🔑 Future-proofing your portfolio career with AI

Today, in 10 minutes or less, you’ll learn:

• 🤖 6 AI workflows to tackle your biggest career roadblocks
• 🎯 How to use ChatGPT as your career coach
• 🚫 What NOT to use AI for in your career journey

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🛡️ Future-proofing your portfolio career with AI

In my late 20’s, I felt like I had hit a wall in my tech career.

I had spent my career thus far pursuing other peoples’ definition of success, but hadn’t looked inward enough to gain clarity of my own success criteria.

I felt frustrated and lost.

But the silver lining of this moment was uncovering a treasure chest of career tools that I use to this day (and also used to help guide tech workers at companies like Meta, Google, Amazon, and Square in their careers).

Now these tools can be supercharged with AI.

Last month, we published editions focused on leveraging AI in your job search (Chris Ming) and landing your first consulting client.

Whether you’re building a portfolio career or not, the future might be looking increasingly uncertain due rapid AI and technological disruption, economic shifts, and changing social norms.

So how do you adapt?

Today, we’re going to show you 6 AI workflows that you can use to help you unlock clarity in your career discovery and accelerate your career growth.

Let’s get into it:

🔮 Career Discovery

“I don’t know what I’m good at”

Understanding your strengths is mission-critical to making good career decisions. Not knowing what you’re good at is like throwing darts with a blindfold on.

👉️ Try these exercises:

1. Think back to 3-5 experiences when you felt like you were thriving. Write down what happened in each experience, then identify the strengths you were exercising in each story.
2. Ask a few people in your circle who know you from various aspects of your life for feedback — including your friends, family members, colleagues, and mentors: “what do you see as my strengths?” and “what career paths can you imagine me doing that would utilize these strengths?”
3. Finally, upload all your reflection/peer interview notes to ChatGPT and input this prompt:

“You are my career coach. I'm going to share my notes from self-reflection and peer interviews about what are my strengths and what career paths utilize these strengths. Synthesize the strengths into a prioritized top 5 list, then help me identify which strengths I may have overlooked in my self-reflection and others may have overlooked in their peer feedback.”

“I don’t know what I want to do”

Struggling to figure out what career path to pursue? Sometimes, we have blinders on due to the role or company we work in.

I personally find it useful to periodically zoom out and think big picture about my career direction. Having a career coach - or AI sounding board - can help trigger fresh ideas you previously wouldn’t have thought of.

👉️ Try this prompt:

“Generate a table of 5 options of career paths by combining the following superpowers, curiosities, and needs:

Superpowers: 1. [insert superpower] 2. [insert superpower] 3. [insert superpower]
Curiosities 1. [insert curiosity] 2. [insert curiosity] 3. [insert curiosity]
Needs: -[insert financial or life constraint]

For each combination, provide a:
- unique career path / role
- list of relevant potential employers”

After you get the results, pick the ones you’re interested in pursing and setting them to the side.

In the next workflow, you’ll learn how to find people on these career paths and use their feedback to validate your career experiments.

“I don’t know whether or not I’d like this career direction”

When I talk to folks stuck at an impasse, I often suggest running career experiments.

What I mean by this is to define a hypothesis about what’d you like - perhaps it’s a new role, business, or employer.

Then validate this hypothesis by either (1) talking to someone a few steps ahead of you or (2) working on a small project in this new direction.

👉️ Try this workflow:

1. Use Happenstance (free) to conduct an AI search on your Linkedin and Google Contacts network. E.g. if you’re looking to break into climate tech, you can search for “climate tech operators” and find out who in your network.
2. Write a short outreach message either using our 11 proven email & DM scripts or Claude. Hint: Leverage commonalities you share like same school, job, etc.

“You are my executive assistant. Help me write a short Linkedin outreach message to [Name], the [Position] of [Company] to ask for their advice on how they transitioned to their current role as someone with a similar background. Ensure it feels personal, helpful, and not salesy.”

