Dear Entrepreneur, It's time to unf*ck your calendar

Three sticky notes to Check Backups, not forget the weekly review and a reminder to send the NPS survey

Let's crush your recurring & repetitive tasks!

Hi there! I'm Amy Hoy and, like you, I run my own business. And like you, I wear an entire haberdashery’s worth of hats: I write, design, market, plan, support, decide, and lead.

But wait, there’s more! There’s also the little matter of all that… other stuff: payroll, paperwork, testing, support, onboarding, editing, analytics, bookkeeping, management. Not that I do it all myself, of course, but I’m the one responsible for making sure it gets done.

Not exactly the stuff that Twitter bios are made of.

But that’s what comes with doing anything like a boss. Being the boss means… The buck stops here. With great power comes great responsibility. Heavy lies the head that wears the crown.

Here’s another cliché for all us #bossmode folks out there:

It’s so hard to find good help these days

Especially when it comes to all this work that keeps on going.

We’ve got lots of tools to help us go from zero to a finished project — Basecamp, Trello, OmniFocus, ticketing systems, spreadsheets, Gantt charts… we’re drowning in project management apps.

There’s just one problem: They’re designed to get you to the finish line.

But when you run your own business, you know that the finish line is a lie.

If you don’t keep up with the marketing, you won’t grow. If you don’t consistently monitor and improve churn, you’ll shrink. If you don’t run tests, you’ll leave money on the table. If you don’t check the backups or test your critical systems, you may find yourself suddenly dead in the water.

And if you don’t regularly talk to your customers and analyze their feedback, well… one day one of your competitors will do it for you.

AGGRAVATINGLY, the same tools we rely on to get our thrilling new stuff “done” give us no help at all when it comes to the ongoing and recurring work that makes our business go and grow:

Basecamp can be configured to send a weekly check-in emails… but it’s one email per task, so RIP your inbox.
Trello cards can be scheduled to recur, but all that does is duplicate an archived task — it doesn’t give you an upcoming agenda, reporting, or continuity between intervals.
OmniFocus has fairly intelligent repeating, but it’s no good for teams, and heaven help you if you break a streak because it won’t let you start fresh.

And if you want to design reusable workflows for those tasks like producing blog posts, case studies, new features, onboarding staff or clients…? Forget it!

After fighting (and failing) to shoehorn this ongoing work into the tools we already use, we have two options:

Wing it — trust your memory, sticky notes, or paper list hung up somewhere in your office, or
Turn to the one tool you know that really does do recurring and configurable alerts (so, even though it won’t actually help you break down a complex task, at least it can warn you well ahead of schedule)

That tool? The calendar.

The calendar is so alluring, but… It’s a trap!

Just like Basecamp, Trello, OmniFocus, and your ticketing system, spreadsheets and your gantt charts…

Calendars are designed for one specific thing. And it’s not this one specific thing.

When you try to make a calendar manage your ongoing and recurring work, you end up in what I call the Calendar Alert Death Spiral.

It goes a little something like this:

At first, the calendar appears to do what you and your team need.

Inevitably, inexorably, you all find yourselves doing the Alert Dismissal Dance:

Should I snooze, or click OK? Will I remember if I don’t snooze? If I do snooze, how many more times will it interrupt my lunch until I’m actually back at my desk and ready to do the work…

Even with perfect discipline, managing-by-calendar sucks

To run your business #likeaboss with ease and confidence — not to mention continual improvement! — you need to know, without a doubt:

what’s on deck
what’s been done
who did it, when, and how… and how it went (like a commit message)
what’s coming up in the near future… and the far future
that each step in a multi-step workflow has been completed (and when, how, and by whom), and, last and definitely not least…
at which step of the workflow each of your individual deliverables are, right now

You also need to be able to trust that the tasks are documented, and in a way that means your team will actually use the documentation, so that sharing the workload, outsourcing, and onboarding new people is quick and easy.

Calendars can't help you with this. And neither can those other tools.

You’ll always have the nagging suspicion that something important has been lost. That things will be late, or undone. That you’re missing something. And you and your team will be endlessly wasting billable hours on verbal checkins (Did x get done? Where are we at with y? What happened last time you did z?).

And on a more mundane note, your calendar is f*cked. And so is your inbox.

As a designer, this offends me!

It’s 2024, my friend! This whole situation is ridiculous. And also, if you ask me, embarrassing for our industry.

It’s not like this problem is new.

The promise of computing has always been to make work easier and more efficient. The earliest, most exciting tech demos have always been about intelligent assistants, from the Knowledge Navigator to Siri. And the big daddy thought experiment that inspired them all all, Vannevar Bush’s Memex, imagined the power of an enlarged intimate supplement to one’s memory. For, like, you know, things you have to do over and over again and tend to forget about.

Vannevar Bush was dreaming this up in 1945.

And he was right:

Humans…	Computers…
…suck at date math and chronology.	…are made of math.
…suck at at being triggered by the passage of time.	…are literally driven by a clock.
…suck at remembering and correlating information.	…excel at databasing and querying.
…suck at disseminating information to the right people at precisely the right moment.	…have messaging in their DNA, thanks to APIs.
…suck at being objective about their success rate.	…have no feelings, and they will happily give you cold hard facts.

Conclusion: These are things the computer should do for us. And we’ve known this for at least 73 years.

Yet here we are in 2024, suffering the whims of our calendars (a metaphor that is literally hundreds of years old). Here we are, jamming our work into vessels that aren’t up for the job, contorting ourselves around our tools, dancing the Alert Death Spiral. Here we are, too, doing the same work over and over in slightly different order and every so often, forgetting a step. Here we are, wasting hours of our lives on verbal check-ins with our team to see if work has been done (and when, and by whom, and in the right order)…

Here we are, struggling, rather than being supported, served, informed, and aided.

Here we are, running like mad, drowning in busy work, instead of using our limited energy to create.

Is this really the best we can do? Abused by systems that demand we jump when they say jump… and if we don’t, all the power and promise of computing is lost?

I reject this idea and the interface metaphor it rode in on!

The tool we deserve didn’t exist… so I decided to make it

I set out to create a trustworthy system.

What is a trustworthy system?

A system that gives you the big picture: what’s done, what’s not done, what’s late, what’s coming up? all in a single glance
A system that ensures no tasks can get lost in the depths of nested lists, and surfaces all coming-due tasks right where you will see them
A system that reports on your team’s successes or failures over time (both positive and negative streaks)
A system that tracks the evolution of a given task over time, so when the documentation or process has hiccups or bugs, that insight is not lost in the mind of a single employee or an overly chatty Slack channel
A system that puts the documentation next to the doing, nobody ever has to “enter a task cold” (and so you don’t have to fetch your process manual from the digital equivalent of a filing cabinet in the basement)
A system that does not rely on a spray-and-pray alert system, but offers you a daily and weekly agenda, and a visual menu of work options whenever you are ready
A system that understands that a lot of work is more than a single task, but less than a whole project — like producing a new case study, or shipping a new feature — and makes it easy to design a reusable workflow that includes and tracks each of those steps
A system that gives you a “boss view” into all the workflows currently in flow
A system that meets you where you are, whether that’s email or Slack (with a panoply of other communication options coming soon)