Jimmy's Jobs of the Future

Lyndsey Simpson: Challenging the stereotypes of tech and How to create purpose later in life

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Episode notes

You may have a stereotypical image of a tech founder. Chances are it’s someone from East London, with a Hipster beard who lives in something like a houseboat…

But as we’ve seen before, founders come in all shapes and sizes. We’ve previously had Anne Boden on, who founded the billion-dollar company Starling in her 50s.

And that is what today’s guest is all about. Lyndsey Simpson is the founder of 55 Redefined and it’s all about finding purpose later in life.

Lyndsey was suggested to us after we made a call out for more diverse guests after International Women’s Day earlier this year and I couldn’t think of a better guest suggestion to reflect this.

Thank you to our partners The Octopus Group for making this show possible. The Octopus Group is a collection of 8 entrepreneurially minded businesses that look to back the people, ideas and industries that will change the world.

Get in touch with us at [email protected]

In this episode we talk about:

  • Where did the name come from.
  • How her entrepreneurial experience has lead to constant consumer feedback loops .
  • The importance of the personal touch.
  • Her journey into the world of work- including work in her dad’s butchers and post office.
  • Why first hires reflected her weaknesses.
  • How to persuade someone to take the jump with you- and why transparency is key.
  • What jobs she is hiring for in this round of growth.
  • Why Instagram is key to reaching older generations.
  • The misconceptions about over 50s .
  • ‘Returnships’ from retirement.
  • The culture of a company with older demographics in mind.
  • Where to find careers at 55 Redefined.
  • Why they went completely remote working.
  • How to maximise in-person time.
  • The sectors Lyndsey is going to disrupt next.
  • Lyndsey’s most inspiring content- a TV show, a book and a newsletter.


If you'd like to see more information about the job roles being offered please look at my Twitter @jimmym