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My Dopp kit and I have been having a love and hate relationship. I’ve been carrying the Filson Tin Cloth Travel Kit, which is fantastic in shape and size, but lacking in any organization. All too often I have gear spilling out, and I am unable to quickly find what I need to the point where it feels like I constantly empty the bag out to find the one small thing I wanted.

So I started the search again for a new Dopp Kit, and the Hardgraft Brothers Dopp Kit Duo seemed like it might check all the boxes. Two pouches, both slightly smaller, seem in theory to be a really clever solution — in practice, these two pouches are tantalizingly close, but miss the mark for a cohesive Dopp Kit. They do make excellent add-ons if you can stomach the price.

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Some quick thoughts on Hardgraft’s Small Brick Card Case, which I picked up a while back to hold some overflow cards and cash where it would be living in my briefcase/bags most of the time. I did use this for a couple of weeks as my primary wallet, so I could get a sense of how it works in a more standard use case.

Hardgraft makes many small cases like this, and it’s hard to get a sense of why you might choose one over the other. I could see some loving this as a primary wallet (I would if I didn’t have the Whisky), but I also think it fills my use case perfectly.

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Back in December, my wife gifted me a pair of these R.M. Williams Dynamic Flex Craftsman Boots which I had been drooling over for some time. A perfect gift. The jump from Blundstone to R.M. Williams is akin to the jump from Seiko to Rolex — both great, but you know, there’s an upgrade there.

What I didn’t expect is how comfortable and easy these boots would be, and generally how good they are. So allow me to expand some on that.

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I have already mentioned my love of a good loafer, and while a classic Sperry is a loafer of sorts, it is very much in a class of its own (i.e. Boat Shoe). I was looking for a shoe I could use to replace a sneaker for any given activity outside of sports-related-things. I wanted to look a little more adult, as I was no longer feeling comfortable wearing sneakers.

A boat shoe was the top recommendation which kept coming up for me. I started to look around — you can spend a lot — but the Sperry is the OG if you will. I went with this Boat Shoe, Gold Cup variant with the classic brown leather and a white sole.

I have no regrets replacing my sneakers with these boat shoes.

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Watches are expensive items, no matter what your budget is, they are an expense you could forgo your whole life, but when you want one you tend to spend more than you anticipate. If you are fishing in the deep end, dropping $10,000 on a watch is a starting price bracket. For others you might top out at $1,000, or even $100. When it comes to watches people tend to buy towards the top of their budgets if they are going to buy a watch — it’s a purchase made out of desire, and rarely out of need.

If you hang around the watch world long enough, you start to see a pattern in the questions asked — a commonality of the editorials. With the most common of the lot being questions around a what someone should or should not have in their ‘collection’, or what watch should be the singular watch someone should own.

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In the fall of 2023, Leica announced the Sofort 2. This is a point and shoot Leica, with the primary idea of this camera being one which prints an instant image for people to share. It’s also inexpensive (by Leica standards) at $389.

I bought three of them when they were announced. One in each of the colors (white, red, black) and gave one each to my kids as gifts, (keeping one for me). Well, my black Sofort 2 only recently arrived due to all the backlog. So, let’s talk about the worst camera I own, and what and why someone might want this.

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For the last couple of months, I’ve had the feeling that this WWDC would be a big one. ‘Big’ in the sense that it is going to create mountains of work for Apple developers across the globe, while giving people a lot of great things to use come September. Yes, there’s all the AI stuff — but there’s loads more Apple announced as well.

Rather than rehash what was said, I wanted to dive into a few things of note. Apple has put developers on quite a roller coaster with these announcements.

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MIC CLICK

Mostly Incomprehensible Gate Agent: “If you are flying with us today on flight FU666, this is a completely booked flight, and we are looking for volunteers to check your bag at the gate. We are looking for 129 volunteers, as all 65 seats are booked. If you are not in the most expensive group, you likely will not find space for your bag because instead of enforcing bag sizes, we push that pain right down to you, our ‘customers.’ You are allowed one carry-on, but we won’t bother to count. Thank you for flying with us.”

