Dennis was in the lobby for a conference, doing what he usually did at conferences. He trying to find someone to buddy up with, so he could brave the storm of personalities and bullshit that he found most conferences created.
Conferences were always a bit of an edge for Dennis; it always felt like everyone knew each other, and he was the new-comer, trying to gain everyone’s approval and have everyone like him.
It felt awkward, at times lonely, and most of all, draining. Dennis knew how to make people like him, having a natural wit and an interesting background story to share, but in large group settings like this one, it tended to feel like a lot of “being on”. By the end of the evenings, he usually sought out some solace in a good scotch at the hotel bar.
Dennis usually had the other members of his leadership team with him at conferences like this, but this time it was different. He’d come here desperately seeking a solution to the woes ReggieCorp Inc. were experiencing. Secretly, he was also hoping he would find some solutions to the woes he was personally experiencing as well.
ReggieCorp’s leadership team had been at each other’s throats lately. Their growth curve had leveled off, and their profits were now static. In the realm of business, staying static was the same as dying. The executive team had sat and brainstormed solutions for hours, arguing bitterly over potential solutions, only to half-heartedly attempt to implement them and start back over. All of the members of the executive team were putting in long hours and felt absolutely exhausted. While they had gotten into this business for the love of the work and the freedom entrepreneurship promised, it would be fair to say that by this point, they all felt trapped.
In the process of banging their collective heads against the wall in an attempt to find the silver bullet solution, they had sought out round table management groups, gotten personality profiling done, and even hired consultants to come in, diagnose what was going on, and provide them a recipe for what was next. Try as they did, these approaches only ever seemed to resolve in temporary changes, before sliding back into the same pattern as before.
At the same time all of this was going on, Dennis was experiencing an inner crisis. At least, he might have called it a crisis if he was able to feel it to that extent. More accurately, Dennis felt detached from life. Like he was floating by, as an observer. He was frustrated and annoyed that he couldn’t find a solution to ReggieCorp’s woes, but more concerning than that was that life felt empty and meaningless.
ReggieCorp’s early success had left each of the co-founders with a sizable amount of wealth. Certainly not putting them in the top one-percent, but Dennis knew he could live comfortably for a few years without having to do very much. And this fact actually exacerbated the problem for Dennis. He simply didn’t have much to worry about — but he also didn’t have much to be excited or hungry for.
Dennis had been debating moving on from the company and doing something different, in the hope that it would create a new experience. Light a fire under his ass again, and get him excited about life.
Finally, Dennis had been a serial dater for the last decade or so, and while he was reliable to create brief, romantic interludes, he also had a creeping sense of loneliness in his life.
Most worrying to Dennis was that he found he was alright with all of this. Very zen about it, he had joked to himself.
The problem was that Dennis had come to the realization he was no longer alright with being alright with this. He wanted more from his life.
Hoping to discover something that might make a difference, he had taken it upon himself to register for Busyness 2.0, a conference that ostensibly combined a focus on good, effective business principles, mindfulness, freedom and many other aspects of what it meant to own and run a company.
So far, the conference had been fine.
Which meant that it was going poorly.
Fine for Dennis meant that he had met some people, had charmed them and left them feeling that he was delightful and funny, and had then left them when he couldn’t “be on” for any longer.
Dennis had been retreating to the bar earlier and earlier, putting his head in his phone and responding to e-mails to give himself a sense of some degree of productivity. He had made a promise to himself to attend one more day of talks, and if nothing shifted from there, he had decided he would catch an earlier flight back home and give his departure notice to his fellow leaders.
Looking at his schedule, Dennis saw that the next talk he’d signed up for was on time management and mindfulness for business leaders. Dennis had been excited about this talk when he had first signed up for the conference. Dennis could certainly use more time, as could most of his team, but the notion of mindfulness really appealed to him. Dennis had already concluded that one of the solutions to his problems might be practising more presence in his life. If he just did that enough, Dennis reasoned, then he would start to see all of the meaning that was already there, and would feel less aimless and fine about life.
Dennis took his seat toward the back of the room, and pulled out his phone to occupy himself while everyone else took their seats.
“Are you making money right now?” A voice next to him asked, mildly startlingly him out of his e-mail daze.
Dennis looked up and saw that a man had taken the seat next to him.
“Sorry, what?” Dennis stammered, quickly regaining his composure, but unsure what the stranger was asking him. It sounded like a sales-pitch, and, correspondingly, Dennis had already loaded his anti-sales-pitch verbal-missiles into their docking bay. While he didn’t enjoy being sold to, he did love the opportunity to absolutely destroy someone, verbally, that was being obnoxious and trying to push something inappropriately.
The stranger smiled, “Whenever I see people at conferences like this staring at their phones, I like to think they’re all ‘MAKING MONEY RIGHT NOW!’ Like they’ve attained some higher level of money transcendence. They just look at their phone and will money into existence. The only caveat is they have to frown their eyebrows a lot and bury their head in their phone. It’s silly, but it makes me laugh.”
It made Dennis laugh too. He smiled back. “Ha, yes. The only cost is that I have to tape my phone to my face, but otherwise I have transcended all money issues and am a billionaire. Buy my special facetape, and you too can be a billionaire!”
At this, the person sitting next to Dennis laughed joyously. He extended his hand, delight at Dennis’ joke still dancing in his eyes. “That’s good stuff. I’m Jonathan.”
