If sharing your work feels hard, let's make it easier

How to move past the mental roadblocks that keep you from sharing

The other day, our kitchen sink clogged. It happened late in the day on a Saturday, and I immediately knew that most plumbers in the area generally work half day on Saturday and take off Sunday. Not great timing for a clog.

I thought I had prepared for this type of situation. I love plumbing, and had three different drain cleaning machines on hand, and a cursory knowledge of how to use them. But I soon found out: I was wrong. So instead, I paid $714 for emergency sink unclogging a couple hours later.

This has me reflecting on how writers and creators need to prepare to reach their readers differently than they might think. To not wait until you absolutely need to share and reach people before order to do so, such as right before a book launch.

So often, we collect the tools we need (“I setup a Bluesky account!”), or we collect the strategies we think will work (“I downloaded a worksheet on how to pitch podcasts”), but we miss the most important ingredients: practice. To test out strategies and tools, try new ideas and iterate on them, and move past the emotional and psychological barriers to sharing our work.

Today I want to explore how to develop those muscles so that you can share your work when it matters most: a book launch, publishing a newsletter, a dream pitch, or that time you happen to be in an elevator with your first choice for a literary agent. Let’s dig in…

Emotional and Psychological Preparation

It’s one thing to have a plan, and something else entirely to have tested the plan, running drills, uncovering the unexpected ways that you and others respond in the situation.

An example of this is a case study of a bestselling author that I shared 14 years ago. You can read the full version here, but these are the basics:

• Eric Ries set a specific goal to become a bestselling author.

• He took the entire year prior to his book launch off from his consulting firm, spending that year testing ideas for what would sell books.

• The only form of payment he would accept that year is book orders.

• He tested his marketing ideas prior to book launch, through promotions and events with real people.

• He was surprised at the results, and if he had relied on these ideas at launch, he likely would not have become a bestseller.

• In the process, Eric — a highly successful guy already — had to challenge his own assumptions, and accept that some of his “best” ideas simply didn’t work as he hoped. So he kept trying new things until he found what worked for his book at that time.

Too often, we justify that the ideas and plans alone can lead to success. If we just LOGIC this enough, it will work. It’s easy to feel that a good logical plan is enough. Here are some examples::

• “Oh, I’m preparing this incredible promotion that I think #bookstagrammers are going to love. I saw another writer do this and it worked so well.”

• “My podcast pitch to get me as a guest on shows is A-MAZ-ING. My friend is a podcaster and she loves it.”

• “I grew up with _____ who is an influencer, he has a huge following. He said he would support my book launch.”

But in the process, people tend to avoid preparing for the most difficult aspects of this work: emotional and psychological reactions from themselves, and their intended audiences.

Now, I love it when people plan a good cohesive strategy, and I spend my days helping writers do this. But we also go a step further into taking small cycles of action, learning from experience, and honing our strategies again and again based on real world results.

Without testing, you are unsure of what will work. I have talked to countless writers whose biggest strategic plans flopped, leaving them bereft, confused, and jaded.

For many writers and creators, the important thing to prepare for is social fear. I wrote about this in my book, Be the Gateway, that often the biggest barrier to success in sharing is our own innate fear of social situations. This can appear in a wide number of ways, including:

1. Fear of looking like a fool, so we don’t test anything before hand. Then, when we need people the most (like during a book launch), we take the smallest possible action so that if it doesn’t work, we save face.

2. Waiting too long to start. We justify this as “not putting the cart before the horse,” or trying to optimize people’s attention into a tiny window of time around book launch. E.G.: “Why share about my book now? It’s not even on sale for a couple weeks.” But that also creates an inordinate amount of pressure to get it right in one precise moment.

3. Communicating too infrequently, and asking too much at once. Often this is justified as, “Well, I don’t want to bug people or look desperate, so I will send one email to my friends and network, and tell them exactly what to do.” The result is an overly long email, with too many asks all at once, and zero follow up. A writer in that situation may get tons of responses where people say, “Congratulations on your book!” but they take no other actions that the author requested.

