Tales & Trails of a Traveling Wiseguy

Today's my first day of vacation. Yeah, I wrote over the weekend about starting vacation, but that was the weekend. Weekends don't count as vacation. Today, Monday, is my first real day of vacation. And today, on my first real day of vacation... I worked. 🤣

Oh, I didn't work a full day. Good grief, I'd never do that. Not unless I was getting a day comped somewhere else— which I have done before. Twice this year, even! Once in March and once again later in March. 😅 But this time it was just 1 hour of work. I figured I can give the company an hour on my day off in exchange for all the flexibility I enjoy during regular workweeks.

Me feeling charitable, or reciprocal with flexibility, isn't the only reason I took a meeting and did some followup work today. It's that, as I've pointed out many times before, work doesn't stop just because I'm on vacation. Especially in sales, work doesn't stop. Customer projects keep moving forward, and frequently the deadlines are set without regard to my availability.

When that presents a big problem I push back and/or call for backup. Indeed, there was another customer meeting today I let my boss handle for me. So he's working a bit today, too— which absolutely factors in to my charitableness / reciprocity calculus. A colleague was even willing to cover this meeting for me. But I volunteered to do it myself even on a day off because, honestly, the alternative is worse.

You see, the alternative if I let this going a week or longer without touching it is not "I'll do it later, when I return," but rather, "While I'm out for a week, other people will try to do it, and they'll do something wrong and break it, so when I return I'll have to spend 3x as long fixing what's broken. Oh, and when it broke someone pressed the panic button, so now I have to join multiple status calls with managers who are demanding explanations." 😣

Texas Trip log #6
AUS Airport · Thu, 13 Nov 2025. 4:45pm.

It has been a busy day for me with meetings galore in Austin.

My day started with a morning alarm at 6:15. I had to get ready for the day, pack my suitcase, and be downstairs for an informal meeting at 7:30am. Luckily it was informal as I fell behind schedule— I got sucked into reading too many work emails early this morning— as I didn't get downstairs until 7:40.

Then there was an 8:30 meeting at a prospective customer's office. We were annoyingly late for that, too. When we started leaving the hotel at 7:50, maps said we'd be there by 8:20. By 7:05, as we sat in traffic, our arrival time had slipped out to 8:25, then 8:30, then 8:40. Fortunately it all worked out as it was a very productive meeting. And the customer was understanding of our tardiness as some of them arrived late because of the same bad traffic (there was an accident in a construction zone).

Later in the morning I took a meeting from a picnic table on the edge of a parking lot outside a beer bar.As I've remarked many times, working remotely isn't just "Work From Home", it's work from anywhere you can set out a computer and get a network signal!

After that I took a meeting inside the bar. It was with a customer who'd picked the bar. Though oddly I was the only one (of the six of us total) who drank beer. I drank sparingly. Then after the customer left and it was just me and my sales colleague, I hit the bottle harder. 🤣

From lunch I headed over to the airport with a stop back at the hotel to drop off my colleague and pick up my suitcase. Here at AUS I cleared security surprisingly fast considering how busy the airport is. I bought a soda as a pretext for sitting at a table in one of the food court areas then conducted two more meetings sitting in the airport food court.

Now it's rolling up on 5pm and I consider myself done for the day. I've been working since before 6am, and I've still got at least 4 more hours to go before I get home tonight.

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.

L.A. Trade Show journal #4
At the show · Wed, 17 Sep 2025. 5:30pm

Today has been the trade show. AWS Summit - Los Angeles. The show's now winding down for the day. People started disappearing around 3pm, presumably to try to beat the traffic home, though the show formally goes through 6pm. This has been my first chance today to catch my breath.

I only got to the show just after 10am. I was busy with other tasks, time-sensitive ones, working in my tiny hotel room on the children's chair at my combination nightstand/desk. I had intended to get to the show at 9 but that didn't work out. So at about 9:55 I zipped up my bag, rode the elevator down to the ground floor, and... walked across the street.



That's right, my morning commute today was a walk across the street. Okay, it was kind of a walk across two streets because I had to get to the diagonally opposite corner. 🤣 This is the entire reason why I booked that tiny hotel room knowing it was tiny— and paid a pretty penny for it. Because it's Right. Here.

Minutes later I'd picked up my badge and registration and was ready to hit the show floor.



Traffic at our booth was steady across the day. That was frankly a relief— from a value-for-our-dollar perspective— from last week's trade show, where we had stretches of an hour or more with no meaningful conversations in the booth.

Things did get busy for me in the middle of the afternoon when I had three scheduled demos in a row with different customers. One brought a group of 9-10 people, ranging from devops engineers to a devops lead, to a manager and a VP. And they kept me busy, firing tough questions at me from all sides. I think I did pretty well, though. I look forward to us moving to the next stage with them.

