Daily(ish)

Hockey is back and I’m still feeling chilled after being at the rink, especially with the gray, foggy weather. But this is not a weather podcast. I’m genuinely enjoying recording, publishing, and even editing every day, and the repetition has made it easier to turn on the mic and find things to talk about.

Links Mentioned in This Episode:

Topics:
00:00 November Check In
00:20 Hockey Rink Chill
00:47 Six Days A Week
01:07 Finding The Groove
02:29 Guests And Discord
03:03 Treadmill Habit
03:55 Supporter Shoutouts
04:41 How To Subscribe
04:55 Closing Thoughts

Did You Know?

• I've got a newsletter you can subscribe to here that I send out most Tuesdays.
• I've had a blog for 20+ years you can check out here.
• If you don't like listening to me, you can find me elsewhere on the internet.
• You can check out some other podcasts I recommend here.

Support the Show
There are three ways you can support what I do online:

• Share the podcast with friends who might like it.
• Join other supporters on my Patreon with a monthly donation.
• Send a one-time donation via Stripe.

I talk with Dan Ryan, a software developer who also volunteers in digital equity work in Chattanooga, about using AI cautiously, political manipulation via social media data and AI-generated personalization (including podcast intros), a smart-home setup using Home Assistant, and how Dan finds hope for the future in the midst of all the things going on in the world today.

Links Mentioned in This Episode:

• Home Assistant
• Organize Against the Machine Podcast
• Obama Presidential Center in Chicago
• Django.com
• The Newsroom TV series
• Barack Obama’s 2004 “Audacity of Hope” speech
• dryan.com
• The Mammoth by Dave Rupert
• ShopTalk Show Discord
• Daily(ish) — Episode 293
• Daily(ish) — Episode 294

Topics:
00:00 Intro
00:22 Meet Dan Ryan
01:45 Day Job Explained
02:54 AI Ethics and Use
06:00 Local Models and Old Algorithms
08:20 Home Assistant Setup
13:52 Obama Campaign Origins
16:47 Campaign Tech Chaos
21:43 Politics Tech and AI Threats
28:45 Finding Hope and Organizing
31:49 Where to Find Dan
34:24 Wrap Up

Did You Know?

• I've got a newsletter you can subscribe to here that I send out most Tuesdays.
• I've had a blog for 20+ years you can check out here.
• If you don't like listening to me, you can find me elsewhere on the internet.
• You can check out some other podcasts I recommend here.

Support the Show
There are three ways you can support what I do online:

• Share the podcast with friends who might like it.
• Join other supporters on my Patreon with a monthly donation.
• Send a one-time donation via Stripe.

I’m venting about Canadian banking frustrations, especially with CIBC business banking and TD’s Visa site. I spent hours on the phone with CIBC for a simple request, got bounced between numbers without direct transfers, and was hung up on while they looked up my account. After paying monthly business fees since starting my freelancing account in 2008, it’s been extremely frustrating to get decent support, especially as branches disappear in favor of poor online/phone experiences.

Links Mentioned in This Episode:

• Sign up for WealthSimple

Topics:
00:00 Intro
00:42 CIBC Support Runaround
01:26 Fees Without Service
02:24 Why Banks Went Online
02:54 Alternatives for Sole Props
03:20 Switching to Wealthsimple
04:11 What You Really Need
05:01 TD Visa Website Woes
05:33 Share Your Grievances
05:35 Subscribe and Tomorrow's Guest

Did You Know?

• I've got a newsletter you can subscribe to here that I send out most Tuesdays.
• I've had a blog for 20+ years you can check out here.
• If you don't like listening to me, you can find me elsewhere on the internet.
• You can check out some other podcasts I recommend here.

Support the Show
There are three ways you can support what I do online:

• Share the podcast with friends who might like it.
• Join other supporters on my Patreon with a monthly donation.
• Send a one-time donation via Stripe.

A few late night thoughts and comments on the passing of Sir Patrick Stewart.