4. Starting every effort to share with an apology. This often looks like, “So this is the email I’m supposed to send asking you to pre-order my book, so here I am, begging you. Sorry, but that’s the publishing game!” Here, one frames the idea of communicating only because you were told you have to in order to serve the book, that it is a dreaded obligation.

5. Stopping way too soon. The moment one item doesn’t take off in a viral way, we feel embarrassed, and start sharing less, not more. We start justifying, “Word-of-mouth marketing is the only thing that works, and I’m not going to shout about my book, so if it was meant to be, it will just happen on its own.” So many writers share about their book only in the few weeks around launch, then abandon their efforts entirely.

6. Concluding that your one big idea or connection is enough. That this single plan is your big shot, and if that doesn’t work, then why bother with piddly other plans that feel like small potatoes (and also like a lot of work.)

The Problem of Knowledge Without Practice

In my plumbing story above, the thing is, I was so close to success with my effort to clear the drain, but didn’t know it. On the day of the clog, I knew how to undo the pipes under the sink and use the drain cleaning machine I had. But I sent it in and out of the pipe a few times, but I didn’t fix it.

Knowing that the later it got in the day, the less likely I could get anyone to come help before Monday, I panicked. I stopped trying to unclog it and got on the phone.

I called 4 plumbers, including 2 that I have good relationships with. None picked up. I called a 5th plumber who actually picked up, but he said he couldn’t help today, and told me to reach out to the big drain cleaning company in our area, giving me their number.

They answered, and she gave me two options: they can come first thing Monday morning, for around $400, or if I wanted to pay their “Saturday emergency service charge,” I would have to add an additional $300 to that, bringing it to around $700. She encouraged me to wait until Monday.

I was frozen. That was a lot of money to spend. I asked her if I could speak to the technician, which she graciously allowed me to do. He was super generous, and he too suggested I wait until Monday. Then he spent time telling me exactly what he would do, and in the process, mentioned how thoroughly he does the job, not just clearing the clog, but snaking the entire drain line to the sewer to ensure the broken up clog doesn’t clog again further down the line.

I told him to come over now, justifying:

1. Fix it once, fix it right.

2. $400 and $700 are both a lot of money. There is no cheap way out of this, so just get it done now, saving my family a day not being able to cook or do dishes.

3. I wanted to start our school and work weeks on Monday off right, not with zero clean dishes, and a clogged drain.

4. I told myself I would observe what the technician would do, and try to learn in the process.

Yes, I overthink things. Then I write essays about it! (I think that may be my new Substack tagline)

You see, I had bought the tools, but I didn't have experience with them. I didn’t adequately prepare for the emotional and psychological aspects of having to clear a clog. This is why I encourage you to prepare more fully for what it means to share your writing and how to ensure it truly connects with readers.

Unexpected Consequences

Another reason to prepare is to become aware of unexpected consequences of sharing. You see, attention can be a double-edged sword. I want to provide two examples of this.

Recently I shared a case study on how a 7-Eleven employee grew an audience of 200,000 subscribers. He spent 12 years dreaming of doing well on YouTube, when a video of his went viral, and his audience expanded rapidly. However, the other day, he uploaded a video talking about how he was considering quitting making videos. Why? Because of the psychological and emotional issues of having people suddenly care about his videos.

He says, “I'm struggling to make videos, because everybody has an opinion.” He’s not just talking about strangers, but is specific about how members of his family suddenly are taking interest, people he hasn’t spoken to in years are reaching out, and every single one of them is sharing their opinion on what he is doing.

So often, we want our work to be seen, but are unprepared for the unexpected consequences when that moment that happens.

Another example are one hit wonders in the music world. How a musician may spend years working so hard to achieve their dreams of success, only to find that they were not prepared for the reality of it.

I remember hearing the story of how the band New Radicals had a huge hit in the 1990’s with “You Get What You Give.” The guy behind the band, Gregg Alexander, had pushed so hard for years to find success. But soon after he hit it big, he broke up the band, got out of his record deal, and canceled the release of his newest song and video — which shocked his record label. The work was already done on it.

As Wikipedia puts it: “It was not long after New Radicals' success that Alexander became tired of the constant media attention and an exhausting touring schedule.”

