Automating the Portfolio of You

AI won’t replace you; if used well it can scale you.

Every job I ever had was handed to me. I never had to market myself.

Now, I am figuring out how to do that from scratch.

For years, I didn’t have to prove my worth—it was obvious.
My work spoke for itself. I was in the room, had the title, was on the invite list, shaped the decisions and directed the teams.

The day I left corporate, that all stopped.
No more Slack pings.
No more urgent emails.
No more packed calendar.

At first, I told myself I needed a break.

Then the silence set in.

And the self-doubt rose like bile I tried to keep down:

• How do I prove my value now?

• I’m great, so why aren’t people calling?

• How do I not fade into irrelevance? That question ends with a haunting view of my father, who in his later life is experiencing a perfect storm of loneliness and dementia.

Waiting wasn’t an option.

I needed to get clear on my next move — and fast.

February is Pivot Month at Optionality, and this month’s webinar can help you start on planning yours. Join former executives Susan Mernit and Fran Hauser, who have parlayed their years of experience into their latest respective passions: Running an AI tech consultancy for nonprofits and opening a local bookstore! Join us, and learn how they planned their pivots. Click the image for details and to register.

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Assuming the World is Waiting for You is a Losing Game

I knew I needed to stop thinking about what I’d lost in my career and start thinking about what I could gain by leveraging my past experience and future work models. As a former enterprise tech executive, I naturally gravitated toward the possibilities around AI.

Many people use AI as an outsourcing tool for writing emails, summarizing meetings, or automating grunt work.

That’s not how I use it.

AI and automation won’t replace your voice, but it can make sure your expertise is seen, systemized, and scalable.

This is a lesson I learned building and running huge manufacturing operations: You won't scale by building one perfect widget.You will scale by building the system that makes thousands of them.

Your expertise should work the same.

But you may not know how to scale your expertise. As an advisor, you're custom-building solutions for everyone who asks. You're giving away your best thinking in "quick chats" and "coffee meetings."

Here's what I learned from 25 years of scaling massive operations:

When your system depends on you showing up every time, it's not a business, it's a really expensive habit.

Stop chasing and start getting paid.

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This is what I did:

🔹 I turned AI into my Knowledge Vault
I uploaded my best work—strategy decks, decision memos, insights from years in my field into a project.

I asked AI: “What do I know that’s valuable? How would you distill my insights? Find me patterns others won’t see.”

It helped me define the repeatable methods I could turn into advisory work, content, and offers.

This became a workbook called the “Business of You”.

🔹 I used AI to identify my Marketable Edge
Instead of sitting in "What should I do next?" paralysis, I used AI to define my niche.

I asked AI: “Who would be best served by my insights? Help me define their hopes, dreams, challenges and fears. What is their 3AM question that I solve, the one that keeps them up at night?”

This gave me the words on how and what to talk to my ideal client about on LinkedIn and YouTube.

🔹 I built my expertise into Scalable Systems and Offers.
AI helped me productize how I work into frameworks that could be purchased.

I turned the workbook into the “Business of You” beta course.

The first session sold out, so I added another.

Another system helped me write five top-selling books in five months.

Systems matter.

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Your Next Chapter Isn’t a Job. It’s a Portfolio of You.

Your next chapter isn’t about ensuring you get another W-2.
It’s about owning your expertise and designing work that fits your life.

No one is coming to tap you on the shoulder; if you don’t define your expertise, others don’t pay attention.

The biggest risk isn’t trying something new—it’s becoming invisible.

I wasted months overthinking what I should do next.

I tried on many hats, contemplated countless possibilities.

The difference between feeling stuck and moving forward isn’t time; it isn’t knowledge.

It is execution.

It is iteration.

This guide can help you get started for free. And if you want to explore further, there’s a special offer for Optionality members.

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Betsy Tong is a five-time international best selling author. She trained AI on her in the process of creating the books, three of which are about AI from the personal journey: The Edge: Your Brain on AI; The ADAPT Framework: A C-Suite Guide to Thriving in the Age of Shadow AI; and Unstoppable Advantage; A C-Suite methodology for adapting governance and processes to AI.

Betsy works with people and companies on how to create the best AI/Human partnerships. Her CustomGPT Tell me about you - acts as a conversational partner that draws out the most interesting, meaningful, and authentic parts of your story—whether for a book, a personal project, or even just for deeper self-reflection.

Betsy’s Executive AI Mastermind enables students to engage with fellow leaders in mastering AI as an essential career partner. Sessions are Thursdays at 12pm PST/ 3pm EST. Optionality members can get one month free.