The Second Intermission

Welcome to The Second Intermission—a place for men in their 40s, 50s, and beyond who've lived enough life to have stories, questions, and something worth talking about.

I'm Jack—a retired Boston firefighter and lifelong maker. Around here we might talk cigars, travel, craftsmanship, getting older, make something in the workshop, or start with one subject and discover the interesting part somewhere else entirely.

The subject starts the conversation. The conversation is the point.

I like information. I just think it's better when it comes with something else—a story, experience, personality, and perspective earned by living awhile. I don't have all the answers. I have questions I'd like us to figure out together.

So pull up a chair. We've got some life behind us, plenty still ahead of us, and a lot worth talking about.

The game isn't over yet.

Business & Collaborations
📧 oldwax@dirtbagassociation.com

📦 The Old Snowboarder
PO Box 320130
1834 Centre St
Boston, MA 02132


The Second Intermission

Should you snowboard alone? I think every skier and snowboarder should experience the mountain solo sometimes.

Last season was one of the best snowboard seasons of my life, including an unforgettable trip to Niseko, Japan. At 50, I started wondering how I could possibly make this season better. My answer was simple: go more often. And sometimes that means going alone.

2 weeks ago | [YT] | 2

The Second Intermission

I've spent a lot of time thinking about what The Second Intermission is supposed to be and why anyone would want to sit down and watch me. On the surface, this channel can look like it's all over the place. One day I might be talking about cigars. Another day it's Scotch and clear ice, restoring cast iron, snowboarding, travel, retirement, getting older, or whatever else happens to be sitting on the workbench that day.

2 weeks ago | [YT] | 3

The Second Intermission

I took the smallest pension they would give me and retired early from the Boston Fire Department. Why would anyone willingly do that?

2 weeks ago | [YT] | 2

The Second Intermission

How do you get rid of cigar smell after smoking? If you enjoy cigars but your wife, girlfriend, family, or anyone else in your life doesn't enjoy the smell that follows you back inside, the answer isn't necessarily giving up cigars. For me, it's about mitigation.

3 weeks ago | [YT] | 2

The Second Intermission

When you hear someone say “that guy,” what’s the first thing that pops into your mind? Is it negative or positive?

3 weeks ago | [YT] | 4

The Second Intermission

We’ve all heard it: “Don’t be that guy.” But what guy are they actually talking about?

Because sometimes “that guy” is the loud, obnoxious person nobody wants in the room. Other times, he’s the guy everybody calls when something needs to be fixed, figured out, or understood.

I’ve spent a good portion of my life being “that guy,” and at this stage of life, I’m starting to think maybe that isn’t such a bad thing.

3 weeks ago | [YT] | 4

The Second Intermission

We’ve all heard it: “Don’t be that guy.” But what guy are they actually talking about?

Because sometimes “that guy” is the loud, obnoxious person nobody wants in the room. Other times, he’s the guy everybody calls when something needs to be fixed, figured out, or understood.

3 weeks ago | [YT] | 2

The Second Intermission

There are plenty of premium cigars I can buy. But at 50, I'm starting to appreciate that enjoying a cigar doesn't always have to be about finding the perfect cigar.

4 weeks ago | [YT] | 1

The Second Intermission

I sat down to roll a quick cigar and ended up talking about life, craftsmanship, producing instead of consuming, and why I created The Second Intermission.

The ideas are old. The sentences are not.

Thanks for watching.

1 month ago | [YT] | 1

The Second Intermission

It's been almost 10 years since I rolled a cigar.

This isn't a tutorial and it isn't a review. It's a workshop conversation while I get my hands dirty and rediscover a craft I used to practice every day.

The cigar isn't perfect, but it's one I'd be proud to hand to a friend. Sometimes it's nice to slow down, make something with your hands, and realize the skill is still there.

1 month ago | [YT] | 3