👋 Hiya, job sneakers!

Dani had the tab open again.

The same tab she always opened on slow afternoons when the urge to see what else was out there got too loud to ignore. HealthForward’s careers page. She’d bookmarked it eight months ago, told herself it was just in case.

She scrolled through. Saw nothing new. Closed the tab.

The email landed in her inbox a few days later. HealthForward Summit, coming to Chicago. Two days, forty speakers. Tickets were $1800. No way was her company sending her. And her bank account could only send thoughts and prayers.

Her friend texted her a link an hour later. She almost didn't open it. The conference was looking for volunteers. Free t-shirt, free meal, and more importantly free admission.

But did she really want to burn a vacation day on a registration desk at 7am?

She signed up anyway.

Dani smoothed the front of her blazer one more time.

The coffee cart wasn’t even set up yet, but she had found her spot behind a folding table stacked with lanyards and badge sleeves. Not exactly where she’d imagined breaking into her dream company. But here she was.

The first hour was a blur of printing badges, handing out tote bags, pointing down the same hallway over and over. By 9am, her feet already hurt.

Then a woman walked up, frantically scrolling through her phone, clearly looking for her registration email.

“I can’t seem to find it.”

Dani pulled up the list, found her in a few seconds, printed a new badge.

“Thanks,” she exhaled. “I couldn’t find that email to save my life.”

She looped the lanyard around her neck.

“Do you work for HealthForward?”

“No, just volunteering.” Dani hesitated. “I work in marketing at ClearPath. I’ve been following HealthForward for a while though. Couldn’t swing the ticket price, so.”

The woman smiled. “Smart. What kind of marketing?”

They talked for a while longer. Dani didn’t realize until later that she’d described her last marketing campaign in the kind of detail she never managed in interviews. It hadn’t felt like a pitch. It just felt like talking.

The woman handed Dani her business card as the line picked back up.

“Send me your resume. I mean it.”

Her name was Eve Wollman. VP of Marketing, HealthForward.

That night, Dani sat down to write the email.

She opened a draft, stared at it, closed her laptop. Made tea she didn’t drink. Opened it again.

The first version ran four paragraphs. She cut it down to two, then decided two was still too much. She deleted the line about how their meeting felt like it was straight out of her favorite movie. Too much.

She landed on five sentences. Read them until they stopped making sense. Hit send at 11:47pm before she could talk herself out of it again.

Two weeks went by.

She checked her inbox with the specific kind of obsession only job seekers understand. She also double checked her spam folder and triple checked that she’d sent the email to the right person.

She started to make peace with it. A VP at a fast-growing healthtech company probably gets dozens of emails after every conference. The moment at the registration table had felt significant, but not every coincidence is magic. Sometimes you're just two people reaching for the same glove. That's all.

Eventually, the reply came.

Eve had been traveling. She apologized for the delay and got right to it: she’d mentioned Dani to their Head of Marketing. Would Dani be free for a call the following week?

One video call. One panel interview. One take-home project that felt more like the type of work she’d love to be doing than the work-flavored work she’d been used to.

The offer landed in her inbox a couple slow afternoons later.

She closed her eyes, let out a long breath, and let herself feel it.

Then she closed the careers page for the last time.

The door prize? If you know what you want, stop waiting for it. The clear path may never present itself. But somewhere out there is a strange, awkward step forward that most people would talk themselves out of, and that step is the one that puts you somewhere the universe can actually work with. You can't engineer the serendipity. But you can show up somewhere it might find you.

Go grab a lanyard,

✌️ Steve

👋 Hiya, work besties!

My boss said something to me the other day that I’m still sitting with.

Not because it was harsh. Not because it was a shock. But because it was just... true. And I hadn’t really prioritized it before he said it out loud.

“You need to get outside of your team.”

I knew he was right. But also... wasn’t that kind of on him? Like, isn’t it his job to direct me where to go? Isn’t that how this is supposed to work?

Spoiler: that’s not how this works.

The room you’re not in.

Right now, somewhere in your company, a group of people are working really hard on something super important that is perfectly aligned with your strengths.

Are they going to think of you?

If you can’t answer that with some confidence, that’s the thing worth fixing. Not your resume. Not your LinkedIn profile. That.

The three circles.

Think of your reach at work like three circles.

The first circle is your immediate team. The people who see your work every day. You’re known here. Probably very well known. And that’s great.

The second circle is your manager’s world. The meetings they’re in, the stakeholders they talk to, the cross-functional relationships they have. You might show up here occasionally, if your manager is a skilled delegator or actively focused on your development. But you’re probably an afterthought.

The third circle is everyone else. Not just your boss’s boss. Your counterparts in product, in sales, in ops, in engineering. The people owning the big projects that actually move the needle. The people who don’t know you or why they should loop you in.

These cross-functional relationships are often where the biggest impact happens. And where the best opportunities come from.

Most of us are doing incredible work inside circle one. And wondering why everyone else seems to be getting the exciting projects.

Why your manager can’t do this for you.

Here’s the thing about managers: they can advocate for you, but they can’t build your relationships for you.

If your counterpart in the product team has never worked with you, your manager saying “they’re really good” only goes so far. Trust is built through doing things together, not through someone else’s recommendation.

I gave someone feedback not long ago that they weren’t ready for a bigger role. Really talented person. But when I thought about who outside of our immediate team knew what they were capable of... nobody. Not because they weren’t doing great work. Because the work was done in a room with the door closed.

That’s a frustrating place to be. And it’s fixable.

What to actually do.

A few things that work, in my experience.

Ask your manager to bring you to one of their meetings that you wouldn’t normally attend. Not to sit quietly and look engaged. To contribute something.

Figure out where the cross-functional chatter happens. A weekly business review, a shared Slack channel, a working group on a big initiative. Show up there with something useful to say.

Once you’ve started to build some relationships, look for the gaps. What’s the thing that everyone is struggling with that nobody is solving? Do that. The people who step into those gaps get known fast.

And honestly? Keep your manager in the loop with what you’re doing. Tell them who you’ve connected with recently. Tell them what you contributed. Don’t assume they’re tracking it. Help them help you.

The one question.

Ask your manager this: “Who outside of our team knows what I’ve been working on?”

If they have to think too hard, you have your answer.

And your next project.

The deep dive? Adam Grant’s Give and Take is the most compelling case I’ve read for why the people who reach across team boundaries, help others without keeping score, and invest in relationships outside their circle end up with the most credibility and the best opportunities. And it’s a great read.

Get your name out there,

✌️ Steve

👋 Hiya, work bestie!

You know that sick feeling you get right before an interview? The one where you’re convinced you’re the World’s Biggest Imposter and you’ll probably throw up all over your keyboard on this Zoom call?

Yeah, I used to feel that way.

But now, here’s how I keep my lunch where it belongs.

Interview Mixtape

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Interview Mixtape

I print out this mixtape template the night before every interview. I can usually work through it in about 30-60 minutes. But then I can go to sleep knowing I’ve got the perfect playlist to pop in tomorrow to boost my confidence.

• The Gig: This is just the company and role you’re interviewing for.

• Audience: These are the specific people who’ll be in the interview.

• The Theme: This is the overarching thing that they’ll be evaluating.

The A/B Sides of Your Career

Think of the A-side as the good times where you really shined. The B-side is the dark times where you got beat up a little, but learned a lot.

Here’s the thing: you’ve got tons of stories you could tell. So when your audience hits you with one of those inevitable “Tell me about a time when...”, you’re likely to come down with a case of analysis paralysis as your entire career flashes before your eyes.

My life hack... choose your stories beforehand. And by that I mean pick one A-side and one B-side story and limit all of your responses to just those.

Poof, you’ve just lowered your heart rate by 45 bpm.

Now when your audience asks, you just have to decide if your A or B-side is a better fit for the scenario. And then what angle of the story you’re going to tell.

But that sounds too easy, right? And what if they ask about more than two scenarios? Or your story doesn’t perfectly match their prompt?

It is in fact that easy. Nearly every behavioral interview question falls into one of two buckets: showing what you’re capable of (A-side) or demonstrating resilience and growth (B-side). The key is choosing bigger, stronger stories that can stand up to more than one scenario.

And don’t worry about circling back to the same story. That’s actually a good thing. Your audience already has some context as a jumping off point. And they get a fuller picture of what it’s like to work with you than a bunch of disjointed, vague examples.

And close enough is good enough. Just tell your story. They care more about how you think and communicate than getting a pixel-perfect answer. If they need more, they’ll ask for more.

Pro tip: Test your stories beforehand. Ask AI for 50 examples of “Tell me about a time when…” prompts based on the theme of this interview. Go through the list and see if you can quickly decide which story you’d pick and the angle you’d use. If you’re getting stuck a lot, you probably haven’t found the right stories yet.

Three Good Questions

Here’s another way to stand out: come up with three good questions. These are questions that make your audience say “That’s a good question,” and then pause for a few seconds while they think about their answer.

It’s a bad look if you don’t have anything to ask, but it’s also not helpful if you’re just regurgitating every other candidate’s throwaway questions.

For example: “I noticed the team recently switched from X to Y framework, what drove that decision?” is way better than “What technologies does the team use?” The first shows you’ve done your homework and you’re thinking critically. The second could’ve been answered by skimming the job posting again.

More inspiration: look at your audience’s LinkedIn profiles, at the company’s Glassdoor reviews, or just pretend this is your second week at this gig. What sorts of things would you be asking your audience?

Hype Song

One last thing (and this might sound weird):

Pick a hype song. Then right before you get on the call, blast it at full volume and move your body. Dance. Do jumping jacks. Go full inflatable tube man like at a car dealership and wave your arms around.

I know it sounds ridiculous, but getting your body moving literally changes how you feel. Our bodies and minds are connected in ways we don’t even understand. Get your energy up. Get your blood flowing. And you’ll show up as the version of yourself you want them to meet.

The deep dive? If you need even more help with what to do before, during, and after the interview, grab a copy of The Job Closer by Steve Dalton. You'll also want to check out the FIT Model and CAR Model that he and his former colleagues at Duke University put together.

You got this,

✌️ Steve

PS That extra space at the bottom? All yours for notes. And keep your mixtapes throughout your job search. You’ll start to see patterns in what’s working and what’s not as you go from interview to interview.

👋 Hiya, work bestie!

Most of the time, when someone gives job search advice, it goes something like this: “Apply to everything within the first week that it gets posted. And make sure you’re tailoring your resume specifically for each company.”

