You Can’t Rush Deep Work

July 21, 2026July 20, 2026 ~ Sasha ~ Leave a comment

Deep work isn’t just about setting aside time in bigger blocks, or about putting down the phone and turning off notifications—though those are good places to start.

Deep work is about the qualities of this sacred time you’ve set aside.

Think of the adjectives you’d use to describe deep work: focused, calm, exploratory, curious, lateral, creative, settled, playful, generative, spacious.

While there’s some overlap with how we’d describe our “non-deep” work— with words like efficient, bounded, clear, pace, and decisive—this overlap is probably small.

When moving between the two types of work, I sometimes struggle with how I experience time.

In regular work, time comes in small(er) increments. It exists as a helpful constraint to drive clarity and decisions. I’ve trained myself to get a lot done in 10 or 15 minutes, and that feels both comfortable and normal.

For deep work, I create blocks of time, but that’s just the beginning. My job is to hold the space I’ve created: the larger block of time is permission, so when I enter that larger space, I have to adhere to a different set of rules. I’m not checking the clock. I’m not looking for efficiency. I’m not thinking about what came last or what comes next. I’m not judging the success of the last moment against any criteria other than presence and engagement. This is a big shift, and it can be difficult to maintain.

Paying attention to how time feels is a good clue for whether we’re “in it” or not.

For “regular” work, time keeps us on task. It is a metronome that drives forward progress. Quality and quantity play together, and both are equally important.

For deep work, time is a buffer that protects us, creating the space we need for exploration and for leaps. The quantity of our insights and decisions does not matter; what matters is quality. Our job is to force ourselves to slow down, to move deliberately, to sit with what we’ve come up with and keep asking “is this good enough?” Our goal, for a block of deep work, is one great outcome, not 5 or 15 small but (only) good outcomes.

Here’s a hint: if you’re 10 minutes into a deep work task and you notice you’re 10 minutes in, you probably haven’t fully shifted gears yet.

Two Extra Hours

February 23, 2021February 22, 2021 ~ Sasha ~ 2 Comments

When this pandemic is over, I will start commuting back in to work.

My commute is a 10-minute walk to the train, a 40 minute train ride, and another 10 minute walk to the office. That adds up to one hour each way, twice a day, five days a week.

The question is: where will I find that time?

Right now, my days feel full. It doesn’t seem like there are extra minutes, let alone hours, waiting to be claimed.

And yet, two full hours a day, 10 hours a week, are apparently there for the taking, from one day to the next.

Which means that if I have something really important to accomplish, today, I apparently have 10 available hours per week that I could find if I really wanted to.

The point is: the barrier between what we are doing now and what we’d like to accomplish in the future is not a lack of available time.

The barrier is the myth of scarcity.

The barrier is our need to hang on to other seemingly essential tasks.

The barrier is our unwillingness to say that this thing is something I’m going to do, no matter what.

No fuss, no drama.

Like riding a train each day, just start doing that new thing, today.

Math Class

September 17, 2020 ~ Sasha ~ Leave a comment

In most of my math classes growing up, you’d get partial credit for showing your work. This was a boon for me because I was sometimes prone to careless errors.

Giving credit for the work makes good sense in grade school math: the concepts matter more than getting the arithmetic 100% right.

Along these lines, working hard each and every day—what used to be face time in the office—can also be a way to show that you care, that you’re trying your best.

On the other hand, this can go too far.

As we get grooved into the habit of hard work, we start to measure ourselves in terms of hours spent rather than results achieved.

The hours, once a means to an end, become an end in and of themselves: look how hard I’m working (you say to yourself and others).

The problem is, this can become a negative spiral: we can slip into the bad habit of being less disciplined with how we spend our time, lose sight of the difference between urgent and important tasks, and (ironically, despite all the time we’re spending working) give short shrift to the best things we have to offer.

Letting your work stand there, to speak for itself, is an act of bravery.

