High School Cafeteria Part 2: Turn Every Job Hunt Conversation Into Multiple Opportunities

High Level Concept:

You can transform every job-related conversation from a single shot at one specific role into a gateway that opens multiple doors. Building relationships that lead to referrals, contract work, future roles, and connections throughout the company.

Some Context: The High School Cafeteria Analogy for Job Hunting

Picture a big cafeteria full of round tables, each with a group of people building something different — one’s working on a puzzle, another’s building a Lego tower, another’s sewing, etc.

Your goal in job hunting is to find a table where you (1) are excited about what they’re building, (2) enjoy working with the other people around the table, (3) have unique value they need that you actually want to bring everyday, and (4) are set up for success and can work in a way that matches your lifestyle needs.

You could walk up to every table and say “hire me! I’m great!” - but in this market, you’ll likely be drowned out by the noise. Instead, start with these two steps.

• Part 1 - Get clear on what you want and what you have to offer before walking in.

• Part 2 - Have conversations and explore a mutual fit.

If you follow this, you’ll soon tell if what they’re building excites you, if you like the people enough, and if you could see if they’re working style could align with your lifestyle needs. If yes, keep exploring. If not, thank them, reflect on what you learned (maybe back in your study room), and move on to other tables a little bit more clear on what’s important to you. You're searching for a mutual fit.

In this blog post, we’ll talk about Part 2.

How to get the most out of your conversations once you’re in the cafeteria. Just having one conversation is fine. But what if you could turn every conversation into a node that connects you to other potential conversations that are a true fit? Or what if you each conversation built a stronger network of people working behind the scenes to send jobs your way, especially when they’re not even posted yet?

If you haven’t already, check out “Job Hunting is like a High School Analogy” first.

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Level 1: The Traditional Approach

Cold applying + asking connections to push your resume up the pile.

What happens if you stay at Level 1:

• You pitch yourself for the one open job in the conversation. If it's not a fit, you say thanks and walk away. Move on to the next job and repeat.

• High School Cafeteria Analogy: That’s the equivalent of walking up to a table, asking "Do you have space for me here?" If they say no, you say thanks and leave.

• Result: They likely forget you within minutes. You’ve limited yourself on how else they could help you.

This isn't wrong, but it's limiting. You're capping your opportunities at the exact number of 1:1 conversations you can have, and the timing has to be perfect.

Level 2: Uncover Needs & Genuinely Offer to Help

Goal: The goal of this is to genuinely offer value and build a relationship with this specific person. This is not transactional. This person you’ll talk to is doing a job that matters to them. Be yourself and build a relationship with them as you would with anyone else new. Discover what they're struggling with and offer to help in a shorter-term capacity while you continue your search.

How to do it:

1. Express genuine interest in helping them:

   • "I'd love to learn more about what you're building—maybe I know someone in my network who could help, or there's another way I could be useful."

2. Ask discovery questions to understand their hopes and dreams:

   • "What are you trying to build?"

   • "What would success look like if you knocked this out of the park?"

   • "If you got the perfect hire, what would you want them to accomplish?"

3. Identify what's missing:

   • "Where do you think you're short on resources or know-how?"

   • "What would be most helpful to you right now?"

4. Offer help - a connection, a resource, an idea, or even some contract/fractional support if you see a fit:

   • I might have someone in my network who could help - can you tell me more about specifically what that issue is? Or who would be a most helpful?

   • "While I'm job searching, I'm taking on some contract work. If you're interested, I'd be happy to talk about helping you with [the specific need they mentioned] on a short-term basis. Would that be useful?"

Maybe this conversation will turn into nothing. Or maybe it’ll end up being the most valuable conversation you’ve ever had. You can’t know. But assume you’ll talk to 10 people and you only need 1-2 people to make connections or share a new job rec to make all the difference.

Level 3: Build Your Brand & Get Connected

Goal: Make it really easy for this person to know how you could help them, and how they could help you. They’re much more likely to open doors for you and see opportunities for you within their team or elsewhere if you’re clear and speak to your audience.

How to do it:

• Clearly communicate who you are, what value you offer, and why you're excited about the company/team—confidently but with flexibility

• Explore any potential roles that could be a fit

  • If there’s an existing rec, explore if the role could be reshaped (more senior, different location, expanded scope)

  • If not an open rec, see if they’re considering expanding their team to tackle that particular thing - explore that with them as far as you can go.

• If it can't be reshaped, ask them to connect you elsewhere in the company:

  • "Who else is working on [X type of work you want]?"

  • "Is there a team focused on [new products/launches/whatever excites you]?"

  • "Do you know anyone who might need someone with my skillset?"

• You can always leave with a clear ask that would help you:

  • Connect them with people who could help

  • Share relevant resources

  • Provide value to what they're working on

  • Make a specific request:

    • "I think I could help you with X on a contract basis. If that sounds useful, we could talk through what you really need. Are you open to that?"

    • "Is there someone within this company working on [launching new products/starting something new]? I'd love an intro if it's not too much trouble—I'm really excited about what you're building."

What you're hoping for:

• They reshape the current headcount to fit you better, OR

• They remember you when a senior role opens up, OR

• They connect you to a colleague in another department, OR

• They tell you about other teams/projects that might need you

Level 3 should be your goal for every conversation. Aim to leave every conversation with a connection to another person or information about other opportunities within the company. It may or may not happen, but make the ask clearly and they can say yes or no.

Why this works:

• You're playing in the sandbox with them—getting to know their work, their challenges, their world

• You're being genuinely helpful without expecting anything back

• You might earn income while job searching (reducing any thoughts of desperation and building credibility)

• You're building your network with external-facing work

• You might convert it to full-time down the line, or they might refer you elsewhere

Core Guiding Principles

• Be human - Build relationships. Don't view this as transactional. People want to help people they've connected with.

• Learn their hopes and dreams - Understand what they're trying to accomplish and why it matters to them.

• Explore what's missing - What do they already have vs. what's standing in their way?

• Be genuinely helpful without expecting anything back - Share articles, contacts, resources. Be useful in the moment and after.

• Be crystal clear on what YOU want - What you're great at, what you're looking for next, what excites you.

• Offer clear next steps and specific asks - a connection, information on the company, etc.

The Bottom Line

The more helpful and compelling you are, the more popular you become in that high school cafeteria. People will advocate for you behind your back. Jobs you didn't know existed will surface. You transform from a forgettable resume into someone people want to help, connect with, and pitch for opportunities—even ones that haven't been posted yet.

Job Hunting is like a High School Cafeteria

The High School Cafeteria Analogy for Job Hunting

Picture a big cafeteria full of round tables, each with a group of people building something different — one’s working on a puzzle, another’s building a Lego structure, another’s sewing, etc. Consider these different companies / teams you might join.

Your goal in job hunting is most usually pretty straightforward. You ideally want to join a table where you…

1. are excited about what they’re building

2. enjoy working with the other people around the table

3. have unique value they need that you actually want to bring everyday

4. are set up for success and can work in a way that matches your lifestyle needs.

You could walk up to every table and say “hire me! I’m great!” - but in this market, you’ll likely be drowned out by the noise. There are too many applicants and too much risk. People are looking for applicants with specific skills that meet their specific needs right now. To stand out, you need to be intentional about who you’re reaching out to, build a strong message and brand about who you are and what you have to offer, and get to know people - connecting the dots between what they’re working on and what you want to offer.

Plus - if you become extremely popular in the cafeteria, you’ll more likely have people seeking you out or sending you opportunities that aren’t even posted yet. The dream.

Start with these two steps:

• Part 1 - Get clear on what you want and what you have to offer first.

  • In this market, you can’t be a jack-of-all-trades ready to learn anything. Companies are hiring for what they need. And value people who are clear on that. Before you walk into the cafeteria and start having conversations, take a moment outside (maybe in a study room down the hall?) to get clear on what you want — the kind of work you enjoy, the type of people you like to collaborate with, what matters most to you in your next chapter, etc.

  • Develop a list of criteria - must haves and nice to haves about any job you’ll want next.

  • Practice a pitch to communicate clearly what you want.

  • Map out what tables you would explore first on a theory they’re most likely going to fit your criteria while also needing exactly what you like to offer.

  • Start researching who you’re connected to at those tables and how best to get connected.

  All of this makes it much more likely your time in the cafeteria will be useful and maybe even a tad fun.

• Part 2 - Have conversations and explore a mutual fit.

  • Then you step inside the cafeteria and start visiting tables intentionally. You’ve already done the research and have a sense of what they’re trying to build and what the person you’re talking to likely cares about most.

  • You sit down and explore, “Hey! I love what you’re doing. It really resonates with this part of me. I have a sense of what you’re building and I think I could really be helpful. I’d love to explore this with you.” Then ask them thoughtful questions. “What are you hoping to build in a dream world? Why is that important to you? What’s going really well? Where are you’re struggling / missing resources?”

  • Then help them. Offer a resource. Give them a tip. Workshop a problem with them. Start working alongside them now. It’ll showcase your value, build a relationship, and begin to test out if you like to working together. Do this without any attachment to getting anything in return.

  • Along the way, share what you’re great at, and how it could fit with them. Connect the dots of your special talents with the problem they’re solving right now. “It looks like you’re building a lego amusement part for mice! I noticed purple legos could be really helpful here and I’m really strong at purple legos - I’ve done it at my last two jobs in these specific examples. I’d love to explore if that’s useful here.” Workshop with them how you might be able to help them.

  • Make an ask and create follow-up steps. If you’re interested, the goal should be to have another conversation. If it’s not a fit, ask for a connection who might need the help you’re offering; or get more information about the industry / companies you’re excited about. Then go home and follow-up with value wherever you can.

  • Nurture - for people you felt connected to, stay in touch. For others, you can let them go and allocate your energy towards new connections.

If you follow this, you’ll soon tell if what they’re building excites you, if you like the people enough, and if you could see if their working style aligns with your lifestyle needs. If yes, keep exploring. If not, thank them, reflect on what you learned (maybe back in your study room), and move on to other tables a little bit more clear on what’s important to you. You're searching for a mutual fit.

In the next post, we’ll talk about Part 2.

High School Cafeteria Part 2: Turn Every Job Hunt Conversation Into Multiple Opportunities. Just having one conversation is fine. But what if you could turn every conversation into a node that connects you to other potential conversations that lead to opportunities that really meet what you’re looking for? Or what if each conversation built a stronger network of people working behind the scenes to send jobs your way, especially when they’re not even posted yet? You can also stay at level one and apply to one job at a time. But the goal is to increase chances of getting the job that truly meets what you’re looking for. And speed up the time it takes to find that.

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Rocks, Pebbles, Sand: How to Reset When Life Gets Too Full

From a corn pit 🌽 in Connecticut last weekend...and a representation of things on my plate that week 😬

TLDR: If you’re feeling overwhelmed or a bit scatter-brained, this is for you. Especially if you're navigating work alongside a job search, planning for parental leave, or big changes at work. If you’re already feeling great about what’s on your plate, feel free to skip!

More of an audio person? I recently did ​a podcast with my friend Alexis​ talking about this, career changes, and other things (thanks, Alexis 🙏 ).

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I’m coming out of a 2-week overload period.

I woke up in the middle of last week, realizing I had way more things to do than time to do them before heading out on vacation (later today!). And I felt super drained, down and guilty.

This seems to happen at least once every fall. A confluence of things in work and life ramping up at the same time.

My work gets busier in September as people come out of vacation-summer-mode ready to revamp their job search or hit work goals by year-end.

Plus, I made a last-minute trip to New Haven to see friends and sit in a ​corn pit​ (highly recommended), volleyball leagues are overlapping, my close friend is recovering from pneumonia and I wanted to visit, Halloween is coming, etc. etc. etc.

With perspective, I’m grateful to have time to do these things.

But in the moment, it was overwhelming.

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My first reaction when this happens is an old one. Just power through! Do more, faster!

Work late hours. Say yes because saying no makes me feel a mixture of guilt / fear / sadness. Stew in indecision instead of declining plans. Be grumpy and distracted at a volleyball game. Work late and take a while to fall asleep.

It’s only for a couple of weeks! No biggie!

But it isn't sustainable.

I wasn't enjoying what I was doing or able to be present. I was spending too much time ruminating on how to do 20 things with actual time to do 5.

I eventually switched out of “power through” mode and did a reset.

The result was feeling way more present, light, energized, and grateful. I could actually enjoy the corn pit (and my lovely friends and their kids) vs. stewing about my schedule.

How did I reset? I use these 5 steps often with my clients and in my own life. Whether you do it in one sitting or over a few days, I highly recommend it.

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5 Steps to Reset My Workload

1. Remember I can never get 100% of things done in all areas of life. This comes from ​4000 Weeks, Time Management for Mortals​ - a book I highly recommend. TLDR: I’m never going to get everything done, no matter how hard I try. The sooner I accept it, the better my quality of life. I need to pick the most important things and let the rest slide away.

2. ​Rocks, Pebbles, Sand ​This is how I find what to prioritize and what to let go of. The concept:

   • Rocks are your most important priorities—what truly matters to you in life (e.g. family, health)

   • Pebbles are the responsibilities that are important but not critical. They may still need to get done, but you wouldn't want them to crowd out the rocks (e.g. work, hobbies)

   • Sand represents the smaller things that can easily take over if you let them (e.g. email, reading newsletters, tidying)
     
     If you fill your jar (your day, week, or life) with sand first, there’s no room left for rocks. But if you put the rocks in first, then the pebbles...the sand can settle in the gaps or be left outside the jar.
     
     For me, that meant prioritizing family, friends, sleep, exercise, and clients. And deprioritizing the cleanest apartment and the perfect dress for an event.

3. Calendar Blocking I’m not one to stick to a rigid schedule, but calendar blocking keeps me sane. I put blocks for my Rocks, Pebbles and even some Sand. As I need to, I move them around like a puzzle. It makes me (sometimes painfully) aware of how little time I have. But then I can see what I need to make room for (e.g. downtime) or let go of.

4. Resetting expectations and saying no This is a muscle I'm always building, but a magical one. You can start with scripts (examples ​here​ and ​here​), but make them your own. Some of mine this week:

   • “Hey - I’m unexpectedly overcommitted this week. Would you mind if we moved this to next week? I’ll have much more headspace then.”

   • “Unfortunately, I can’t - I have plans. But thank you for the invite 🙏”

   • “I'm sorry for the delay! I'm a bit swamped heading into vacation. I have a window on Thursday to finish this. Let me know if that's too late and I'll find time in the next day. Thank you!"

   • “Not today - but thanks!”

5. Rinse and repeat on the fly As things get done, I revisit my priorities and my calendar, then make adjustments as needed.

Was this a perfect reset with no snags? No! Did I have to apologize for some delayed things? Yes!

But I'm significantly more on top of things than I would have been, and more importantly, I'm able to be more present, productive, kind, considerate, and grateful.

Questions for you:

• What are your 3-5 big Rocks right now?

• What’s one Pebble that you may need to let go of or scale back on?

• What Sand can you just ignore completely? (This can be very freeing.)

Want some help?

I'd love to help you reset and work towards your short-term and long-term goals. This is especially useful if you're juggling a career change or expanding your family amid your already very full life. I have slots for ​Discovery Calls​ starting again in mid-October.

In the meantime, please go find a Corn Pit to play in 🌽🌽🌽. It's the best.