Dear Designer,

It’s been about ten months since I started Dear Designer. It’s been my honour to put my weirdo ideas into the world and to have others, both weird and not, accept those ideas in their inboxes.

I’m planning on doubling down on the writing, and work even harder to create a newsletter that will be of value to you, dear designer. My focus will be increasingly on addressing the opportunities and struggles of designers in a changing and challenging social environment.

But I thought it might be interesting to share a little bit about the hows and wherefores of this newsletter and where I’m struggling to grow and to reach more people.

Writing is a daily activity, even when it’s not

I know this only finds you every week or so. But I actually find myself thinking about this newsletter every single day.

Sometimes, it engrosses me. On those days, I’ll write notes or do some research or plan new posts. On other days, I may be less obsessed about the writing but I’ll stress about you, my reader, and how design is changing dramatically and where we might head together.

I am genuinely worried about how various present and subterranean crises are dividing us designers from ourselves and from one another. These include generative AI’s transformation of our tools, the routinization of tasks that mask our commitments to values, the growing coarseness of our visual discourse, and the dearth of jobs in a market that values platforms over people.

To give you (and I) a sense of where my head is at, I thought I would frame some of my thinking in terms of various dichotomies. Polarities, despite their negative political connotations, provide useful framing devices for challenges; sometimes it’s helpful for me to position my own challenges in light of best versus worst in order to imagine what might emerge as plain old medium-good.

My newsletter challenges in oppositional form

Conceptual vs Practical

While my training and writing proclivities tend to be sadly and slightly academic, I really want this newsletter to speak to any graphic designer. How can I use language in a way that connects to folks while also staying true to my own voice and interests? How do I make sense of what is happening while also creating a newsletter that helps the most people possible in a very challenging design market?

For example, I am developing ideas for a number of useful digital “products” like a workbook to create a better portfolio and a short guide for those seeking jobs who are just out of school. I was able to bridge this conceptual-practical gap when teaching at the university and I want to bring that learning to more people here.

Please stay tuned for more details about these products and, more importantly, do let me know if there is a particular and practical topic of interest that you might want me to cover for you.

Audience vs Authenticity

While I desperately want Dear Designer to be helpful to individual designers, I also struggle with reaching a larger audience.

After all, who doesn’t want a smashing audience these days? There are influencers selling eye shadow application who have hundreds of thousands of followers while many lowly newsletter writers connect with a handful of folks. It makes no sense — and yet, and yet, there are dozens of people on Substack, Ghost, Beehiiv and Medium who are also rapidly growing their audiences with no advertising, no videos, and no fancy fanfare.

How do you keep your writing personal and honest while also ensuring it’s useful and deliberate in a cacophony of social media that tends towards the fake and fallow?

I’m sure that I can thread this needle because others (Joan Westenberg, Erin Kissane, Ethan Marcotte) do this so, so well. I and we are fortunate to have excellent online writers to emulate. This was not the case five or ten years ago to be honest. The meteoric rise of this platform (despite its ethical flaws) and others like it allows me to ask this question.

Free vs Paid

My vantage point is and will always be built around the indie web, which is where I started. I believe in independent, free, open, and unlimited expression, whether it is in print, online, live or some admixture of the three.

And while I ran a business for 20 years and continue to help drive agency growth today, I find it queasy-making to sell my own “content”. I believe in offering ideas freely. But like all weirdo writers, I need money to live and grow and shape the next stage of this newsletter. I don’t like the idea of creating false stratifications through tiered newsletter offerings — but I do want to be able to be paid for this work I’m doing.

Going paid (as of today)

Today, I’m opening up paid subscriptions to Dear Designer. To be clear, the newsletter will remain free at least for the time being. But anyone who wants to support my efforts will be wildly rewarded with my utter gratitude and a few other perks. I’ll be creating a shorter weekly newsletter to all paid subscribers about two areas which I find both most important and most helpful

1. Al and Design: My personal take on how Al is actually showing up in design from a practical and ethical standpoint.
2. Personal Practice: Short lessons from my work and career with a focus on ethics and typography.