The Forever Problem

August 21, 2018August 20, 2018 ~ Sasha ~ Leave a comment

On the days I’m really sleep deprived everything seems impossible. White space is useless. My patience is low. I overreact.

And if I’m having a week or weeks with something that is physically wrong–an illness or an injury–my “impossible” stories get amplified. Especially in the case of illness, “What if I feel this way forever?” is a crushing thought that can spiral.

And then, if I’m lucky, I get better. Enough sleep or adjustment or medication or healing makes an ailment go away. My new “now” is replenished with possibility.

It’s the most human of reactions to over-attribute to our present “now.” We’re so confused about how time, and it’s passage, works that “now” often feels like forever.

So when we’re dealing with an unresolved problem, when we’re making sense of the “no way” that we thought would be a “sure!”, when a key decision maker is a long way from agreeing with our position, when ten potential investors all turned us down in a row…

…we jump, without noticing, to forever.

“What if this ‘no’ is forever? What if I will always be told ‘no’!?”

You won’t be.

You’ve just been told “no” now.

With some combination of good fortune, new information, different tactics, and the simple passage of time, forever things will shift.

Tomorrow’s now won’t be the same as today’s.

10 Minute Meeting Hack

April 3, 2018April 2, 2018 ~ Sasha ~ Leave a comment

The next time you mess up your schedule, get wires crossed, or are simply slammed for time, turn your hourlong 1-on-1 meeting into a 10 minute one.

“I’m sorry, I messed up, we only have 10 minutes, what do we absolutely need to cover?”

Then cover it.

And see what happens with those remaining 50 minutes, for both of you.

This isn’t a profound idea, but it’s a really useful one.

Unless, of course, you file it away under “someday.”

No Rush

July 6, 2016July 5, 2016 ~ Sasha ~ 1 Comment

It’s summertime. If you’re not on vacation, then you’re probably making space for some bigger, longer-term projects.

Inevitably, our work time is split into two broad categories: the busy things we need to get through efficiently, and the labor that requires our thoughtful, soulful engagement.

We routinely struggle to create the right balance between the two, which is an important fight.

We also cannot forget that the qualities that serve us well in one area serve us poorly in the other. It’s great to be focused, urgent, and keeping an eye on the clock when tearing through our inbox. But striving to be driven, focused and efficient when we are engaging in bigger questions and in harder topics that don’t yield to quick and easy answers is, with due credit to Indiana Jones, like bringing a knife to a gun fight.

There’s no “hurrying up” when we’re working through big, complex problems.

Make the time, take the time, and don’t rush it.

Tick tock

July 28, 2015July 27, 2015 ~ Sasha ~ Leave a comment

There’s no half hour longer than the one we spend waiting for something: our table to be ready, the show to start, the gun to go off.

We know this when it comes to the small things, but not the big ones.

So we’re content to sit back and wait for that next big project to land on our laps. We’re happy to cool our heels until we get promoted, because we believe the new title will get folks to listen to us in a new way. We’re OK with holding court at the water cooler while we wait for our boss to figure out what we already know.

Speak up. Act now. Stop waiting.

The Tyranny of Outlook

October 8, 2013October 7, 2013 ~ Sasha ~ 5 Comments

Last week, as I rushed, apologetically, to start a meeting five minutes late, the person with whom I was meeting nodded knowingly and said, “hey, it’s OK. That’s the tyranny of Outlook.”

Thank goodness for a bit of perspective.

As I reflect on the ineffectiveness of trying to transition from one meeting to the next in a matter of seconds, I’m contemplating a different approach. One idea is to schedule all of my meetings to start at 10 past the hour. (I think this would work better than scheduling them to end 10 minutes before the hour, because then they’d just run over). 10 minutes to shift gears, or to prepare, to take a step back, and also not to run late.

Manually retooling each outlook meeting would create more work, and it would probably take a while to explain to everyone that I’m serious that I really want to start at 10:10 (or, more importantly, 4:10). Most important would be my holding up my end of the bargain by being on time for 95% of the meetings.

