my embarrassing newsletter blunder

When Morning Brew sold to Business Insider for $75m back in late 2020…

I had an idea:

What if I started a newsletter that was like Morning Brew, but for freelancers?

Clearly the model was viable…

Freelancers & remote workers were a fast-growing audience…

And running an email-based business where the email WAS the product sounded very enticing.

So in March of 2022, I launched what is now The Freelance Gig.

I designed it to mirror Morning Brew in every way possible…

Which meant:

- Sharing news stories with a twist of sarcastic humor
- Including lots of GIFs and memes
- Dropping tips & tricks in a playful tone

And, most importantly:

Mailing every day from Monday to Friday.

Because that’s what Morning Brew did.

More sends = more ad inventory to sell…

And sponsorships are how this type of newsletter makes money.

So, over the next 18 months, I published 277 editions of the newsletter.

… Which is when I realized I’d made an embarrassing blunder of epic proportions.

Yet before I reveal exactly what it was…

Let me first share how this epiphany came to club me upside the head:

I’ve kept a journal since 2015.

Every Sunday, I’d crack it open and write a long stream-of-consciousness entry about whatever was going on and how I was feeling about it.

It’s been an immensely helpful tool.

But in early 2023, I decided to formalize this habit into more of a “personal review.”

So I designed a simple set of questions to ask myself at the end of each week, month, quarter, and year…

To see if my actions were actually in alignment with the goals I’d set for myself.

As I began to implement this …

The fog started to clear….

And what I saw was deeply unsettling:

There I was, toiling away 7 days a week to publish a newsletter that was only going out to ~2,000 subscribers and driving minimal revenue.

I’d blindly copied Morning Brew without realizing the tradeoff I was making…

Because mailing daily meant I had little time to focus on growing the list.

Those two priorities were in direct conflict with each other.

Yet it was impossible for me to see until I zoomed out.

I immediately shifted to a weekly cadence…

So I could reinvest all that extra time into growing the list.

Moral of the story:

Publishing more often will make you more money…

… but only if you’ve solved for list growth and are adding new subscribers every day.

Otherwise, each extra edition you send will only slow you down.

And if you’re just starting out…

I recommend mailing once a week and scaling up from there as your list grows… so you don’t make the same embarrassing mistake I did.

Actually, on that note:

Since my book funnel is converting well and adding new buyers to my list every day…

I’ll be mailing Monday to Friday starting in 2025.

Just wanted to give you the heads up.

As always, I appreciate your time & attention 🙏

I’ve got a lot of exciting stuff in the works for next year…

Stay tuned :)

Jim Hamilton

P.S:

It may sound trite, but:

Conducting personal reviews has been one of the most influential changes I’ve made in the last 5 years…

Because I’m no longer a victim of “drift” in business or my personal life.

I know exactly where I’m going and how to get there.

No more waking up 6 months down the road and going “WTF am I doing??”

And, crucially…

I’m always reevaluating both my destination and my roadmap.

Either of which can lead you astray if you’re not careful.

Anyway, if you’re interested in seeing how my Personal Review System works…

I recorded a short(ish) video to walk you through it.

Along with a shared folder housing all the templates you’ll need to duplicate it for yourself.

You can tap here to check it out:

Duplicate my Personal Review System here