Ben Callahan
@bencallahan.com
Curious guy, systems thinker, Founder of Redwoods, The Question, & Sparkbox, design system consultant and coach. Loves coffee, photography, poetry, volleyball, and cheating at hide and seek.
https://bencallahan.com/
https://sparkbox.com/
https://bencallahan.com/
https://sparkbox.com/
Took a few moments to document my takeaways from @zeroheight.com Converge #designsystems conference.
Fair warning, this is not your standard tech blog post.
bencallahan.com/convergance
Fair warning, this is not your standard tech blog post.
bencallahan.com/convergance
Convergance - bencallahan.com
“A location where airflows meet, characteristically marked by an upwelling of air.” It’s been a while since I’ve had a week like the last week of
bencallahan.com
November 3, 2025 at 1:50 AM
Took a few moments to document my takeaways from @zeroheight.com Converge #designsystems conference.
Fair warning, this is not your standard tech blog post.
bencallahan.com/convergance
Fair warning, this is not your standard tech blog post.
bencallahan.com/convergance
October 30, 2025 at 10:06 AM
The Question Episode 063 is open and ready for your answers! It's about the agreements needed between #designsystems in a system of systems architecture. Should be a nice deep dive into some niche systems thinking!
Answer by Wed to get an invite to the deep dive on Thur!
bit.ly/answerTheQue...
Answer by Wed to get an invite to the deep dive on Thur!
bit.ly/answerTheQue...
October 20, 2025 at 11:48 AM
The Question Episode 063 is open and ready for your answers! It's about the agreements needed between #designsystems in a system of systems architecture. Should be a nice deep dive into some niche systems thinking!
Answer by Wed to get an invite to the deep dive on Thur!
bit.ly/answerTheQue...
Answer by Wed to get an invite to the deep dive on Thur!
bit.ly/answerTheQue...
Reposted by Ben Callahan
We’re going downhill fast, with Design Downtime’s 50th episode!
Chela Giraldo Loves Downhill Longboarding | Podcast Episode on RSS.com
This episode is going downhill fast, as Chela Giraldo joins us to talk about her love of extreme longboarding. She describes her journey from discovering longboarding while working at a skate shop in ...
rss.com
October 16, 2025 at 3:02 PM
We’re going downhill fast, with Design Downtime’s 50th episode!
@johnonolan.bsky.social truly enjoyed your presentation at @penpot.app fest. 🙏
October 10, 2025 at 9:58 AM
@johnonolan.bsky.social truly enjoyed your presentation at @penpot.app fest. 🙏
Jumping into an accessibility workshop with Layshi Curbelo at @penpot.app Fest!
Great storytelling right out of the gate!
Great storytelling right out of the gate!
October 9, 2025 at 12:58 PM
Jumping into an accessibility workshop with Layshi Curbelo at @penpot.app Fest!
Great storytelling right out of the gate!
Great storytelling right out of the gate!
Wildly impressive demo of Token Script at @penpot.app fest from @mikekamminga.bsky.social
October 9, 2025 at 10:06 AM
Wildly impressive demo of Token Script at @penpot.app fest from @mikekamminga.bsky.social
Watching @gloria.design share some designer ↔️ developer nuggets at @penpot.app fest!
October 9, 2025 at 10:02 AM
Watching @gloria.design share some designer ↔️ developer nuggets at @penpot.app fest!
Reposted by Ben Callahan
Turns out Design Systems Office Hours is quickly becoming the hey-we're-still-here-design-system-podcast.
We need more design system podcasts folks. Grab a mic and record.
We need more design system podcasts folks. Grab a mic and record.
October 7, 2025 at 2:29 AM
Turns out Design Systems Office Hours is quickly becoming the hey-we're-still-here-design-system-podcast.
We need more design system podcasts folks. Grab a mic and record.
We need more design system podcasts folks. Grab a mic and record.
Reposted by Ben Callahan
You know it's gonna be a good week when you start it off talking to DESIGN SYSTEM WIZARDS @nathanacurtis.bsky.social and @bencallahan.com!
October 6, 2025 at 10:46 PM
You know it's gonna be a good week when you start it off talking to DESIGN SYSTEM WIZARDS @nathanacurtis.bsky.social and @bencallahan.com!
