I feel inadequate when I see many founders’ schedules. Their calendar has 2 blocks, mine looks like a game of Tetris. They have 4 hours of daily deep work, while I spend days responding to Slack pings.
I sometimes feel guilty because the “sage advice” around deep work never stuck: I’ve blocked my calendar, worked with interval timers, tracked deep work time, but always returned to doing what’s top of mind.
For a long time, I thought it was, something I needed to fix. But then I embraced chaos. There are the days I spend in Slack, there are days where something blows up and I spend all day in meetings to fix it. There are days where I sleep 4 hours and do dopamine work the whole day (hi, docs!). And there are the days where I go heads down and do hours of deep work.
I don’t feel guilty anymore for not doing 4 hours of daily deep work. Even worse, I want to kill a sacred cow and convince you that you should be less obsessed with deep work as well.
Here’s why:
How I manage deep vs. shallow work
Deep work isn’t a binary. It’s not like some people spend all day on one task while the rest has 8 tabs open at the same time and never spends 10 minutes in either.
Personally, I do deep work, though not religiously. When I start my workday, I ask myself what the highest-impact thing in the company is. From that follows what I need to do.
Sometimes, that means doing deep work for a few hours. Other times, it means spending all day in Slack to coordinate something.
That’s why I find the obsession with deep work so frustrating: The point of running a company isn’t meditation training where you train yourself to resist distractions. The point of running a company is to build a great product and grow it.
I want to be spending my time on the best way to do that - not on what productivity Twitter threads tell me.
If you can unblock a colleague in 10 minutes by answering a question, that might enable them to do 4 hours of deep work. If you can do that 6 times in an hour, that might not be a deep work hour, but you’re unleashing more growth than you would’ve if you’d spent that hour writing a memo about a proposed company value.
Speaking of deep work - I’ve often considered getting assistance from a research paper writer to help balance the demand for high-quality work with the constant need to switch tasks. I actually don’t think deep work is always a positive.
The downsides of deep work
We romanticize deep work, but I don’t think a 100% deep work day is optimal. That’s for a few reasons:
Deep work is exhausting
The point of deep work is to solve hard problems with single-task focus. And that’s cognitively hard. After a few hours of deep work, your brain is exhausted and you’re probably going to spend the rest of the day doing less taxing stuff.
This means deep work hours are a precious resource we shouldn’t use on trivial things, because…
Startups (often) don’t need high quality
Deep work improves the quality of the work you do. But at a startup, a lot of things don’t need to be that great.
In the seed stage, we always talk about building MVPs and validating before spending a ton of work building something people might not want. But that attitude often vanishes once the company is off the ground.
But if you’re doing something for the first time, you should have the same attitude of building a minimum viable version and validating.
This is especially true for ICs on your team. You might hire great engineers, designers, etc. who take pride in doing high-quality work with lots of deep work hours. This is a good trait, but not when you don’t need perfection.
Spending your deep work hours on things that don’t need to be that great also has a corollary problem.
Things often take longer
Parkinson’s Law states that "work expands so as to fill the time available for its completion". So if I schedule 90 minutes of deep work to code a new feature, but get done in 30 minutes, I might waste the next hour on hover animations or find something else because my calendar dictates 90 minutes for the task.
That doesn’t mean I’m anti deep work. It’s an important tool.
Who needs deep work?
Deep work is kind of like potions in a video game: You don’t want to finish the game without ever using them. But you also don’t want to use them for a random skeleton in a cave. You reserve them for the bossfights.
Deep work is the same way. I think there are three charateristics that mean you should focus on deep work:
You create concrete deliverables
If you write articles, design UIs or build features, you probably benefit from doing more deep work (provided you expend them on the high-leverage, we-know-this-is-valuable parts of what you do).
But as a manager/leader, you rarely have concrete deliverables. Your deliverables are decisions.
And decisions often require the opposite of deep work: They require back and forth. They require reviewing. They require ad-hoc feedback.
You know it matters
Everyone’s tasks exist on a spectrum of leverage. We all do high-leverage things and things that just need to get done.
Imagine you’re a designer who needs to design:
a) The marketing site
b) A social media post
The marketing site is persistent and directly helps get new customers. The social media post is ephemeral and is at best an intermediate step at getting customers. The marketing site is worth spending deep work on. The social media post is probably best done as an 80/20.
How to implement this: Energy management.
Energy management
Human bodies and minds don’t work like machines. But we make schedules as if we do.
Sometimes we lack the energy for certain things. Other times we feel a ton of energy for something else.
But when our Friday 9am-11am deep work block doesn’t line up perfectly with what we envisioned on Monday, we feel bad.
I’ve actually seen better results (both measured by how I feel and how things go overall) by leaning into where my energy is. and I think more founders should do the same instead of believing what works for someone, somewhere, will also work for us.