Do you think they have that speech memorized? Because I have it memorized. Sometime around 2012, I stopped checking bags. Carry-on only, roller bag. Then, I fell into the one-bag trap — you can check the site archives for that content — before stabilizing with carrying a large duffle and a smaller personal item onto the plane for the last few years.

During that time, my bags were never lost, and I never had to gate check — but I also paid to ensure I got on the plane in the first half of boarding.

It had been a long time since I made a proper ‘one bag,’ personal item only, trip — but a short business trip at the start of this year made for an easy one-bag journey. Traveling with a personal item only was a breeze getting to my destination — the type of thing that can lure you right back in. And then, coming back on the same trip triggered something for me.

The return trip had a massive gate line. The airport had many service members flying, who were allowed to pre-board before the first ticketed group on the airline I was flying. I was in the second labeled group and didn’t care when I boarded because ‘personal item’ travel means you don’t need to. I heard another couple in line talk about how the last time they flew out of this airport; the second group had to check their bags due to how many people pre-boarded. That was wild for me to think about.

I wasn’t stressing about the bag I would keep at my feet, but it was something I had never really thought about — what a stressor to have to gate check even in the highest boarding groups I could pay for. As I flew back, I realized how much less stress I had on this trip, with no baggage needed to compete for the overhead bin. It was a stress reduction I didn’t expect.

The problem is, I don’t love traveling with a small personal item-sized kit, so I knew personal item only wasn’t in the cards for me — but what about checking bags?

Many horror stories have been about lost baggage in the last few years. I dug into the stories to determine if lost baggage was a blip or a real issue — it appeared that lost baggage was declining again. This matches up with something I believe strongly in: it’s generally a safe move to do something a company offers if that is an area where the company makes a lot of money. Put another way: soda doesn’t make restaurants much money, so the mixes can be off, and the restaurant is generally meh about it. But restaurants make a lot of money on cocktails, so those are usually on point.

Likewise, airlines don’t make money off your carry-on, which is a trash experience. But they do make a lot of money off checked bags, so they are very incentivized to convince people to check bags. It makes sense; follow the money.

So I checked my bag. And then I did it again. And then again.

Checking a bag is travel magic.

You get the best of both worlds: the ability to pack nearly everything you want to pack while still only carrying a personal item onto the plane — albeit a much lighter personal item. Granted, none of this is new; this is how the air travel experience was initially designed to be. So instead of rolling your eyes at this less-than-novel approach, allow me to remind you how we all lost our damned minds being obsessed with personal item carry-on situations and instead should be embracing the checked bag.

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The hardest part of checking a bag is trusting the system — getting over the anxiety that your bag might be lost. My wife declined to check the first time we checked, so it was only me and the kids. I split our stuff between two rolling bags, added AirTags, and still had the kids (as did I) pack an extra pair of underwear and toothbrushes in our carry-on bags. Just in case.

A friend gave me a tip: whatever you do, don’t bother trying to follow your bags with the AirTag; it’s very stressful.

So, I followed the bags with the AirTags.

It was weird and slightly stressful as the bags weren’t moving together. However, I could see they made it on the plane by the time I was on the plane, and off we went. Everything went without issue.

These days, we pack in our own bags, and I don’t think much about the process. All the underwear is safely in the checked bags, too.

But recalling the above, where I said this is a profit center for airlines, there are also some upgrades to the system, which I didn’t know about before I started checking. Upgrades remove even more pain from the flow of checking a bag.

I must add a caveat: I have the base level ‘status’ with United and only fly with United. As such, I don’t know how other airlines handle things (though United is not particularly highly rated), and I don’t know what does and does not come with status. I get one free bag per person because of my status, which is great for me.

When you check in for your flight and indicate you are checking bags, the app enables a “bag drop shortcut.” I thought this would be a silly non-perk perk, but it’s huge. Each airport handles this slightly differently, but there’s a particular United area labeled “Bag Drop Shortcut,” all you do is take your phone app and bags right there and hand them off. In Denver, this is curbside; you tap an NFC tag, which prints your bag tags, and someone takes the bags, tags them, and puts them on the conveyor. In Houston, there is a line where they scan your boarding pass near the ticket area, and you hand off the bags.