🚀 Career Growth

"I don't know which skills to prioritize"

Let’s say that you realized you’re super excited about transitioning into the AI software industry. But your background is primarily in health tech.

How do you know which specific skills you’re missing? And how do you build them?

👉️ Try this prompt:

“Based on current market trends, analyze the skills required for roles in [your profession] in the [your industry]. What skills are important, but you’re currently missing? Give me a ranked list of 5 skills I should prioritize learning, with specific learning resources for each.”

"I can't see my blind spots or growth areas"

Sometimes we're too close to our own performance to see the harsh truth.

This is a good use case for AI can help synthesize feedback from multiple sources to surface insights you might miss.

👉️ Try this prompt:

"You are my career coach. I'm sharing feedback from multiple sources [paste performance reviews, peer feedback, client testimonials]. Analyze these for recurring themes about my strengths and development areas. Then identify 3 blind spots I should address and suggest specific actions to improve each area."

"I struggle to position myself uniquely in the market"

Standing out in a crowded market is hard. Think of it like selling a product — except the product is yourself.

Similar to packaging a product, this requires understanding both your unique value and what the market needs.

👉️ Try this workflow:

First, answer the following reflection questions (I used to share a version with career coaching clients):

1. Your unique selling proposition: What specific value do you bring that other candidates don't?
2. Employer needs: What gaps is the employer trying to fill with this role?
3. Market research: What are are the strengths, weaknesses, and experiences of other candidates for this role?
4. Competitive advantages: What are your top 2-3 superpowers that make you stand out?
5. Packaging: How do you package yourself in a convincing, understandable way for employers?

Next, grab a link to your desired JD, attach it and your notes into ChatGPT, and try this prompt:

"You are my career coach. Help me craft my unique positioning for [your desired role] at [your desired company]. First, review the attached JD to understand what the company is looking for.

Then review my positioning exercise responses and tell me what’s working and not working about my approach. Then create 3 different positioning statements that highlight my unique value proposition, each targeted ate the role and company in the JD."

❌ What not to use AI for

While AI is amazing, I don’t recommend relying on it for EVERYTHING:

• Relationship building: Nothing replaces genuine human connection and networking
• Final decision-making: Use AI for analysis, but make major career moves with your own critical thinking
• Replacing human feedback entirely: AI can synthesize feedback, but can't replace seeking out real mentors and peer connections
• Treat AI like a smart intern: It’s not a genius. Always review and customize the output

💡 In Summary

In my late-20’s, I spent many months soul-searching. But perhaps with the tools we have now, career clarity might’ve come faster.

In this edition, we covered 6 AI-powered workflows to tackle the most common career roadblocks:

• “I don’t know what I’m good at”
• “I don’t know what I want to do”
• “I don’t know whether or not I’d like this career direction”
• "I don't know which skills to prioritize"
• "I can't see my blind spots or growth areas"
• "I struggle to position myself uniquely in the market"

Start with 1 pain that resonates with you. Pick a workflow. Test it out this week and let me know how it goes.

We live in more volatile times than ever, but the flip side of the coin is we have loads of new tools to help us adapt quickly.

Don’t use AI to make career decisions for you, but do leverage it as your thinking partner to navigate uncertainty with more confidence and speed.

Thanks for reading! Which AI workflow will you try first? Hit reply and let me know.

💎 Last Week’s Gems

🧠 ChatGPT's Impact On Our Brains According to an MIT Study (TIME)

💭 The Next Great Distribution Shift (Substack)

🤔 Hybrid Still Isn't Working (HBR)

👪️ The Portfolio Career That Made Him a Better Parent | Ben Erez (Dad of 1, PM Coach/Product Advisor) (Youtube)

✨From Our Community

• Join our Community Beta: Apply to join our upcoming invite-only community beta kicking off June 23, 2025 → Apply Now
• Get Past Replays: You can access our vault of community call recordings here

💌 Reader Notes