New #designsystem recaps and articles from the last week or so:
- Episode 062 Recap (video): bit.ly/4nUMNYh
- Evolving DS Skills (article): bit.ly/3KQLnz0
- Episode 061 Recap (video): bit.ly/46NadaA
Currently working on the article for 062 on the constant pressure to go faster. More soon!
- Episode 062 Recap (video): bit.ly/4nUMNYh
- Evolving DS Skills (article): bit.ly/3KQLnz0
- Episode 061 Recap (video): bit.ly/46NadaA
Currently working on the article for 062 on the constant pressure to go faster. More soon!
Recap: Design System Speed Pressure (The Question, Episode 062 with Jeremy Elder)
A recap of The Question Episode 062 with co host Jeremy Elder on the pressure to go faster that so many design system teams are feeling. We explored some new concepts to help frame our perspective on this common challenge. Links for you to check out: • Our sponsor, zeroheight (https://bit.ly/4pMqQvI) • The Episode 062 FigJam (https://bit.ly/42kcatB) • The Episode 061 Raw Data (https://bit.ly/4nsIlj6) • Ben on LinkedIn (https://bit.ly/3T6rd5S) • Ben's Studio, Sparkbox (https://bit.ly/4a4Gg6G) • Jeremy on LinkedIn (https://bit.ly/3WkY4W6) • Redwoods Design System Community (https://bit.ly/redwoods-ds) Join the next episode of The Question here: https://bencallahan.com/the-question Join Redwoods design system community here: https://bit.ly/redwoods-ds Stay in learning mode!
bit.ly
October 6, 2025 at 12:31 PM
New #designsystem recaps and articles from the last week or so:
- Episode 062 Recap (video): bit.ly/4nUMNYh
- Evolving DS Skills (article): bit.ly/3KQLnz0
- Episode 061 Recap (video): bit.ly/46NadaA
Currently working on the article for 062 on the constant pressure to go faster. More soon!
- Episode 062 Recap (video): bit.ly/4nUMNYh
- Evolving DS Skills (article): bit.ly/3KQLnz0
- Episode 061 Recap (video): bit.ly/46NadaA
Currently working on the article for 062 on the constant pressure to go faster. More soon!
New article live: Evolving #designsystem Skills, how our tools are shaping the necessary skills needed to be a thriving design system practitioner and what we can do to bring up the next generation of systems thinkers.
bit.ly/3KQLnz0
bit.ly/3KQLnz0
Evolving Design System Skills - bencallahan.com
Any artist will tell you that the tools they use impact their art. The same is true for us—the tools we use in our design systems work certainly
bit.ly
October 3, 2025 at 9:34 PM
New article live: Evolving #designsystem Skills, how our tools are shaping the necessary skills needed to be a thriving design system practitioner and what we can do to bring up the next generation of systems thinkers.
bit.ly/3KQLnz0
bit.ly/3KQLnz0
Would love to spend the day with you in Bristol, UK!! Grab a spot in my #designsystem culture mapping workshop!
Alrighty, that's Converge officially sold out! See y'all in three weeks! 🥳 @zeroheight.com
October 2, 2025 at 10:10 AM
Would love to spend the day with you in Bristol, UK!! Grab a spot in my #designsystem culture mapping workshop!
Episode 062 of The Question with Jeremy Elder is LIVE. This week, we’re considering how #designsystem teams can deal with the pressure to go faster.
Answer (bit.ly/answerTheQuestion) to join the deep dive!
👏 Thank you to @zeroheight.com, the organizers of Converge, for making this one possible! 👏
Answer (bit.ly/answerTheQuestion) to join the deep dive!
👏 Thank you to @zeroheight.com, the organizers of Converge, for making this one possible! 👏
The Question is a weekly conversation for anyone seriously interested in Design Systems.
Each Monday, you’ll receive an email from me with a design system related question. You’ll have 48 hours to answer. If you choose to do so, you’ll receive an invite to the deep dive on Thursday (or Fr...
bit.ly
September 29, 2025 at 3:17 PM
Episode 062 of The Question with Jeremy Elder is LIVE. This week, we’re considering how #designsystem teams can deal with the pressure to go faster.
Answer (bit.ly/answerTheQuestion) to join the deep dive!
👏 Thank you to @zeroheight.com, the organizers of Converge, for making this one possible! 👏
Answer (bit.ly/answerTheQuestion) to join the deep dive!
