A ton of great content yielded nothing for my side business, and after one year I closed shop. I was determined to find out what I did wrong and to learn from it. This is a postmortem on why it failed, and 15 considerations I apply to every piece of content I produce.

Put some muscle behind that good content

A killer product isn’t going to amount to much if it never reaches its intended audience. Your product needs a brand, and your brand needs a content strategy to spread the word, engage customers and encourage opt-ins.

For a year I produced a wealth of well-written, finely produced content to promote a side business I was building to connect local entrepreneurs in my state of Vermont. I loved my audience, I knew their interests, and I understood their pain points (I was one of them after all). But growth never materialized. We had a small, dedicated following, and that was it.

I received consistently positive feedback for the content I sent out — a newsletter, a video blog, and in-person consultations, but they did little to grow our audience. What could I have done differently? The answer lies in the lack of a coherent content strategy.

What went wrong?

Following the closure of my side business, I did a postmortem. In retrospect the problem was obvious, but when you’re in the thick of building a passion project, it can be hard to see what’s truly working and what’s just busted.

The problem wasn’t the content, it was the strategy.

I compare our content track record to riding a rollercoaster with tiny humps and steep drop-offs. A pop of content could launch us up to the crest of a hump, but just as quickly send us plunging back to earth. Our content existed in a vacuum with little connection between each piece. And they were infrequent enough that we never earned any mind share. Quality be damned.

Keep this coaster going!

Luckily, the basics of content strategy can work universally for most businesses regardless of the product. Let’s go back to the roller coaster analogy. Think of each cart on the coaster as a unique piece of content. Each is connected to the other, and all are pulled by the work-horse at the front.

Each piece of content builds on the previous one, forging a long-form narrative. Your audience can hop on at any point, and the message is clear and relevant to their interests. Ideally, once they’re seated, they remain invested to see what comes next. It’s at this point that strategic content releases hold their attention, encourage a deeper relationship, and earn their support.

Great content is not good enough

I recently spoke to a husband and wife team who specialized in videography. They had a fantastic body of work, an attractive brand, and a hefty amount of content already deployed to Instagram. Their website was inviting and representative of their quality offering. From my view, it looked like they were doing everything right, but their content was yielding no return, and they were baffled.

I asked them what their content strategy was supposed to accomplish for them and I was met with blank stares. They were spending a ton of time and energy creating beautiful videos, but they hadn’t given thought to the purpose behind the content ie: strategy. Did they want more traffic to their website? Did they want referrals or leads? Did they know who their audience was? Nada.

This deer in the headlights response felt similar to what I went through while evaluating the failings of my own side business. There were no clear objectives guiding the content, and thus no strategy to deliver on those objectives.

Here’s how I turned my content mistakes into lessons learned.

For every piece of content, I produce today, I am clear on why I’m creating it, who it’s for, and how it serves my broader business objectives. This piece your reading is no different. I wrote it to provide guidance to entrepreneurs who are befuddled by content strategy, to position myself as an expert, and encourage interest in the branding and content services that my business provides — yep keeping it real with you 😉

My process in 5 questions, 5 rules, and 5 considerations

5 questions to answer before building content:

  1. Who is this for?
  2. What do I want them to do?
  3. How does this support my objectives?
  4. Does this content encourage action?
  5. Will they be entertained, educated, or intrigued?

5 Rules for every piece of content:

  1. It speaks directly to the core interests and values of my audience
  2. It revolves around the action I want them to take
  3. It reflects positively on my brand
  4. It invites them deeper into the narrative
  5. It shares an empowering, honest, and human message

5 Considerations for deploying content strategically:

  1. Be consistent in message, visuals, and tone
  2. Release content at a reliable and consistent clip
  3. Cast a narrow net -release content only where they are
  4. Weave a larger purpose into each piece of content
  5. Don’t stop, iterate

You can do what the big brands do — seriously

Ever notice the way ads for Coca Cola change depending on where you are? The people, scenery, activities, and tagline are all tailored to specific, localized demographics. But each carries a deeply consistent message “Taste The Feeling.” Or to put it in plain terms, drink a Coke to feel part of something bigger than yourself. This has nothing to do with the taste or quality of the product, and everything to do with the emotional response the brand wants to elicit from its audience.

You’re not Coke and that’s ok. We can learn from them nonetheless.

With your objectives defined, focus wholeheartedly on the interests of your audience when crafting a content strategy. Know their values, what drives their decision making, their interests, and their struggles. Then design content that speaks directly to these attributes and solves them on an emotional level. And be consistent, timely and interesting.


Great content can build awareness for your brand, but to stay top of mind you need a content strategy that deploys your message with intention, consistency, and relevance to your audience. Without a strategy, you might as well forget to hit “Publish” on every piece of content you create.

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