Today’s Agenda
Hey crew, I’m updating the email branding of The DesAI Digest. Let me know what you think.
This week, we’ll cover:
🛠 Career Strategy: Coaching from yours truly, no charge
🤖 AI Tactic: New Updates to Deep Research made it… worse?!
⚡ Execution Insight: I’m hiring
🧠 Curiosity Corner: Dan Young’s Pokemon Resume
💼 Job Board: Scaling Systems, Search, and Spend
Let’s dive in.
🛠 CAREER STRATEGY
Coaching from yours truly, no charge
If you want to talk about a career problem, I’ll give you 15min of my time and try to help you to the best of my ability.
Ideally, you’ll bring a specific, detailed challenge. The more you can think about and define the specific problem the solve, the better it will be.
I’d love to help you. I’m a bit bored waiting for the book to get published, so if I can help folks out in the meantime, that’s really gratifying for me.
🤖 AI TACTIC
New Updates to Deep Research made it… worse?!
When I was writing last week’s edition, I tried ChatGPT deep research to find job posts. I noticed the user interface was completely different: it was the first major change I’d seen since deep research was introduced last February.
Here’s a glance at the new UI for deep research.
It seems like the new deep research is more agentic: breaking down a large project into manageable tasks, hooking up to external apps, and accepting specific sites to look at. And it wrote a meticulous report about its findings.
Seems pretty positive, right?
Except it found nothing! It failed miserably when I asked it to find jobs for last week’s newsletter.
Somehow, the smartest setup of ChatGPT (5.2 Extended Thinking with the new deep research) failed miserably at doing a task that prior versions did easily.
Previously, we talked about AI’s tradeoff between security and helpfulness. It seems there’s another tradeoff just inside of the helpfulness component: rule following vs. expansive creativity.
Hallucinations creep in when AI doesn’t follow rules and just tries to provide an answer via “creativity” (or lying, depending on your perspective). In this new modality of deep research, AI does the opposite, it follows all the rules to a fault.
Instead, the optimal state would be to emulate a human: just try your best with the information you have and show even a partially correct output. If only we could toggle the amount of rule-following by use case…
If you try the new deep research and have tips or tricks I can use, let me know!
⚡ EXECUTION INSIGHT
I’m hiring!
My wife and I buy group travel businesses. One of our brands, Women Travel Abroad, is looking for a Part-Time Event Marketer.
Core Responsibilities:
Host Weekly Community Calls – Host or co-host Community Calls each Saturday from 12-1pm ET, facilitating engaging discussions and fostering connection among potential Women Travel Abroad travelers. Note: these calls are a sales touchpoint. The goal is to educate and inspire women about solo travel, plus a soft pitch for why to travel with WTA. Learn more about our Community Calls here: https://womentravelabroad.com/community-call/
Conduct Trip Info Sessions – Present trip details and answer questions during scheduled info session calls, showcasing destinations and itineraries to prospective travelers. Check out past info session recordings here: https://www.youtube.com/@women-travel-abroad
Post-Call Reporting & Follow-Up – Provide with weekly summaries including attendee names, trip interests, questions asked, and any follow-up needs. Coordinate intro emails between attendees and Katherine when specific questions or interests arise.
Manage Private Facebook Community – Actively engage in the Women Travel Abroad private Facebook group by creating regular posts with travel-related questions and prompts, and responding thoughtfully to member posts to foster community engagement.
Required Skills & Qualifications:
Genuine passion for travel, with solo travel experience preferred
Natural ability to connect with and engage new people, particularly our ICP of women ages 40-70
Quick thinker with strong improvisational and on-the-spot response skills
Excellent verbal and written communication skills
Professional, organized, and detail-oriented in follow-up and reporting
Expected pay is $40/hour, but negotiable for highly qualified candidates. Potential to become a Trip Host or Host Assistant and get a free trip to destinations like Egypt, Bali, Paris, Seoul, etc.
🧠 CURIOSITY CORNER
Dan Young’s Pokemon Resume
A guy named Dan Young vibe-coded an online experience that combines the GameBoy Pokemon aesthetic with his actual resume. You can wander around his digital homestead and ask questions / collect lore about Dan.
I think this is fun, but not particularly effective. Recruiters spend 7.2 seconds reviewing a resume. Unless you have a lot of time to kill, this experience flies in the face of the resume-reviewing reality. If every resume coming across my desk was a video game, I’d never get anything done.
I think this experience would be better as a staged Pokemon battle, with Dan as the player trainer, fighting against an enemy trainer with Pokemon themed after the big problems / challenges in Dan’s career. Dan’s own Pokemon could be his roles and their moves could be his relevant skills.
In any case, I am excited for a future where we can reimagine what’s possible.
💼 JOB BOARD
Scaling Systems, Search, and Spend
Here are the 3 most interesting remote job openings I’ve seen this week, all paying $150k or more:
If you want the jobs, please sign up for the newsletter :) That’s it for this week.
-Rahul from The DesAI Digest
P.S. Reply back to this email with a business challenge you’re facing! I’d love to help.
P.P.S. if you liked this, forward it to a friend. And if you hated it, forward it to an enemy.