To be clear, Dear Designer will still be free. But paid subscribers will get a little something something more.

You can upgrade by going to the homepage of this newsletter.

Social vs Spiritual

I believe that design is an inherently spiritual endeavour. I know I’m a little odd that way. But design has to be about more than information and ideology.

Yes, it is a political act to create new communications and to put ideas into the world. But design, with its deep roots in aesthetic investigation, metaphysical inquiry, religious metaphor, and semiotic history is also a fully psychic practice.

Design cannot be just about what it looks like and how it is received. It is also a form of mark-making that digs into and dramatizes and wonders and worries and thrills and trills. Our profession is much more than the sum of its parts — and one of my challenges is how far to profess, how far to press, and how far to stress in promulgating this arcane idea.

Minimalist vs Maximalist

I am planning on revamping my own portfolio site using Ghost and bringing a new journal there to the surface. That blog may be slightly different than Dear Designer; it will complement what I’m trying to do here. At some point, my plan is to bring Dear Designer over to Ghost, which is open source, nonprofit, and part of the growing fediverse.

This move may take six months or a year and, in the meantime, I’m trying to figure out how to keep this project of supporting designers minimal in personal effort and maximal in designer reach. I am also potentially bringing in other platforms like Gumroad, Kit and Tally to grow this newsletter, depending on how my strategy and planning continue to evolve. And depending on what you, dear designer, tell me along the way.

Me vs AI

I do not use generative AI to write Dear Designer. There are dozens of people on this platform and elsewhere arguing persuasively that writers should use AI to create and create quickly.

I refuse to do that.

Why would you want to be a writer if you don’t want to write?

Do you value your ideas enough to write them?

Do you want to learn from writing or just put words into the world?

AI provides the most critical challenge to creating since the advent of the printing press.

For but me, writing helps me to think, to study, to obsess — and to let go.

AI is, at its best, a writing crutch.

But I also refuse not to use AI. I will use AI on occasion for research, ideation, planning, and critical thinking. AI can be helpful to pressure-test some of my ideas. It can offer new perspectives on where I might focus my energies. And it can introduce new organisms into the Petri dish that is my brain.

Thank you

Again, I want to thank you for being a subscriber, dear designer.

If you have any thoughts on the above, please consider putting them in the comments below. And if you want to support this little project through a paid subscription, I’d be ever so grateful to even more in your inbox.

Wishing you a good Labour Day week ahead.

Yours,

Image of the Week

Growing up in the Philadelphia suburbs, you couldn’t help but not hear about Dorney Park, an amusement park in Allentown. I think I went a few times with my family as a kid but it was very, very strange. I probably became an early fan of David Lynch because of Dorney Park.

You can get a sense of what it was like from this poster advertising Labor Day Weekend.

“Free Ox Roast”? “The Original Rube band”? “King & Queen of the Apple Butter Party”? “Sauerkraut Village”? “Schnitzing Party?” Big clown head?

I am positive that Dwight Schrute went to Dorney Park as a kid. Founded in 1884, even the name “Dorney Park” gives me hives.

Quote of the Day

“If you have not yet learned the skill of absorbing rejection, court it deliberately: Apply for some jobs you really don’t think you’ll get so you can learn to decouple ‘no’ from surprise and dejection.”

— Cate Hall (1 September 2025)

Note: I started TypeQuote about in May 2025 to collect and share inspirational and otherwise opinionated quotes from and about designers, artists and writers.

Every day, a new and unproven quote appears on the site. These are not automatically generated, however; I literally copy and paste quotes I find across the web into this website — and I do my utmost to find a true attribution and source for every one of them.

Moving forward, I’ll re-use the quote of the day from TypeQuote here. That way, you can more easily find and share that quote — and perhaps discover a few others along the way.

To share this post with someone, here is a tiny, little button 4u 2 use.