Instead, he turned his attention to producing other bands, working behind the scenes. Now, this isn’t to assume his success was a misadventure. He has probably lived a deeply fulfilling life since that time, and has no regrets. But just imagine the years of efforts to achieve something, only to realize that it isn’t what you wanted after all.

What Preparing Looks Like

So how do we prepare? Well, this is how I am preparing for the next clogged drain:

• Before the plumber left on that Saturday, I showed him the machine I was using. He spent 10 minutes carefully explaining to me exactly what to do next time, and even made a modification to my machine so that it would be more effective. He said, “We love it when homeowners try to fix clogs themselves, so I’m happy to try to share some advice.”

• I have been watching dozens of videos on YouTube where plumbers show you how they unclog drains in various real-life situations.

• I created a step-by-step checklist for how to approach a clogged drain, and printing that out to put next to my tools in the basement.

• This is embarrassing, but for the largest and best drain cleaning machine I bought years ago, I had never actually taken it out of the box. So I did that, got it setup, and tested everything on it.

• I am clearing the area around our primary drain cleanout. Previously, I would have to move an entire shelf of my kids’ toys to access it, plus move a huge spare sink that we have down there. So even before I would try to clean the drain, I would have to make a huge mess to access the cleanout. No more.

• I am practicing. Actually going through the motions of using the machine, even if I don’t have a clog to clear. This helps identity simple problems that I can address now, when I’m not stressed.

• Storing the drain machine right next to the cleanout, and then putting a container next to it that has needed supplies such as gloves, accessories, checklist, bucket, towel, headlamp, extension cord, etc.

Our drain will clog again. Maybe tomorrow, maybe in 10 years. Regardless, addressing it will not require me to find the tools, move furniture, and have me trying to remember steps. Plus, I will sleep better knowing I am more prepared than I was before.

How do you prepare to share your writing and creative work before you really need to? As I’ve encouraged many times before, view sharing as a craft, a process that you can practice and slowly hone over time.

Let’s say you have a book launch coming up in 8 months. Perhaps you are planning to ask other authors for a blurb, or you want to pitch yourself on a podcast for the first time, or ask a friend to preorder or the book, or any number of items. Consider the emotional place you will be in if the very first time you do this is the moment you absolutely need these things to work.

How to prepare? Perform smaller less mission-critical versions of these tasks way before you need to be good at them. Then hone and repeat.

This is the time period where you can make mistakes and they won’t matter. When you can learn a valuable lesson and not feel it cost you anything. Where you can work through emotional and psychological angst.

Here is a simple example: let’s say that you plan to email each person in your network asking them to pre-order your book, and you want to do this 4-weeks before the book comes out. But right now, you are still 6-months away from launch. Why not send some of these people a “I was thinking of you” emails? It can be personal, it can be professional, it can be focused on their work or your own. But get used to reaching out to your network via email.

Besides this process helping you improve your communicate skills, wouldn’t it be nice if your network heard from you via email before they get an email that says, “Hi! Remember me? Well, I really need for you to spend $20 right now to buy my book.”

Or if you hope to pitch yourself on a few mid-sized podcasts that you love, why not pitch yourself to a smaller podcast first, or to a podcast that you won’t worry if you don’t get on. Just to work through the entire process before it truly matters to your book launch.

I’ve worked with thousands of writers in the past twenty years, and find that preparation is never going to be wasted effort or time. Those writers that I know who are especially good at how they share and engage with their readers tend to view how they share as a craft, one where they slowly improve over time by experimenting, learning, and showing up for their readers.

Please let me know in the comments: what scares you most about the idea of sharing?

For my paid subscribers this week, I shared Mini-Case Study on Lessons From Plumbers on Growing an Audience. Clearly, it’s “Plumbing Week” on my Substack. See a preview here.

Reminder: if you want to explore working with me, there are two ways I collaborate with writers and creators:

1. One-on-one consulting

2. My Creative Shift Mastermind, whose doors open up again in April

As always, thank you for being here with me.
-Dan

Kids of the Week: This is often where he is when I come home from work, straddling the typewriter:

A trip to the library for books on electronics:

Magic Tree House before bed: