Medium Rare turns 250: Five things I've learned from five years of blogging

Medium Rare turns 250: Five things I've learned from five years of blogging

On July 13th, 2014, I published my first Medium Rare blog post right here on ChicagoNow. Since that time, I’ve written 249 posts ranging from philosophy to comedy to whatever bucket you’d put my four-part sandwich saga into. Each time I’ve hit a milestone (100th post, 200th post) I’ve taken a second to reflect on what I was thinking about at those exact moments.

My two previous posts rambled and bounced around between multiple topics. I was trying to squeeze too many thoughts together. So, today for #250, I’m gonna try to at least keep things organized.

But first, a look at the previous mile markers. My 100th post ended with this:

This last piece of advice is as much to you as it is to myself: Don’t worry about whether or not you can make a career out of blogging or writing. That stuff is out of our control and isn’t a reason not to get started. Instead, get your voice out there, because even if you have just one person saying, “I was thinking the same thing!” well, that’s a pretty awesome way to start the week.

And the 200th post:

For the next 100 posts, I’m going to try and change my fuel. Keep up the production, but also focus on the post-production too. I’m going to see what I can learn about marketing, try some new things out, and see what happens. I’m not sure what I’ll have to report two years from now, or whenever the 300th post will be. I may have a three-part series on how to market your blog, or I may finally publish that three-part series on why you should give tomatoes another chance.

It’s funny to read that last line because it turned out to be pretty prophetic. On one side, I have spent a lot of time learning Facebook, LinkedIn, and Instagram marketing. And my day job has switched from sales to content marketing. But I’m also fresh off writing a four-part series on a fictional sandwich battle. That’s not very far off from a three-part, “Why you should give tomatoes another chance” series.

The overarching theme in both of my previous mile marker posts was all about finding a higher purpose for the blog. I seemed to be wrestling with the question: If my blog posts are never going to have 100,000 views, it’s still worth it because of X. I was trying to solve for X like I was back in high school algebra. Was it the writing itself? The process? The connection with readers?

When I was compiling a Top 5 list for post #250, I found the dominant thoughts were all about the creative process itself.

1. Everything is a blog post

For me, the biggest difference between Year 1 and Year 5 is the depth chart. By depth chart I mean all of the ideas that are written down, hanging out “on the bench” for a future post.

This isn’t true for each idea, but I’m finding a lot of enjoyment scrolling through my list and remembering where I was for the initial lightbulb moment.

A few examples:

Diet Coke courtroom battle – This one hit me last week. I was sitting at Halal Guys working up the courage to add their blistering hot sauce onto the gyro meat platter. For some reason, I chose to get a Diet Coke instead of a regular Coke. I was looking at the can of Diet Coke and remembered my parents having it on the boat when we were growing up. But also how many people my age and younger are huge Diet Coke fans. So, is Diet Coke for millennials or baby boomers? Maybe that could be a debate. What if the debate took place in a courtroom? Reach for my phone. Jot it down. Not sure what it will become, but I know there’s something there.

We’re overusing the “is back” advertisement – I was in Quiznos about to order the $5 sandwich of the day. I looked up at the menu and they had two signs hanging from the ceiling. “The lobster roll is back!” “The bread bowl is back!” And I thought to myself, “I never knew those things were gone.” Are we overusing the “is back” slogan? Reach for my phone. Jot it down. Not sure what it will become…

Maybe “just have fun” was secretly profound advice – Had this one, literally seconds ago. I went to the bathroom, was thinking about where I’d go with this post, and wondered, “Am I going to end up with the cliche` advice of ‘just have fun?'” I thought back to the little league coaches who would say, “Hey, just go have fun out there” or, “As long as you are having fun.” These expressions get a bad rap because we’ve kind of merged them together with the “everyone gets a trophy, the score is zero-zero” philosophy. But I think “just have fun” is a different idea altogether. You can have that be the guiding light and still be extremely competitive. Reach for my phone. Jot it down…

I mean those are three incredibly mundane moments. Two lunches at work and a trip to the bathroom at home. But in Year 5, I carry Medium Rare around with me everywhere. When I’m publishing regularly, it literally changes the way I see the world. Even in the most regular everyday moments.