Links Mentioned in This Episode:

• All Good Things

Topics:
00:00 Intro
00:15 Busy Day Filler Episode
00:39 Addams Family Night Out
01:09 Remembering Patrick Stewart
01:33 2026 Losses Reflection
01:53 Where to Reach Me
01:59 Subscribe and Sign Off

Did You Know?

• I've got a newsletter you can subscribe to here that I send out most Tuesdays.
• I've had a blog for 20+ years you can check out here.
• If you don't like listening to me, you can find me elsewhere on the internet.
• You can check out some other podcasts I recommend here.

Support the Show
There are three ways you can support what I do online:

• Share the podcast with friends who might like it.
• Join other supporters on my Patreon with a monthly donation.
• Send a one-time donation via Stripe.

I talk about my ongoing struggle to find a to-do list/CRM system that actually sticks for both client work and home life. Looking back, I found a 2014 episode where I was dealing with the same problem and using Trello and Todoist. Now I’m experimenting with Finalist. Finalist looks great and helps roll unfinished tasks forward, but it also tries to be a journal/planner, which can feel like too much.

Links Mentioned in This Episode:

• Todoist
• TickTick (stuck with it the longest)
• Apple Notes
• Apple Reminders
• Notion
• Trello
• Things
• Obsidian
• 2Do
• todometer (from Cassidy)
• Finalist
• Daily(ish) Ep 38 from 2014 - Managing Ideas and To-Dos

Topics:
00:00 Intro
00:15 Why To Do Apps Fail
01:29 A Tour Of Past Tools
02:13 Repeating Tasks And Follow Ups
02:53 The Real Problem Avoidance
03:26 Two Systems Family And Work
04:48 Trying Finalist This Month
05:44 Obsidian Temptation And Complexity
06:29 Wrap Up And Listener Feedback

Did You Know?

• I've got a newsletter you can subscribe to here that I send out most Tuesdays.
• I've had a blog for 20+ years you can check out here.
• If you don't like listening to me, you can find me elsewhere on the internet.
• You can check out some other podcasts I recommend here.

Support the Show
There are three ways you can support what I do online:

• Share the podcast with friends who might like it.
• Join other supporters on my Patreon with a monthly donation.
• Send a one-time donation via Stripe.

Reflecting on two recent conversations with two different friends - one who is having to switch to a work from home situation, and another who is setting up a new coffee shop business - and how my own situation compares.

Links Mentioned in This Episode:

Topics:
00:00 Welcome to Dailyish
00:16 Why Solo Work Fits
01:12 Linear Workflows Thrive
02:05 Missing Coworker Moments
03:31 Hiring and Business Cycles
04:26 Coffee Shop Contrast
06:02 Your Take

Did You Know?

• I've got a newsletter you can subscribe to here that I send out most Tuesdays.
• I've had a blog for 20+ years you can check out here.
• If you don't like listening to me, you can find me elsewhere on the internet.
• You can check out some other podcasts I recommend here.

Support the Show
There are three ways you can support what I do online:

• Share the podcast with friends who might like it.
• Join other supporters on my Patreon with a monthly donation.
• Send a one-time donation via Stripe.

I missed recording on Sunday because I felt low-energy and uninspired. I’m trying not to beat myself up, and this year-long daily project helps me keep going even when I don’t feel inspired. A cool highlight that came out of doing this show was Transistor.fm’s customer service after a listener contacted them with an interesting request.

Links Mentioned in This Episode:

• Transistor.fm

Topics:
00:00 Intro
00:26 Low Energy Weekend
01:34 Analytics And Motivation
02:40 Recent Guest Chats
03:06 Transistor Shirt Story
04:23 Supporters And Memberships
05:23 How To Subscribe
05:38 Sign Off

Did You Know?

• I've got a newsletter you can subscribe to here that I send out most Tuesdays.
• I've had a blog for 20+ years you can check out here.
• If you don't like listening to me, you can find me elsewhere on the internet.
• You can check out some other podcasts I recommend here.

Support the Show
There are three ways you can support what I do online:

• Share the podcast with friends who might like it.
• Join other supporters on my Patreon with a monthly donation.
• Send a one-time donation via Stripe.

For today’s Saturday chat I’m joined by Josh “Triple Threat” Collinsworth (design engineer at Cloudflare, blogger, and game designer), who I know from the ShopTalk Show Discord. We talk about Josh’s former company Deno was acquired by Cloudflare, remote-work continuity, and dig into the daily puzzle-game renaissance including Josh’s new browser-based PWA puzzle game Tupo.

Links Mentioned in This Episode:

• Deno runtime for JavaScript
• Cloudflare
• Tupo
• JoshCollinsworth.com
• Wordle
• Clues by Sam
• Inkwell Games
• 25c: A Video Game Podcast
• ShopTalk Show podcast
• ShopTalk Show patreon

Topics:

• (00:00) - Welcome and Guest Intro

• I've got a newsletter you can subscribe to here that I send out most Tuesdays.
• I've had a blog for 20+ years you can check out here.
• If you don't like listening to me, you can find me elsewhere on the internet.
• You can check out some other podcasts I recommend here.

Support the Show
There are three ways you can support what I do online:

• Share the podcast with friends who might like it.
• Join other supporters on my Patreon with a monthly donation.
• Send a one-time donation via Stripe.

I asked my friend Spencer to play hockey correspondent and help me understand the ramifications of the Winnipeg Jets trading goalie Connor Hellebuyck, break down the players they got in return, and how the Hellebuyck drama compares to Spencer’s favourite team, the Detroit Red Wings, own drama involving Dylan Larkin as well as other players tied to last year’s U.S. Olympic team.

Links Mentioned in This Episode:

• Hellebucks
• Spencer on Bluesky
• Spencer’s blog

Topics:
00:00 Intro
00:47 Hellebuyck Trade Fallout
01:38 Breaking Down The Return
04:03 Jets Outlook After Deal
07:10 Heritage Classic Timing
07:57 League wide Trade Requests
10:41 Olympic Team Drama
14:56 Next Jets vs Devils Game
17:39 Wrap Up

Did You Know?

• I've got a newsletter you can subscribe to here that I send out most Tuesdays.
• I've had a blog for 20+ years you can check out here.
• If you don't like listening to me, you can find me elsewhere on the internet.
• You can check out some other podcasts I recommend here.

Support the Show
There are three ways you can support what I do online:

• Share the podcast with friends who might like it.
• Join other supporters on my Patreon with a monthly donation.
• Send a one-time donation via Stripe.

I got a YouTube comment asking if I’d ever bring back my old podcast about podcasting, Show Me Your Mic. It ran from 2013 to 2020 for about 130 episodes (mostly interviews) and eventually slowed down due to scheduling fatigue, work, and COVID. The show was an open invite for podcasters to talk about their gear, motivations, and whatever was happening in podcasting, and it also let me meet people I otherwise wouldn’t.

Links Mentioned in This Episode:

• The Structure of a Podcast (ep319) - YouTube
• Show Me Your Mic
• Paul Kafasis Talks Rogue Amoeba
• Part 1 with Lindsay Patterson
• Aaron Mahnke - Caring About All the Parts
• The Podcast — Lore
• Raygan Kelly and Nate Heininger of The Short Game
• Tyler Stalman - The Most Minor Celebrity Possible
• Justin Jackson
• Lex Friedman - Your Stats are Totally Bogus

Topics:
00:00 Dailyish Intro Setup
00:19 Show Me Your Mic Origins
00:51 Why The Show Ended
02:02 Memorable Guests Highlights
04:00 Could It Return
05:09 Interviewing Today Saturdays
05:44 Where To Listen

Did You Know?

• I've got a newsletter you can subscribe to here that I send out most Tuesdays.
• I've had a blog for 20+ years you can check out here.
• If you don't like listening to me, you can find me elsewhere on the internet.
• You can check out some other podcasts I recommend here.

Support the Show
There are three ways you can support what I do online:

• Share the podcast with friends who might like it.
• Join other supporters on my Patreon with a monthly donation.
• Send a one-time donation via Stripe.