It's OK to Meet Local Friends at Faraway Conferences

Why we let our guards down on the road, and what happens next

Welcome back to The Workaround. I’m Bob 👋

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My friend Steph meets all the coolest people at conferences.

I spent last week at an industry conference on another continent in a wonderful setting.¹ Of course, it’s got to be a wonderful setting to attract industry titans at a time of year when we celebrate Father’s Day and take time off for vacations.

This was my sixth time attending, and the third company I’ve represented at this conference. But I haven’t been there in eight years, and it was the first time I went as an investor rather than an operator.

This meant I had a lot less pressure and a more open calendar. My mind was clearer, so I filled it by making observations.²

Today, I’m sharing one that sticks with me the most, and one I hope we can keep in mind as we return to reality this week.

That Recurring Icebreaker

“Funny how we have to come all the way out here to meet.”

That’s what my friend, Jack, says as we sit down for breakfast on a beautiful, sunny morning at an outdoor cafe across from the ocean.

It’s Monday of the big conference, and most people are just landing now. Jack and I got in on Sunday, and this is the first meeting for either of us.

His observation is one that we’ve all heard a hundred times in conferences around the world. It never gets old to hear this self-owning joke because it’s so true and so strange. But no one goes past the observation to break down why we meet out here more often and what that means.

But, like I said, I’ve got some time to observe…

Jack and I live in the same city, about thirty minutes away from each other. We’ve known and liked each other and worked in the same industry for more than twenty years. Yet we’ve gotten together locally only four or five times. I’ve seen him more in out-of-state conferences than I have in the place where we both live.

That is odd. But that’s not all.

Our conversation this morning—and all of our conversations away from home—are so much more interesting. Neither of us is pitching or being pitched. We don’t have a meeting to run to next. Our phones remain in our pockets. So we’re much more real with each other. We share deep stories about our families, our companies, and our hopes, dreams, and struggles.

It’s not that we’re going somewhere special. It’s that we’re getting away from somewhere. We’re escaping our offices and daily work routines that often feel like they strangle us with schedules and deliverables. But more importantly, we’re getting away from our usual selves.

We Let Our Guards Down

At home, we’re stuck in our roles. Senior executives in fancy offices are protected by administrators and chiefs of staff who safeguard their valuable time and attention. Vendors with quotas to hit run to hit their numbers. Managers have people and processes to manage. And everyone is stuck in meeting, email, CRM, and group chat hell. There is no time for relationship building—even if a watercooler or keg-erator is just down the hall. We just want to log off and go home.

Escaping to a work conference takes so much pressure off. Everyone at the home office knows you’re out here, “doing important stuff” and in a different time zone. They tend to leave us alone.

But this is just the first step. Once we land, the real magic happens as the walls of our egos begin to dissolve.

Everyone here is part of a shared community of individuals who have achieved a measure of success in the industry. Through some combination of skill, passion, luck, and climbing over the competition, we’ve made it past the velvet rope and into the VIP section. We relax a bit, give everyone a friendly nod, and try to act like we’ve been here before.

In some cool clubs, there’s still a lot of preening and pressure to stand out. But this is still a work conference, and we’re all here to sell something. We’re trying to deepen our relationship with a client or hoping to open the door with a new prospect. Or we’re speaking on a stage, hoping to convince the financial markets that our company deserves a higher share price.

Everyone feels a little bit smaller—and more real—when they are hustling for attention.

I go see the CMO of the world’s largest marketer make his way to a small stage hosted by the world’s largest retailer, the one he sells more than $10 billion of products to each year. That retailer is hosting the event in the hopes of selling billions of dollars in new advertising products to this CMO. They need each other.

Riding in the elevator to this event with me is the CEO of the largest and hottest advertising agency holding company. He’s frantically pushing the elevator close door button because he fears he might be late for a front-row seat to see his biggest client on this tiny stage.

You’ve gotta serve somebody, and any good servant is humble. Our egos slip down another notch…

We’re all a little bit naked out here, and it’s not just because it’s sunny and hot. As our guards come down, we see that we are just fellow humans living the struggle and the dream.

The more exotic the location, and the farther away the time zone from home, the better the bonding. The setting may be lovely, but we’re out of our comfort zones and cling more tightly to each other. We need to start doing conferences in the hills of Tanzania or the jungles of Brazil. We’ll boost more deserving local economies and move people farther away from their regular selves.

