Tales & Trails of a Traveling Wiseguy

Today was another workday for me. I mention that because a lot of my peers at other companies in the industry are off until Monday, 5 Jan. For me this week has been a workweek. ...Though Jan. 1 was a holiday, and I used a vacation day on Dec. 31. So it was a workweek of just 3 workdays.

Shortening the week to just three working days made it an easy ramp back in to working after having a week-plus off around Christmas. Also making it easy is the fact that things are slow. Lots of people in the industry being off this week means a lot of my customers are off, too. Or only part of their staff is back so they're moving slowly on things.

Next week will be the start of the new year in earnest, work-wise. It's unclear right now whether I'll be slammed right away as people pile back in to the office and want updates on everything, or ramps up slowly because people returning after 2 weeks away will need time to sort things out from their end first. I'll see next week. For now... it's a weekend already!

One of my sales colleagues has given me gifts each of the past few years. I've helped him make a lot of money, so it's understandable. (It's a professional custom in enterprise sales that the account executive, the one who makes big bucks on big deals, gives gifts to technical staff who were key to winning the deals.) The past few years the gifts have been bottles of liquor— which is fine, because I enjoy liquor! This year's gift was another bottle of whiskey.



This one's a bit different because, unlike the past few years' gifts, it's not a Scotch whisky. Yamazaki is a Japanese distiller, and this particular variety, Legent Cask Finish Blend Bourbon Whiskey, is distilled in Kentucky from American grains and aged for 8 years then sent to Japan for secondary aging and blending.



I was surprised to learn this is a $200+ bottle of bourbon. No, I didn't go rummaging through the box for a receipt. I'm not the kind of person who checks the price tag when receiving a gift. But when I searched online to learn more about this liquor, well, there was the price, right there.

I haven't opened the bottle yet. I will, soon. I'm certainly not going to make the mistake my grandmother did in saving beautiful gifts for a special-enough special occasion that never came. Perhaps I'll enjoy a drink, tomorrow, on Christmas, since this is a Christmas gift. I haven't celebrated Christmas in over 30 years... but at least I can raise a glass to good friends.

"Global Bonus Holidays for [Company] Employees" read an email that was sent out 2 months ago.

I didn't get it.

I literally didn't get it.

I only learned about it today when a few colleagues and I were making smalltalk at the start of a meeting. "Are you going anywhere next week when we have the whole week off?" they asked.

"WhAt WhOlE nExT wEeK oFf?!?" was all I could reply.

Goddammit.

God DAMMIT.

I could have planned a vacation if I'd known about this TWO FUCKING MONTHS AGO. Instead I learn about it with less than a week to go. After Hawk made a conflicting plan... and even if we change that conflict, travel is 2x - 3x as expensive to book now as TWO FUCKING MONTHS AGO.

Texas Trip log #2
41,000' over Nevada · Tue, 11 Nov 2025. 7pm.

I'm not even halfway to Texas yet and already my plans for the rest of the week have changed. The customer I intended to visit in San Antonio on Friday couldn't get all of their people together on the same day. Instead we'll meet with them virtually, and probably next week. That means I should go home Thursday instead of Friday, and I don't need a rental car to drive to San Antonio.

Unfortunately this is the way enterprise selling is in 2025. Face-to-face meetings are rare anymore. Scheduling them with customers and prospects is like pulling teeth, and even once they agree to a meeting date they often renege on it. It's like nobody can commit anymore.

Fortunately I know it's 2025, not 1995 unlike a certain senior politician who seems to think "Bring back Johnny Carson [to host the Tonight Show]" is a reasonable demand. (Johnny Carson stepped down from hosting that show in 1992 and retired to private life. He died in 2005.) I anticipated that the customer in San Antonio had at least a 50/50 chance of flaking on us, so I held onto two homeward flight reservations: one on Thursday and one on Friday. I simply canceled the one on Friday. And, as I got the news of them flaking out just before boarding the flight, I was able to do that from my phone while sitting in my seat while the aircraft was still parked at the gate.

Cancelling my rental car reservation took a bit longer. I waited until I could take out my laptop computer for that. Though by the time we were 41,000' feet above Nevada I couldn't get my computer to connect to Southwest's flaky wifi. So I went through "Sorry, that username or password couldn't be found" purgatory on my mobile phone trying to pull up the booking site to cancel the car.

Yesterday my boss suggested a plan to help me reach elite status. At first I thought he might be joking because he brought it up in a laughing manner, but as he explained it there's a real there there.

His idea was that our AE (account executive) counterparts often seek to "protect" us from having to travel as we head into the end of the year. Except those of us who do travel as part of our jobs are concerned about reaching elite status. And as we head toward the end of the year we're keeping an eye on how many more miles/points/trips we need to qualify. He talked about getting his team together to discuss how much more each person needed for the year then telling the AEs, "Hey, you need someone to help you cover a meeting? Reach out to Chris, he needs 4 more trips this year for elite status!"

