The 14-Day “One Shortcut a Day” Experiment: Automating Tiny Frictions in Your Digital Life

We tend to think productivity breakthroughs come from big changes: a new app, a new system, a new routine. In reality, a shocking amount of your daily drain comes from tiny, invisible frictions—those small, repetitive digital tasks you do dozens of times a day without thinking.

The good news: you can chip away at those frictions with equally tiny automations. One shortcut. Per day. For 14 days.

In this post, you’ll learn how to run a simple 14-day experiment using MacOS Shortcuts and text expansion tools like TextExpander to systematically reduce digital friction in your life—without needing to be “good with tech.”

Why Tiny Automations Work So Well

You probably:

Type the same phrases over and over (email intros, client replies, your address)
Click the same menu options every morning (open tools, arrange windows, join a meeting)
Repeat the same online actions (saving files, renaming documents, uploading screenshots)

Each action might only cost a few seconds, but multiplied by days, weeks, and years, it’s a massive time sink and attention killer.

Tiny automations flip that script. Instead of trying to redesign your whole workflow, you:

Notice one annoying, repetitive behavior.
Build one shortcut to remove or reduce it.
Repeat tomorrow.

The result: compound gains from very small changes.

Meet Your Toolkit: MacOS Shortcuts + Text Expansion

MacOS Shortcuts: Visual Automation for Normal Humans

MacOS Shortcuts is Apple’s native automation tool, built into macOS and iOS. It gives you a visual, drag-and-drop interface for building workflows—no coding required.

With Shortcuts, you can chain together multiple actions that interact with:

Apps (Mail, Safari, Notes, Calendar, etc.)
System functions (Wi-Fi, Do Not Disturb, screenshots, Focus modes)
Websites and URLs
Online services via APIs or third-party integrations

Think of it as LEGO blocks for your digital routines. You stack actions like:

Open App → Resize Window → Move to Display → Set Volume → Start Timer
Get Current URL from Browser → Save to Notes → Add Tag → Archive Tab

Once you build a shortcut, you can trigger it via:

A keyboard shortcut
The menu bar
Spotlight search
A dock icon
Siri (on Mac, iPhone, or iPad)

Text Expansion: Turning Short Snippets into Full Sentences

Now add a second tool: text expansion. Tools like TextExpander let you type a short snippet (like ;addr) and automatically expand it into a longer phrase (like your full mailing address).

Common uses:

Email replies (;ty → “Thanks for your email! Here’s what I can do…”)
Support responses
Meeting templates
Signatures
Frequently shared links

Where Shortcuts automates actions, text expansion automates words. Combined, they form a powerful toolkit for your 14-day friction-removal experiment.

Step 1: Map Your Digital Friction

Before you automate, you need to know what to fix.

For one day, keep a simple log. Whenever you feel a tiny spark of annoyance, ask:

“Did I just do something I’ve done at least 10 times before?”

Write those down. Examples:

“I keep digging through folders to find the same project file.”
“I type my Zoom room URL every time I send invites.”
“I always rename screenshots manually.”
“I copy text, open Notes, paste, and add a tag.”

Don’t judge the size of the problem. If you do it frequently, it’s a candidate.

Step 2: Borrow from “Dynamic Personas” to Group Your Tasks

In workplace design, there’s a concept called dynamic personas. Instead of grouping people by job title, you group them by shared digital behaviors—like how they use tools, how often they collaborate, whether they’re mobile-first, and so on.

You can use the same idea for yourself:

Look at your friction list and sort tasks into behavioral groups, such as:

Communicator – emailing, messaging, scheduling, responding
Researcher – reading, clipping, saving, annotating
Coordinator – organizing files, renaming, tagging, archiving
Creator – drafting documents, writing content, preparing slides

These become your personal dynamic personas. Over 14 days, you’ll build shortcuts that serve different “you” modes. For example:

On days when you’re mostly in Communicator mode, focus on email + messaging shortcuts.
On Creator days, focus on writing and content tools.

This gives your experiment structure and ensures your shortcuts match how you actually work.

Step 3: Design Your 14-Day “One Shortcut a Day” Plan

Here’s a sample roadmap you can adapt. Each day, build just one thing.

