Time Management is Broken—Here’s What to do Instead

I admit it - I was lying. For more years than I care to admit I promoted the well-worn myth that there is time for everything. It goes like this…

With some good planning and loads of perseverance (cue soundtrack of Chariots of Fire) you can achieve anything. 

It’s a delightfully appealing promise. It’s also dangerously wrong.

You might remember the demonstration of Boulders, Pebbles and Sand. The late Stephen Covey popularized this metaphor in his book First Things First and it’s been used ad nauseam in productivity lessons ever since. 

The idea was that if you tried to first cram all your menial work (sand) and tasks (pebbles) into a jar that represents your available time, there was no room left over for the big projects (boulders).

Instead, Covey taught us, you need to start with your projects, followed by important tasks, and then - like a game of Tetris - all the small tasks would find a home on your calendar. The trick behind this sleight of hand is it starts with just the right size boulders and a perfect combination of pebbles and sand. 

But that’s not how life works.

The photocopier

In the early 1990’s, when Covey popularized this approach, we were still learning how to use the Internet, email was yet to become ubiquitous, and we didn’t have smartphones, social media, Slack, Team, or Zoom to interrupt even the best-laid plans. Instead, we sat at a desk typing memos, attended meetings, and talked on the phone. 

The fanciest office technology we had was the photocopier.

The problem today, “isn’t that we are bad at prioritizing the big rocks”, writes Oliver Burkeman in his wonderfully sardonic book Four Thousand Weeks “It’s that there are too many rocks and many of them are never making it anywhere near the jar.”

The Inbox

Most people in my workshops start their work day with the same ritual: they open their Inbox. Their planning is a mix of long-term goals, sprinkled with a long list of more immediate tasks all competing for whatever minutes remain between meetings—it’s hard to get a sense of progress. 

Email offers a more immediate reward. As you plow through your Inbox, you’re solving problems, helping co-workers, and answering client’s questions. Not always, but there’s enough gold in the coal mine to keep bringing you back for more and to keep the dopamine flowing. So, like a fisherman trying to fill the day’s catch, you keep clicking, hoping for a bite

“There are few things ever dreamed of, smoked or injected,” writes Kelly McGonigal in The Willpower Instinct, “that have as addictive an effect on our brains as technology.” 

Instead of driving the bus - keeping it pointed towards your goals - you’ve let other people grab the steering wheel. 

Good luck with that.

Over the last decade, my goal with clients has shifted from productivity to effectiveness - getting the right work done. And it’s hard—effectiveness is all about creating a road map before you get behind the wheel.

The solution is a simple 3-step strategy to get better results immediately. You don’t have to work more hours, learn fancy software, or buy a treadmill desk - instead, you need to think like a pilot.

Think like a pilot

There’s a reason commercial flights are safer than driving your car - even (in most big cities) safer than crossing the street. It has to do with routines.

Before they fire up their engines and taxi down the runway, every pilot carefully examines their load, fuel, route, weather conditions, and air traffic. Even if they’ve flown the route a hundred times, they go through the same planning routine. 

They are creating a Flight Plan. 

Note, that a Flight Plan is not an endless list of miscellaneous tasks, priorities, and left-over good ideas. It is what Greg McKeown described in his insightful book Essentialism, “your highest contribution towards the things that really matter.”

Let’s get into how this works.

1. Your Flight Plan

Just like a pilot, your first job every week is to create a flight plan for where you need to land on Friday. There are four sections:

1. Goals - your goals for the quarter or year. This is your North Star—constantly refer to them, and update at least quarterly.
2. This week - work to complete this week. 
3. This Month - opportunities (goals, tasks, research, communications, etc.) that fall in this month.
4. Someday - a holding area for unprioritized, miscellaneous tasks and projects. 

Your job is to update the “This week” section by reviewing what needs to carry forward from last week, add new priorities from “This Month” and consider what needs your attention in your “Someday” bucket.

I’m highly motivated by crossing tasks off my lists, so I like to limit “This Week” to 12, or fewer outcomes—any more and I risk over-committing. Everything else goes into “This month”, or “Someday”.

Note: it doesn’t matter where you create your Flight Plan. Some clients use Outlook, others OneNote, or Notes - even a page in their journal. As long as it’s easily available it works.

What matters is that you pay yourself first.

2. Pay yourself first

In the world of personal finance, paying yourself first is the first rule to creating wealth, With your Flight Plan, that happens by blocking time.

Blocked time is like a meeting - you plan to be there on time, ready to do the work, and complete some measurable progress by the end time. Respect blocked time.

Once you have your Flight Plan, turn to your calendar and block time for activities that require “deep work” (work that requires undistracted concentration) or work that you might procrastinate about.

For example, I block time for writing, research, client work, and volunteer work. 

Learning how to work with block time might take some practice. For example, its easy to populate your calendar with lots of colorful time blocks reserved for important work and then, as soon as something unexpected comes up, blow it off as if it’s of lesser importance. 

Instead, you need to work your plan.

3. Work your plan

The third step is to work your plan. Just like the pilot constantly correcting for unexpected weather conditions, you need to correct course for impromptu meetings, client requests, staffing shortages, and work that took longer than expected. 

The easy reaction to plans that go astray is to metaphorically “throw out the baby with the bathwater.” Instead, you need to adjust. After all, you have a Flight Plan—your goal to reach by Friday. Instead of throwing up your hands and burying yourself in your Inbox, adjust. 

If the 11:00 report writing time block got bumped by a request from your boss, move it to 11:30. If your morning was overrun with client requests, shift your sales call block to the early afternoon. Expect the unexpected, adjust, and get back on track. 

Like a pilot, practice navigating around that storm, move your blocked time to a new spot, and get back on course.

Pay attention

“Your experience of life”, Burkeman writes, “consists of nothing more than the sum of what you pay attention to.” 

When you allow technology and having unlimited access to take over your attention it’s hard to get anything significant done. You’re firing a lot of bullets, but not knocking down many targets. 

The Flight Plan model is simple. But it’s also field-tested and it works, Instead of trying to cram all the Boulders, Pebbles, and Sand into your day, you choose what you want to pay attention to.