The sandbox of work - Looks Like Work, Season 1, Ep 17
What happens when a well-known name in tech decides to go solo—not just to scale, but to breathe?
In this thoughtful, energizing conversation, I reconnect with Efrat Dagan—founder of Workaround, ex-Google and Lyft talent exec, and one of the most beloved mentors in Israel’s startup scene. We talk about what it really means to build a business from the inside out, with curiosity, spaciousness, and a sneaky amount of joy.
Efrat shares how she turned her side hustle into her main gig, why she doesn’t believe in “bringing your whole self to work,” and how the workplace has permanently changed post-pandemic (spoiler: the employees are not going back). Plus, we explore what freedom really looks like—beyond the buzzwords—and how challenge, growth, and stability can actually coexist.
What We Talk About:
How Efrat went from big tech exec to independent mentor and founder
The difference between intrapreneurship and entrepreneurship
Why “freedom” is about way more than remote work
Building a lifestyle business without compromising ambition
The emotional realities of challenge, identity, and growth
Roe v. Wade’s ripple effect inside HR and leadership spaces
Redefining success on your own terms—and learning when not to scale
Why some parts of yourself are not for the workplace (and why that’s okay
Efrat’s Compass Question:
“What part of the job do you love the most—and how can you do only that?”
If you're building your own thing or reshaping your current role, let this question lead the way.Key Takeaways:
Freedom is strategic: Designing a career around flexibility is power, not compromise
Intrapreneurship counts: Even inside big tech, creativity and autonomy are possible
Challenge ≠ burnout: You can stretch yourself and stay sane
You are not your job: Detaching identity from work is a deeply stabilizing move
You can build before you quit: Side hustles are sandboxes for sustainable growth
Not everything belongs at work: Keeping some parts of yourself private is an act of care
Follow the joy: Prosperity isn’t just financial—it’s about energy, relationships, and impact
“Bringing your whole self to work? I’m not sure workplaces know how to treat that.”
Listen to this episode on Spotify | Apple | Wherever you get your podcasts
Resources & Mentions:
Visit the WorkAround website (Hebrew)
Catch up on previous seasons of Looks Like Work wherever you get your podcasts: Spotify | Apple | Podbean
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