Hey, I get it. That's straight-forward advice. It even feels productive. You feed ChatGPT the job posting and your LinkedIn profile and blammo… out pops another perfect resume.

But here’s the thing most hiring managers aren’t saying out loud: “Resumes rarely decide who gets an interview.”

To understand why, think about what they’re actually dealing with.

Resumes are junk mail. Referrals are Yelp reviews.

Imagine the worst junk mail day you’ve ever had. The one when the mailbox wouldn’t even close. I bet you brought that mail inside and tossed it on the kitchen table. What if that happened every single day for a month?

Now imagine it’s winter. Your furnace just died and you need help NOW.

Are you going to sift through that towering pile of junk hoping to find an HVAC company, or are you going to jump on Yelp to find the best reviewed one in your area?

Your perfect resume is just one more piece of junk mail. Maybe the hiring manager looks at it, but even so, it was likely only for six seconds before it ended up on their kitchen table.

The Yelp review? That’s someone inside the company telling them: “Hey, I worked with this person before. They’re friggin’ awesome.”

And it’s how most interviews are happening in the real world. I mean, companies are giving their employees referral bonuses for a reason. They’re literally paying to not have to sift through that pile.

So why do most people avoid the referral route?

Because it’s uncomfortable. It’s awkward to reach out to someone you haven’t spoken to in two years. You don’t want to bother them and you don’t want to be rejected.

I hear you. I don’t like asking for favors either.

But here’s the thing you need to hear: you’re not asking for a favor. You’re offering them an opportunity. They’re likely getting some cash in their pocket if you get hired.

So here are my suggestions:

• Prioritize jobs where you know someone who works there.

• Reach out to them before you submit an application.

• Tell them you’re interested and ask questions about the company.

• They usually connect the dots and offer the referral all on their own.

• But don’t hesitate to ask directly. Remember, it’s a win-win.

If you want a referral, there’s an app for that.

I built Side Doors specifically to solve this problem. It's a Chrome extension that cuts through the noise on LinkedIn's job board and helps you find the right companies, the right people to talk to, and the best opening lines to land that referral. It's completely free, so go ahead and give it a test run and see why sending out junk mail is no longer necessary.

The deep dive? If you want to go even deeper on leveraging your network to find job opportunities, I highly recommend The 2-Hour Job Search by Steve Dalton. It's a practical system for organizing your search, identifying target companies, and getting referrals without feeling sleazy about it.

Remember, feeling productive isn't the same as being productive. When it comes to job searching, it's often just one person putting in a good word that creates the momentum you need to get to the finish line.

Referrals > Resumes,

✌️ Steve

👋 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,

✌️ Steve

👋 Hiya, work bestie!

Lately, everyone's asking the same thing: What's gonna happen to our jobs as AI gets smarter? Fair question, and yeah, some folks are getting a bit sweaty about it.

Here's my hot take. Our jobs aren't vanishing into thin air, but they're definitely getting a makeover. The real winners in this next leap forward won't be the traditional code wizards. Nope, it'll be people who can use AI tools to tackle the right problems.

We're entering the golden age of generalists with solid product thinking. Ya know, someone who can sniff out what’s broken, decide if it's worth the trouble, and whip up a quick prototype to test in the wild.

So how do you level up your product thinking?

Let’s break it down. A product mindset is getting nosy about problems, caring deeply about the people you're helping, and staying flexible enough to learn and pivot.

It means asking stuff like:

• Who's pulling their hair out over this?

• What's the actual headache we're solving for?

• How will we know if our solution slaps or is just mid?

Quick caveat before we go any further... I’m not saying everyone should get an MBA and ride off into the Product Manager sunset. There will always be a need for deeply specialized technical experts. But if that’s not the path you’re drawn to, I’m recommending you start borrowing from the Product Manager’s mental toolkit.

Ready to start building those product thinking muscles?

No fancy degrees or ten thousand hours on Udemy required. Just grab these four books, read ‘em in order, and you’ll have product juices flowing through your veins in no time.

📚 The Lean Product Playbook by Dan Olsen. This is your beginner’s guide to product thinking. Dan walks you through a clear, step-by-step playbook for identifying the right problems, testing ideas, and making decisions based on real learning.

📚 Sprint by Jake Knapp. Once you’ve grasped the basics, Jake shows you how to turn an idea into a testable prototype in just five days. Perfect for solo or small teams, this method helps you skip the fluff and get real feedback fast.

📚 Continuous Discovery Habits by Teresa Torres. After launching or testing, how do you keep learning? Teresa teaches you to regularly engage with users, gather insights, and make discovery a sustainable habit instead of a one-off effort.

📚 Inspired by Marty Cagan. This one zooms out to cover what makes great product teams tick. Marty dives into strong leadership, how top teams operate, and staying focused on solving real problems. Save this for last to see how everything fits together.

Reading is cool and all, but knowledge isn’t sticky until it’s put into action.

Here's your homework assignment:

1️⃣ Spot a daily pain. Look around and find something that makes coworkers groan. Maybe it's a process that drags, a meeting that feels pointless, or a handoff that always goes sideways. Don't overthink it. Just find what makes people roll their eyes.

2️⃣ Think like a PM. Instead of jumping straight to solutions, pump the brakes and ask: Who's suffering here? What exactly is the trainwreck? What do people actually need? You're not fixing yet, just getting clear on what's broken.

