes, just finding and laying out the tools is all I have time for. That's ok. That's progress. Sometimes makers are consumed with the end result, we need to be satisfied with incremental steps toward that result."

- Lauren C., CEO (and resident maker/manager)

Break those projects down and add them to your day plan, then use them as mental health breaks throughout the day. No more harried, distracted mornings and no sacrificing hobby pursuits for the privilege of a smooth entry into your workday.

2. Plan while you're hot.

There’s also some unintentional disruption in the way Mark plans his days. He does it in the morning, some twelve hours or so after he last sat at his desk immersed in design work. He’s planning cold, when he’ll have to exert more mental effort to decide on his tasks/schedule for the day than he would if he were already knee deep in work and well up to speed. Complicating that is the fact that he’s starting out the day with communication trickling in … because he has no plan in place, whatever requests are coming his way are more likely to win top spots in his day plan whether they really belong there or not.

A better approach, we think, is to bookend each workday with these two chores:

  • Startup
    This is your on-ramp, your entry into your workday. During startup, we’re loading necessary apps and programs, reviewing our plan for the day—created the night before in the next step—checking messages and adjusting our plan as needed. (There are plenty of folks out there preaching the no-email-in-the-morning gospel, but we’ve found that avoidance usually isn’t necessary when we start the day with a roadmap.)

  • Shutdown
    This is your off-ramp, your time to plan the next work session and close up shop. Instead of just putting a pin in things and hoping we can get back to the right mental headspace the next day, we take ten minutes or so to jot down next steps, ideas we’re mulling over, and any other notes we may have, that way we can comfortably close the door on work for the day, knowing we have what we need to reorient when the time comes.

In a nutshell: End each day by setting up your plan for the next one. This habit helps you both disengage at the end of today and re-engage more efficiently tomorrow.

3. Plan to plan.

Mark’s last mistake is that he doesn’t treat day planning like the worthy, stand-alone, daily task it really ought to be if it’s to have any chance of bringing him consistent returns.

"The key to developing a deep work habit is to move beyond good intentions and add routines and rituals to your working life designed to minimize the amount of your limited willpower necessary to transition into and maintain a state of unbroken concentration."

- Cal Newport, Deep Work

Dedicate a little time to planning every day. Do it at around the same time each day. It won’t take long before it’s a habit that, like brushing your teeth, requires very little of you but makes a big difference, especially in the long run. Transitioning in, through, and out of your workdays gets easier, requiring significantly less clearing a path to work and more just showing up and working.

The planning challenge:

It sounds too simple to have much of an impact, but we’ve found that effective day planning can spell profound productivity gains and an overall greater sense of fulfillment. If, like us, like Mark, you chose your field because you love it, day planning may be even more impactful for you because it protects the work you love from some of the everyday frustrations that can turn a passion-driven pursuit into a daily grind. Here’s our challenge to you: adopt our three planning tips for thirty days. Just try it.

Our recommendation for first-timers: use pen and paper. If that's too retro for you, use a spreadsheet, or if you want an app to help, try ours. The main thing is to keep it as simple as it sounds. At the end of each work session, consider what you accomplished that day, what you’d like to work on next, and make a plan, stacking work tasks earlier in the day and weaving personal projects in later. When your thirty days are up, evaluate: How’s your job satisfaction level compared to a month ago? Are you spending more time on what you love and less clearing away obstacles in the way of it? Is transitioning into, through, and out of your workday easier?

It’s not flashy, and it doesn’t come with the bragging rights that intricate, ultra-disciplined approaches to getting things done earn you. But when you love what you do, who needs ‘em?


Photo by Glenn Carstens-Peters