What Work Should Remain Hard?

What work should remain hard?

If you've decided to use AI tools in your business, this is the question I want you to ask:

What work should remain hard?

Not everything that can be made easier should be.

Which parts of what you do are challenging, messy, inefficient, or full of tension—and should stay that way—because that's how you get to the good stuff?

AI tools promise to make things easier, faster, cheaper. What they don't help us assess is the potential cost of that ease.

What is the cost—short and long-term—of not having my hands and heart in this?

Where is my emotional, intellectual, and physical labour warranted?

If writing makes you a better thinker, don't ask Claude to write your drafts. If reviewing your clients' financial statements every month is what keeps you connected to the heart of their business and makes you an indispensable advisor to them, it's okay to say no to the shiny new reporting tool.

One of my foundational beliefs in business is: choose your hard, let the easy things be easy.

This means knowing what hard parts are worth honouring and protecting, because that's where creativity, critical thinking, innovation, trust, or connection comes from.

Not all friction should be removed.

What part of your work should stay messy or challenging because that's where your value actually lives?

By answering this, you'll also get to the core of what parts of your work are worth protecting as you grow.

As always, I welcome your thoughts on this,

— Kate

P.S. This assumes you've already worked through other ethical considerations around AI use. I'm not addressing that here, because I don't think it's the part of the conversation I can add the most value to. This is.


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Kate Smalley

Kate Smalley is a small business advisor, facilitator, and educator based in Toronto, Canada. She writes about growth and business development for principled, industry-shaping entrepreneurs.

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Am I Willing to Maintain This?