"I need just 1 more trip, possibly 2 if it's a short/cheap one," I said right away. I needed no delay to think about it because I've already been tracking it. I explained to my boss how I created a spreadsheet years ago, modeling it kind of like a sales forecast, to track progress toward elite status.

I also told him about how hardcore frequent flyers do Mileage Runs (MRs)— trips they take purely to earn status. I did an MR, just once, years ago.

I gently pushed back, though, on the idea of telling AEs to help book work trips for us. I did that because I don't want to create or perpetuate a notion that we're arranging business trips for personal benefit. I do push for meeting customers and prospects face-to-face, by traveling to visit them, instead of meeting via videoconference. I do that because it makes business sense, because it's more valuable for the company, not because it's a boondoggle or for status bragging rights.

This week, since returning to work on Wednesday morning after a relaxing long weekend in Phoenix, I've been developing a customer workshop. The deadline was short... It was decided early last week ago that I'd have to deliver it today. And not only that but I was on the road for 3 days last week with a business trip and then had 2 days of PTO planned this week. Thus the work in earnest on the creating the workshop began Wednesday morning. To run it for an audience of 6-8 devops engineers today at 9am. 😳

TBH I could have started before Wednesday. Although at the same time, not really. Mon-Tue were out because I was on vacation. Last week Thursday afternoon I'd just gotten back from a business trip and was tired out. And Friday I was both still tired out and had at least half a day of regular work to do. So I started this week Wednesday.

At first I was kicking myself for not starting until Wednesday. Despite the reasons above I kept scolding myself, "This would be so much easier if I'd done even 1 hour per day of it last Thu-Fri." That made me feel down. But at least I got going Wednesday. And I made steady progress at it, ultimately working until after 6pm because I was in the zone on it. That made me feel good.

Thursday was another "in the zone" day— at least up through lunch. After lunch I paused working on the workshop because I had a few important meetings to attend. When I got back to the workshop development work around 3pm I found that my infrastructure had gotten borked. 😰

My systems were wedged. About 95% of what I'd built was unusable. It wasn't anything I'd done; I hadn't touched it for 3 hours. And it seemed like it wasn't somebody else's fault, either; nobody else was using my infrastructure. Something had just failed on its own. And while I know enough about the infrastructure underpinnings to figure out, in broad strokes, what was wrong, I'm not expert enough in the details to have fixed it. Fortunately I still have one colleague— I used to have three, until the layoffs of a few weeks ago— who is familiar with the infra. Unfortunately it was already after 6pm for him and he was offline.

I messaged my boss to let him know. He was understanding of the predicament. He encouraged me to do as much as I could the rest of the day, and he'd help get my east-coast colleague involved at 9am EDT (6am my time) today. I finished the day Thursday pleased with how much I'd built in 2 days but crestfallen that a system snafu at the 11th hour might force us to push the seminar off to next week.

Well, I woke up at 5:40am today. It's not that frustration made me unable to sleep; just the heat. But the frustration was definitely there so I decided I might as well put on a shirt and log in to see if my colleagues were active. They'd just logged in a few minutes earlier. Logan, the guy who setup the infra originally, had just messaged that he was starting to take a look. Within 10 minutes he'd diagnosed the problem. It was basically what I'd figured out, but at a more granular level. He knew the specifics I didn't, so he knew which part had failed and how to reset it. He reset it, and within another 10 minutes everything was back up and running. The path was clear for me to deliver the workshop seminar today at 9am!

The seminar went well. We had a good number of attendees at the start, though half were called away less than 15 minutes later when part of their infrastructure went down. Oh, the irony! I even joked with them about my infra outage. But their infrastructure runs the e-commerce site for a small retail brand you might have heard of, so "down" for them means it's all-hands-on-deck for their infra team.

Their infra team was about half the attendees. The other half were apps people whose app was behaving just fine, so they could stay. I ran the workshop with them. It went really well. We ran until just after 12pm. The customer appreciated it, my sales counterpart said I did a fantastic job, and my boss really liked it, too. Good times!

I've been pretty sanguine about the layoffs at my company this past week. I'm surprised how sanguine I've been about it. That makes me wonder, why am I so sanguine, this time? And yes, it's "this time" because this isn't the first layoff we've had this year. We had one in January that also impacted my team heavily. And while there were none in 2024, there were two in 2023 and one in 2022.

I think an obvious dimension of the answer for why I'm so sanguine is that, after all of these rounds of layoffs, I've become numb to it. Each one of them has hit my department, along with others. Each one has resulted in the dismissal of decent workers who were getting the job done, along with some who weren't. It's always when good people get whacked that I take it harder. This time there were more good people whacked, as a proportion of those dismissed, than last time. That tells me I should be taking it harder. And that's where the numbing effect comes in.

