Daily writing retrospective

June 02, 2026

Back in April, I decided to write daily for my newsletter. Up to that point, my newsletter was mostly a delivery mechanism for my blog. But I wanted to change that. I wanted to write more.

This is what I said in my first post:

It’s been a while since I’ve written in my newsletter (hope you’re still here!)

In this age of AI, I find that I want to write more (not less) in my own voice. To me, writing is thinking, and I have a lot of thoughts rolling in my brain that I want to clarify and solidify – so what better way to do that than to write?

But I have to dust some cobwebs.

Well, I love Martin Fowler’s “if it hurts, do it more often” aphorism. I frequently say it in programming or business circles. Why shouldn’t it apply to writing as well?

So, I’m going to try to write daily (for 30 days) and see if it sticks. At least for week days (weekends might be tough). If that’s not interesting to you, you can always unsubscribe. But before you do so, give me a chance!

I hope that what I write is useful to you.

More than anything, I’d love to also hear from you.

If I write something that interests you or sparks something in your mind, I’d love to hear it. Maybe this can become more of a conversation than me screaming into the void.

Well… that’s it. Hope you enjoy the ride with me.

Best,

German

In my typical retrospective format, I’ll ask:

What went well?
What went wrong?
What could we improve?

What went well?

First, the wins.

I wrote a lot more!

I wrote 29 posts in a span of ~40 days. I missed some days. But for the most part, writing daily – and publishing daily – was a tremendous forcing function.

Nothing like a good deadline to force yourself to just ship.

It wasn’t easy. I had to make time for writing (typically at 5am), since I didn’t have time otherwise. And it took about an hour to write each short post. But I loved being able to ship daily, even when I wasn’t fully satisfied with what I wrote. (Don’t let perfect be the enemy of good, right?)

I published blog posts

Out of that daily writing, I also created three blog posts:

It helped me think

In my first post I said “to me writing is thinking”. And boy did it get me thinking.

Because I had to write daily, I was constantly thinking of what I would write the next day, jotting down some ideas and notes, and it did help me work through some of the “thoughts” I had in my head (the ones I mentioned in my first post).

It helped me connect with readers

One of the coolest things was when a reader responded to a post. I love connecting with others over ideas. And a few people responded to some of my posts excitedly agreeing, asking questions, or offering their perspective.

It was honestly one of the best surprises about writing daily. Before I started, I didn’t know what to expect: either utter silence or perhaps outrage (those are the fears in our heads). Instead, people were interested and excited.

To those of you who wrote back, thank you!

Because I connected with readers, and because I have now made my newsletter into a vehicle that is more than just delivering blog posts, I feel comfortable writing there.

That may not seem big, but it’s a huge win for me.

Before this exercise, I felt like my newsletter had an implicit agreement that it was purely a delivery mechanism for blog posts. After 29 posts, I think the people who only wanted it for that reason have unsubscribed. :)

So, overall, I’m very glad I did it. But I want to make some changes. So, on to the what went wrong section.

What went wrong?

It’s costly

I loved the forcing function of writing daily. But the reality is that it is hard to always wake up at 5am and write.

Sleep is very important to me. Due to previous health issues, I try to prioritize sleep as much as possible, and my kids are also grateful when I’m not grumpy and tired. And though I wish I didn’t need as much sleep as I do, I think making sure I sleep well is the right trade-off.

I also have a bad habit of wanting to do too many things. So, as I was writing daily, I was also exploring new AI workflows, recording a couple of remote pairing sessions (which I’m still editing), and trying to get more information on how other teams are using AI. Oh, and I also had to do my regular consulting job. That’s a lot to fit into a single week.

So, even though I love writing daily, there are days when it is more important that I get an extra hour of sleep or that I edit a video.

I forgot to decouple deployments from releasing

Another huge problem was that by writing daily, I meant publishing daily.

In software, I always encourage teams to decouple deployments from releasing software to customers. We tend to use feature flags for that. That way, you can deploy whenever you want – ideally continuously. But you only release a feature when it’s ready.

Well, if I’d done that with writing, I could have written daily but only published when I felt ready. In that case, I might have felt differently about some of my posts.

Which brings me to the next point.

Some ideas need more space and time

Publishing daily meant I couldn’t fully work out some of the thornier ideas in my head.

Some writing just doesn’t fit into a single day – or into a single email, for that matter. Many thoughts are just complicated, and I feel like I have to untangle them before I can write about them.

I mean, that’s part of the beauty of writing: it forces you to work out those complicated topics until you can explain them simply. But because I had to publish something every day, I just couldn’t spend the time I needed on the thornier ideas.

So, publishing daily sometimes forced me to write about a simpler idea at the cost of refining a thornier one.

Posts are siloed

This is a good and a bad thing.

Because posts are not available in the general internet (unlike a blog post is), I felt more okay with publishing things that I wouldn’t have otherwise. I don’t mean that the posts were bad, but there’s an internal pressure when I publish a blog post that I have to make sure it’s really good because some unknown masses will read it.

In reality, for all I know, more people actually read the newsletter posts than my blog posts. But because the blog posts are “out there”, I feel that pressure. And that pressure can lead to not writing. So, the siloing can be a good thing.

But it’s definitely sad that they’re siloed.

I want to write to communicate with others. And I love blogs because to me they are part of the beautiful fabric of the internet. People sharing learnings, lessons, and ideas without gatekeeping. So, I’m a little sad that I have things written that live in emails and cannot be easily shared.

What could we improve?

Having said all that, I hope to make some tweaks.

I won’t continue to put the must-publish-daily pressure on myself. I wish I didn’t have to remove that (I like the forcing function), but I have to prioritize other things right now.

But that doesn’t mean I’ll stop writing!

On the contrary, I hope to continue to write more. I’ll still make 5am my writing time. It works most days. I just might not be able to hit it daily.

And I will continue writing in my newsletter. But I hope to publish a lot more to my blog as well. In a way, I would love it if I could write daily on my blog. That’s a bit wild, but I think it’s the ideal.

And I also hope to make my newsletter more of a 2-way channel.

I want to continue connecting directly with readers of the newsletter. That was one of my favorite parts of writing daily, so I’m really hoping I continue doing that.

Write to me or send me your blog!

Finally, some parting thoughts.

First, if you’re reading this, thanks for reading! Thank you for giving me some of your precious time.

Second, I encourage you to write more! (Make sure you write, not the robots!)

If you’d like a reader, send me an email and send me your blog. I love discovering new blogs to read.