3️⃣ Talk to actual people. Talk to folks who deal with this pain every day. Ask open questions and soak up their perspective. What drives them bonkers? What have they tried? What would make them do a happy dance? Your goal is to listen, not pitch your idea.

4️⃣ Sketch a rough fix. After soaking up their insights, draft a possible fix. No need to be fancy. It could be a quick diagram, a process tweak, or a one pager. Just make sure it gets the idea across clearly enough to test.

5️⃣ Ask for real feedback. Share your sketch with the folks you spoke to. Ask what lands, what feels off, and what they’d change. Listen more than you talk. The goal is to shape ideas with real feedback, not just your own hunches.

This isn’t about launching the next iPhone. It’s about building the muscle: spotting problems, understanding people, and making smart moves that actually help. The product mindset starts small and that’s exactly the point.

The deep dive? If you want one solid resource to keep building your product chops, check out Lenny's Podcast. His chats with product leaders are gold every time. Start with these three episodes: Ethan Smith, Elena Verna, and Brian Balfour.

Product thinking isn’t just for fancy product managers. It’s for anyone who wants to solve better problems and create things that truly matter. Spend some time learning this mindset, and the payoff will be huge, not just for your career, but for the quality of work you produce.

Go sniff out those headaches,

✌️ Steve

👋 Hiya, job sneaker!

The senior leadership team was huddled around the latest five-alarm fire. The CEO shook his head, weary from weeks of acquisition negotiations and a seemingly endless stream of contractual red lines. He looked like he hadn’t seen a pillow in three weeks. Tommy jumped in to take point—he was always the first into the flames.

After the meeting, he lingered by the window, watching the morning traffic thin out. The last four years had been a revelation—trading the suffocation of enterprise bureaucracy for the beautiful chaos of building something from scratch.

When the acquisition papers were finally signed, champagne corks littered the floor. Tommy sat at his soon-to-be-someone-else’s desk, facing an uncomfortable truth: he’d just orchestrated his own funeral. The parent company already had all its executive boxes thoroughly checked. His impressive collection of hats had suddenly gone out of style.

Late one night, nursing a scotch in the office speakeasy, he scrolled the job boards with the enthusiasm of someone shopping for a casket. The thought of being reincarnated as a corporate cog made him take an even bigger sip. He’d gotten hooked on startup adrenaline—that everything’s-on-fire-but-isn’t-it-thrilling energy. No way was he going back to a world where “that’s not my job” was considered a core value.

His inbox buzzed. Outplacement services, courtesy of his severance package. The sender’s name looked familiar—of course it did. Many years ago, in a job far, far away, Tommy had spent two painful weeks calling everyone in his boss’s Rolodex to confirm their contact information. Those names had been popping up in his life ever since. He chuckled at how small the world still seemed.

With a heavy sigh and a little muscle memory, he began assembling his job search survival kit: LinkedIn alerts, tailored resumes, strategic outreach over coffee. The process hadn’t changed—still soul-crushing, just with a broader network. This time, though, he had Crunchbase. He could look up startup investors he knew and spot potential warm intros to founders.

His first promising lead—perfect on paper. It practically screamed you belong here. He ran his resume through the ATS checker included in the outplacement package.

Twenty percent match. TWENTY.

“Seriously?” he hissed at his laptop. Two decades of experience, reduced to a failing grade by an algorithm that probably couldn’t tell a term sheet from a grocery list.

He word-smithed to match the keywords and got a better score, but it read like it belonged to some other guy named Tommy who wore beige. Not the first responder, he knew himself to be. Off it went anyway, into the void—dozens more to follow.

Cold apps disappeared without a trace. Networking yielded mostly radio silence, with the occasional well-intended “I’ll keep an eye out.” It felt like launching flares into a thunderstorm—desperately hoping someone would see them before he ran out of chances.

When a former investor emailed him about a startup that seemed like a perfect fit, it felt like the clouds might part. The founder took a meeting. Thirty rushed minutes later, the call ended—surface barely scratched. The rejection hit his inbox before he could close Zoom. Apparently, that’s all it takes these days.

His confidence smoldering like the last embers of a campfire, Tommy widened his search to include—big gulp—enterprise roles.

A director position at a major bank caught his eye. Not his dream, but at this point, worth a look. He noticed a former colleague on the team and reached out. One LinkedIn message later, they were catching up over a video call.

“Remember when you volunteered to update our old boss’s contact list?” she said. “I think I mysteriously got food poisoning that day and hid in the restroom.”

Tommy laughed. “Hey, someone had to do it.”

“That’s exactly what I need in this role,” she replied. “Everyone thinks enterprise means staying in your lane. I need someone who brings that get-it-done-no-matter-what energy.”

“Wait—you’re the hiring manager?” Tommy blinked.

Now he’s back in a cubicle, sleeping with his eyes open while onboarding videos play: how to spot phishing emails, how to avoid injuries while sitting in an office chair, how to be a human that interacts with other humans. He wonders if he’s made a colossal mistake.

Then a shrill alarm pierces the quiet.

As he joins the procession to the stairwell, Tommy grins. Maybe this is just the fire drill before the real blaze. Maybe he won’t have to choose between job security and the thrill of putting out the flames after all.