👏 Thank you to @zeroheight.com, the organizers of Converge, for making this one possible! 👏
Nice addition to our deep dive from yesterday!
Side chat from this week's The Question with @bencallahan.com and @natalyathree.bsky.social triggered another hot take. 🔥
blog.damato.design/posts/design...
blog.damato.design/posts/design...
Design Attractors
Chaos theory meets design systems.
blog.damato.design
September 27, 2025 at 3:42 AM
Nice addition to our deep dive from yesterday!
The Question Episode 061 with this week's co host @natalyathree.bsky.social is LIVE!
Answer here bit.ly/answerTheQue... and join us on Thursday at Noon Eastern for the deep dive into how our skills as #designsystems practitioners are evolving.
See you Thursday!
Answer here bit.ly/answerTheQue... and join us on Thursday at Noon Eastern for the deep dive into how our skills as #designsystems practitioners are evolving.
See you Thursday!
September 22, 2025 at 12:06 PM
The Question Episode 061 with this week's co host @natalyathree.bsky.social is LIVE!
Answer here bit.ly/answerTheQue... and join us on Thursday at Noon Eastern for the deep dive into how our skills as #designsystems practitioners are evolving.
See you Thursday!
Answer here bit.ly/answerTheQue... and join us on Thursday at Noon Eastern for the deep dive into how our skills as #designsystems practitioners are evolving.
See you Thursday!
Last chance to answer this week’s #designsystems survey!
bit.ly/TheCoreSampl...
We’ll close it at noon Eastern 🙏
See you Friday at The Redwoods Quarterly!
bit.ly/TheCoreSampl...
We’ll close it at noon Eastern 🙏
See you Friday at The Redwoods Quarterly!
September 10, 2025 at 11:54 AM
Last chance to answer this week’s #designsystems survey!
bit.ly/TheCoreSampl...
We’ll close it at noon Eastern 🙏
See you Friday at The Redwoods Quarterly!
bit.ly/TheCoreSampl...
We’ll close it at noon Eastern 🙏
See you Friday at The Redwoods Quarterly!
Reposted by Ben Callahan
Where AI Is Failing Design Systems, and Where We Are Failing AI, by @bencallahan.com:
https://bencallahan.com/where-ai-is-failing-design-systems
#ai #designsystems
https://bencallahan.com/where-ai-is-failing-design-systems
#ai #designsystems
Where AI is failing design systems, and where we are failing AI - bencallahan.com
For a design system program where the goal is often stable, high quality, durable output, how much instability, lack of quality, or impermanence can
bencallahan.com
September 9, 2025 at 7:30 AM
Where AI Is Failing Design Systems, and Where We Are Failing AI, by @bencallahan.com:
https://bencallahan.com/where-ai-is-failing-design-systems
#ai #designsystems
https://bencallahan.com/where-ai-is-failing-design-systems
#ai #designsystems
Time is almost up!
Happy Monday, system nerds. You have until Wed at Noon EST to answer The Core Sample (an industry-wide, #designsystem pulse survey).
I want to hear how you're doing. 💚
We'll unpack it at The Redwoods Quarterly, but we need your help to make it happen.
bit.ly/TheCoreSampl...
Happy Monday, system nerds. You have until Wed at Noon EST to answer The Core Sample (an industry-wide, #designsystem pulse survey).
I want to hear how you're doing. 💚
We'll unpack it at The Redwoods Quarterly, but we need your help to make it happen.
bit.ly/TheCoreSampl...
September 8, 2025 at 12:31 PM
Time is almost up!
Happy Monday, system nerds. You have until Wed at Noon EST to answer The Core Sample (an industry-wide, #designsystem pulse survey).
I want to hear how you're doing. 💚
We'll unpack it at The Redwoods Quarterly, but we need your help to make it happen.
bit.ly/TheCoreSampl...
Happy Monday, system nerds. You have until Wed at Noon EST to answer The Core Sample (an industry-wide, #designsystem pulse survey).
I want to hear how you're doing. 💚
We'll unpack it at The Redwoods Quarterly, but we need your help to make it happen.
bit.ly/TheCoreSampl...
