The Best Part About “Cringe-Worthy” Beginnings

Ever had one of those moments where you look back at something you started a long time ago and just think, “Man. I really sucked back then?”

Because last week I had one of those cringe-worthy experiences.

I’ve been writing the Caffeinated Entrepreneur newsletter for just over a year now, and a few months ago, I decided to start the podcast as a way to go “behind the brew” of certain issues.

The idea is that I am sharing what was happening in my business when I wrote it, and what I’ve learned since I wrote it… 6 months, 8 months, sometimes a whole year later.

Pick which newsletters to “brew into episodes” based on which past issues got a lot of engagement (higher open rates, more replies), the ones you people apparently couldn’t get enough of.

So when I pulled them up, I was ready to be inspired, but the irony was that some of the highest-engagement issues were some of my very first newsletters, and instead I was like… “oh my gosh, these are terrible!”

Like, I read them and genuinely thought, “How did I get anyone to keep reading when I was putting this out into the world with my whole chest?”

And when my podcast co-host, Bernie, and I started recording last week’s episode, I told him just that. I was laughing while cringing because I’m half proud and half mortified.

And Bernie just goes, “But that’s how everybody does it. You have to suck when you start.”

Which is annoying because he’s right, and the podcast we just started is the perfect example!

We are only 9 recorded episodes in, and it’s been like fumbling around in the dark without a flashlight, trying to find our groove.

We’ve had moments where we absolutely nailed the topic. And we’ve had moments where we’re like, “Where were we even trying to go with that?” Thank goodness for editing software!

I imagine we’ll still be figuring it all out in real time for the next 6 months, but we’re also having fun in the process and, somehow, people are already listening and enjoying it (or so they tell me with purely unsolicited feedback, so I’m going to assume it’s genuine).

Cringe is proof of growth

So here’s what I want you to steal from my little cringe-fest:

You can’t improve what you won’t start.

If you don’t put anything out there, you’ll stay stuck in your head forever, tweaking a version that doesn’t exist. Starting gives you real feedback, real reps, and something you can actually make better.

Your first draft / first launch / first anything? It’s allowed to be bad.

Version one isn’t supposed to be polished. It’s supposed to be proof you showed up. The people who win aren’t the ones who nailed it on day one, they’re the ones who kept publishing long enough to get good.

You don’t need to be “ready.” You need to be moving.

Readiness is a moving target perfectionists use to keep themselves safe from judgment. Momentum is what builds confidence, not the other way around.

One of my all-time favorite quotes is this…

Weekly Challenge

1) If you’ve been doing your thing for a while:

Go look at the beginning. The first post. The first client. The first launch. The first “please don’t judge me, internet” version. Then give yourself credit for how far you’ve come.

I’m not asking you to not cringe. I’m telling you to give your past self a well-deserved pat on the back for plowing through the hardest part and embracing the suck so you could get where you are now!

2) If you haven’t started (or you keep stopping):

Put a date on the calendar to start, publish, or launch…whichever one you are getting ready for. And I mean a real date. Not “soon.”

Then ship the first version knowing it’ll be clunky and imperfect, and that’s literally the point.

But a little word of advice from someone whose been through this process a time or two or ten:

You don’t get good just because you started. You get good because you stay in it long enough to build the muscle.

But staying in it is hard when you’re relying on motivation, and that’s why you need systems.

Systems are how you keep showing up on the days you’re tired, busy, distracted, or questioning every life choice.

Systems are how you use discipline when inspiration is nowhere to be found.

So if you want to build AI-powered systems that make consistency easier, whether that’s your newsletter, your podcast, your lead gen funnel, your promotion plan, your client delivery, or your team ops, literally ANYthing business related, reply to this email or DM me the word SYSTEM.

I’ll ask you a couple of quick questions, and we’ll map what systems your business actually needs and how AI can support them so you can stop starting over and start getting momentum.

So yeah, cringe a little if you need to and keep going anyway.