And let’s HOPE for a travel snafu. On my previous trip to this conference, an Uber strike turned all of our travel plans upside down. Guess what? Strangers united in a common cause figured it out together. We shared precious car rides, split helicopter costs, and helped each other navigate the train system. Challenge breeds camaraderie.

On our own, without the mediating shell of our hometown and corporate ecosystem, we become more open to others. A shared baguette, bottle of wine, or vape pen helps unlock bonding. A full belly and looser headspace shift our ego down another notch. It’s what humans have been doing with campfires and peace pipes for thousands of years.

What Happens When We Open Up

Many interesting things happen in these temporary spaces once people become real again.

Senior executives spend quality time with suppliers and their own junior employees. There are many unscheduled minutes when senior leaders are forced to engage in conversation and learn about what their support staff sees on the ground. I must have heard “How can we improve?” a dozen times from the lips of C-level captains of industry. It’s a bit like an annual Undercover Boss Conference.

Ruthless competitors build bridges when isolated together. I’ve seen:

• Investors admit their biggest mistakes

• Agency competitors discuss ways to raise the waters of their entire category together

• Competing brand managers advise each other on their career prospects

• Startup founders compare notes on which clients to embrace or avoid

As our guards fall, we have the kind of conversations we always wanted to have. We realize no one knows what they’re doing, but we can get a little closer to the truth by helping each other find some shortcuts.

Together again, we recall the special place we have in each other’s hearts. In 2008, I delivered the first keynote speech for my book at a conference. I met a great guy named Sean there. Last week we met for the first time since. I can still remember our years-ago half-drunken conversation about industry trends while closing down the bar. He told me a copy of my book is still on his desk.

We confront some of our biggest enemies. Last week at the conference, a friend moaned to me about wanting to avoid—or punch—a former boss who betrayed his trust. The next day, we all ran into each other in a hotel lobby. Guess what came out of it? They shared a Bro-Hug.

We’re trapped here, we see we’re just people—flaws and all—and we get over ourselves.

While on the road, I’ve offered and accepted countless apologies for real and perceived slights with co-workers, clients, and business partners. We hug it out, let it go, and laugh at how silly we were in our careers’ youth.

Can We Take It With Us?

Alas, when I arrive at the airport at 6:30 a.m. on Thursday to begin my first of three flights home, I see that my peers and I have already slipped back into our regular work personas. In the departure lounge, several people who had been relaxed and laughing just hours earlier are now hugging their laptops close and dialing into conference calls.

But what if we nudge our conversations further, and keep keeping it real?

The next time you’re in Cannes, or Vegas, or Tanzania for a work conference, and someone says, “Isn’t it funny how we come all the way here to meet?” Reply:

“Yes! It’s because we’re outside of our bubbles, and it means we become more open, trusting, and value human connection. How can we keep this feeling together when we get back to our offices?”

Maybe a little progress will be made back home…or maybe we’ll make this an excuse to get together here again next year…

If you like my writing, feel free to click the ❤️ or 🔄 button on this post so more people can discover it on Substack 🙏

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BONUS: Cool Content of the Week

A little something I found meaningful. You might agree…

Status Games Rule Everything

One of the downsides of writing about fancy conferences is that it can stir up all the negative emotions about our place in the office hierarchy. Not everyone can attend, so those with the largest budgets and most prestigious titles tend to win the free trips. They seem to be living the dream while we can’t help to feel FOMO—until it’s our turn to step on that rung of the corporate ladder.

Jack Raines recently wrote an insightful look at the status games we play. It begins with the colleges we attended and the degrees we earned. And it continues through every title, perk, award, and the number of people you manage. We human beings are constantly judging ourselves by how we stand in comparison to others. It’s natural, and can have positive sides. But Raines points out a massive pitfall:

“This desire for approval makes status dangerous, because we can fall in a trap of chasing status for status’s sake, with little regard for the kind of status that we actually desire. And unlike money, status is domain-specific.”

The funny thing is, once we “win” a status game, we end up wondering, “Now what?” There is always a bigger pond, a higher title, a more velveteen rope. And the people you meet at those higher levels are just as self-conscious as the rest.

Status games are all around us and can play a role in helping us advance in our careers. The key is playing them to get to something truly meaningful. Otherwise, you’re just getting played.

Status Games Rule Everything Around Me.

1. If you must know, it's the Cannes Lions International Festival of Creativity. I’m sure whatever industry you’re in, there’s a big, sexy, exotic industry conference like this.

2. Apologies to the real operators on this trip, Rob and Steph, for having to listen to my many observations, mostly shared after 1 am.