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Workflow Automation

The Unforgettable Art of Doing Less

The first time I automated a part of my workflow, I felt like I’d discovered fire. I was spending three hours every Monday morning sorting through spreadsheet data before a team meeting. One Sunday night, instead of dreading Monday, I stayed up until 2 AM writing a script that did the work for me.

The next morning, I ran the script. Four minutes later, what would have taken me three hours was done. I felt like I’d stolen time from the gods.

But here’s what nobody tells you about automation: that feeling never gets old. Never. Ten years later, I still get that same rush watching a machine do what used to consume my precious time.

The Real Currency of Creation

Time isn’t your most valuable asset. Mental bandwidth is.

Every decision you make, every task you juggle, every notification you process—they all drink from the same limited pool of cognitive resources. Once depleted, your creative well runs dry.

Workflow automation isn’t primarily about saving time. It’s about reclaiming your attention.

When I interviewed top performers across industries—from bestselling authors to venture capitalists to Olympic athletes—a pattern emerged: they all ruthlessly automated the predictable to make space for the exceptional.

They understood that genius rarely emerges from busy work.

Automation Mindset: Think Like a Lazy Genius

Before we talk tools and systems, let’s rewire your thinking.

The automation mindset begins with a simple question:

“Should I even be doing this at all?”

Not “how can I do this faster?” but whether the task deserves your involvement in the first place.

I learned this lesson the hard way. For years, I meticulously tracked business expenses, spending hours categorizing transactions. I became efficient with keyboard shortcuts and templates. I even felt virtuous about my discipline.

Then I hired a bookkeeper. For $150 a month, everything was handled better than I could do it. The hours returned to me generated exponentially more value in creative output.

Sometimes the best automation isn’t technology—it’s delegation.

For tasks that must remain yours, ask:

  1. Does this need to be done more than once?
  2. Does it follow consistent patterns?
  3. Does it require minimal judgment calls?

If you answered “yes” at least twice, you’ve found automation gold.

The Three Levels of Workflow Automation

Level 1: Template Automation

The 80/20 approach to reducing friction

The simplest form of automation comes from templates and snippets—minimal technical skill, immediate returns.

Examples:

On macOS and iOS, built-in text replacement is surprisingly powerful. Go to System Preferences > Keyboard > Text to create shortcuts for email responses, addresses, or any text you repeatedly type.

For more robust needs, consider:

Quick Win: Identify your three most common email responses. Create templates for each, saving them as text expansions. What once took minutes now takes seconds.

Level 2: Trigger-Based Automation

When this happens, do that

The next level connects triggers to actions—when one thing happens, another follows automatically.

Tools that excel here include:

Real-world example: When a client pays an invoice (trigger), my system automatically:

  1. Marks the invoice as paid in my accounting software
  2. Sends a thank-you email with next steps
  3. Creates a project folder with the client’s name
  4. Adds the project to my task manager

What used to be a 15-minute process now happens while I sleep.

Quick Win: Set up an automation that saves email attachments to a specific folder, naming them consistently based on sender and date.

Level 3: Intelligent Workflows

Contextual systems that adapt and learn

The most sophisticated automation uses conditional logic and AI to make decisions based on context.

Examples:

One of my most valuable systems analyzes my calendar, task list, and project deadlines each morning, then generates a daily schedule based on my energy patterns, meeting preferences, and priorities.

The magic isn’t in the technology—it’s in the thinking. The system encodes my best decision-making about how work should flow.

The Hidden Cost of Automation

Let me tell you what the productivity gurus won’t admit: automation has costs.

Building good automations requires:

  1. Upfront time investment
  2. Maintenance when systems change
  3. Troubleshooting when things break
  4. Mental overhead to remember what you’ve automated

I’ve built elegant automations that saved me hours, only to have them break when a service updated its API. The time spent fixing them sometimes exceeded what I’d saved.

The honest automation equation is:

Value = (Time Saved × Frequency) - (Setup Time + Maintenance)

Only automate when this equation delivers positive value.

Common Automation Pitfalls

After a decade of automation obsession—and countless mistakes—I’ve identified these failure patterns:

1. The Complexity Trap

Building systems so intricate that only you understand them. When they break, you’re the only one who can fix them.

Solution: Document your automations simply. Better yet, share them with colleagues who will benefit.

2. Premature Automation

Automating workflows before you understand them fully, encoding inefficiency.

Solution: Manually perform a process at least 3-5 times before automating. Map the workflow on paper first.

3. Automation Addiction

The disease where you spend more time building systems than doing the actual work they’re meant to support.

Solution: Set time boundaries for your automation projects. Respect the line between meaningful efficiency and obsessive tinkering.

The Automation Hierarchy of Needs

Not everything deserves automation effort equally. I use this hierarchy to prioritize:

  1. Customer-facing processes - These directly impact revenue and reputation
  2. Data transfer between systems - Errors here multiply downstream
  3. Repetitive administrative tasks - Classic time-wasters
  4. Personal convenience automations - Nice-to-haves

Start at the top and work down. The value diminishes as you descend.

Digital Ecosystem Integration

The most powerful automations bridge the gaps between your digital tools. For Apple users, this includes:

  1. Shortcuts app - Available on iPhone, iPad, and Mac
  2. Universal Clipboard - Copy on one device, paste on another
  3. Handoff - Start tasks on one device, finish on another
  4. iCloud automation - Share automations across devices

A simple but powerful example: I have a Shortcut that captures ideas in any app through the Share menu, formats them with relevant tags, and appends them to my idea document—identical behavior whether I’m on iPhone, iPad, or Mac.

For creative professionals, these cross-device workflows eliminate the friction between inspiration and documentation.

The 5-Minute Automation Rule

If a task takes less than 5 minutes and you only do it monthly, don’t automate it.

But if a 5-minute task happens weekly? That’s 4+ hours annually. Automate.

This simple heuristic prevents automation rabbit holes while directing energy to high-impact opportunities.

Start Here: Your First Automation Projects

Ready to begin? Here are three starter projects with exceptional ROI for creative professionals:

  1. Email processing rules
    • Create filters for routine messages
    • Auto-file newsletters and subscriptions
    • Set up canned responses for common inquiries like project requests
  2. Creative asset management
    • Auto-organize incoming files by type, client, or project
    • Rename files following your naming convention
    • Create standardized project folders with templates for briefs and deliverables
  3. Meeting and client management
    • Eliminate scheduling back-and-forth
    • Connect calendar to a booking tool like Calendly
    • Auto-create meeting prep documents with client history and talking points

Embracing the Automation Mindset

The tools will change. The platforms will evolve. But the mindset is timeless.

Ask yourself daily: “Am I using my uniquely human capabilities right now, or am I doing work a machine could handle?”

Your creativity, empathy, insight, and vision—these are what make you irreplaceable. Everything else is a candidate for automation.

I’ve spent thousands of hours building systems to save hundreds of thousands of hours. But the true value isn’t in the time saved. It’s in what that time makes possible.

Automation isn’t about efficiency for efficiency’s sake. It’s about creating space for the work that matters—the moments of creative flow, deep thinking, and human connection that no algorithm can replicate.

In a world that constantly demands more, the most revolutionary act is to automate the mundane so you can focus on the meaningful.

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