Claude, can I pull you for a quick chat?
5 career conversations to explore with your AI-bombshell 🏝️
I hate to admit this, but I am SO locked in on Love Island. Twenty plus hours of my time wasted, and counting. Just me in my room with the illegal stream I found on Reddit.
Apparently, my life is now:
Watching people in bikinis pull each other for chats
Me pulling Claude for career chats
So naturally, these worlds had to collide. I present you:
Five prompts to turn Claude into your career coach, Love Island edition. 🏝️
Mandatory background music:
📌 New to Claude? Use this guide to get started.
First chat: Where’s your head at?
📍 By the pool
You and Claude need to build a connection. And no, not by turtle tongue kissing. Or by “getting some French fries.” (Thank Kenzie for both of these)
Before Claude can be your work therapist, it needs to know where your head’s at.
Things like:
What does an ideal Tuesday look like?
When do I feel most useful?
What compliments do I brush off?
What does success look like if money weren’t the only scorecard?
Or, would you rather have a disability and become deaf than listen to country music? (Bea = 👑)
📱 Text Claude
I want you to become my long-term career coach. Before giving me any advice, interview me to understand who I am, what motivates me, what drains me, and the kind of life I’m building. Keep asking follow-up questions until you genuinely know me.
Claude replied, asking me to do what I do best: ramble.
📌 Tap the microphone to talk out loud and your words will be transcribed.
The more we chatted, the more “seen” I felt. Whatta Man, as Salt-N-Pepa would say.
Yikes. I mean, it’s not wrong. Am I chasing something because I think I should?
The quality of Claude’s advice is directly proportional to how honest you are with it. Introduce yourself, flaws and all.
Once Claude knew my good sides and minor flaws, it was time to unleash the crazy.
Second chat: My type on paper
📍 The Speakeasy
Tell me this: What’s your type?
Did the answer include tall, dark, and handsome?
OMG! It did?! 😉
We all “think” we have a type. The Islanders did too. Then voted Sean off the island.
I mean, someone explain:
Turns out: What you think you want isn’t always what you actually want.
It’s like Corey telling Melanie: “There’s a certain type of man who can handle you, and it’s not Sincere.” (which, agree. girl run) 🏃♀️
Same for jobs and companies.
You might be tempted by big bucks and ambitious plans (Corbin), but much better off starting your own wholesome small business (like Gal).
Claude can help figure out what you romanticize and what you would actually enjoy.
📱 Text Claude
Based on my experience, strengths, personality, and ideal lifestyle, what companies or roles are the best fit for me? Ask any clarifying questions about my requirements, personality type, constraints, and preferences.
First, Claude asked me a few questions:
What’s your preferred work structure?
Which type of company energy fits you best?
What matters most in your next role?
Not bad. But I wasn’t sold.
So I asked Claude: “How do you think I’d be most fulfilled?”
That answer felt much more me. It suggested a few high-value retainer clients, combined with producing original work. Meaning:
“You go deep into spaces where people feel lost or left behind, make sense of what’s happening, and build resources — written, editorial, structured — that help normal, curious people navigate those spaces with confidence and even enjoyment.”
We’re definitely onto something.
Claude spotted patterns and made observations I hadn’t made myself.
We all have a type on paper. Let Claude challenge the story you’ve been telling yourself about your career.
Just two chats in and Claude seems to know me pretty well. Our connection was cute.
Then ten minutes later, I started spiraling about AI. 😵💫
Third chat: Give me 10! Give me 10!
📍 The glam room
It’s this season’s most memorable moment: Melanie needing 10.
A moment all too real. We all get overwhelmed. We all need to emotionally regulate.
Heck, it’s me every day when I open LinkedIn or try to keep up with AI.
When life is life-ing, Claude can be your voice of reason. Your personal Aniya.
📱 Text Claude
Based on everything you know about me, if I disappeared from the internet for a month and could only learn five things about AI before coming back, what would they be and why?
You can insert any topic. Dump all your worries. Paste your list of 21 all seemingly urgent tasks.
Claude can prioritize tasks. Build an interactive to-do board. Read and summarize PDFs. Create a 30-day curriculum. Or tell you which 20% of topics to study to learn 80% of the skill.
When your brain has 48 tabs open, let Claude close 43 of them.
Or, as Jen would say:
Third chat done. Feeling much calmer. 🧘♀️
Then made the mistake of asking Claude to roast me.
Fourth chat: Do I have 20/30 vision?
📍 Soul Ties
Which is better: 20/30 or 20/13 vision?
Let’s ask nursing-school-graduate Kenzie.
Like Kenzie, sometimes our vision is blurred.
Are we really not qualified enough? Too old to pivot? Too young to apply?
Let Claude assess your strengths and blind spots. It does this well because it has no emotional attachment. Unlike Aniya, who was scrolling through her selfies with KC while he was busy hoeing at Casa Amor. 🙄
📱 Text Claude
Review my LinkedIn profile, resume, and portfolio as if you were hiring for my dream role. Tell me what I'm underestimating, overestimating, and what my biggest blind spots are. Be constructive, but don't spare my feelings.
When using this prompt, make sure Claude knows your dream career. Explain it or attach job ads.
📌 Upload a dream-role.docx to your project, so it can always refer to it.
But be aware: Things can get messy. Claude’s response might land as hard as Corbin saying, “Nah, I haven’t thought about Kenzie since I’ve been here”.
When I sent my text, Claude said (verbatim): “I sprinkle in personality, lots of it” is charming for a freelance writing pitch, not your LinkedIn about section. 😶
Ask Claude to bruise your ego before the job market does.
Like your typical Islander, Claude buttered me up and then hurt my ego.
Which left us with one final decision…
Final chat: Who’s your strongest connection?
📍 The Fire Pit
You’ve explored. You’ve chatted. You’ve got to know yourself better.
Now it’s time to decide: Will you keep exploring, or are you ready to couple up? 👀
AI is like a 22-year-old boy from Miami. Give it more options and it will entertain them all. Ask it to commit, and it gets uncomfortable and finally starts assessing.
📱 Text Claude
If you had to bet your own money on one version of my future, which career path would you choose for me? You can only pick one. Defend your answer, tell me what I'd have to sacrifice, and explain why it's a better bet than my other options.
As for me? Claude told me not to commit. At least not to a corporate job.
And while that feels scary as hell, Claude’s right. Freelance suits me.
To ease my anxiety, it told me that “job happiness depends entirely on who your manager is, whether the company hits a rough quarter, whether priorities shift. You’d be one reorg away from losing the life you built.”
And shit, ain’t that right. Corporate job ≠ stability.
At some point, the answer isn’t another conversation. It’s to stop dilly-dallying on an island, get back to the real world, and start doing!
Final thoughts on coupling with Claude
Did I waste 20+ hours of my time watching Love Island? Maybe not. All these villa chats got me thinking about the chats I need to be having in my life.
Turning to Claude for career advice was a 10/10. Much better than ranting to my mom, who starts a come-back-to-the-Netherlands rally every time I share mild concerns.
I weirdly trust my AI-match that, yes, I should continue freelancing rather than looking for a “safe” corporate job. I’ll figure out the 401(k) and maternity leave later.
Let’s see where Claude’s career plan takes me. I’ll keep you posted 🤗
Over to you! If you pull Claude for a chat this week, tell me how it went. I have a feeling we’ll all learn something from each other’s career chats. 🫶