The door prize? The job you land probably won’t come from a perfect resume or a flawless application—it’ll come from the reputation you built when you thought no one was watching. Your value can’t be measured by an algorithm, but it can be remembered by someone who saw you step up and deliver. Reach out to those people. They’re your best referrals, your strongest advocates.

And hey—if you ever find yourself staring down a severance package, try negotiating. I’ve talked to HR leaders—there’s often more wiggle room than you think. Worst case, they say no. But you don’t get what you don’t ask for.

Onward through the smoke,

✌️ Steve

👋 Hiya, job sneaker!

Kim sat cross-legged on the living room floor, her eyes flicking between her laptop and the chessboard in front of her. The gray hum of her company’s all-staff meeting played in the background, reporting quarterly financials in that same monotone drone she’d heard a dozen times before. Cash burn, runway, projections—mumbo jumbo.

“Sure you want to do that?” her partner asked, leaning in with an inquisitive smirk.

“I think so,” Kim said, removing her hand from her bishop.

Two moves later, her partner slid their queen across the board. “Checkmate.”

Kim blinked. “Seriously? Again?”

The next morning, Kim stared at her boss on the screen. He wore the tired face of someone who’d been up all night rehearsing their lines.

“We have to make some tough decisions, and unfortunately… your role has been impacted.”

Impacted. What a word. An understatement for the floor opening up and swallowing her whole. She nodded, trying to stay composed, but was already in a free fall.

With only three weeks of severance, she immediately started pinging people from her network. Old coworkers, mentors—anyone who might help open a side door. Stability, she thought. I just want stability.

Another game of chess. This time, Kim leaned in. Watched her partner more closely. Noticed how they built walls, protected their queen, and stayed patient.

“You never go for a big move early,” she said.

“Nope. I wait. I set up the board. Then I strike.”

A week later, their kitchen was gutted. The contractor they’d paid upfront vanished. Thousands of dollars gone—their savings, her backup plan.

She had to take a short-term, throwaway contract to cover bills. That work gutted her. She told herself it was temporary—just a pawn sacrifice in a long match.

Three months passed like a losing endgame. But her network came through. Interviews finally turned into an offer. She cried when the email arrived—relief, exhaustion, a breath she’d been holding finally let go.

The new job was promising. Kim felt like herself again, solving problems side by side with other engineers, trading ideas, and pulling each other out of dead ends. But a week in, a teammate left.

Then came her first all-hands. Financials again. This time, she listened.

“We’re seeing a recalibration in the market… reassessing growth trajectories…”

Buzzwords. But between them, a story. Kim heard it now.

One more teammate left the next week. This is the setup, she thought. And I’m not getting caught flat-footed.

She upgraded LinkedIn to Premium. She started messaging hiring managers directly. Bold, strategic moves. She thought like her partner. Like a chess player.

She sent a connection request to the hiring manager at Shopify—simple and direct. It felt like a long shot, but what did she have to lose?

To her surprise, they responded almost immediately. Character interview. Technical interview. Reference checks.

Wait—where were her references? No one was picking up the phone or responding to emails. Panic stirred. Was this going to slip away right at the end?

The night before the deadline, the checks came through. Her references had finally delivered. She got the job.

Now, a month into the new role, Kim wraps the chessboard in bubble wrap. The sun filters through the window, warming the cardboard boxes lined up like pawns.

They’re moving to Chicago. Everything still feels uncertain. But her gut tells her this is the right move. She knows now that stability isn’t about staying put. It’s about staying alert. Being strategic. Willing to move before you don’t have a choice.

“Hey,” her partner calls out. “Your last company just did a round of layoffs.”

The door prize? Stability isn’t static—it’s a strategy. Standing still is how life catches you flat-footed. True stability is an illusion. It comes from continuously thinking ahead and making bold moves, especially when you sense disruption on the horizon. Even if you’ve already faced a career setback, it’s never too late to make a bold move. You never know what could happen next.

Who dares wins,

✌️ Steve

👋 Hiya, job sneaker!

Joe watched an empty two-liter bottle of Faygo Arctic Sun skip down the alley behind his house like it had somewhere to be. The alley was always littered—styrofoam takeout containers, broken toys, soggy cardboard. Even if he cleaned it up, more would respawn, like clockwork.

He stood at the bedroom window, sweatpants sagging, his favorite gamer shirt—a faded black tee with pixelated hearts—clinging to one last thread of optimism. If the shirt actually reflected reality, he’d be one heartbeat away from a game over.

Behind him, his wife walked in, already showered, dressed, and halfway through her first cup of coffee.

“Do you have time to feed the dogs? I want to log on early,” she said.

“Yep,” he mumbled, not even pretending to hide the fact that he’d taken a hard left down Hardly Working Way months ago. There’s a quiet rebellion that forms when you know your employer has no ambition for your skill set.

Then came the flooded kitchen. Again. “You’ve got to be kidding me,” he groaned, his socks already getting to work with the cleanup. Déjà vu from a year ago—busted pipes, sunken ceiling, the shit smorgasbord all over again. Problems didn’t come knocking anymore; they had a key.

Weeks passed in a haze of presidential campaign sound bites and half-naps on the couch. Joe was either watching the news or just trying to sleep through it. The couch had officially become his command center for spiraling.

His wife, with a concerned tilt of her head, suggested a change. “You’ve got to find a new job. Something that actually challenges you. I’m upgrading your LinkedIn account to Premium.”

