Observations and Inferences

This week, I got a question on TikTok asking me how I feel about the idea of "building a personal brand."

To me, when people talk about personal brands, what we’re really talking about are things like name recognition, credibility, associated value and ultimately, the degree of trust you hold with an audience.

The way I see it, there are two ways to make money with an internet business: You can build an audience and then charge companies for access to that audience (think influencer, affiliate marketer, podcaster with ads) or you start the company and sell products and services directly to those people (the entrepreneur).

Most business owners I know sit somewhere in the overlap between these two, ensuring a variety of income streams. Which is convenient, because in both instances, your #1 job is to build an audience of people that trust you — people that trust your recommendations, your ideas, your insights and/or your taste.

I won’t lie, there’s something...

Working with creative people, one of the questions I hear most is "Should I start a Substack?" 

It’s not hard to understand why. We hear stories of people making hundreds of thousands of dollars per year with the platform, some even receiving 6-figure advances from Substack itself.

To the creative mind, this sounds like a no brainer. After all, "getting paid well to write about stuff I care about" is what all writers want, and, frankly, is not always that easy to find.

But are platforms like Substack all they're hyped up to be? Or is it another quintessentially American "Hope you got there early!" money rush?

That's the question I'm hoping to help you answer in today's blog.

Substack: The latest big new thing

A little background: I’ve worked in content marketing for the last 8 years. I started in 2014, right at the very beginning of the “pivot to video” era that drained newsroom budgets and led to thousands of talented...

If you ask the Instagram ads, an evergreen marketing strategy will save your life. It will clear your acne, clean your house and get your entire family out of debt. Needless to say, it seems like “evergreen marketing” is the latest mythical, top-secret strategy in the entrepreneurship industry.

But what is this evergreen thing all about? The truth is, it’s not as complicated (nor as foolproof) as it sounds.

They name “evergreen marketing” comes from the evergreen tree. Evergreens, as they’re called, grow and hold onto their green leaves all year. They don’t turn orange and lose leaves in autumn, nor do they go dormant in winter.

So in essence, an evergreen marketing strategy is one that aims to attract, nurture and make offers to people all year round. The strategy, which acts like a hypothesis, asks you to experiment with an automated marketing system.

In this article, I'll offer you the structure of that experiment. We'll do it the old...

I spend a lot of time thinking about science fair projects.

I grew up in middle schools, so the aesthetic is familiar to me. Tri-fold project boards, scalloped trims, staying up 'til 2 am cutting dolphins out of a picture book because you left it for last minute, trying to be quiet because Mom had to drive to Walmart at midnight so now she's annoyed and probably exhausted but also you both know it's funny.

As a teen girl who was explicitly uninterested in anything involving the use of numbers, the simplicity of the science fair process was good for me: Problem/Question, Hypothesis, Observations, Results, Conclusions.

Even if you found yourself making up a month's worth of observation logs about a cucumber growing process that never technically happened, the science fair formula was easy enough to work with. Plus, you got to make it pretty, which I am intrinsically good at.

All in all, my relationship to...

Surprise: I'm leaving New York! I'm in the process of packing up my whole life (again) and moving down to the Washington, DC area. This transition has me thinking a lot about coping with change, or the idea of being in-between.

We've been talking a lot about this at Pretty Decent this month, mainly because it's a question so many people struggle with. When we're in-between, in the messy middle, it can get real anxious real fast.

After all, if you're always waiting for the next thing to happen, you inevitably start sweating a little wondering when it'll arrive (or how it'll feel when it finally does).

When it comes to coping with change, or being comfortable in-between, to me it becomes a question about tension.

What do we do with the tension that comes up when we're in-between big life changes?

The feeling I've had for the past few weeks is almost like the moment right before a big sneeze. My body feels taught, rigid — like it's waiting for something that hasn't...

Last night, I found myself scrolling through Pretty Decent's Instagram feed. If there had been a microphone in my head at the time, I'm certain it would've picked up the rumblings of...

...well, to be frank, a hater.

"This looks like shit," I thought bitingly to myself.

Naturally, I then went and looked for all of the Instagram accounts in my industry who were clearly doing a much better job than me at branding. Their perfectly kerned text and color-coordinated feeds sneered at me from the other side of my phone.

I felt my body tense. I'm sure if I had done a scan at that moment, I would've noticed clenched shoulders, a tightened chest. One thing I know for certain: It didn't feel good.

Luckily, I caught myself before I archived my entire feed and decided to quit social media and give up on all of my hopes and dreams. As I decided to be intentional about my reaction, a single thought popped into my head:

"No, it's not as good as it could be. But it's good enough for...

How do sites like Patreon and Substack work? Are they right for me as an independent creator?

I spent yesterday on a VIP Day with a client who was brilliant, deeply educated and insightful — exactly the type of person who could walk into a classroom and deeply impact the lives of anyone in the room.

There was only one problem: When she decided to branch off and create a Thing online to offer her expertise and share her gifts with the world...

...she did it on Patreon.

Tell me if I'm right here: You like the idea of getting paid to write. Or create. Or facilitate learning. Or host a radio show.

In your research (I know you research), you've noticed that platforms like Substack and Patreon present themselves as a vehicle to make that creative dream happen.

And yes, theoretically, they could be.

But for solo creative thinkers, or even small teams, in my consulting work I've noticed that when idea-stage creative entrepreneurs head to these platforms...

I sat down with Founding Member Lenéa Sims to discuss her experience since joining The Study. Here's what she said...

Pretty Decent: Let's start from the beginning. Where were you at when you first found Pretty Decent?

Lenéa Sims: We met at the very beginning of my business. I was at the point where I was finally ready to make a leap of faith, but I had no fucking idea what I was doing in terms of the business side. I just knew that I wanted to create my own space. And that I wanted to make something I hadn't seen before.

I didn't know, like, how to write my sales page, I didn't know how to actually find my audience. I didn't know how to do anything in any sort of strategic, structured way.

I remember feeling really lost all the time, like I was in the middle of the ocean with not a clue what direction to go in.

PD: Direction! Everyone says we help with finding direction. So what would you say was the first transformation that you noticed?

LS: So the...

This week at the Pretty Decent Internet Café, I taught the second part of our Sales module. Or I should say, the second part of what was supposed to be our Sales module.

About 20 minutes into last week’s lesson, it became clear that we liked the word “OFFER” better.

When I asked why “Offer” felt different than “Sales”, the chat exploded:

“Seems more friendly”

“Feels like you’re helping, like it’s reciprocal”

“It’s like a gift!”

And so, simple as that, we changed our language and the conversation changed direction.

The whole class reminded me of a question I got last week about designing online courses.

I’ve been running a question box on my story the last few weeks to inspire content ideas and find out where folks are getting stuck.

One person asked:

“How can a small biz compete with big businesses who offer online courses at almost no money!?”

Such...

I want to talk about why I think you should make an online course, despite how saturated you might feel the industry is. But to do that, we need to talk about Steve Jobs.

In 2005, Steve Jobs stood in front of an audience of new Stanford graduates and told them a story from his brief stint at Reed College. Although he dropped out after only a single semester, the college still permitted him to drop in on certain classes. Most notably, Steve Jobs dropped in on a calligraphy course.

It was in these calligraphy classes that Jobs learned about the archaic beauty of fonts — the difference between serif and sans-serif, how spacing and kerning influence the experience of viewing the design. He was entranced.

To quote him directly:

“None of this had even a hope of any practical application in my life. But 10 years later, when we were designing the first Macintosh computer, it all came back to me. And we designed it all into the Mac. It was the first computer with beautiful...