Why does it have to be uncomfortable?

• • •

That’s my friend Marcus Blankenship asking about The Expertise Incubator. He said it’s fine for me to attempt to answer his question in view of my email list. Here’s his full question:

Why does it have to be uncomfortable?

Isn’t there another way?

If you convince me there really isn’t, then how can you prepare people for the type of discomfort they will experience?

Financial discomfort
Psychological discomfort
Physical discomfort
Emotional discomfort

Where on the “pain scale” does this discomfort lie? A 1 or a 10? What should I be ready for?

Finally, though it might cause great emotional discomfort, what steps do you take to reduce that? Novocane? Ibuprofen? Recovery room? Cold compress?

How long is the “recovery” period? When does it start becoming comfortable again?

When the process involves discomfort, it seems like selling the process is as important as selling the outcomes.

I’m sure you know all this – and now I do too. Thanks for listening. 😉

It’s 6:28am on December 27 as I start to answer this question. By 7:30 or so I am sure I will have written an honest answer to the question; one that will also read like an advertisement to some people.

I’m biased, of course. I remember starting the practice of daily publishing around the second week of January, 2016. Let’s call January 20th my daily-publishing-aversary. I’ve been doing this for 4 years as of Jan 20, 2020. And it’s been extremely beneficial for me, so it’s hard to conceive of not doing it.

Those 4 years have taught me: it’s uncomfortable. Hell, it’s uncumfortable to me right now, 4 years in, for a combination of reasons (got sick for a few days before Christmas, lost momentum, recently shut down the paid segment of the list, feeling a bit at sea about what would be the ideal combination of serving me and serving y’all).

There was a time when it wasn’t uncomfortable! That was maybe 18 or 24 months in, for a glorious ~12 month period of time. Hard to be sure exactly when, but I remember the feeling: I felt like a badass. I could pump out these emails that followed a pretty narrow format of wacky/fun story -> transition to making a point about positioning/specialization -> transition to a call to action to sell something. If I had 20 minutes, I’d get it done in 20 minutes. If I had more, I’d probably indulge because it was fun, challenging-enough-but-not-overly-challenging, and it produced tangible short and medium term results (conversations with list members, product sales, services sales). That’s the flow state on a platter 5 days a week!

I earned that extended flow state state. The first 3 months of publishing daily were brutal! The next 15 or 21 months were easier, but still an education. It took real effort, applied over time.

And then I wrecked that flow state in April/May of this year with the paid list experiment. I learned a lot and wouldn’t do it any other way, but it destroyed the status quo, and I’m still seeking a new, improved status quo. I feel self-conscious about the experimentation and changes. That’s uncomfortable too.

And now I’ve led 9 TEI participants through this daily publishing practice in the first challenge of that program. And I’ve been a student of others and their daily publication. I’ve seen a pattern.

Month 1 to Month 3: You’re “feeling the burn”. The discomfort is largely mechanical, meaning you’re incorporating a new time-consuming activity into an already-full schedule, so the source of the discomfort is the change required to accomodate the writing.

A wiry, jumpy, caffeinated sort of enthusiasm for the challenge pushes you through this mechanical discomfort, and while the writing is not easy, but it’s relatively easier than it’s gonna get because you’re writing about what’s easiest for you to write about.

I call this the Expertise Enema because you’re flushing out of your system the easiest-to-describe but easiest-to-replicate version of your expertise.

Month 4 to Post #100: Your writing, time management, and other “muscles” have adapted to this new practice. You’re no longer feeling the burn, and the Expertise Enema continues at a good clip. Look at all those stinky posts accumulating! The discomfort level has declined to that equivalent of a brisk walk up stairs.

Then at some point, probably before post number 100, you hit the wall. The Expertise Enema has concluded, and you’re out of things to say. Or so you think. That modest level of discomfort you were enduring spikes, and you see your whole tidy world of daily publishing threaten to crash and burn in front of you.

You feel shame about that. You feel doubt about the depth, value, and relevance of your expertise. I pray you keep publishing, even in the midst of this new psychological and emotional discomfort.

If you follow my advice, you keep publishing and you take some risks in your content. Maybe you risk repeating yourself; you revisit an old topic, but with a renewed attempt to explain it through analogy or in a more fundamental way. And you have a breakthrough the third or tenth time you try this.

Or maybe you risk speculating about a topic of value to your clients, but you move from speaking from firsthand experience to speaking from your point of view (the place where you stand). And a list memember writes back saying “I’ve never seen it this way. Thank you!”.

As you take these risks, you develop new capabilities and assets:

  • Unique content that comes from your point of view (POV).
  • Unique ways of explaining things that feel like how genuine experts explain things. You’ve heard that old saw about how any fool can make something complicated, it takes a real expert to make it simple. You start to lay hold of this capability to simplify.
  • A deep rumble of confidence begins to resonate through your writing.

After Post #100: You might start to innovate in your content. Your writing has become equal part marketing tool and expertise laboratory, and you start trying some risky experiments in your laboratory.

Not every daily publisher proceeds to this third phase of discomfort and achievement. Some avoid this level of risk-taking entireley. Some restrict this experimentation to their client work under the umbrella of prototypes or “this is a good idea; let’s hedge things carefully but try it and see what happens”. Some do it only in their personal side projects.

The discomfort here is also a doubt about relevance, but unlike the previous doubt (about the depth of your expertise), now you question whether you’re going too far. Too far into edge cases? Too far into philosophy? Too far into untested speculation?

• • •

That’s a map of the discomfort you’ll probably experience if you commit to publishing daily for let’s say a year or two. It’s like the Middle Eastern Meal at El Gamal restaurant here in Taos (highly recommended restaurant, BTW): it’s a big platter with a variety of forms of discomfort laid out on it, each with its own unique flavor.

The least discomfortable place is after post #100 and before you experiment with innovation content. I don’t know what his take on it would be, but I see Seth Godin as parked in this spot. Because his topic (marketing writ large) is broad, he has plenty to deal with even without committing any list bandwith to innnovation content.

There’s no shame in doing what Seth is. It’s likely to deliver an ideal ROI on the time you invest in the daily publishing. Innovation content is quite risky by comparison. But some of us go there anyway. We don’t mind the discomfort in light of the potential reward.

This is getting long, so let me answer the rest of Marcus’ questions in a lighting round.

How can you prepare people for the type of discomfort they will experience?

  • The aforelinked podcast at is an attempt.
  • This email is an attempt. 🙂 That’s why I went into as much detail as I did.
  • I can invite them (you?) to join a paid cohort of The Expertise Incubator and be among a small group of others who are embracing the same series of challenges and feeling very similar discomfort. In other words: don’t do it alone.

Where on the “pain scale” does this discomfort lie? A 1 or a 10? What should I be ready for?

  • It’s less painful that even an un-messy, un-acrimonious divorce. My first marriage ended when my wife left me for a cult leader. The divorce was remarkably “clean”. That was way more painful than daily publishing ever has been for me.
  • I needed to end my first business partnership in order to experiment more without risking another person’s wellbeing. That was more painful than daily publishing has ever been for me.
  • Back when I was doing copywriting work, a client said he was disappointed in my work. That was momentarily very painful, but if we could take that momentary pain and dilute it over a 6-month time period, maybe we have an equivalent for the discomfort of publishing daily.

The bottom-line discomfort of publishing daily, and therefore of TEI, is the discomfort of being visible in a new way. There are safer ways to earn visibility for your business. I haven’t found any with more profound long-term rewards, though.

A TEI cohort starts up on January 13. Please REPLY if you’re at all interested and we’ll talk about whether it makes sense for you.