She Left London to Travel, Think, and Start Over
How Niluka Kavanagh Built a Founder Community After Saying No to the Safe Path
When Niluka left her corporate job in London, she wasn’t burned out.
She wasn’t pushed out.
She just knew something else was calling.
“The job was fine. The people were nice. But I could see the trajectory. One day I’d wake up with a nice title and think… I never took a risk.”
So she booked a one-way ticket to Valencia.
And started from scratch.
Today, she runs Imagine That Club, a global community for first-time founders, especially those making the leap from corporate to self-employment. And she’s quietly building one of the most thoughtful founder spaces I’ve seen.
From comfy career to uncertain freedom
Niluka didn’t hate her job. But she had a question she couldn’t shake:
What if I never try?
She didn’t want to be the person who always wondered what could’ve been.
She wanted to work for herself.
And from anywhere.
“A director told me, ‘Maybe focus on just one.’ But I wanted both. So I went for it.”
She left. Moved to Spain. Built her first public speaking business.
Then launched a community for others doing the same.
Starting lean, pivoting fast
At first, Imagine That was for digital nomads, people chasing location freedom.
But she quickly realized something.
The real pain wasn’t travel logistics.
It was the emotional and practical shock of going solo.
“I realized I connected more with people like me. From corporate. Now going into entrepreneurship. That’s who I could really help.”
So she pivoted. Tightened the positioning. And kept building.
Not with ads. Not with fluff.
With people. With connection.
Real talk: the hardest part of leaving
Niluka had a secret weapon: a soft sabbatical clause that let her return to her job if she needed.
“I always share that, because not every leap needs to be extreme. If you’re not competing with your company, have the conversation. Many will welcome you back.”
And yet, even with that safety net, the hardest part wasn’t leaving.
It was deciding to leave.
The overthinking. The what-ifs.
That quiet fear that maybe you’re not ready.
Maybe you’re being naive.
“But once you start doing, the fear shrinks. The worst-case scenario is usually the one you’re already in.”
Burnout isn’t just overwork
Niluka didn’t burn out from long hours.
She burned out from too much movement.
“Two years. Eight countries. A dating app. A startup. It was amazing… and unsustainable.”
So she slowed down. Learned to check in with herself.
And built a lifestyle that didn’t need escaping.
Her routine now is simple:
Move in the morning. Work in focused blocks.
Avoid meetings on deep work days.
Make room to breathe, think, rest.
What she’s seeing in the market
She works with dozens of new founders each month. And here’s what she’s noticing:
The AI boom lowered the barrier to build, but not the pressure to sell
Boomers are the most underestimated segment in tech
Communication and relationship-building are the real unlocks
Content that’s “too perfect” doesn’t convert, real wins
You don’t need perfect planning. You need momentum
“So much of this game is take action, read the feedback, improve. Then do it again.”
Her stack and workflow
She uses GPT daily, not to outsource her voice, but to speed up her work.
For content: ideation, tone tweaking, caption brainstorming
For sales: templates, CRM updates, light prospecting
For balance: writing clarity, not writer’s block
“It’s my sparring partner. But I never let it speak for me.”
What success means now
It’s not about a million dollars in Bali.
And it’s not about escaping work.
It’s about doing meaningful work, on your terms, without sacrificing your health or your relationships.
“I want to make as much as I can, while still having time freedom and quality of life.”
That means choosing clients carefully.
It means knowing when to say no.
And it means building a life you don’t need a vacation from.
My takeaway
Niluka’s story isn’t about breaking out.
It’s about tuning in.
To yourself.
To your energy.
To the kind of life you want to build.
She didn’t wait until burnout.
She didn’t wait for a fundraise.
She just started. And she kept listening.
And in the middle of a noisy, AI-driven world, she’s quietly building something that can’t be automated:
Belonging.
Connect with Niluka on LinkedIn: https://www.linkedin.com/in/nilukakavanagh/
Learn more about ImagineThat: https://beacons.ai/imaginethatclub
Become a Club Member: https://www.imaginethatclub.com/club
Full episode: https://youtu.be/VdjSD2MVta4