That was just the kick in the sweatpants he needed. Joe knew to skip the job board trap and go straight to tracking down hiring managers, sending them short, sincere messages alongside his résumé.

Then one day, on his favorite Discord server, he scrolled past a post: Want to move to Finland? A stunning lake photo, birch trees reflected in water, so still it looked painted. He laughed. “Yeah, that’d be nice,” he thought. He’d never even been on an international flight. Hell, he barely left the block those days. Still, something made him reply to the ad—just for fun, just to feel something.

To his shock, the guy replied. They jumped on a video call that same day. They clicked instantly. Turns out the company was filled with expats from around the world—people who’d taken leaps Joe hadn’t even dreamed of. Maybe they knew something he didn’t, so he kept the conversation alive.

And then the offer came. A real one. For a real job. In Finland.

Panic joined the party. “How do we even get there? What about all of our stuff? The dogs?” Change being too hard had always been a trusty excuse to stay put. But the employer offered relocation services. Friends could take most of their things. But the dogs? That was the line in the snow.

Then the election results dropped. And the stress he thought had peaked? It just achieved a high score. Suddenly, moving halfway across the world felt less like a daydream and more like the reset button he’d needed to press all along.

They called the vet. “Trazodone,” she said. “For the dogs. It helps.”

They mapped out a plan: drive from Detroit to NYC. One direct flight to Helsinki. Less time for the dogs to be trapped in the airport or on a plane.

Two days after the election, Joe finished accepting the offer.

Finland buzzes in a language they don’t yet understand, but beauty doesn’t need translation. They walk the cobbled streets, the dogs surprisingly calm, as if they too know it’s finally okay to exhale.

Joe spots a lone cigarette butt on the sidewalk. It sticks out like a sore thumb in the otherwise pristine city.

He bends down and picks it up.

The door prize? Pain without purpose is just suffering—and suffering is exhausting. It’s no wonder we shut down and check out. But if the reason to take action is strong enough, tenacity and resilience can take over. So don’t just dismiss an off-the-wall idea during your job search. Just remember to first get serious about your why, so you can turn potential breaking points into stepping stones.

Be bold out there,

✌️ Steve

👋 Hiya, work bestie!

It’s that time of year again, performance review season. And if you just groaned, I totally get it. Most people see performance reviews like a trip to the DMV: an annoying box to check before getting back to the real work. But I'm seeing them differently now. As a manager, this isn’t just another thing on my to-do list—it's honestly one of the most important parts of my job. And it’s one of the best tools I have to help people grow.

While performance reviews are a natural time for feedback, no one should ever feel blindsided. If that happens, that manager really needs to step their feedback game up. They need to start thinking about feedback like driving a car—you don’t wait until you’re in a ditch to jerk the wheel. You make the little nudges along the way to keep the car on the road.

You also don’t just stare out the windshield the whole time—you check your mirrors and ask the other people in the car to check your blind spots. That’s exactly what a good performance review does. You’re getting insights from your manager and your peers because no one person ever has the full picture.

How would you rate your performance lately? Have you been keeping a steady pace, following the road signs, and getting to your destinations on time?

How do you think your peers feel about the trip? Have you been letting them take the wheel every now and then, or at least help pick the playlist?

Managers, in particular, aren’t just looking at how you’re doing right now—they’re thinking about your future potential. They usually have a pretty good view of where you are and where you should be going. A lot of them even use a 9-box grid to sort things out. Think of it like a simple chart that maps out high, medium, and low performance vs. potential.

Which box do you think you’d land in right now? Are you flooring it in the fast lane, cruising at a steady speed, or pulled over on the shoulder somewhere?

How others see you can shape your career in big ways. If you’re looking for a new job, a solid referral can make all the difference. If you’re after a big promotion, having your manager in your corner is key. The best way to make that happen? Consistently showing that you're a strong performer with a lot of potential.

So when your next performance review rolls around, don’t treat it like just another formality. Use it as a chance to get the full picture of where you stand and what nudges you need to make to keep moving forward. Don’t just think about how you feel you’re doing—get real feedback on how others see your work and trajectory. The best way to do that? Show up to your review with honesty, openness, and curiosity.

The deep dive? If you feel like you’re not performing at your best or aren’t reaching your full potential, it might be time to check in on your motivation. If performance is the output, motivation is the fuel in your tank. Check out Drive: The Surprising Truth About What Motivates Us by Daniel Pink.

Keep moving forward,

✌️ Steve

👋 Hiya, job sneaker!

It’s July, and once again, Kent plops down in the chair with the weird tear in it. His boss leans forward, all smiles. “Kent, you're doing great work. We want to renew your contract.”

Déjà vu. Same spiel, five years running.

Which makes Kent wonder why he’s been low-key job hunting these past few months. Sure, the work is getting stale, but the job market is brutal. Maybe it’s best to let the open roles go to people who really need them.

A week later, he’s sipping coffee with an old friend, a new ritual he started when he first began looking. Meet up, catch up, see if they know of any opportunities. “Maybe I should take a break from these, now that I’m staying put?" he muses. His friend shrugs. "Hey, do whatever you need, man. You know I’m always here.”

Then August hits, and Kent finds himself back in that same torn chair. Only this time, his boss isn’t smiling. “The position dried up. We can’t renew.”

