👋 Hiya, job sneaker!
Sidney was doing that awkward grocery store stretch, trying to reach the good maple syrup on the top shelf, when someone's cart crashed into hers.
“Oh, sorry!" She spun around, ready to give whoever it was the stink eye, but froze. “Randy?”
“Sidney! Holy crap, how long has it been?” His face broke into that same grin she remembered from those endless leadership meetings where they'd actually solved things instead of just talking in circles.
They stood there blocking the condiments aisle, catching up like no time had passed. That was the thing about Randy. Conversations with him just flowed. Always had. Before they knew it, other shoppers were shooting them dirty looks.
“We should grab coffee soon," Randy said, stepping aside for an impatient dad with a screaming toddler. “Seriously, let's not do the whole 'we should totally hang out' thing and then forget each other by the time we get our groceries loaded in our cars.”
Sidney laughed. “Deal.” But even as she said it, she knew how these things went.
Later that night, she stood at the stove stirring pasta sauce while her partner wrestled their two-year-old into her high chair.
“So they want me to rewrite the onboarding docs again," Sidney said, not looking up from the bubbling tomatoes. “Third time. And get this, Thing One said the complete opposite of what Thing Two told me last week. Guess whose fault that is?”
“Let me guess. Yours?” Her partner finally got the kid strapped in and kissed Sidney's cheek. “The Startup Bros are the worst.”
Sidney shrugged. “Could be worse, right? Remember when I quit without having anything lined up and then, surprise! Found out we were pregnant?”
They ate to the soundtrack of tiny fists smashing peas, Sidney's mind drifting to those brutal months of job interviews. The moment she'd mention her pregnancy, she could practically watch hiring managers' enthusiasm deflate like a punctured balloon.
The next morning, coffee in hand, Sidney opened her laptop at the kitchen table. Just browsing, she told herself. But then she saw it, a customer success role at a fertility benefits company. The kind with amazing culture, flexible work, the whole deal. Even better? Her old teammate worked there now.
Sidney fired off an application and shot her former colleague a quick message. “Hey! Just applied for the open CS role at your company. Would love to catch up!”
A week later, she sat in her favorite coffee shop watching her phone. The automated rejection email hurt, sure. But what really stung was the silence from her old teammate. Not even a “sorry, too busy” response.
“Traffic was insane, sorry I'm late.” Randy slid into the chair across from her, slightly out of breath.
“No worries.” Sidney closed her laptop. “I was just wallowing in rejection emails anyway.”
They caught up on work, life, the usual stuff. Then Sidney mentioned the big news. “We're actually thinking about moving to Toronto. My partner and I love it up there.”
“That's awesome! Though job hunting internationally sounds like a nightmare.”
Randy's eyes suddenly lit up. “Wait. One of my clients is a startup in Montreal; they're incredible. Growing like crazy, really solid leadership team. Want me to put you in touch?”
Sidney hesitated. “I mean, sure. It would be nice to at least learn about the Canadian market.”
The following Tuesday, Sidney's laptop chimed with a Zoom notification. The Startup Bros wanted a “quick sync.”
“So we've got awesome news," one of them said, leaning back in his gaming chair. “My buddy is looking for something to do before he starts his MBA. We figured he could run customer success for a bit, you know? Give you some direction.”
Sidney's face stayed perfectly neutral while her brain screamed. She nodded and made appropriate noises, already mentally updating her resume.
That evening, she dove into research about Randy's Montreal client before her call. While digging around their careers page, she stumbled across a customer success posting. The job description named the hiring manager, so Sidney took a shot.
She crafted a LinkedIn message. “Hi! I noticed your CS role and, coincidentally, have a call with your colleague tomorrow. I'm also friends with Randy, not sure if you know him, but he speaks highly of the company.”
The response came back in two hours. The hiring manager was pumped, asked Sidney to apply immediately, and suggested coffee the next week when she'd be in town. Even better news, they wanted to open a satellite office in Sidney's city.
Meeting the hiring manager felt like finding a long-lost friend. They finished each other's sentences talking about customer success strategy. She even introduced Sidney to one of the co-founders that same afternoon.
Just one more step, meeting the CEO.
Then... nothing. Days turned into weeks. Sidney's optimistic follow-up emails got swallowed by the void. She was back at her kitchen table, staring at her laptop, when her phone rang.
“Hey, just checking in." Randy's voice was a lifeline. “I actually took on a fractional role with them, crazy, right? Everyone's still talking about you bee tee dubs. They just launched a big product update, and it's been chaos, but the CEO said he was for sure going to call you.”
Sidney felt her shoulders unclench for the first time in weeks.
When the CEO finally called, his energy was infectious. And his offer floored her, not just the customer success role, but leading the entire team build-out.
“Okay, what's the catch?” Sidney asked. “This sounds too good to be true.”
He laughed. “No catch. Randy vouches for you, and honestly, your network is exactly what we're going to need for our new location.”
One month later, Sidney sits at a table in the lobby of her Montreal hotel, watching real maple syrup pool golden around her pancakes. First day at the new job, and she can't stop smiling.
The Startup Bros never spoke to her again after her resignation email, probably for the best. But she did send personal notes to the colleagues who mattered, promising to stay in touch. This time, she means it.
The door prize? Relationships don't survive on good intentions. They need nudges, check-ins, and shared pancakes now and then. Even if you're not plotting your next career move, start reconnecting now. Not to ask for anything. Just to remind people you exist. Because when the right opportunity shows up, it's usually someone else who opens the door.
Go warm up your griddle,
✌️ Kirby