No matter which airport I check my bags at, dropping them off typically takes under 5 minutes. That might be on the high end, too. I budgeted an extra 25 minutes for checking bags the first time, but now I don’t add extra time. It’s very smooth — which is the antithesis of a typical air travel experience. Whatever time I spend dropping my bags is easily saved by being able to move more freely and walking through TSA security with far fewer things needing to be scanned.

Once you drop your bags, United allows you to track the bag tag scans in the app. This is an excellent way of knowing a general location instead of an AirTag, though I still recommend an AirTag as a low-cost, high-reward addition to the process. The scans will tell you significant checkpoints, and it is mainly helpful to know if they have your bag and whether it is at baggage claim or not.

Alright, but what about waiting to get your bags at the end? The longest I’ve had to wait is about 20 minutes, but I was among the first people off the plane and walked right to baggage claim without a stop — and it was amid a bad influx of flights landing after some big storms in Houston. So that’s not too bad.

On average, we wait under five minutes after we get to baggage claim (which can be a trek). My current status has my bags labeled ‘priority,’ and I am not sure what that means, but it appears this label gets them to baggage claim among the first tranche of bags. This likely helps a bit with the timing of waiting for the bags.

One last bit on the process: the condition of the bag. I have checked our hard-sided polycarbonate Rimowa, soft-sided TravelPro, and hard-sided TravelPro. The hard-sided bags tend to get some scratches. The soft-sided ones have some marks. It is what it is. Nothing has been damaged, though none of it looks pristine any longer.

But for my stuff, I’ve been checking a Medium Rugged Twill Duffle from Filson — which is not the typical bag you check. The one I checked is dark brown, and I removed the shoulder strap when I checked it. There are marks on the bag, but there’s no discernible damage, and it’s been through 4 individual flights already. I’ll keep using this bag.

Your bags won’t come out pristine, but they don’t look too bad, certainly nowhere near what I initially feared.

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I don’t see myself going back to carry-on. Even for shorter trips, I check a bag. By doing this, I have removed all my anxiety around boarding the plane. I carry one small bag, which fits nicely at my feet.

The overall benefits of traveling with a checked bag:

• No boarding group anxiety, you don’t need the overhead bin, and your seat is assigned because you fly a proper airline, so there’s no worry about when you get on the plane.
• You can take a pocket knife in your checked bag.
• You don’t have strict liquid limits, so you can pack all the toiletries you want and need.
• As long as you stay under the weight limit, you can pack anything you want or need to bring.
• Moving through security with a small bag with no liquids makes the process faster and easier.
• It’s easier to move about the airport post security as you are carrying/pushing/dragging less weight and luggage around with you.

The downsides:

• You’ll always have to walk to baggage claim and wait for your bags. This will add some amount of time.
• If you don’t have status, you are likely paying for the privilege of checking a bag. And those checked bag fees can be considerable.
• There is potential for losing your bag, which you should mitigate with AirTags.
• Your bags will suffer more wear and tear than in a carry-on situation. This will necessitate a more durable bag to ensure you don’t end up with a torn suitcase at the end of your trip.
• You might have issues if you have connecting flights with a short connection window. (Though with the help of AI, airlines are getting more savvy about this.)

Overall: net positive by a lot. I didn’t think carrying more would make me much happier, but it feels like magic to have that one or two extra things you never had room for before. An alternate jacket or a second pair of shoes are the primary two items I never had room for, but I now always pack.

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If you are going to give checking a bag a go, here are the bags we use:

• Travelpro Maxlite 5
• Travelpro Maxlite Air
• Rimowa Cabin Essential
• Filson Medium Rugged Twill Duffle

The Rugged Twill Duffle might be underrated here, but if you were a staunchly pro-rolling bag, the Maxlite Air is the one to go with; it’s a great bag and a great price.