Welcome to Post Anyway: the newsletter for entrepreneurs & creatives who are great at what they do, but terrible at talking about it.

I have a client who recently celebrated 100 newsletters in a row.

That’s 100 weeks with ZERO missed issues. That’s NUTS, and most certainly something to be proud of.

And when I think about that, I spiral into a mental gymnastics routine, convincing myself that because I don't have that level of consistency, I must not be serious about my work.

While that’s obviously untrue, it’s easy to feel that way. Take this newsletter, for instance: We’re 12 days into 2026, and you’re just now hearing from me.

Mistakes and slip-ups offer an open door for negative thinking. Specifically, thinking along the lines of: You broke the streak. You ruined it. Why bother starting again?

In their own way, these negative voices believe they’re helping you.

They’re offering you an out. A reason to throw your hands up and remove yourself from whatever uncomfortable goal that you’ve set.

Weirdly, this makes me think of a TikTok I’ve seen recently, where someone asks: “If the only reason you aren’t going vegan is that you don’t want to give up bacon… why don’t you just go vegan, plus bacon?”

@addietheoptimist

this idea applied to so many aspects of your life - stop making arbitrary rules for yourself, it prevents you from actually reaching your ... See more

This applies to anything! Why anchor yourself to an all-or-nothing mindset when you can just compromise? We treat our creative habits like fragile glass that shatters once we miss a day.

In 2026, I want to be the type of person who tries again.

It is much easier to quit than to fail, feel bad for a moment, and show up the next day.

How to try again (when you've "broken the streak")

I love these little freaking penguin gifs.

This advice applies to newsletters, but it also applies to all the other commitments we make in life: Workout plans we abandon three weeks in, business ideas we shelf after a single “no,” content we stop posting right before we start seeing returns.

Here’s what I’m doing — I hope it helps you, too:

1. Kill the comparisons

That 100-week streak isn’t mine, but not because I suck. It simply belongs to someone else with different circumstances, different brain chemistry, and a different life.

Comparing myself to that is like comparing my body to someone with a completely different genetic makeup and then feeling bad that I don't look like them.

Your version of consistency doesn't have to look like anyone else's. Last year, I barely managed one newsletter a month. This year, if I hit two a month, I'm literally doubling my output. It’s all about perspective, people!

2. Reframe "starting over" as "continuing"

Taking a break isn’t the same thing as quitting, which is something I need to get through my thick skull.

When you miss a week, you're not back at zero. You're at week [however many you actually did]. The habit didn't disappear just because you skipped once.

Now, if it helps you to think of things as “fresh starts,” you can ignore this one. But, to me, a fresh start means zero foundation, and that’s more daunting than picking things up where I left them.

3. Remove friction from your habits

What's the thing that makes this sustainable for you? For me, it's giving myself permission to write shorter newsletters when I need to, or to send something imperfect, because “imperfect and sent” beats “perfect and stuck in drafts.”

What's your “bacon”? What small compromise makes the thing actually doable instead of theoretically perfect?

4. Get comfortable with disappointing yourself

I know, woof. But it’s true: You're going to fall short of your own expectations sometimes. And you have to be okay with that person, the you who didn't meet the goal, and still show up for them next week.

5. Remember there's a version of you who did nothing

This one is, perhaps, the most important. Somewhere in the multiverse, there's a version of you who never tried at all. Who never published that first newsletter, never posted that first piece of content, never started the thing.

You're already beating that version of you!

Real talk: I have a ton of lofty goals in place for 2026.

I want to grow my LinkedIn to 12K, book speaking gigs, and of course, finally hit that first $100K year. I want to host ten events through my new community here in Pittsburgh, and I want to travel internationally at least once.

I'm probably going to fall short on some of them.

But the alternative, protecting myself from failure by not even trying, would be the only real loss, you know?

I’d love to know: What are you trying this year?

Reply and tell me. I want to know what you're picking back up, what streak you "broke" that you're restarting, what you're doing even though you're scared you'll mess it up again.

P.S. If you're struggling with what to post or how to make your content strategy actually work without selling your soul, reply to this email. I read every single one.

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