Ilana Golan Leap

Techies encouraged to chase 'portfolio careers' to outrun AI job displacement

Those looking to expand their professional or personal development should focus on a myriad of skills to compete with the effectiveness of artificial intelligence.

Those in tech intimidated by the role that artificial intelligence will play in their jobs or careers are encouraged to chase ‘portfolio careers’, defined as a career compromising of a variety of roles rather than one position at a single organization. In the same way that financial advice may include ‘diversifying your portfolio’ to create a stream of different incomes, portfolio careers are built around combining multiple paid roles to ensure consistency and that workers remain invaluable against the threat of AI.
“The way I look at it, we're in front of a massive cliff, and I think we are going to see 10s of millions or 100s of millions of people losing jobs because of AI,” said Ilana Golan, founder of Leap Academy. “There's a lot of reskill schools, and we're going to help you reskill your things, [but] I bet most people can actually lean on the skills they already have and move them to something else, and nobody teaches that. There's not a single entity that teaches how to create ‘portfolio careers’, which is where I think the future is going. Every single leader that you see will have a portfolio of things, not just one, and there's not a single entity that we know of that teaches that.”
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Ilana Golan Leap
Ilana Golan Leap
Ilana Golan Leap
(Photo: Leap Academy)
The concept of portfolio careers was first popularised by philosopher and organizational behaviorist Charles Handy in his 1994 book The Empty Raincoat. In the decades since, groups of Generation X and millennials often sought alternatives to full-time employment as “a more efficient path to self-discovery and finding the right career." The idea is that those in more creative industries, or those who prefer to freelance their services, can make the most of work-life balance, job security, and income streams by dividing their work. In an increasingly AI-dependent world, the concept may be seeping into more tech-focused industries as workers face the threat of job replacement in their full-time positions.
It’s a feeling felt by many, especially in turbulent times in Israel and across the world. Tech booms come and go, and macroeconomic events like pandemics and war can cause instability within careers. Jobs can be lost, companies can sink, and it can cause individuals to seek a new path forward, either professionally or personally.
While Israel’s high-tech sector saw roughly $12 billion of funding in 2024, an increase of 27% compared to 2023, there are still risks of ongoing job cuts. Even sure-fire brands like Meta confirmed the dismissal of 40 employees (5% of its Israeli workforce) alongside 3,600 global job cuts to meet changing market trends. With the fast adoption of AI lurking over every employee’s head, companies can be seduced by its ability to cut costs amid shaky geopolitical and economic times.
A surprise change in life circumstances encouraged Golan to start Leap Academy, a course helping professionals reinvent their careers through guidance, training, and offering the tools to help individuals who seek to enhance their professional journeys. In the 21st century, growing professionally doesn’t just mean securing your job - it means growing in a myriad of ways to build your talents and networks and creating ‘portfolio careers’ that encapsulate several different areas of work and life.
“I suddenly realized for the first time in my life that my identity was always attached to my title,” she told CTech when thinking back to a time when she suddenly lost her job. “It was always attached to the company I was with, and without it, I felt like a complete nobody. I never built myself. I never built my own personal brand. I never had anything to stand for. And this was a complete shock. The other element was that suddenly, I had no clue what I wanted to do next.”
One of the ways those in the tech space can expand their portfolio careers is by taking on freelancing positions or by tapping into creative ventures outside their traditional work through new media like podcasting or establishing Substack publications. New Media outlets offer possibilities to explore creative opportunities traditionally associated with portfolio careers this time in the guise of tech.
Leap Academy, which is offering a three-day course for anyone who has been recently laid off either in the tech space or from the ongoing cuts due to the new American leadership undergoing spending cuts across several programs, has tapped into this model. Its podcast has welcomed prominent guests including Israel’s Eynat Guez, CEO of Papaya Global, and Richard Branson, Co-Founder of the Virgin Group. The course is also open to Israelis who may be suffering from PTSD and war-related issues in the workplace and who may want to change their professional or personal pathways.
Originally from Haifa and who started her career in the Israeli Air Force before moving to San Francisco and tech, Golan was one of the first women to become an F-16 flight instructor commander until pivoting to what she does now. “In this era, I think we're going to start leaping again and again faster than we've ever had before,” she told CTech. “People will change not just jobs - because even if it's the same job, it's different function and different responsibilities. If you don't have it down, if you're not leaping again and again, and if you don't know how to reinvent, we lose relevance at speeds I've never seen before.”