What Black Friday taught me (not what you'd expect)

Jason here.

Now that we're about a week past Black Friday and our inboxes have finally calmed down a bit... I wanted to share something I've been thinking about.

Black Friday is actually one of my favorite times of year as a marketer, and not because I love getting sold to—trust me, I was as exhausted as everyone else by the end of it.

But here's the thing... it's like getting a free masterclass delivered straight to your inbox. You've got hundreds of smart marketers all trying to convince people to buy things at the exact same time, using every angle and tactic and hook they can think of. Some of it works brilliantly, some of it falls completely flat, and if you're paying attention you can learn a ton from watching what happens.

This year I kept notes on the stuff that caught my eye. I wanted to walk you through five lessons that stood out—things that got me thinking about how we position offers, how we treat our audiences, and how we can cut through the noise even when everyone's getting absolutely hammered with promotions.

Lesson 1: Change the terms and you change the game

There's a legendary copywriter whose training I'd been eyeing for a while now.

One of those "I should really get around to buying that someday" situations that just never quite happens because life gets in the way and there's always something else demanding your attention and your wallet.

In the past, this training had sold for anywhere from a few hundred dollars up to over a thousand depending on when you caught it and what bonuses were included.

Always a one-time payment, always a decent chunk of change upfront, and always something I told myself I'd circle back to eventually.

This year they did something different though.

Instead of the big upfront investment, they opened it up as a monthly subscription—I think it was something like fifty bucks a month, and you could cancel anytime without any strings attached.

Same training, same content, same everything... just a completely different offer structure.

And here's what's interesting about that—the shift in terms turned what had been a perpetual "maybe someday" into an immediate yes for me.

Because suddenly I wasn't sitting there trying to decide whether this training was worth several hundred dollars of my money right now. I was just deciding whether it was worth trying for a single month.

That's a much easier question to answer, you know?

It got me thinking about how often we get stuck obsessing over the what of our offers when the real opportunity might just be in rethinking the how.

Same product, different terms, and you've got a completely different psychological equation for the person on the other end deciding whether to pull out their credit card.

Lesson 2: Old assets + creativity = new income

Here's the thing about that training I mentioned—it wasn't even new material.

These were recordings from live programs and workshops they'd run years ago, stuff that had already been created and delivered and was basically just sitting on a digital shelf somewhere collecting dust.

Not generating any revenue, not reaching any new people, just... existing. Dead inventory, essentially.

But by getting creative with the timing of the offer — Black Friday creates this built-in urgency and attention that you can ride — and by restructuring the payment terms to lower the barrier to entry…

They found a way to breathe new life into something that had already done its job once before.

I think a lot of us are probably sitting on stuff like this and don't even realize the opportunity.

Old webinars we ran once, past trainings we put together, workshops or challenges we created that got great feedback but then we moved on to the next thing.

We assume that because we already sold it or because it's been a while or because it feels "old" to us, there's nothing left to do with it.

But the reality is that most of your current audience probably never saw it the first time around—they weren't even on your list back then. And even the people who were around might not have been ready to buy at that particular moment.

Makes you wonder what's sitting on your own shelf that could be repackaged or repositioned or just offered again with a fresh angle and a creative twist on the terms.

Lesson 3: Addressing subscription fatigue

I've been getting emails about a copywriting mastermind for a while now — one of those communities where you pay a monthly fee ($49/month)…

And you get access to a bunch of trainings and a community of other copywriters where you can get feedback on your work and ask questions and all that good stuff.

Pretty standard membership model, nothing revolutionary about the structure.

But this Black Friday, they did something that really caught my attention.

Instead of just offering a discount on the monthly rate or throwing in some bonus content, they put out a lifetime deal—pay $200 once and you're locked in forever with no more monthly charges ever again.

And here's why I think this was particularly smart timing...

I think in 2026, people are going to become real sticklers about more subscription fees.

Every month there's another charge hitting my card for something I signed up for six months ago and barely use anymore, and I think a lot of buyers are starting to feel that same fatigue creeping in—this sense of "do I really need another recurring charge showing up on my credit card statement?"

So when I saw that lifetime option, it hit me differently than it might have a few years ago.

$200 is basically four months of membership, and if I was planning to stick around anyway, why wouldn't I just lock it in and never have to think about it again?

I took the deal. And I'm betting a lot of other people did too, because they were reading the room on what buyers are actually feeling right now instead of just doing what they've always done.

Lesson 4: The list hygiene disasters (self-own edition)

Okay, this one's a little uncomfortable to talk about—partly because I'm pointing fingers at other people, and partly because I'm not exactly innocent on this front myself.

During Black Friday week, I got hard-sell emails from people I didn't even realize I was subscribed to.

Aggressive, urgent, "last chance before the doors close forever" type pitches coming from names I genuinely didn't recognize when they hit my inbox.

Either these were people I'd opted in with a year ago and then never heard a single word from since... or I legitimately have no memory of subscribing in the first place.

Honestly not sure which scenario is worse.

And look—I'm as guilty as the next guy for not emailing my list as often as I should.

I know what it feels like to let weeks go by without sending anything and then feel weird and awkward about showing up again out of nowhere. I get it, I really do.

But I would at least think I'm smart enough not to come completely out of the blue with an aggressive sales pitch after totally neglecting the relationship for months on end.

That's like ghosting someone for a year and then showing up at their door asking to borrow a thousand dollars.

You might technically have the standing to make the ask, but you've burned through all the goodwill and trust that would have made them actually want to say yes.

If you're going to sell to your list during a high-intensity period like Black Friday when everyone's guard is already up, you really need to have been showing up before that moment arrives.

Building the relationship bit by bit, providing value consistently, staying somewhere in the general vicinity of top-of-mind.

Otherwise you're just another stranger screaming into an already overcrowded inbox, and people are going to treat you exactly like one.

Lesson 5: Reading the room/Standing out in crowded markets

This last one made me smile, because it was so completely different from everything else landing in my inbox that week.

In the middle of all the 50% off promotions and the BOGO bundles and the "doors closing in three hours, this is your FINAL warning" countdown timers... I came across an offer that made me do a double-take.

It was essentially a partnership offer—something along the lines of "we'll connect you with our promotional partners and get you in front of their audiences," and they were offering it for free.

100% off, as they put it.

It wasn't a course they were trying to sell me or a product I needed to purchase.

It was a straight-up offer to help people get more exposure by tapping into their network of affiliates and promotional partners, without any money changing hands.

Now I don't know all the details of how they structured it on the backend or what they were getting out of the arrangement long-term, and I'm sure there was some strategic thinking behind it beyond pure generosity.

But what I do know is that in a week where absolutely everyone was screaming "BUY NOW" as loud as they possibly could, this one stood out by doing the exact opposite.

It takes some guts to run that play during the biggest selling week of the entire year when everyone else is going hard on promotions.

And it takes some real awareness of what people are actually feeling in that moment—overwhelmed, skeptical, tired of being pitched at from every direction they turn.

Reading the room matters. Sometimes the best way to stand out when everyone's inbox is overflowing isn't to yell louder than all the other people yelling... it's to be the one person who shows up and doesn't yell at all.

What I'm taking away from all this

There's been a lot of interesting stuff happening in the market lately—things I've been watching and thinking about and learning from as I observe what's working and what's falling flat.

I'm excited to share more of it with you over the coming weeks as I process it all.

And no, I don't have some high-ticket program to pitch you at the end of this one. Just some observations from a fellow marketer who spends way too much time reading emails and probably overthinks all of this stuff more than is really healthy.

But hey, that's what makes it interesting.

Talk soon,

Jason