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A Self-Inflicted Wound

Jay Baer
Jay Baer
Nov 5, 2019 · 7 min read

It would seem that a lot of people found my latest email to be very relatable. Here’s what I had to say last week. Have you ever been there?

My father was a very smart man. He was very loquacious and had a lot of sayings. I’m sure he heard them from someone else, but I heard them from HIM, so to me, they are his sayings.

Two, in particular, I find I revisit quite often.

The first is, “You can only sit in one chair at a time.”

As my wife and I downsized a lot this summer when our youngest headed to college, I found this saying to be of great solace. “How much room do I really need?”

And the second became all too relevant last week.

I have been on 1,332 airline flights since 2009, according to the new app Flighty (which sucks in all my data from TripIt — another indispensable app). That totals to more than 3,000 hours in the air. And after all that time, I finally made the BIG mistake business travelers can never make….

I was in Scottsdale, delivering a seminar for Investments & Wealth Institute in front of 1,000 wealth managers (my Dad’s occupation, ironically). I flew home from Phoenix, with a connection in Minneapolis. I used to always fly direct on American or Southwest to Phoenix from Indy, but I’m a Delta guy whenever possible, and the new Terminal 3 in Phoenix is amazing and tranquil, whereas Terminal 4 (where American and Southwest are located) is NOT.

We had some kind of interplanetary headwind on the way to Minneapolis because even though we left on time, our flight was somehow 30 minutes late on arrival. Many passengers — like me — had VERY tight connections. And if you haven’t been to the Minneapolis airport, it’s chock full of great restaurants and shops, but it’s about 17.1 miles long. Of course, my departure gate for home was on the exact opposite side of the airport, and time was ticking away.

It was one of those flights where the “ding” sounded, and people leaped out of their seats like a jack-in-the-box. Much jostling and scurrying. I grabbed my stuff and bolted for the door.

As I emerged, I noticed a small sign, held by an airport worker in an orange safety vest. It read: “J. Baer”. Hmmm. “I’m Jay Baer,” I stated. “Come with me,” he replied, and we went OUT the jetway via the magic steps that only baggage handlers and captains ever use. It’s like Narnia, but with a lot of baggage carts.

At the bottom of the stairs sat a gleaming, black Porsche Cayenne SUV. “Hop in,” said airport hero, and away we went! Dodging planes, and tugs, and safety cones, we traveled a secret highway. Evidently, there is a Delta service (American and United do this too, I’m told) that whisks VIPs between gates, so the hoi polloi don’t bother them for autographs. I don’t have anywhere near that kind of swag, but he told me that when they are VIP-less, they look for Diamond-level Delta flyers in danger of missing a connection and save them from that fate. Fantastic!

We arrived all the way on the other side. He escorted me up the magic steps, and I just WALKED ONTO THE PLANE! No boarding pass. Just sit down. Wow!

So giddy was I to not only make the flight, but to be the recipient of such a customer experience, I grabbed my phone and posted about (a bit braggy, really) the secret Porsche ride on Facebook, and then watched two episodes of Bar Rescue. I didn’t work one bit on that connecting flight home (unlike this flight to Houston, where I am writing you this update).

After landing safely in Indy, I got my car and drove the 57 minutes home. A late night, I arrived at 1:45am. Unloading my bags from the trunk, I thought, “geez, this bag feels lighter than usual.” I checked. And then again. And again, with more urgency. And now, with great concern.

My laptop was GONE. I left it on the first flight.

Worried about missing my connection, I forgot to notice I had left my laptop in the seat pocket. D’oh!

I rushed inside and called Delta. No word. Lost and found at Minneapolis was closed. I went online and filled out the lost items form. And then I tried to go to sleep.

My Dad’s second saying was: “It’s never going as well as you think it is, and it’s never going as bad as you think it is.”

No kidding. Within 90 minutes, I was pampered beyond belief, AND I made a colossal blunder that caused a ton of stress and drama.

Yesterday, I spent 15 hours buying a new laptop (no word on the missing one from Delta) and rebuilding my digital life. Not my best day.