Dennis shook Jonathan’s hand, “Pleasure to meet you Jonathan. I’m Dennis.”
Dennis and Jonathan exchanged some more pleasantries before the speaker came on stage and began her lecture.
Dennis found the content mildly interesting. The speaker was okay, but her material did have plenty of merit. Although Dennis had heard a lot of these tips before, he reasoned with himself that he could never heard this stuff enough, and maybe if he really just took diligent notes and put a lot of willpower into following the advice being given, he would create the breakthrough he was looking for.
He leaned over to Jonathan to make a joke at one point during the lecture, and was surprised to see that in Jonathan’s notebook, he was simply doodling. No notes, nothing written out — he was just drawing.
Dennis, relating to Jonathan as a cautionary tale, redoubled his efforts to take diligent notes. “I can’t imagine a crappy picture of a cat is going to help me be more mindful.” That being said, Dennis did notice that Jonathan seemed to be enjoying himself.
At the end of the segment, Dennis and Jonathan walked out together, and headed to the coffee shop for some refreshments. On the way there, Dennis decided to ask Jonathan about his notes.
“Hey, I couldn’t help but notice, instead of taking notes, you were drawing shitty pictures of cats.”
Jonathan laughed again, genuinely, “Well, actually, I was going to see if you were interested in buying some art for your office.”
Dennis laughed in kind, before Jonathan continued.
“Actually, I just doodle because I find it relaxing. It shuts my brain off and stops me from thinking about all of this stuff too much.”
Dennis responded, “But… aren’t you worried about not absorbing this material? Is your memory that good?”
Jonathan ordered his coffee, then turned to Dennis, “May I buy this for you?”
Dennis nodded and waited while Jonathan paid the bill.
“I’m not actually here for any productivity or mindfulness tips. It’s not that there’s anything wrong with them, it’s just that I’ve noticed, after years of trying to ‘become more productive and mindful’, no amount of following a recipe gets me somewhere unless I shift who I’m being underneath that.”
Dennis stopped Jonathan. “I’m not sure I understand.”
Jonathan nodded, directed them to a table, and sat down with Dennis.
“It’s like hiring a consultant to solve a problem in your business. They can tell you all of the right things to do, but if the problem isn’t actually a lack of knowing what to do, and instead is something deeper, like say perhaps a fear about scaling too big, or a concern about getting so big you have to work fourteen hour days… Well, no amount of having the right answer is going to overcome that fear. It’ll just stay in the shadows, quietly and effectively sabotaging all of your efforts. You know what I mean?”
Dennis took a sip of coffee to mask his astonishment. He knew exactly what Jonathan meant. He had just summed up a significant part of how it had been going with his fellow leadership team.
“So… well, what are you doing here then?”
Jonathan smiled and looked out at the crowd. “Oh, I’m here to serve someone. I don’t know who yet.”
Dennis felt his brain split in two. On the one hand, that sounded like such a new-agey bullshit response that he wanted to dismiss Jonathan immediately. On the other hand, there was something about the way Jonathan sat and spoke that felt honest and true. Almost simple, in a way, though powerful in his simplicity. Dennis realized the experience he had with Jonathan was that he trusted him. When Jonathan said he was here to serve someone, Dennis believed him.
Dennis chose his next words carefully, trying to skirt around the part of his brain that was shouting “That’s frigging bullshit!” at him.
“What does that mean?”
Jonathan turned back to Dennis and laughed again. “Oh, it’s okay to tell me you think what I just said is bullshit — there was a time when I would have felt that way too!” Dennis laughed and relaxed. He noticed how much easier this conversation felt than many of the others ones at this conference, and realized it was because he wasn’t running the “Dennis-show” — the routine he used to make sure people liked him. Jonathan just seemed to genuinely like Dennis.
Jonathan continued, “No, what I mean is that I come to these events to meet people, and what I care about is making a difference for someone. I’ve learned that if I do that, everything else kind of takes care of itself.” He held out his hand, as though to stay the response Dennis might have had ready. “And I know even that can sound silly. There was a time in my past when I would have torn that to pieces. But I’m a different person these days.”
Dennis’s curiosity was piqued. “What kind of difference do you hope to make?”
Jonathan finished his coffee and said, “I’m not sure — that depends more on the kind of difference that person is hoping to create in their life. What I’m interested in is supporting them to get beyond doing the right things, and instead creating the experience of life that seems to be eluding them.”
Jonathan got up from his seat. “Hey, I’m due for a talk about turning your art into masterpieces,” Jonathan smiled wryly at Dennis, “but if you’d like, I’m happy to share more, and even explore what that difference would be for you. Whether or not that’s what you’re here for, I find it’s always powerful getting present to what’s possible in our lives, on the other side of what’s predictable. Want to meet for drinks at the end of the day?”
Dennis was fighting with the reactive part of himself that was concerned about a sales pitch. He didn’t want to sit through the equivalent of a time-share presentation. But, again, he noticed he trusted Jonathan.
“Sure, I’d love that.”
Jonathan nodded, “Cool, and I promise I won’t turn it into a sales pitch to get you to buy my cat doodles. How about we meet back here at the end of the day for a cocktail before dinner?”
Dennis laughed and nodded his head in agreement. “That sounds great — see you at 6:30”.
Jonathan gave a thumbs-up, turned and walked into the crowd.
Dennis sat with his thoughts for a while, and then got up to go to his next talk.