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Change is also the theme of this edition. Let’s dive in.

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

• 🎭 Why "So what do you do?" becomes your worst nightmare after quitting

• 🧰 7 unconventional tools to rebuild your identity beyond job titles

• 🔬 How to run "tiny experiments" to discover what actually makes you come alive

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🪞The identity crisis no one warns you about when you quit

"So what do you do exactly?"

In 2019, this question made me break into a cold sweat.

I had just left my full-time SF tech job to travel the world, and my parents were convinced I'd become unemployable forever.

Every month, they'd call asking when I was getting another "real job."

Up to that point, so much of my identity had been wrapped up in being a “PM at Dropbox.” I didn’t know who I really was because I hadn’t carved out space to allow my own dreams to percolate.

I’d be lying to you if I said I didn’t feel anxious, self-doubt, and like I was making a huge mistake.

Fast forward to 2023. I left my Singapore tech job again, this time to build my own business and creative projects.

When industry associates and VCs questioned, "so what are you doing exactly?" I just shrugged.

This time, I felt more comfortable in my own skin.

What changed? Well, to start I learned about untangling my self-worth from my work.

But the real breakthrough was learning about the importance of Person-Path Fit.

In this newsletter, I'm sharing the tools that helped me (and dozens of others) navigate this identity shift towards Person-Path Fit after leaving a full-time role.

🤝 It’s an identity party

After chatting with readers and researching online, it’s clear I’m FAR from being the only one grappling with identity when faced with many different paths in front of me.

Take:

• Tim Huang, former PM in the Bay Area and Portfolio Path reader, shared that after leaving his full-time role to travel, “the hardest part was learning to stay indifferent to other people's expectations, so I could figure out what I actually care about.”

• Youtuber Ali Abdaal wrote about his struggle with what to call his identity after he quit his high-prestige job as a doctor.

• Andy Johns, former tech executive in Silicon Valley, wrote about leaving behind his highly successful tech career and learning how to reconstruct his sense of value and self-worth.

• Here’s a Reddit thread from a tech leader echoing the above:

And that’s just the tip of the iceberg.

But let’s say that you’re in the messy middle - stuck in the valley after leaving behind the last mountain peak of your career.

How do you navigate through the valley to reach the second peak?

After going through this twice myself and talking to dozens of others, I’ve found a handful of tools to be powerful:

🧰 An unconventional toolkit for identity shifts

First, you’ve probably heard the standard fare like “lean on friends and family”, “get a hobby”, “build a side hustle,” yadda yadda… So I’m not going to talk about those.

Instead, let’s get into the non-obvious stuff:

Tool #1: Self-reflection

As you can probably tell from my last edition on AI prompts for career coaching, my favorite questions zoom in on clarifying your strengths and curiosities — key ingredients of your Zone of Genius:

When I left my SF tech job, I realized I had perceived my Zone of Genius only in the context of one company for the past 4 years. Now it was a chance to redefine what it was for a broader industry over the next 4 years.

👉️ Try out exercises like:

1. Strengths: “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. Curiosities: “What are the problems you’re obsessed with solving?” “Why are they so interesting to you?”

This works because often we struggle to identity our own attributes, but can easily recall experiences when we felt the most alive.

If you want to supercharge these exercises with AI, grab my free prompts here.

Tool #2: Peer feedback

I’ve also found it very helpful to get a trusted friend or colleague to share how they perceive my strengths.

👉️ Try sending these questions to a friend:

1. “What do you see as my strengths?”

2. “What can you imagine me doing that would utilize these strengths? It doesn’t have to be a job title.”

Sometimes we have total blind spots. And our closest circle can just see things that we can just can’t.

Tool #3: Social validation

A FAANG product manager who left his job recently shared with me that connecting with others in the midst of similar transitions helped him validate his new path.

👉️ How to get this validation:

1. You can join communities of entrepreneurs, career changers, and portfolio careerists (like our very own!)

2. Share your on-going tiny experiments (more on this below) and get feedback

3. Collect insights on how your peers are approaching their tiny experiments, informing your own direction

4. Hire a coach who is a few steps ahead of you

Unlike only asking for peer feedback, this is much more focused on your experiment hypotheses (and theirs). Instead of reflecting on the past, it’s more forward looking.

Tool #4: AI brainstorming

Additionally, you can leverage your favorite LLM to pick up blind spots, share feedback, or generate new ideas. This works especially well if you’re using one with long-term memory.

Or once you have greater clarity on your strengths, you can do some fun stuff.

👉️ Try this prompt:

If you want to play around further, you can grab more of my AI prompts here.

Tool #5: Identity expansion

Many tech workers are also struggling with fear of AI.

And if you believe AI is inevitable, then this is something we’re all going to have to deal with whether we like or not.

Julie Zhou, former VP Product Design @ Facebook, suggests focusing on identity expansion instead of attachment instead:

While her advice is targeted towards adapting to AI, substitute “tools” for “job title” and these lines apply quite nicely.

Tool #6: Tiny experiments

Many high-achievers I know struggle with “all or nothing” thinking.

Anne-Laure Le Cunff, neuroscientist and founder @ Ness Labs, suggests that instead of setting rigid long-term goals about who you "should" become, start with small 1-2 weekly experiments.

👉️ Try these 3 steps:

1. Design the action: Define the hypothesis.

2. Set a specific number of trials: Run the test multiple times to collect enough data and see if there’s anything interesting to learn from it, e.g. do you actually enjoy writing or was it just that 1 time?

3. Collect the data: Do [the action] for [a set duration of time].

This experiment recipe gives you a great tool for testing different aspects of your identity to help you move towards Person-Path Fit (e.g., "I'll try writing daily for 30 days to see if I actually like writing.").

The data is your internal feelings - do you feel a sense of joy doing the activity?

Tool #7: Creative work arrangements

Finally, crafting a unique work structure that fits you can be powerful.

Elena Verna, Head of Growth at Lovable, writes about how when she decided to go full solopreneur, “stepping out on [her] own was brutal on [her] identity.”

However, she derisked by crafting a unique work structure that mitigates the risk that her experience languishes (therefore her credibility):

1. Structuring her advising work to maximize learning

2. Taking on full-time roles but as an interim leader (predetermined end date)

3. Creating alternative income streams to smooth out pipeline volatility

At Portfolio Path, we don’t believe in limiting ourselves to just “consulting.” Consider the full menu of options - FT work, fractional, teaching, etc.

Don’t be afraid to get creative.

In Summary

Quitting your high-powered job often triggers an identity crisis no one warns you about.

But this uncomfortable valley between career peaks is actually the perfect time to explore your Person-Path Fit.

We walked through 7 unconventional tools to help you go beyond the job title and discover who you really are:

1. Self-reflection

2. Peer feedback

3. Social validation

4. AI sounding board

5. Identity expansion

6. Tiny experiments

7. Creative work arrangements

Remember - the goal is NOT to identify another dream job title.

It’s about expanding your identity beyond the socially acceptable constructs (like job titles) and reveal what actually makes you come alive.

That’s what real success feels like to me.

Thanks for reading! Are you going through an identity shift? Reply and let me know how it’s going. I response to every email.

💎 Last Week’s Gems

🚀 When are the best and worst times to join a startup? (Dan Hockenmaier)

🤖 When AI Has Better Taste Than You (Julie Zhou)

🤯 A solo founder just sold his 6 months old AI startup for $80M (Substack)

👫The Separate + Joint Method: How My Spouse and I Manage Our Money (ODAD)

✨From Our Community

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💌 Reader Notes