But here I am. I got pretty much everything fixed. I caught up on my to-do list, and I’m back in the game!

“It’s never going as well as you think it is, and it’s never going as bad as you think it is.”

Words to live by. Maybe they’ll help you, as well?

Now Hear This

I’m very glad I was able to get my unexpectedly new laptop set up for today because I recorded two terrific episodes of my forthcoming new podcast: one with Mark Scharenbroich and the other with Neen James. Both spectacular speakers and good friends. The new show is called, “Standing Ovation: Where Professional Speakers Tell the Stories of Their Stories.”

In each episode, I interview a world-class speaker about their signature on-stage story. Where did it come from? How has it changed? When does it bomb?

It’s an intimate, inside look at how the world’s best speakers go about their craft. There’s no show like it, and I hope you’ll give it a listen when it debuts mid-November or so. I’ll let you know. My new website will launch at the same time.

My New Speech

Meanwhile, I’m also polishing up my new keynote speech.

It’s called, “THINK SMALL: How to Achieve Big Business Growth Results by Improving the Three Specific Things Your Customers Truly Care About.”

I’m booking events for “THINK SMALL” right now. Interested? Please contact Michelle Joyce at

Ask Jay: Where Do Great Stories Come From?

This isn’t a question I’ve been asked, but rather I question I’ve been asking. On the tapings for Standing Ovation, I sometimes ask my guests whether the best stories are great because the story itself is so remarkable, or because the story has been polished and perfected.

You’ll hear the exact answers on the podcast, but in general, my guests believe it’s mostly the latter. The best stories on stage aren’t necessarily the most fantastic (few of us have climbed Everest, or whatever), but the best stories are always well told.

Nothing in your life is “too small” or “too mundane” or “too normal” to become a story. Whether you’re a speaker, a corporate communicator, or just want to make good conversation at an airport bar, the power is in the telling, not necessarily the tale.

Maybe I’ll tell my “Magic Porsche and Missing Laptop” story on stage someday!

Making it Happen

I don’t talk much in this email about the work my consulting team and I do for major brands and organizations, but if you indulge me for just a paragraph, I’d like to do so in this issue. I am incredibly blessed to have a group of extremely bright and experienced strategists at Convince & Convert that do the heavy lifting when we deliver content marketing, social media, digital marketing, and customer experience strategies to clients all over the world.

I get a lot of the credit, but I deserve practically none.

Right now, as I write this, they are finalizing amazing programs for Vanguard, Arizona State University, Purdue University, University of California, Kaiser Permanente, Oracle, Cisco, Kite Realty, Visit California, and several more.

It probably goes without saying, but I am extremely proud of the work we do. If you ever need anything on the strategy side, please visit us over at

On the Road

As always, this is a busy time for speaking, and I appreciate every opportunity that comes my way. Recently, I’ve been in San Antonio for Caterpillar, Santa Barbara for Appfolio, Houston for NRG, a podcast festival in Indiana, MarketingProfs in D.C., the aforementioned Phoenix trip, and now back to Houston. Followed this week by Nebraska, Philly, and Chicago.

TONS of great events lined up. And I’d love to work with you too (maybe we can talk about the new one: THINK SMALL)?

Speaking of which, my calendar is rolling for 2020. Please contact Michelle if I can help you with a keynote, workshop, emcee, or other.

If you need a speaker, #PickPlaid

Speaking of my suits, my friends at Appfolio were the first event to order me a custom suit with their logo as the pattern to wear on stage. That’s next level!

I appreciate your time and your trust.

All my best,


Jay Baer

Written by

Jay Baer

Founder of Convince & Convert, a digital media and marketing company. NY Times best-selling author, global keynote speaker. New book: Hug Your Haters

Convince & Convert

Convince & Convert: content, social, customer experience

Jay Baer

Written by

Jay Baer

Founder of Convince & Convert, a digital media and marketing company. NY Times best-selling author, global keynote speaker. New book: Hug Your Haters

Convince & Convert

Convince & Convert: content, social, customer experience

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