Days 1–3: Communication Frictions

Day 1 – Email starter templates (TextExpander)
Create snippets for:

Common greeting + context
Common “sorry, I’m busy” responses
Meeting follow-ups

Day 2 – “Start Email to Myself” shortcut (Shortcuts)
A shortcut that:

Opens your email app
Starts a new email to your own address
Pre-fills subject line like “Inbox dump”

Use it as a fast capture system from anywhere.

Day 3 – “Daily Check-in” snippet + reminder
Use TextExpander for a daily summary template, e.g.:

What I worked on
What blocked me
What’s next

Trigger it in your notes app or email.

Days 4–6: Research & Reading Frictions

Day 4 – “Save article for later” shortcut
From your browser, a shortcut that:

Takes the current URL
Saves it to Notes or your read-later app
Adds a tag like “to read”

Day 5 – Quote + source snippet
TextExpander snippet that inserts:

“Quote:
Source:
Date:”

You’ll paste quotes and fill the fields—much faster than typing from scratch.

Day 6 – “Research session” focus shortcut
A Shortcuts workflow that:

Turns on a Focus mode
Opens your browser with specific research tabs
Opens your notes app

One click to “enter research mode.”

Days 7–9: Coordination & File Frictions

Day 7 – “Clean up screenshots” shortcut
A shortcut that:

Moves desktop screenshots into a "Screenshots" folder
Optionally renames them with date + project

Day 8 – “Project folder starter” shortcut
Ask for a project name, then:

Create a folder
Add subfolders like Notes, Assets, Exports

Day 9 – File path snippet
TextExpander snippet for frequently referenced paths, such as:

;proj → /Users/you/Documents/Client-Projects/

Days 10–12: Writing & Creation Frictions

Day 10 – “New blog draft” shortcut
A shortcut that:

Opens your writing app
Creates a new file with today’s date and a prefix like blog-

Day 11 – Writing boilerplate snippets
TextExpander for:

Standard intros
Calls to action
Legal disclaimers or footnotes

Day 12 – “Focus to write” shortcut
A Shortcuts workflow that:

Enables a Focus mode
Closes distracting apps
Opens your writing app and a research doc

Days 13–14: Personal Quality-of-Life Frictions

Day 13 – “End of day shutdown” shortcut
A shortcut that:

Closes work apps
Opens tomorrow’s to-do list
Starts a short reflection note

Day 14 – “One-tap meeting setup”
A Shortcuts workflow that:

Opens your calendar
Joins the next Zoom/Teams call
Adjusts volume or mic settings

Step 4: Keep It Frictionless to Maintain Momentum

To make this 14-day experiment stick:

Aim for 5–10 minutes per day. Don’t over-engineer. Simple is better.
Save and name clearly. Use verbs: Start Writing Mode, Save for Later, Clean Up Screenshots.
Test as you go. Run each new shortcut immediately and tweak any step that feels clunky.
Use them daily. Place high-value shortcuts in easy reach: the menu bar, Dock, or a reliable keyboard shortcut.

Remember: the goal isn’t perfection. It’s reduction—of repetitive effort, clicks, typing, and decision fatigue.

What You’ll Likely Notice After 14 Days

If you commit to one shortcut per day, you’ll probably experience:

Less context switching – starting or switching tasks becomes a single action, not a sequence of clicks.
Faster writing – text expansion quietly shaves seconds from every email and document.
Cleaner digital spaces – fewer random files, tabs, and loose ends.
More mental bandwidth – fewer tiny decisions about “how” to do things.

You’ll also build something more valuable: an automation mindset. You’ll start automatically asking, “Do I really need to do this manually?”—and often the answer will be no.

Conclusion: Small Frictions, Big Leverage

You don’t need to become a full-time productivity hacker to benefit from automation. A simple 14-day experiment—one shortcut a day—is enough to:

Expose where your real digital friction lives
Show you how powerful MacOS Shortcuts can be for chaining together everyday actions
Reveal how text expansion tools like TextExpander dramatically speed up your writing
Give you a set of tailored, behavior-based workflows that fit your own “dynamic personas”

Start small. Today, watch yourself work and pick one thing that annoys you. Tomorrow, turn it into a shortcut or snippet.

In two weeks, your computer and phone will feel noticeably more cooperative—not because you bought a new device, but because you taught your existing tools to work more like you do.