Weekly Dispatch – Thinking About a Better Web

Weekly Dispatch - Thinking About a Better Web

The web is a prickly place. Its facets are infinite—some lustrous, like the opportunity to discover fascinating people and ideas. Other facets are opaque, like the abuse and hatred that threatens people’s safety. It can be a dark place. And yet, people continue to build community, create art, share ideas, and tell stories. I’m curious about that impulse — the impulse to build a better web.


A List Apart does an amazing job of collecting and publishing long-form, thoughtful essays about building a better web. Here are a few I’ve enjoyed:

The Pastry Box Project, Natasha Lampard – Such a lovely story about building companies that stand the test of time: “What if, instead of focusing on exits, we focused on sticking around?”

The Friend and the Follower, Closr.to – “Why do we feel so alone when we’re supposed to be more connected than ever?”

Designing Platforms (For) Trust, Gunther Sonnenfeld – “…it’s one thing to want to trust someone, but it’s another thing to hold trust, earn trust and share trust with other people … So, it seems we can design for trust, but we don’t actually design trust itself, nor do we really ‘engineer’ its mechanisms.”

The Web’s Grain, Frank Chimero – “What would happen if we stopped treating the web like a blank canvas to paint on, and instead like a material to build with?”

The Internet’s Original Sin, The Atlantic – “It’s not too late to ditch the ad-based business model and build a better web.”

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My Anti-Victory Story

Caligater - My Anti-Victory Story

I’d like to tell you a story about the last few years. A story about anti-victory.

I was feeling good: I had left my job at a marketing agency in order to go to graduate school full time. I blazed through my master’s classes. In just a handful of semesters I knocked my coursework outta the park. I was set to finish my degree quickly, and then go for a terminal degree in my field. I planned for a career in academia. I had a great plan in place. I was pursuing a dream to get my master’s.

While I worked on the classes required for my degree, I started freelance work in marketing communications. I figured freelancing would give me a flexible schedule and room to focus.

So as I worked on classes, I also grew my freelancing work, which grew my income, which grew my business skills. Although working for myself was challenging, I had happy clients and forward momentum.


Then, I walked off a track just a few feet from the finish line.


The track: grad school.

The finish line: graduating with a master’s degree.


With classes complete, I was ready to work full-time on my thesis—the culminating document for my degree that would take at least two semesters and lots of hours to complete. I had no classes to attend and no one to report to, and I believed that sort of academic flexibility would work perfectly with my flexible freelancing. I was confident that I just needed six months or so of focused time to research and write the thesis, and then I could earn my degree. The flexibility of freelancing and unrestrained research would empower me.

But all that flexibility turned into a neglect vortex. I didn’t realize how all-consuming working for myself would become. As I focused on freelance work, week by week and month by month I lost sight of my thesis work.

So here’s what I did over the next three years:

Freelanced, built a steady and fruitful business

(Ignored thesis research and writing)

Joined a startup

Got laid off from the startup

(Continued to ignore thesis work)

Joined a high-growth company

Changed careers from marketing to business development

(Realized I was no longer enrolled in the grad program)

Hired an executive coach

Reapplied to grad school, on the urging of my executive coach

Got back into grad school

I stepped back on the track. I had to do a couple extra laps to make up for my time away, but I’m back in the race. But it doesn’t feel as victorious as I might have thought. Stepping back on the track feels a bit shameful.

Well-meaning family and friends tell me I’m in the home stretch. But I don’t feel like it. I’m not sure I’ll ever feel like it.

I still fight resistance, impostor’s syndrome, and shame, including but not limited to the following types of moments:

Not finishing something I started

Having to answer “How’s your thesis going?” one more time

Failing to meet expectations (mine or others’)

Disappointing loved ones

Disappointing myself

Being my own saboteur


But, I’m doing more laps on the track right now. I have:

Finalized my committee, which is made up of three interesting (and challenging) scholars

A regular weekly study night

A monthly study date with other grad students

A whole bunch of loving people holding me accountable


Still, finishing my degree no longer holds any luster.

The possibility of completing my thesis—and thus finally finishing my master’s degree—doesn’t look like success. It looks like… completion.


I’m often thinking about how I define success and failure. And frankly, I’m not sure that there is a difference between winning and losing. If there is a difference, it’s ever so slight.

I doubt I’ll feel victorious when I finish my thesis. And I’m okay with that.

It will feel like an anti-victory.


Immeasurable, immense gratitude to Sandy Grason (@sandygrason) for being the impetus and the driving force of this writing.
Thank you, @joecardillo, for your feedback.
Photo credit. 

Weekly Dispatch – Love and Things

Caligater - Weekly Digest - Love and Things

Hey there. If you would indulge me for a bit, I think you’ll enjoy this digest.

I’ve been thinking about love, and the curious and magnificent shapes it takes.

My nephew wrapping his arms around my neck in a hug

The older man who gently took his wife’s elbow as they crossed the street

A text message that simply says, “Hi. Was thinking boutcha”

The barista pouring hot milk onto a shot of espresso just so

A friend asking for help

Discovering a herd of deer on a morning walk

And this list of heart-swells goes on. All of these are simply moments of connection.

And now, on to the digest.


If you read only one thing from this dispatch, let it be this: From Afghanistan, With Love by Mujib Mashal

Write a hand-written letter to someone.

“Walking around a city you’ve loved someone in can break your heart with every corner you turn.” Learning How to Love Again is Like Learning How to Walk Again by Austin Gunter

On “strange truth” in the movie InterstellarLove and Gravity on The New York Times

This article has made the rounds online. I find it fun and fascinating. To Fall in Love With Anyone, Do This

For love of place, and seasons: Mountain Snow, Fire Prayer by Craig Mod

Some poetry: On Love by Kahlil Gibran

(If you can’t see the video, click here to watch on YouTube.)

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