Wait, what? How does a job just disappear overnight? Wasn’t this the same guy telling me I was crushing it last month?

Kent goes home and tells his wife. He’s not ready to hit the market full throttle. He knows how rough it is out there. But they’ve got eight kids to put through school. So, ready or not, it’s go time.

He pounds the pavement. No networking rock left unturned. Coffee meetups, church handshakes, handing out resumes to other parents at speed-skating practice.

And it works. One to two interviews a week. A night-and-day difference from his other strategy—customizing resumes, blindly firing off applications, and getting one phone screen out of a hundred.

Then October rolls in, and finally, “Kent, we think you’d be a great fit. We want you on board.”

But the offer? Laughably low. Then he replays something the execs said—how they frown on candidates interviewing elsewhere, how they despise job-hoppers. Huge red flags. He trusts his gut and declines, betting on his remaining interviews.

Which promptly fizzle out. Then the callbacks stop. The job market goes quiet.

By the holidays, nothing. No leads. No movement. Just silence.

Late one night, while his family sleeps, Kent lies awake, replaying that rejected offer over and over. Was I an idiot? Should I have just taken it? What if that was my only shot?

Come January, he can't sit in this despair any longer. He heads to a familiar tech meetup, one he used to love, hosted at his former employer. The moment he walks in, familiar faces light up. The energy is contagious. For the first time in months, he feels something other than stress.

So, he keeps showing up. Not for networking, just for the camaraderie. The boost. The reminder that he’s still Kent, still valuable, still part of a community.

And then, one day, the phone rings.

It’s the recruiting firm that placed him in his last contract. “Hey, we’ve got something. ML Ops. They want seven years of experience. Interested?”

Kent laughs. “Has ML Ops even been around for seven years? Whatever, throw my name in the hat.”

A month later, he’s sitting in a new chair, in a new boss’s office. “Kent, you’re doing great work.”

But this time, the work is exciting. Challenging.

And this time, if he ever has to do it all over again, he’s ready.

The door prize? The job came through a traditional path, but it took time for the stars to align. The real takeaway, though, wasn’t just about his network aiding in the job search—it was about leaning on those connections for emotional support during the long layoff. Without that camaraderie, the wait would have been much harder to endure. If you can be that support for someone else, don’t hesitate—offer encouragement and affirmation. It can make all the difference.

Support one another out there,

✌️ Steve

👋 Hiya, job sneaker!

How did I get here? I was stuck in a never-ending cycle, training a revolving door of new hires while my growth sat impatiently in the waiting room. I was too early in my career to coast.

Maybe it was time to be selfish for once? That agency down the road, promising an endless flow of cool clients and even cooler colleagues, sounded like exactly what I needed.

A few rounds of interviews later: Challenging work? Check. Smart colleagues? Check. Chilling on a downtown rooftop in flip-flops instead of being stuck in an interior cubicle attached to a warehouse? Check, check, check. I could totally picture myself enjoying every minute at that place.

“They love me, they really love me!” At least that’s how it felt when the offer letter arrived. It was time to put in my notice. Hold up—counteroffer. More money, too much to turn down. So, I apologized and did my best to say goodbye on good terms. They couldn’t match the offer but were very understanding and even said they’d stay in touch.

Chained to my cubicle once more, my golden handcuffs felt a little shinier.

At first, I convinced myself I had made the right call. What’s wrong with more money, right? But every morning, I felt it. That nagging question: Did I just sell my future for a little extra on my paycheck? The weeks stretched into months, and the feeling didn’t go away. I coasted, doing the same work, feeling like I had hit pause on my career.

Months later, a new LinkedIn notification popped up. “Remember me from the agency? You gotta check out my new place. Want to come in for lunch?” Come in for lunch? Like, you don’t have to pack it or pay for it? I had heard rumors of that new place where all the devs around town were flocking. Why not at least check it out?

If I thought wearing flip-flops was cool, this place was next level. They basically treated their engineers like royalty. This was it. The kind of environment I had been craving. The kind of energy I thought I’d missed out on when I signed that counteroffer.

Another push to get through the gauntlet of interviews. Another offer letter in hand that matched my current salary. Time to put in my notice. But wait—another counteroffer with a higher salary and a $20K retention bonus.

I won’t lie. I hesitated. A lot. It was tempting. That kind of money was no joke. But then I thought about where I was a year ago—making the same decision. Did I really want to go through this cycle one more time? Another year of feeling like I was just trading time for money instead of building something bigger for myself?

Nope. Not this time. I shut my eyes, took a deep breath, and said, “Thanks, but no thanks.” Then I signed the offer letter.

Best. Decision. Ever. Every skill, every connection, every opportunity I have today? These were all seeds that I planted the day I said yes to that job.

The door prize? Growth isn’t optional. If you’re stagnating, you’re actually moving backward. Counteroffers are just handcuffs in disguise, keeping you from real progress. Never underestimate first impressions because the most unexpected connections can open the right doors. And above all, the path to your next opportunity probably won’t look the way you imagined. The universe has a weird way of working things out if you let it.

Stay open to the strangeness,

✌️ Steve

👋 Hiya, job sneaker!

I grab my first cup of coffee, saunter into my office, and log on, fully expecting just another day of Slack messages and status meetings. Then my boss’s boss pings me: “Got time for a quick chat?”