Reposted by Ben Callahan
Our friend @bencallahan.com, who runs The Redwoods Quarterly - an online design systems event happening Friday, 12th September from noon to 3.30pm (ET), is offering us a discount. Simply fill out the core sample survey linked below and secure a 50% off code with: 'zeroheightDeal'. hubs.li/Q03GSxRq0
September 4, 2025 at 12:58 PM
Our friend @bencallahan.com, who runs The Redwoods Quarterly - an online design systems event happening Friday, 12th September from noon to 3.30pm (ET), is offering us a discount. Simply fill out the core sample survey linked below and secure a 50% off code with: 'zeroheightDeal'. hubs.li/Q03GSxRq0
Reposted by Ben Callahan
Love seeing you all at Converge! Please buy a ticket 👇 #designSystems
Very excited to launch Converge 2025! This year we're bringing a day of design systems goodness to Bristol, UK on October 30th, with some of the best speakers from around the world. 🤩 Super-early birds tickets are available now for £99 + VAT. Don't miss out: converge.zeroheight.com?utm_campaign...
April 8, 2025 at 11:19 AM
Love seeing you all at Converge! Please buy a ticket 👇 #designSystems
Reposted by Ben Callahan
I'm really excited to be participating in the upcoming virtual #DesignSystems webinar - The Redwoods Quarterly!
I'll be presenting about using #WebComponents in design systems. Hit me up if you'd like a discount code.
www.tickettailor.com/events/learn...
I'll be presenting about using #WebComponents in design systems. Hit me up if you'd like a discount code.
www.tickettailor.com/events/learn...
Select tickets – The Redwoods Quarterly – Zoom
The Redwoods Quarterly is an interactive online design systems event presented by Redwoods and hosted by Lauren LoPrete and Ben...
www.tickettailor.com
August 29, 2025 at 7:13 PM
I'm really excited to be participating in the upcoming virtual #DesignSystems webinar - The Redwoods Quarterly!
I'll be presenting about using #WebComponents in design systems. Hit me up if you'd like a discount code.
www.tickettailor.com/events/learn...
I'll be presenting about using #WebComponents in design systems. Hit me up if you'd like a discount code.
www.tickettailor.com/events/learn...
Reposted by Ben Callahan
How to convince executives not just to fund the initial push of design system work, but to keep funding it.
alistapart.com/article/sell...
alistapart.com/article/sell...
The Never-Ending Job of Selling Design Systems
You didn’t start your web career to be a politician or salesperson. But if you want to work on design systems, you have no choice. Ben Callahan shows you how to convince executives to fund the init…
alistapart.com
August 26, 2025 at 5:11 PM
How to convince executives not just to fund the initial push of design system work, but to keep funding it.
alistapart.com/article/sell...
alistapart.com/article/sell...
I sat down with @nathanacurtis.bsky.social to process what we both took away from The Question, Episode 060 on where #AI is failing #designsystems.
TLDR: the amount of work to get AI to solve certain problems well may be more than what most folks are willing to put in.
Watch here → bit.ly/45OYI1A
TLDR: the amount of work to get AI to solve certain problems well may be more than what most folks are willing to put in.
Watch here → bit.ly/45OYI1A
Recap: Where AI is Failing Design Systems (The Question, Episode 060)
A recap of The Question Episode 060 with co host Nathan Curtis on where AI is failing us as design system practitioners. We settled on this idea: until an AI model can guarantee the promises your design system makes, AI is best treated as a collaborator that scaffolds, accelerates, and proposes—not a factory that ships. Links for you to check out: • The Episode 060 FigJam (https://bit.ly/4fIwbzs) • The Episode 060 Raw Data (https://bit.ly/4mrPBv9) • Ben on LinkedIn (https://bit.ly/3T6rd5S) • Ben's Studio, Sparkbox (https://bit.ly/4a4Gg6G) • Nathan on LinkedIn (https://bit.ly/4aG68Vs) • Redwoods Design System Community (https://bit.ly/redwoods-ds) Join the next episode of The Question here: https://bencallahan.com/the-question Join Redwoods design system community here: https://bit.ly/redwoods-ds Stay in learning mode!
bit.ly
August 25, 2025 at 2:45 PM
I sat down with @nathanacurtis.bsky.social to process what we both took away from The Question, Episode 060 on where #AI is failing #designsystems.
TLDR: the amount of work to get AI to solve certain problems well may be more than what most folks are willing to put in.
Watch here → bit.ly/45OYI1A
TLDR: the amount of work to get AI to solve certain problems well may be more than what most folks are willing to put in.
Watch here → bit.ly/45OYI1A