Observations and Inferences

If you want your creative business to make money, your job is to find the point. This is what people mean when they tell you to develop a "messaging strategy."

Messaging is one of those words you'll start seeing everywhere once you know to look for it. But to the artist who just wants to sell art, it may seem confusing. Isn't messaging just copywriting? Is this another piece of jargon made up by consultants who want to sell things?

Answer: No and probably yes. But it's still worth digging into, if only for the sake of giving you something to think deeply about the next time you get outside for a walk.

What are you offering and why should anyone care?

This is the foundation of your messaging strategy. The business books will call it your unique selling proposition (USP), but it's less complicated than acronyms make it seem.

The easiest way to figure out your answer is to get into conversation. Maybe you're telling someone what you do and you get that tingly feeling inside,...

When's the last time you designed something for yourself?

I know, I know – we're in business to help other people. That's what the podcasts and courses and service offerings and products and commissions and 1:1 calls are for, right? To offer a solution or answer a question or respond to a need.

But what about you? What about what you need?

If you're not paying yourself a living wage, either because the business isn't generating enough revenue or because you don't think you're "ready to" yet...that's a systems problem.

If you're working long hours without any breaks, waking up in a cold sweat and reaching for your phone to see what passive-aggressive client email you received overnight...that's a systems problem.

If you want to take a sabbatical next year but don't know how you'll be able to step away from constant social media posting and come back to a surviving business...that's a systems problem.

That might seem redundant until you...

I spent last weekend at a bachelorette party. One of my best friends is getting married in January, and our little group reunited for the first time in five years. 

As you can imagine, we fell right back into place—in large part because we're all still fluent in our own hyper-specific language (made up mostly of Vine references, inside jokes and catchphrases coined after one too many bottom-shelf vodka crans).

In other words, we all just get it. When Makenna, the nurse, starts explaining the internal function and process behind a hangover, we all laugh when someone calls her "The Science Side of Tumblr." 

These inside jokes unite us, solidifying our existence as a "we." When we all giggle at a niche reference to a random night in 2014, we affirm to one another that we share the memory, that we all still belong.

This is a powerful human experience. The quest for belonging is one of our most powerful intrinsic motivations— as social creatures, we are...

If you want to "start before you're ready," plan for the you that doesn't feel ready. If you want to "do it scared," design a system for the you that feels scared.

This is what we talked about for the last 20 minutes or so of Big Paper Planning Day last Sunday. After spending the day together dreaming and planning and studying the science of motivation, a question appeared: How do I know if I'm ready to pursue this goal?

At Big Paper Planning Day, we employ a version of the 12 week year—a concept coined by Brian P. Moran and Michael Lennington that essentially boils down to "What if you get a new year (and all of the rituals and excitement that come along with it) every 12 weeks, instead of just once a year in January?

The 12 week year offers us a constraint. Constraints are good for creativity, provided we have space first to think divergently, without naysaying or judgement on the basis of "practicality." 

When we're in the divergent thinking stage, we don't...

I am sitting at a desk in my bedroom writing this to you. In a little less than an hour, a group of people will join me on Zoom for Big Paper Planning Day, and together we will plan out the next 12 weeks of our life. On Sunday, again, I will sit here at this desk and facilitate the same experience—holding conversations with people all over the world on what it means to try and how it feels to pursue the life we want.

This is my job, yes. 

And. 

You can imagine how absurd it feels right now.

The truth is, I feel ridiculous promoting the idea of life design and planning in the face of so much suffering and injustice. There is a large part of me that wonders whether there's any point in trying at all. 

This part of me is, I believe, frozen solid at 22 years old. That's how old I was on August 7, 2017, the day my Dad died. In moments like this, when grief is everywhere and beauty is hard to find, it is this 22 year old part of me that cries out...

I don't know how to tell you this, but running a creative business by yourself from your bedroom or office or phone is not always easy.

I know. Shocking, right?

Who would've thought that developing products and services, asking for feedback, negotiating rates, reviewing financial statements, designing a website, writing persuasive copy, performing on social media, managing a team and/or making constant decisions about what to work on or prioritize next would be challenging?

Sure, there are perks: I can shower whenever I want, for one. I have total creative freedom and almost no hoops to jump through in order to get an idea out.

But it would be unfair (to myself and to you) not to acknowledge that there are days when everything is hard and nothing feels like it's working.

After all, if we just ignore these hard parts and keep sharing highlight reels on social media, what happens?

Oh, right: We all go on thinking we're the only one struggling.

But...

You walk into your local café, excited to sit down and get some deep work done. Your usual seat is taken, so you glance around for another free one. That’s when you notice:

Everyone at this café is barefoot.

They’re seated at tables, sitting criss-cross-applesauce in booths, even walking into the bathroom…with no shoes on.

You glance down at your own feet, delicately laced up in your favorite pair of sneakers. You briefly wonder if this is some kind of practical joke. Then a thought crosses your mind:

Is it me? Did I miss something? Am I the weird one…for wearing shoes?

How Social Proof Influences Our Decision-Making

As humans, we tend to look to others for insight and clues on how to behave. This is a social and psychological concept called social proof, and it’s why we’re so obsessed with reading reviews and Reddit threads about products before we buy them.

Social proof is a strong form of influence. There are two...

I can't tell you how often people come to me and tell me they're ready to burn it all down and start over.

Usually these are people that have been in business for a while, growing their audiences and networks, selling a particular set of products or services. They've almost always come to "be known" for something, reaching a degree of success offering cooking tips or coaching sessions or parenting advice to people who trust them.

Then they get the nudge.

If you've felt the nudge, you'll know what I'm talking about. It's an inkling—an idea that just won't go away.

Sometimes the nudge is a name. Other times it's a stack of seemingly unrelated books that feel totally "off topic" but irresistible all the same.

For me, it was the phrase "Big Paper Planning Day." I just couldn't get it out of my head. I walked around (literally) for two years, wondering what it wanted to be, this cute little turn of phrase that felt so accurate to the way I organize my life....

You probably know the feeling. You’re stumbling across the Internet, maybe on the toilet or in a late night scroll hole, and a flashy 7-second video pops across your screen. Blue light fills your eyes as dollar signs and commas beg for your attention.

“How I made $7,345 today without leaving my bed”

“My client just had a $65,782 launch!”

“The morning routine of a 7-figure business owner”

“This, too, could be yours,” the captions often urge. “Learn how in my signature online course.”

These content assets reflect a strategy called income claim marketing, the practice of sharing earnings in an effort to build trust and affinity with an audience of potential buyers.

Like a lot of content marketing strategies, income claims are used to pull those who want to achieve a desired result into a sales funnel. That sales funnel will, eventually, sell them a product or service that promises to deliver upon the desired result...

A few weeks ago, a friend of mine burst through the door brimming with the joy of a new idea. I won’t spill the beans here, but it’s a good one—it solves a problem and is perfectly aligned with what he enjoys offering the world. It’ll stretch him a bit—he’s gonna have to learn a new skill in order to make it happen—but ultimately, I believe that creating this thing is going to be both fun and good for him as a person and an entrepreneur.

There’s only one problem:

He doesn’t know whether or not it’s going to work out.

How can entrepreneurs overcome the fear of failure and embrace the unknown?

People come to me with ideas. A lot. I have a tendency to get really excited about whatever the person who’s talking to me is really excited about, and I’m good at the Internet (launch strategy and marketing), which gives me something to offer founders.

The elephant in the room is, of course, always the potential for...