Break big things into small t.h.i.n.g.s.
How you can get more done less painfully, and run big projects without frantic last-minute changes
Warning: At first, you’re going to think the advice in this article is obvious, and want to skim through. I’m putting this at the top as a reminder that obvious =! easy, and this one really is a gamechanger.
In college, I had a secret.
Every day I would tear a page from my notebook, fold it up til it fit in my left jeans pocket, and split it into two columns:
The day’s schedule of classes and tasks
A “new to-dos” column to keep track of stuff for later
That wasn’t my secret — plenty of people saw and asked why I kept a crumpled, ink-smudged piece of paper in my jeans. (Also, not very green. I switched to digital when I got my first smartphone).
The secret was a ~150 page book by Cal Newport: How to Become a Straight-A Student. I’d lifted my painfully simple system right from the book, and wow did it turn me into a pain in the ass.
My favorite spot on campus was the “Grille,” basically on an on-campus coffee shop. You could find me there any time I wasn’t at class, the dining hall, or the gym — and although I did homework there, I also watched the latest How I Met Your Mother and played dumb browser games. Shoutout TagPro.
This is not what people writing papers want to see. In my third year I discovered MOOCs and started taking classes about anatomy and exercise science alongside my normal work, which also was probably annoying. One friend said “how is it that you always seem to have your work done and never seem to be working?”
I recommended the book to people. But no one ever followed through, so it stayed “secret” and I graduated with a great GPA while spending more time on ultimate frisbee than on schoolwork.
I know there’s a ~75% chance I’m sound like an ass right now, so I want to clarify — none of this is because of natural talent or intelligence or even a particularly strong work ethic, and I wasn’t trying to bother anyone. I just found someone whose advice seemed good and then followed it.
And I got better at following it over time.
When I entered the working world, the same lessons applied and made a massive difference in what I can get done. One difference I didn’t see coming is that these skills were actually more valuable at a company, because you need to coordinate multiple people across multiple teams.
Here’s the advice I got and followed: break big things into small things.
If you ever hear “we just need to figure out…” it’s time to run for the hills
Break big things into small things. A big project becomes small tasks. Simple enough.
And yet...I watch it not happen all the time. One of the most dangerous phrases I hear at work is “we need to figure out…”
“We need to figure out our plan for agencies”
“We need to figure out the process for sending work to design team”
“We need to figure out what our brand will be”
These aren’t to-dos.
They’re too vague. How will you figure it out? What steps do you need to take to figure it out? How will you know that you’ve successfully figured it out?
When people tried to copy my notebook-paper system in college, they’d write a schedule like:
10:00: Class
11:30: Lunch
12 - 5: Work on paper
I’d write a schedule like:
10:00: Class
11:30: Lunch
12 - 12:45: Confirm 4 new sources to cite in psych paper
12:45 - 1:30: Outline paper, with paragraph topic sentences and sources assigned to specific paragraphs
1:30 - 3: Write (minimum: the introduction)
3:00: Go do whatever the fuck I want
“Work on paper” is vague, just like “figure it out.” When I got more specific, I could get stuff done faster — because once I’d hit the milestones I marked, I knew I’d made enough progress.
If you need to “figure out a process with design,” you’ll sit around for three weeks until the next urgent project comes up, send it to design (who will be pissed), and complain afterwards about the process still being busted. Maybe you, dear reader, won’t do this, but look around. It happens constantly.
What if you could break “figuring it out” into steps like:
Create a Jira ticket template that makes it easy for your team to include all the info design needs
Map out the process that would work best for you and your team, including the lead times, stages of review, and meetings
Talk to the head of design about what works best for them
Schedule a weekly design sync as a failsafe to review work and make sure new projects are accounted for
You can choose whatever approach makes sense for your situation. As long as you break down the steps like that, it will get done.
When you lead bigger projects with multiple teams, breaking into steps is even more important. I’ve been in soooo many meetings where all the right people were in the room, lots of good ideas were thrown around, and...nothing happened.
The steps weren’t well defined. Which meant that person B couldn’t start their work until persons A and C got their bit done, there was no plan to share with executives (so the execs poke their noses in unproductively, which is the project owner’s fault, not the execs’), and the next “status” meeting was basically “the status is the same as last time.”
