Ditch Planning and Start Increasing Your Luck as A Content Creator

We can’t fight chance. Let’s make it our ally.

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Photo by el pepe on Unsplash

Chasing certainty is a waste of time. Oh, how I wish to know what the future holds! How I wish to control it!

No more fears. And plans would finally become useful…

All the time and money we waste spend on courses and planning has just one goal: reduce uncertainty. But we can just trim its edges. So many things are out of our control.

In the last five years:

• my child took away multiple hours of sleep every week for at least a couple of years,

• platform changes have killed the reach of my content,

• a once-in-a-century pandemic and, soon after, oversized inflation cripple my business.

Guess how many of these highly impactful events were on my plans?

We need acceptance (but not resignation)

Maybe the most important skill I gained after 13 years of doing business is acceptance. I had to change my plans and pivot so many times. I’d be in an asylum (or in rehab) if I didn’t learn to let go.

But that doesn't mean giving up. We can still push the odds in our favor. We do it through planned serendipity.

(Thanks to

Russell Nohelty

for bringing this term to my attention.)

You probably know about serendipity. The Cambridge dictionary defines it as:

the fact of finding interesting or valuable things by chance.

For content creators and entrepreneurs, it means:

1. noticing unexpected waves (like an online trend),

2. riding them.

Now, you probably noticed the contradiction. How can you plan the finding of interesting or valuable things by chance?

It's like being in many places at once to increase the odds of getting struck by lightning. (Assuming that's a good thing, like, for example, when you need to turbocharge your trusty DeLorean and travel through time.)

As content creators, we have many ways to practice planned serendipity.

Take more shots

I've published over 100 posts on Substack Notes with varying results—some vanished into obscurity, others received dozens of likes and, most importantly, comments. Ask any creator, even the big ones, and they'll tell you the response to their content never stopped surprising them.

The note about the article that inspired this article.

A couple days later: comments and 3X likes.

Over time, you can raise your baseline. You form a clearer picture of what your audience wants and appreciates. So, content that completely bombs becomes rare.

But to reach this level, you need a large sample size, which means publishing dozens, possibly hundreds of pieces of content, and reaching thousands of people. You’re like a scientist testing a new drug. You need thousands of subjects to find reliable patterns, medians, and averages.

With a small sample size, outliers lead you to the wrong conclusions. For example, suppose you’re publishing recipes:

• one day you release a video about a beetroot salad,

• it gets 3 times your usual views,

• you conclude that people love beetroot,

• you post only beetroot content for a month,

• your views plummet and subscribers gather in front of your house to throw rotten bettroots at your walls.

What happened? That salad recipe was an outlier. It was beetroot day. Some beetroot influencer stumbled into your recipe and shared it with his following.

But when you collected a larger sample, with more beetroot recipes, you got far more reliable results. (Enough with the beeroot, I promise.)

This is why pushing your quantity up is always valuable.

But, beware, I’m not advocating for forgetting about quality. My philosophy is: aim for the highest level of quality that still allows you to publish frequently enough to quickly gather data.

All the data and repetitions you amass accelerate your improvement. So, in the end, quantity increases quality. Win-win!

Be everywhere (or at least in more than one place)

This is tough advice to give for me.

To succeed on any platform, you can't just publish. You also need to:

• learn the platform's rules and language,

• get to know other creators,

• sometimes learn new tools.

It's a lot of work, and it multiplies with each new platform you try. That’s why I always advised my clients and followers to limit themselves to only one platform. Otherwise they can’t put in the necessary effort to make a dent.

But if you find the time, appearing on multiple platforms exposes you to different audiences and makes it seem like you're everywhere. Eventually, people can't ignore you.

The only caveat is to choose platforms that support your efforts with good organic reach, like Substack and YouTube. Read more about this in the article below:

Don’t Let the Wrong Platform Sink Your Writing

Be a social butterfly

Most platforms reward engagement. Their algorithms amplify the content that gets the most shares, likes and comments.

But here comes the chicken-and-egg problem: when you’re starting out, getting engagement feels almost impossible. The workaround is to “enocurage” engagement from other creators and borrow their audiences.

Of course, I don’t have to remind you that this doesn’t mean bombarding strangers’ inboxes begging them to “please, please, please, share my awesome article, I spent a full 40 minutes writing it!!!”

Do this, instead:

• find interesting creators talking to a similar audience,

• leave sincere and thoughtful comments to their content,

• let them and their audience get organically interested in you and your content.

Some creators will become friends this way. Then, you can organize a more structured “engagement pod”, if you want.

I've done this on Medium, by commenting on articles from people whose attitude I liked. When I later found them on Substack, they recommended my publication and brought me more than half of my subscribers (who exceed 300 now).

Offer a buffet

Monetization is tough for many creators. We love creating and giving away content, but selling always feels like selling out. Yet zero earnings put us in the fast-lane to burnout and quitting.

But monetization can become an obstacle, too. I've seen creators try to imagine the perfect product or service before publishing their first post. The problem is you'll never know exactly what the audience wants to buy until you ask them for money.

Many of my Italian clients followed this path:

• consumed our videos and newsletters for months,

• bought a low-price product, or a single hour of consultation,

• sometimes bought other low-price products,

• subscribed to our membership or paid for multiple months of coaching.

If you don’t yet have a flagship product or service, try smaller offerings until something clicks.

Never stop studying

I started my creator career with a blog about photography that got 300,000 page views a month from Google. The main traffic source for my current project in Italian is instead YouTube. Throughout my career, I also published interview podcasts, sent newsletters, launched ebooks and courses, and wrote sales and ads copy.

Each new skill created more opportunities, kept my work fun, and kept me and my business growing.

To plan serendipity, make sure to always be learning and practicing something new.

Enrich your toolbox

Sometimes learning new tools is tedious but necessary to do our job well. Other times it's procrastination disguised as productivity. But a new tool can also inspire or unlock new ways of expression.

For example, with generative AI you can help create illustrations that enrich your content even if you suck at drawing.

Be curious, but set a limit to the time you spend playing with new tools.

Give away your best content

In the early days of blogging, guest posting was a common practice. By publishing an article on another person’s blog, you got access to a new but aligned audience.

This still works today:

• find blogs with audiences similar to yours,

• look for guest post guidelines (or ask),

• send 1-3 ideas tailored to their audience,

• write and send the best article you can,

• include a CTA pointing to your blog or, even better, to your email list landing page.

You can also expand this strategy to other platforms: you can exchange interviews on podcasts, videos on YouTube channels, and social media posts.

On Substack, after connecting with various authors, I proposed several guest posts. They all brought new subscribers. One in particular attracted at least 30 subscribers 24 hours after its publication:

My guest post is the single cause for this spike.

By finding creators with overlapping audiences and offering valuable guest posts, you gain exposure to new readers and expand your reach.

Here’s my ultimate guide to find guest posting opportunities and make the most of them:

The Ultimate Guide to Guest Posting: Just Write and Grow Your Audience

Call it Lady Luck, call it the Muse

The book “The Creative Act”, by Rick Rubin, is all about how to foster creativity. The overarching message is that you have to prepare yourself for when the muse comes to visit. This means collecting ideas, exploring them, being open to inspiration from every source, and so on.

Planned serendipity is the same. It takes some work. It may be a bit unfocused.

But we can’t fight chance, so let’s make it our ally.

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