Has anyone out there tried these sorts of scheduling hacks? What have you learned?

Time’s passage – Tom Hussey

August 7, 2013August 6, 2013 ~ Sasha ~ 2 Comments

I found these Tom Hussey photographs arresting. They are images of Alzheimer’s patients taken 50 years apart.

Perhaps it is because time’s clock is ticking, because the days are long and the years fly by, because the oldest of my three kids just went off for a month of sleepaway camp and, even though it’s still a long way off, his being out of the house for a few weeks reminds me and my wife that one day he will actually BE out of the house, moving on and living a whole life elsewhere, hopefully visiting us from time to time. And, eventually, so will my other two kids, even our baby girl.

Inexorably, I will, if I’m lucky, continue to live life, experience joy and sorrow, and, I hope, continue to gain wisdom and perspective as I grow older.

All the while I will continue to look in the mirror each morning, and one day (no doubt sooner than I expect it) I will be surprised at the person I see in the reflection. When that day comes I will talk to younger people and they will make the same mistake that I surely have made countless times: not understanding that I old was once young, vibrant, reckless, inexperienced, and brash.

American culture scores low marks in terms of respect for our elders, and I suspect it is because, in the absence of a strong set of norms around how to treat one another, as individuals we routinely forget the arc of the lives that others have lived. Perhaps most of us lack the capacity to see a wizened, cracked face, or a body that moves more slowly than it once did, and see the full life that person has lived.

Yet if we’re lucky, time will pass for all of us and we will grow old. Of course. I sometimes wonder, though, if our inability to truly understand this simple fact is one of life’s biggest practical jokes. I know that if we all felt how precious and fleeting our lives are we’d often act differently.

Seeing such vivid, beautiful images of time’s passage doesn’t make me fearful, but it does help me remember to live now, to experience the richness of life and love and family now, to be courageous in what I do now, because time really is flying, and my chance to make a difference is people’s lives is today, not tomorrow.

90% or 5%

May 12, 2010May 11, 2010 ~ Sasha ~ Leave a comment

I recently heard a speaker who suggested, to a roomful of hyper-productive multitaskers, a radical reorientation of how to spend time. This speaker, a successful investor and investment adviser, doesn’t write emails, doesn’t multi-task, and doesn’t have a Pavlovian response to a Blackberry’s red blinking light. Based on his own experience, he suggested that successful decisions come when we create space for deep contemplation and reflection – when we create the time that allows us to we walk around and look at our problems with the curiosity and reflection of a poet who studies a rock, or a beach, or the morning sky.

A lovely idea that is easy to dismiss, to be sure – and many in the audience had just that reaction. One person went so far as to give an impassioned argument in favor of the efficiency of multi-tasking (while conceding that he agrees with Clifford Nass’ research showing that multi-tasking doesn’t work).

Why are we all so defensive? Perhaps because we kid ourselves into think that we’re almost getting done 100% of what we need to get done. We’re super-busy, but, we tell ourselves, we’re probably completing 90% of what we absolutely must get done, and the other 10% probably isn’t all that important anyway, right? And if we’re getting 90% done, then cutting out half of our meetings or not responding to half our emails sounds impossible. It feels like a move from 90% to 60%. Imagine the impact!

But I wonder if the 90% is an illusion. What if I’m doing 15% of what I could do, or even 5%? What if I’m nowhere near doing everything I could do that would be productive, because “everything” has gotten so big that I’m never anywhere but the tip of the iceberg.

If I’m only doing 5% of what I “could” do, then a radical shift becomes easier. By acknowledging that I’m the one deciding how I spend the time, and by recognizing that my criteria might be really good or really bad, I just might create the space for that radical reorientation.

Am I ready to make a big change? Not yet. But I do think that doing away with the notion that I’m doing “almost everything” will allow more space for doing what I really need to do.

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