Strategy Note 2: Three Questions Worth Sitting With

There are three questions worth sitting with if your brand has never truly answered them.

These questions require honesty, and honesty requires sitting with discomfort long enough to find the real answer rather than the convenient one.

Who are you for?

The obvious, but unhelpful answer is a demographic category. Women 25-45. Small business owners. People who care about sustainability. These answers feel safe because they are broad enough to include almost anyone.

The useful answer is a specific person. What keeps them up at night? What do they want to become but are afraid to admit? What have they tried that did not work? What would they pay almost anything for if they believed it would actually work?

When you can describe your customer's inner experience with such accuracy that they feel seen, you have answered this question. When you are still describing external characteristics, you have more work to do.

What do you stand against?

Brands with enemies are more memorable than brands trying to please everyone.

This is not about manufacturing outrage or picking fights for attention. It’s about identifying the genuine dysfunction in your space—the common practice that harms the people you serve, the assumption everyone accepts that you know is wrong, the way things are done that you refuse to participate in.

What makes you angry about your industry? What do you see other businesses doing that you would never do? What status quo are you rejecting?

That frustration, channeled into positioning, becomes a rallying point for people who share it. They are not just hiring you for what you do. They are hiring you for what you refuse to do.

I stand against the template-industrial complex that promises fill-in-the-blank brand strategy and delivers forgettable sameness. I stand against the advice that tells founders to sand down their edges and appeal to everyone. I stand against the devaluation of thinking in favor of shortcuts.

That position costs me clients who want easy answers. It also attracts clients who have tried templates and found them hollow. The clients who find me through what I stand against tend to become my best clients.

What transformation do you create?

People do not buy products or services. They buy the version of themselves that exists on the other side of the purchase.

The transformation is not what you deliver. It is who they become. The woman who finally has a brand that feels like her. The founder who stops second-guessing every message. The business owner who knows exactly what to say and believes they have the right to say it.

When you can articulate that transformation vividly—when you can describe the after in a way that makes someone ache for it—you have stopped selling features and started selling futures.

These three are inquiries to return to, again and again, as your understanding deepens and your business evolves.

If everyone on your team would answer these questions differently, you need to come to a consensus before you even think about pivoting your marketing strategy. The confusion inside will always manifest as confusion outside. Your audience can sense when a business does not know itself.

But when you can answer these questions with specificity and conviction, everything else becomes easier. Messaging flows from clarity. Content ideas emerge from understanding. The right clients find you because you have made yourself findable to them specifically.

Sit with the questions. The discomfort is temporary. The clarity compounds.

Stay Curious,