Pick a table.

When I landed at a startup job in NYC in 2009, I spent the first six months in what many people called "the worst territory." Staten Island.

I'd commute an hour and a half from Bushwick, which meant two different trains, followed by a ferry over to the island just to get my day started. I had no car, which is still wild to think of. Sometimes I'd have to walk 30 or 45 minutes to get from one cold call to the next. By the end of my first winter, I'd worn giant holes in the bottoms of my dress shoes, and every time I stepped in a puddle or walked through snow, my socks were soaked for the rest of the day.

One day, after I'd finally arrive back at the office in SoHo to log my sales calls, I noticed something interesting going on in the sales pit. Two groups of people. Two very distinct tables.

One group of reps clustered together to complain about how impossible the job was. The quota was unrealistic. Territories weren't fair. Not enough inbound leads. "This place doesn't want us all to succeed," I once overheard. The others nodded in agreement, like it was some brave thing to say.

And then there was the other group of reps. The folks who didn't have time for those types of conversations because they were too busy figuring stuff out. They’d huddle up to compare notes on what was working, borrowing each other's talk tracks, and staying late to prep for the next day. If someone left before 9 p.m., somebody would always yell, "Half day?" across the floor. Nobody in this group talked about whether the conditions were fair. They were determined to succeed.

Early in that job, I sat down at the second table. I wanted to be around the people who were killing it, and I loved the energy. I didn't know at the time that I was making one of the most important decisions of my career.

Michelle

Michelle joined our company on the customer success team a few months after I started. She'd taken a pay cut and a step backward in her career to be there. On paper, it didn't make much sense. She'd come from a job paying more money and a title with a lot more prestige.

I’d earned the opportunity to train new employees (while still having to perform at my sales job), and I remember her first day because of something she said during onboarding. We were going through the usual orientation stuff, and I was sharing the slide decks, when she looked at me and said, "I'm going to move through the ranks here."

Not "I hope to move through..." or "I'd love to move through..." She said it like you'd tell someone your name. Matter of fact, in case I was interested.

I'd already trained a lot of new hires by that point, and most of them spent training nodding along and trying not to look overwhelmed. But Michelle was different. She had this energy where you just knew she was going to be a problem, and I mean that in the best possible way.

And a few weeks later, I watched her prove it. A doctor called in, furious about something that wasn't really our fault. Most people on the CS team would try to get through a call like that as fast as possible. Defuse, apologize, move on. Or, better yet, hand it off to a manager. But Michelle stayed on that call for half an hour, at least. She listened to the rant without rushing the customer off the phone. She worked through the issue slowly and methodically. And by the end of the call, she'd turned that doctor around 180 degrees.

When she hung up, she slammed the phone down, pointed right at me, and yelled, "That's gonna be a renewal!" Then she walked over to a teammate who'd been struggling with a similar situation and walked him through exactly what she'd done.

Michelle and I still say that to each other when we hang out and something goes well. "That's gonna be a renewal!" We remember it fondly.

That was Michelle. Every problem was something to figure out. She eventually brought that mindset and attitude from CS over to the sales team, and from sales into management. And after a few more years, she left and kept going onto bigger roles at other companies with more responsibility and more impact.

Today, Michelle is the CEO of a well-known creative agency doing over $25 million in annual revenue. And I can still hear her on that first day telling me she was going to move through the ranks. She wasn't predicting her future. She had already decided it.

Josh

Josh joined our company around the same time Michelle did. He came from a big pharma company with a recognizable name and a bigger paycheck. And he was resentful about the pay and the job requirements from the moment he walked in the door.

I can remember one day when we were sitting in bean bag chairs, eating seaweed crisps (or whatever "startup snack" was lying around), and Josh was venting about his territory. I asked how his calls had gone that day, and he complained about having to make cold calls in the first place. He thought a junior salesperson should be making cold calls on his behalf so he could spend his time on deals. But there we were, sitting in bean bag chairs at an early-stage startup.

I tried to share what was working for me, but Josh wasn’t interested.

"That's easy for you to say. You've already gotten traction."

It irked me to hear this while I was wearing shoes with big holes in them.

Naturally, Josh found the complainer's table fast. He joined the group that spent time complaining about injustices instead of figuring out how to make some sales. And that group confirmed his beliefs every day. The quotas were unfair, leadership didn't care, and the system was designed for them to fail. They had each other's backs in failure, and it probably felt like solidarity. But nothing about those conversations ever made any of those people better at their jobs. And one day, Josh just didn't show up for work.

Last time I looked, he'd been an Account Executive at a bunch of tech companies for six months here, eight months there, and so on.

What I think about

The thing that jumps out at me about Michelle and Josh isn't that their outcomes were so wildly different. It's that their outcomes were determined before either of them made a single call.

They worked on the same floor, with the same product, quotas, leadership, and pay cut story. They'd made similar sacrifices to walk through the same door. But Michelle viewed her sacrifice as an investment, and Josh viewed his sacrifice as a loss.

They both made that decision early. And from that point forward, every day in their jobs became proof of the stories they’d already chosen.

When I look at the people from Josh's table on LinkedIn today, so many years later, most of them are still bouncing around. A few years here, a few years there. I don't see a lot of upward momentum. I imagine they're still playing the same characters, just at different companies now.

The bottom line

I've been building my own business for almost seven years now. The tables look different. No sales pit or bean bag chairs. But the choice is still there. And candidly, some days I feel like sitting down at the complainer’s table. An article I spent a lot of time writing bombs with readers. My email open rates drop for a few months. The algorithm changes, and my reach tanks. It would probably feel good to find someone who agrees that it’s all so unfair. That the platform screwed me, or the market has shifted. That it's harder than it used to be. And maybe some of that is even true. But I’ve seen what happens when you sit at that table and tell yourself that story.

Michelle chose her story on day one. I remember it because she told me. And I sat down at the same table because I saw a group of people whose future felt bright. I wanted to be around the folks who were jamming out, and I’m so glad I did.

So here's my question for you today:

Which table are you sitting at? Will you find a way to succeed, despite conditions you can't control? Or will you wait for a "fair" that may never arrive?

Reply and tell me what you think. I can't respond to everyone, but Jennifer and I read every email, and we love hearing from you.

That's all for this week.

See you next Saturday.