It's possible I'll be less sanguine about this layoff as take more time to think about it. The effects of January's layoff got worse and worse for weeks as flawed planning and execution became clearer and smart, capable people chose to quit because they lost faith in Management. (In the tech industry we call the latter brightsizing, a play on words against the euphemism "right-sizing" that Corporate America created to put a positive spin on the term "downsizing".) Within two weeks every seasoned manager in my department quit.

Indeed I already see reason for growing alarm over this layoff. This layoff hit the sales team hard. Cutting sales people is a pretty extreme thing in business. Sales people generate the revenue! I mean, cutting development staff has consequences, too, but those consequences often take 12-18 months to materialize. Cutting sales staff means a hit to the company's numbers next quarter.

And it's not like Management was just "trimming the fat". We were already running lean. When you make significant cuts to a team that's lean, you're not just trimming fat— or excess capacity. You're trimming muscle. You're dismissing good people who were doing work that counted. And the people left can't just "pick up the slack". They weren't slacking.

Management even acknowledges that they cut people doing real work. They've told us to think in the coming days and weeks about what we won't do because it's just not high priority enough. And while they've phrased that with empathetic words and intonation, and framed it to imply that we individual contributors have agency, it's starting to stink like 5 day old fish.... Why are they asking us to figure out what work gets cut? That should have been part of their strategy in planning the layoff!

Napa Trade Show blog #8
Back home - Wed, 10 Sep 2025, 5:30pm.

I'm back home from the trade show in Napa. It's earlier than expected. Booth visits were slow again today, tapering off to nearly nil by 2pm, so our event coordinator encourage those of us not already booked to stay overnight to head home early. I left at 3, which was just an hour before the official closing time, and used that early start to mostly beat traffic on the way home. Still, there was some traffic, making it a 2 hour drive. I got home at 5pm. That's 48 hours + 3 hours after I left on Monday.

It's just as well most of us left early. Our team spirit was close to nil as we spent most of the day trying to figure out what's going on with a layoff today. Oh, we totally put on game faces for talking to customers and prospects. Selling was the one thing we all could be positive about. But the moment it was just us coworkers again, the dismal "WTF is going on?" discussions started back up.

Speaking of those dismal discussions, it looks like tomorrow morning is going to be back-to-back-to-back meetings with various levels of leadership "explaining" the layoffs to us. I quote explaining because do we really need 3 hours of meetings on the topic, with each layer of executive management needing to have their own say? That says to me we have too many layers of executives. Maybe they should have laid off one of them. But of course they didn't.

Update: Assembling Details about this Layoff

Napa Trade Show blog #5
Wrapping up Day 1 - Tue, 9 Sep 2025, 7:30pm.

This afternoon I did a costume change at the trade show. During my off-shift time between 1-3pm I shaved my beard down to a mustache, ironed my arm-towel, and donned my tuxedo to become Jenkins.



The show had been extremely quiet up 'til lunch. It was busier, but not busy, at 3pm when I returned. Though right away I started commanding attention in my butler guise. People noticed me and came into the booth to talk. Or they stopped and stared from 20' away, trying furtively to take pictures with their phones, and my colleagues and I beckoned them to come in and talk to us. We even helped them take pictures posing with Jenkins.

Late in the afternoon the conference's technical sessions wound down and there was a reception in the vendors area. There were free drinks offered there— and attendees had to walk past us vendors to get to them! That's part of the logistical strategy of supporting vendors I wrote about in my previous blog.

Throughout the rest of the day, until several minutes after the 7pm closing time, Jenkins continued to be a draw. My cosplay brought people into the booth, people who work at companies we want to turn into customers, who otherwise wouldn't have come talk to us. That is why I rushed out to a fine men's wear shop yesterday afternoon and dropped $50 on a new bow tie and shirt studs.

My company has a split opinion on whether Jenkins should be part of our branding. Our marketing department, virtually all of whom have been hired in the past 2 years, are against it. To them Jenkins represents the past— even though it's the source of 90% of our revenues— and they don't want to associate the company's messaging with it.

I point out, and some of our sales leaders support me strongly on this, that not only is Jenkins the source of 90% of our revenues but it's a strong brand that people recognize. People in the DevOps industry who've never heard of our company have virtually all heard of Jenkins. They recognize the butler on site, they are entertained by seeing a real-life Jenkins the Butler, and they're way more willing to come talk to us. Then, once we get the opportunity to talk to them, we can build on our industry bona fides with Jenkins and then pivot to talking about our newer products— the products we believe represent our future. But to talk about that future we first need people willing to listen. Jenkins creates that willingness.

I emphasize this here because I worry that I am risking my job by dressing up as Jenkins. I'm literally going against the desires of at least one of our C-level executives, the CMO. And quite possibly the CEO as well! But you know what... if they want to fire me over it, it'll be their own colossal mistake.

I'm back to work today after being away for 10 days. It turns out 10 days is enough not just to "clear my head" but to be so refreshed that everything seems a bit new again. And I don't mean that in a good way. 😨 Many things are unfamiliar new. Like, "Is this going to be on the test?" new.