Oh, fantastic. Nothing ominous about that at all.

Turns out, a bunch of folks have been laid off, including my immediate manager. But don’t worry, he says—my job is safe. Safe? Sure. But suddenly, this place feels different. And different isn’t always good.

So, like any rational person facing an existential career crisis, I take a casual peek at the ol’ job boards. Just to see what’s out there, you know? I apply to one. Then another. And another. Before I know it, I’m deep in the trenches of blind applications, convinced that with enough resumes launched into the void, the perfect job will magically materialize.

Days turn into weeks. Silence. Deafening, soul-crushing silence. Damn it, Steve, you fell for it again. You know better than to trust the job boards.

But then, like finally seeing the all-clear message after a late-night production fire drill, a reply. Someone thinks I’m a good fit. They actually want to talk to me. Four rounds of interviews, five weeks of suspense, and then—that email. That dreaded “We love you, but not enough to hire you” email. Second place. They’d totally hire me... if only they had two jobs to give.

This one stings. I usually shake these things off, but my motivation is toast. I declare my job search officially dead. Unstar the job boards. Delete my secret “open to work” banner. Unfollow the recruiters. Done.

And then, in an act of career minimalism, I clean house on LinkedIn—narrowing my connections to just the strongest working relationships I’ve built. Ironically, that turns out to be the game-changer.

Soon after, I spot a post that would’ve been lost in the noise before:

And just like that, I slide into his DMs:

One intro later, I’m chatting with the hiring manager. Four rounds—this time, just one week—and boom: job offer in my inbox.

The door prize? Referrals change the game. Instead of blasting applications into the abyss, what if I had just waited for the right moment and made one strategic move? One DM, one week, one job. Lesson learned.

Yours in service,

✌️ Steve

👋 Hiya, job sneaker!

So, I was coaching this designer, we’ll call him Ken. Poor Ken had gotten the axe from his last gig and then vanished into the job search abyss for three whole months. No interviews. Nada. Zip.

He decided to reach out to me for help. My diagnosis? He didn't actually need coaching. He just needed to talk to someone with a pulse and a hiring budget. I knew his charm and obvious skillset would take it from there.

Ken's fatal flaw? Lone wolf syndrome. He got canned and went full hermit, silently screaming into the void of job boards. A common pitfall.

So, we employed a secret weapon: pure, unadulterated heartstring-tugging. Let's be honest, we're all suckers for a good help-me story. Doing a good deed makes us feel warm and fuzzy inside, right?

One LinkedIn post. Then, bam! A recruiter pounced. Three weeks later? Ken sent me a DM: “I got the job!” He had landed a three-month renewable contract.

The best part? They chopped the interview process in half. He was originally supposed to go four rounds, but they already had their answer after just two.

So, moral of the story? Desperation is a surprisingly effective marketing strategy. Just kidding! (Mostly.) Ask for help, people. It works.

Update: Ken is still killing it and has gotten his contract extended to a full year.

What makes this a great post?

• Vulnerability: Ken openly shared his layoff experience, making him relatable to others in the same boat.

• Positive Framing: While acknowledging frustration, the post quickly pivoted to resilience and problem-solving.

• Growth Mindset: The post highlighted lessons learned and next steps, showcasing Ken as adaptable and reflective.

Why did the recruiter bite?

• Hashtags: A mix of broad (#jobsearch, #hiring) and niche (#careertransition, #layoffheartbreak) increased visibility.

• Flexibility: Being open to contract work signals adaptability, making Ken an even stronger candidate.

• Availability: Recruiters love candidates who can start ASAP, contract roles especially move fast.

The door prize? If you’ve been laid off, don’t ghost the professional world. Let people know. The right person might be just a post away from helping you land your next role. Give it a shot, your future employer might be watching.

See you on the flippity flip,

✌️ Steve

👋 Hiya, world!

Here’s a fun thing about life: just when you think you’ve got it all figured out, it sneaks up behind you, taps you on the shoulder, and asks you a question so simple, but so profound, it flips your brain upside down.

For me, that question was this:

Have you ever had a manager like you?

Cue the internal record scratch. What does that even mean? Was this a trick question? I’m usually the one asking the big, introspective questions, and now here I was, sitting awkwardly with my shoe on the other foot.

As I sat there frozen, my mind spinning in circles, it dawned on me. The way I show up at work isn’t about nailing OKRs, reaching Inbox Zero, or running from meeting to meeting. It’s about people. Specifically, it’s about the growth of the people I lead: not just their professional growth, but their personal growth, too.

I realized something important:

I’m the kind of manager who puts ego aside to help others thrive.

Fueled by this realization, I reached for my old friend: Do More Great Work by Michael Bungay Stanier. If you ever need a career compass and a kick in the pants, this book is it. Rereading it reminded me of the moments in my career when I wasn’t just doing good work, but when I was making the kind of impact that lit me up.

Those were the moments when I helped someone unlock something big in themselves: when I helped them see what they were capable of, often before they could see it on their own. Those moments were my greatest work. And they weren’t accidental. They happened because I showed up with intention, curiosity, and a willingness to invest in others.

So how can I create more of these moments?

The answer is Mindspire, my new adventure to help as many people as possible with their careers. I want to create tons more of those transformative moments and share everything I’m learning along the way.

Stay tuned,

✌️ Steve