Throughout the day I also saw, and chatted with, a few customers I've been working with for years. It was great to see them "in 3D" again... especially because some of them I've been working with for over 4 years and don't think I've ever met f2f. Plus a few people who stopped by the booth recognized me from portraying Jenkins at the other trade show last week even though I was "Clark Kenting it" today.

Well, the show's winding down now, but the day's not over. My company is sponsoring an after-hours reception at a bar a few blocks away. "Grab a drink and some snacks with us and wait for the traffic to die down before going home," we've been encouraging people all day.

It's a nifty way of framing the event. I don't know, though, how much of a turnout we'll get. Many people have already left to beat the traffic. And I don't blame them. I know if I were on the other side of the table today, I'd value getting home by 5pm to have dinner with my family over having a free drink of two on some company's dime and then getting home at 8:30.

Update: Keep reading in Back to the Moxy

Napa Trade Show blog #6
Getting ready for Day 2 - Wed, 10 Sep 2025, 10am.

After staying up too late Monday night at the trade show then having to get up really early for a full day yesterday, I was careful last night to pace myself better. It wasn't so much that I made a mistake in pacing Monday night; I didn't. The problem was that I was already running at full speed when a bit of illness tripped me up for 4 hours. It reminded me that I need to under-schedule my day so that, if and when something goes wrong, there's spare time to devote to fixing it.

Thus last night I bowed out of the celebratory dinner, the post-dinner concert, and the post-post-dinner piss-up at the bar. Instead I went out for a quiet dinner offsite by myself, got back before 10pm, and was lights-out at 11pm. Then this morning I slept in until almost 8am. I was able to do that because I don't have any fixed responsibilities until the show at 11:30am. It felt so decadent getting 9 hours of sleep while at a trade show!

So far this morning I've been catching up on work. One of the things about working trade shows in sales is that sales remains the "day job" while the show is also taking up most or all of the day. So we salespeople are always stealing moments here and there to catch up on emails, respond to Slack messages, and keep business moving forward with all of our customers. It's relaxing, though, having only one day job this morning. 🤣 My shift in the booth begins at 11:30am. Update, 10:45am: Today's keynote ended really early, and my colleagues have called me to come to the booth as it's being mobbed.

Napa Trade Show blog #4
On break in my room - Tue, 9 Sep 2025, 2pm.

Today the vendor part of the trade show kicked off. Yesterday was arrivals and was also a training day for people who wanted classes from the main sponsor. Plus a chance for our team to enjoy dinner together before everyone's worn out from long days.

I was up early today for internal meetings from 7 until 8:30 then walked over to the trade show at 9. It's so convenient being in the same hotel as the show— and that hotel not being a Las Vegas mega-resort with 3,000 rooms in multiple towers where getting from a sleeping room to a conference room entails a walk of a mile engulfed by clouds of 25 years of accumulated second-hand cigarette smoke.

Right now I'm back at my room taking a break after lunch. It's been a slow start at the booth today. Why slow? Frankly, because of poor planning by the conference organizer.

I got to the booth at 9 today... and it was pretty much dead. It was dead until after 12pm because the keynote speeches were running. We knew the keynotes would be going and they'd suck all the attention away from the vendor area. But the keynotes all ran long, gobbling up the breaks between sessions when attendees might come out to visit us. The physical layout of the show disfavored us, too.

Yes, it's important for a show to support its vendors. We vendors help sponsor the show! We're all paying money to be here. ...And I don't just mean spending money on salaries and travel costs. We're paying fees in the five figure range directly to the host company just to be here. That's in addition to what we pay the hotel for our rooms, the construction team for assembling the booth, and all the travel costs of the staff. In return conference organizers need to treat the vendors well.

What does it take to treat vendors well? Give the attendees reasons to visit us. Put ample break times in the schedule for attendees to browse the vendors exhibit area. Put the free snacks and drink in the vendor area, so there's extra reason to come by. Put the lunch and dinner either in the vendor area or on the other side of us, so attendees have to walk past us.

So far today these show organizers have not done the above. There have been no breaks for attendees to come visit us. Everyone's running long on presentations— one ran 30 minutes over— and they're just slotting the next speaker immediately after the previous. Then at lunch today, lunch was in the opposite direction from where we vendors are. People had no reason to walk past our displays. In fact, worse than no reason they specifically had reason not to go near us— because we were in the opposite direction and nobody had extra time because the schedule was still 15 minutes behind.

Now, you might scoff at supporting vendors at the show as the tail wagging the dog. People are here for the show, right? We're just the advertisers everyone would be happier ignoring. But like advertisers in commercial TV, we're paying to help support the show. We're here because we want the opportunity to talk to prospective customers. And we have metrics. We measure the number of contacts in the booth ("raw leads") as well as the quality of conversations ("qualified leads"). And when those metrics are low, especially the qualified leads score, we stop sponsoring the show.

This is our third year at this show. The past two years it was very productive for us. This year, unless things turn a massive 180° later today, may be our last at this show.