2. The very best stuff comes with a fight

It’s weird, some of my favorite posts started with the most resistance. The ones where I eventually got in a flow often began with staring at the screen for a few minutes or writing one sentence, deleting it, trying again, deleting it, and feeling stuck for fifteen minutes. Other times it was the morning when I hit the snooze button four times, felt horrible, had kind of this anxious feeling in my stomach when I sat down and opened the laptop.

It seems like the very best stuff comes with a fight. And not even just the process itself, but when I look back on when the posts were published, I see a pattern of the best stuff usually coming during or right after a tough stretch of life. Granted, not always the case, sometimes life is good, writing is good, everything is firing on all cylinders, but other times writing serves as a light in the dark. If I’m ever going through a tough time at work, in life, maybe it’s just the heart of a Chicago winter, whatever it is, there’s a strange comfort in the thought, “Well, at least the writing will be good…”

3. Notes app and Trello

I love the idea of carrying a physical notepad around with me like Larry David. But I’ve given up on it, at least the pen and paper aspect.

Instead, I’ve fully embraced the phone. In the Notes app, I have one titled “Upcoming Medium Rares.” A little over a year ago, someone introduced me to the Trello app and I think this is an even better option. Especially if you have ideas for a bunch of different things, this helps organize things and functions like the Notes app on steroids.

4. The routine becomes really powerful

I don’t have to publish every Monday. It’s not like Modern Family or Game of Thrones where they have a strict weekly schedule to keep. Millions of people are waiting. The producers at ABC, HBO, they’re waiting. The writers and actors couldn’t just take a year off.

But I could. There’s nothing in a contract, no paycheck dependent on posting every week. And yet, I’ve made it personally feel like there is some sort of pressure, something at stake to publish every Monday morning (except when I’m taking a one-month blog writing vacation).

It’s really interesting to me because it doesn’t make a lot of rational sense. What is that motivation? Where does it come from? I know some people have it with running or working out every day, but man, once that routine takes hold it really does keep the production line moving along.

5. There’s no finish line… and that can be weird

When I first noticed I was at post #240, #241, #242 and started kicking around ideas for a 250th post, I had this thought of, “What’s the finish line for Medium Rare?” Is it when I hit post #1,000? Is it when I’m officially out of ideas? Or does it keep going for the rest of my life?

A blog is different than a book or a script. With those you hit a point where you know, yes, I could still make revisions, still improve it, but the story is complete. It’s finished, I’ve said what I needed to say. A blog is more like a journal or a diary; once it’s really taken hold, once you’re bringing it along to lunch at Quiznos or a trip to the bathroom, it doesn’t have an ending. Maybe the number of posts goes down for a season. Maybe it goes up. But, at least here at the Year 5 mark, I see no end in sight. I don’t think there’s a post I could write that would make me say, “Ok, I’m done now.”

Alright, sorry, one more – If you can, it helps to have a writing day and a revision day before posting. 

This one’s fairly new for me, but it’s helped a lot in terms of creating more cohesive posts. On Wednesday mornings, I write next week’s Medium Rare. On the following Monday, I either finish writing it or revise and edit. The four-day gap helps me see the rough draft with fresh eyes and ultimately cut parts out that I might have kept if I was trying to do it all at once (which is funny to say here at the 1,600-word mark. You’re probably thinking, “This is the condensed version?!”)

But above everything else, thank YOU for continuing to read and support the Medium Rare blog. I love sharing these stories and it means a lot to have you here; whether this is the first post you’re seeing or if you’ve been around for the whole five-year ride. Thank you!

Here’s to the next 250!

I’ll have a new post up on Monday, July 15 called, “I wasn’t ready to love Toy Story 4.” If you’re a fan of the Toy Story films or, better yet, if you’re hesitant to see Toy Story 4 because you think Toy Story 3 was the perfect ending and you don’t want to have that ruined, next week’s post is absolutely for you. Thank you for stopping by and see you next week!

And to see what’s going on with my new storytelling company, Long Overdue, check out the website here

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