Please. No more.
When you break big into small, your items need to be “check-offable”
When I ran standups with my team, I would push them. Someone would say “I’m editing a video for our virtual event,” and I’d ask annoying questions like “what does that mean” or “can you describe the edits.” The most important question I’d ask was:
“How will you know when you’re done?”
Every item on a to-do list or project plan should be “check-off-able.” When it’s done, that means it’s obviously done. You can check it off. A stranger could look at the to-do item, look at the work that had been completed, and say “yup, that’s done.”
“Write paper” became three steps, all of them easy to check off.
In “figure out a process with design” — is there a Jira ticket template or isn’t there? Did you write out your preferred process or not? Did you talk to the head of design or didn’t you?
From a personal productivity perspective, this is helpful. You’ll get more done, procrastinate less, and be less stressed doing it.
All great, none of them the big benefit.
The major benefit of breaking big into small happens when you need to work with other people.
To avoid a “status the same as last time” meeting, all you really have to do is break up work into tasks, have the right people on the job, and establish clear deadlines. If that sounds crazy obvious — it is crazy obvious! Doesn’t stop people from not doing it.
As with most difficult, not urgent, important things — like exercise, diet, good sleep habits, or reaching out to the important people in your life — breaking big into small isn’t actually hard. It’s just easy to not do.
When you have a project plan that reflects the real tasks that people need to get done (not the vague “figure out [thing]”), you can take to the group that does the work. You can take it to people outside the initial meeting, and they’ll understand what needs to be done instantly. And you can take it up to your boss so that they can help at the executive level as needed.
Ok, a couple of caveats.
Most project plans suck, and so do most workback plans. The information on them is generic boilerplate and doesn’t meaningfully inform execution (e.g. “our company mission statement is [statement]”), or the goals are incredibly vague (most people know that “brand awareness” is a scapegoat, but the no-better “engagement” is also popular), or the actions on the workback plan were chosen without input from the people who will actually execute the work.
If you want to make an effective workback plan, just start summarizing. I talked more about summarizing here.
Ok ok but actually forget all the other benefits, because this is the big one
When you break big tasks into small steps you are giving yourself a crystal ball.
Decision researcher Gary Klein is the inventor of the “pre-mortem,” an exercise in anticipating challenges before the beginning of a project. In the pre-mortem, his team tells the experts to imagine that “you have a crystal ball. The crystal ball tells you that this project has gone absolutely off the rails. A total disaster. But it can’t tell us where we went wrong. Can you figure it out?”
What Klein has found in his research is that experts make decisions through “mental simulation.” That is, they imagine the steps that they’ll have to go through to achieve their goal, and see if they run into any problems.
When an emergency response team has to pull a car crash victim out of the battered car, the captain imagines trying to pry off the door, “sees” it will be impossible, notices that the car’s roof supports were damaged, and wonders if they could tear off the roof and pull the driver out through the top. He realizes it will work, but that they’ll need to pull the driver out using a different technique, and the plan goes smoothly. This and other examples can be found in Klein’s book Sources of Power, or in his research publications.
The crystal ball exercise forces mental simulation. When experts aren’t explicitly thinking through how to solve a problem, they don’t simulate — but if you can get them to start walking through the steps in their head, they’ll start to notice points of friction.
Walking through the steps… sound familiar?
When you break big work into small steps, you force mental simulation. You realize “oh shit, this approval meeting is going to go haywire if it's the first time the execs see anything,” and so you build in an earlier stage of review. You realize “yes design can get the mockup done in a week, but rounds of revision could take at least that long again, and we’re only scheduling in a couple of days for feedback.”
This is where most workback plans go wrong — slating arbitrary periods of “review” or “feedback” or “waiting for design” without simulating what’s needed to get those tasks done. Then one deadline is missed, because it never made sense in the first place, and the whole timeline goes out the window.
I think about what will go wrong at the beginning of every project, and that’s how I stop stuff from going wrong.
You know, most of the time.
Breaking big steps into small steps is easy to skip, but powerful if you commit. I attribute my college and career success so far (we don’t talk about high school) to getting hyper specific about what needs to be done.
Break big things into small things.