Chicago Trip Log #6
Downtown Chicago - Thu, 13 Aug 2025, 4pm

This installment of sales training is a wrap! We finished Day 3 a bit early, around 3:30pm. It was both an easy day and a hard day. ...Easy, because there were only 8 of us involved in for Day 3 (versus 40-ish for Days 1-2) and our manager kept it casual. But also hard because we made the whole day about interactive group activities. There was no time to tune out by reading news on a smart phone or blanking out during a dull session.

And we pushed each other hard during our collaborative activities. Yesterday I'd introduced people to the warrior saying, used by famous generals from ancient Greece to the likes of Norman Schwarzkopf, "We sweat in training so we don't bleed in battle." Well, today my boss giddily repeated that phrase when my colleagues balked at how hard he was pushing them.

Most of the 8 of us are now downstairs at the hotel's bar enjoying one for the road. I'll leave momentarily for the airport. Even though my flight's not 'til almost 8pm I'd frankly rather not hang around a hotel bar— especially one where beers on tap are $15! I'd rather find a quiet spot at the airport and cool my heels there. Then, it doesn't matter if something goes crazy wrong with traffic. I'll be less than 5 minutes from my gate.

Chicago Trip Log #4
Downtown Chicago - Wed, 13 Aug 2025, 7am

Just like I figured was going to happen after I stayed up too late carousing with colleagues on my first night in Chicago, Day 1 of training on Tuesday was a long slog. It started at 7:15am with breakfast in the meeting rooms, the training proper running from 8 to 5, and then a small team meeting until 5:45pm. 10.5 hours of being "on"— after me getting only about 4 hours of sleep. Ouch.

I kept a game face on for most of the day. Late in the afternoon, though, I kind of lost it. Around 4pm the person who was speaking was not that engaging, and I nodded off a few times. I don't know if I actually fell asleep for a moment at a time, but I definitely did blank out a few times. I got lost in my own thoughts and suddenly realized that I'd stopped seeing or hearing what the speaker was talking about. Fortunately the next speaker was stronger. And the small team meeting at the end of the day was no problem since that was just 3 of us so I was actively engaged. It's much easier to stay focused when the content of the meeting is actively engaging rather than when I'm passively consuming it.

Those 4pm nap attacks, though, told me that I needed to take it easy last night instead of staying up late carousing with colleagues again. Thus I sent my regrets to our regional sales leader that I wouldn't be able to attend his dinner. I figured I'd instead eat on my own and get back early.

As I was considering where to get dinner solo I saw on Slack that one of my colleagues hadn't been invited to any group dinners and was looking for company. I invited him to join me. We agreed on a Chicago pizza chain (Giordanos, for those keeping score) with a restaurant location a few blocks away and walked over there. We split a pizza and an appetizer and enjoyed a couple beers each while chatting amiably about mostly not-work things. It was a right-sized dinner, both in terms of food, drink, and energy levels.

On the walk back from dinner I spotted a few of my colleagues in the hotel bar. I resisted the mild temptation to join them. I knew that "Hey, come have a drink with us!" would easily turn into 2-3 drinks and likely another evening of staying up too late. Instead I retired to my room for a quiet evening. I was in bed not long after 11pm.

This morning I'm feeling a lot more ready for a full day of training than I was yesterday morning. The difference is today I've got 7.5 hours of sleep behind me rather than just 4. That means tonight I should in good shape for the next group dinner / late evening of carousing with colleagues.
Update: over dinner last night I mentioned to my colleague that I'd been upgraded to a nice corner room with a wrap-around balcony at the hotel. "I'm in one of those, too," he said. 

Chicago Trip Log #1
SJC Airport - Mon, 11 Aug 2025, 11:20am

I haven't even finished blogging from Saturday's trip and already I'm leaving on my next trip. Five trips in August! This one's a flying trip, to Chicago, for work. And since I'm flying on Southwest that means....



...Yup, the flight is delayed. We should've left 10 minutes ago; instead we're only part way through boarding. I figure we'll leave 30 minutes late. Fortunately I'm not counting on a connection and I structured my schedule today so that an ordinary delay won't screw things up.

Oh, but speaking of starting this trip before catching up on blogging from the last, I am so glad we pushed back our full weekend trip to Mammoth Lakes into September and instead did a Friday Night halfway trip to the Sierras. The difference was, we got back tired and late on Saturday night instead of tired and late on Sunday night. If I'd had to get up this morning all achy and tired, after packing a suitcase at midnight last night— or get up at 6am this morning— I'd be miserable right now. Instead I had Sunday to recover.

As for this trip: I'm flying out to Chicago for 3 days of sales training, returning late Thursday night. Various people have asked, Oh, will you have time to visit this friend or that relative while you're in Chicago? LOL, no. On business trips like this, on sales training trips, basically every waking hour is scheduled. If I want downtime even to veg in front of my computer for an hour I have to decide what I'm skipping.