These 5 Content Strategy Mistakes are PAINFUL! (From Experience)

Putting out content reminds me of climbing a mountain. There are false peaks, stretches where the slope gets steeper and more treacherous, and some periods where you have to blaze your own trail. But like climbing a mountain, if you stay consistent and keep going, you’ll look back and see that you’ve made significant progress.

Climbing a mountain is hard enough, so I can personally do without the slips and falls. My goal with this post is to share with you some of my biggest mistakes I made while climbing the mountain of content creation so you can apply these learnings to your content strategy.

Scaling Too Quickly

After I successfully raised a round of funding, I had the resources to increase the quality and quantity of the content I was putting out. My mistake was that we went from one platform (TikTok) to six over the course of 6 months. This included an active blog, Instagram, Facebook, YouTube, a video podcast, and of course TikTok.

While our content was better than most, we were spread way too thin to earn another significant follower base on each platform. Beyond this, we were repurposing content across platforms (i.e. creating one video and posting it across TikTok, Insta Reels, YouTube Shorts, and FB Reels), which actually lowered the effectiveness of each post.

Key Lessons:

  • There needs to be a compelling reason to enter into a new channel. More resources isn’t good enough.

  • Add one channel at a time, get a strong foothold as evidenced by a growing and engaged audience.

  • Study what works on the new channel and tailor your content specifically to that channel. Resist the temptation to simply repurpose content.

Taking a Break

I had two other people on my team, my co-founder and one dev, and I needed to raise another round of funding. I was the only one running with content at that time and there wasn’t a way for anyone else to pick it up. I decided that I needed to pause content creation to try to get the round raised as quickly as possible since I was going to have to carry the brunt of the weight for fundraising. For those who have never raised capital, there’s a common saying among founders: you can either run your company or raise funds… but not both. I tried to prove this wrong on my first round and failed. I came to accept this as truth on the second round.

By the time I closed the round, hired and on-boarded our new team members, I had been on a 3 month hiatus from putting out content and it was pretty nice after being such a massive part of my life the prior 4-5 months. It felt even better when people started commenting on my first post back… “HE’S BACK!!!”

But there was a problem…

Views and engagement was significantly lower than usual.

While I can’t prove this, it’s widely accepted that algorithms reward you if you post more regularly. My experience tells me that the inverse is also true. Engagement did increase, but it never matched the prior levels before I took the break.

Key Lessons:

  • It’s better to slow down significantly than to stop all together.

  • When you completely disengage from the platform you’ve gained traction on, you take your finger off of the pulse off of what is happening on the platform, which is ever-evolving. When you come back, what worked before might not work again.

Letting the Sales Process Suffer

Let me tell you, it is exciting when your content strategy starts to pay off. I saw a massive increase in web traffic and new account registrations that would have cost us tens of thousands of dollars had we gone the paid ads route. So naturally, I wanted to capitalize on it and grow it.

For context, our product was supposed to be self-serve and we were about to monetize it. I expected that if I kept focusing on content, registrations would continue to grow, which would grow revenue.

Unfortunately, I was wrong.

Revenue didn’t truly begin increasing until I implemented a direct sales motion, but by this time I had to scale back my team. Since I was the one who owned content, and now sales, I swung hard to the other side and went all in on sales.

I wrote an entire article about this one, because it is arguably the most critical mistake I made. You can read it HERE.

Key Lessons:

  • Content is not a substitute for sales. It’s important to be realistic on how far into your funnel your content can push someone, then make sure there’s a smooth handoff between your content and sales strategies.

  • Dial your sales process, then layer on content to drive more leads into your funnel.

Too Much Time per Post

I like to call myself a recovering perfectionist. Admittedly, I tend to overthink things in an effort to get them as close to perfection as possible. This can be the enemy of content creation because the goal is to be consistent, not perfect. And if you’re aiming for perfection, being consistent will be more difficult by an order of magnitude.

When I was scripting, editing, and producing content alone, I put a lot of effort in. But some of the posts I felt most confident in actually flopped. All that additional time and energy didn’t pay off.

Every once in a while, my co-founder would say “Work expands to the time allotted to it.” When applied to content, I believe it is a tactical hack. So, if you give yourself 3 hours to get a post out, there’s a pretty good chance it’s going to take the better part of 3 hours. But what if you set that deadline at one hour? You will have saved 2 hours and I guarantee you the post will be 80-90% as good as the one you spent 3 hours on.

Funny story: my best post, which received 65M views, 3.4M likes, 100k+ comments, and 40k saves was a total random thought that took me ~15 minutes to put out. In hindsight, it makes sense but I had no idea how well that one would do!

Key Lesson:

  • Set a time limit on how much you’ll spend on each piece of content. This will need to be different for each platform, as some call for higher quality content than others.

Not Taking More Creative Risk

When I was starting, I put effort into learning what the baseline for quality and production was in my industry. I used this to envision the type of content that would stick out. I noticed that no one was using a 360 camera yet. This type of videography had always captured my attention, so I decided to buy a GoPro Max to introduce 360 footage to my industry. I even dreamed up this backpack-mount that didn’t exist and made the bootleg prototype out of an old toolbelt, a piece of deck board, a drumstick holder, a selfie stick, and some landscape staples. The result was capturing footage like no one had ever seen before. I’m convinced that taking this creative risk was a large part of my early success.

Some of my posts were also pretty risky. With one in particular, I spent a ton of time writing a rap, producing my own beat, and filming a silly music video in an effort to become the go-to “sound” for all posts in my industry since having people use your sound was a way to grow your account. It flopped.

Taking creative risk requires more energy, and it doesn’t always pay off. However, it’s still worth budgeting in time to think outside the box and aim for moonshots. I took a decent bit of risk, but I wish I would have been more intentional about investing time to being more creative.

Key Lessons:

  • Creating content can become monotonous especially when you slip into a regular cadence. Budget 10-20% of your content time to thinking outside the box and putting together a more intricate, extensive, or labor intensive piece of content.

  • Finding a new way to introduce content to your audience (the equivalent of my 360 camera) can be an easy way to boost engagement.

Here’s Your Assignment

Take some time to abstract at least one of my mistakes and develop an action item to strengthen your content strategy.

If you need help crafting your own content strategy, or if you want me to review your content and provide some coaching on it, please let me know! Hit that “book a call” button and let’s talk.

Keep Creating.

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