The Liberation of Beginner’s Mind. From Tax Accountant to Comedian

EP002 with Samantha Day & Alison O'Leary

When the wildly impossible, becomes possible

Have you ever dreamt of making a wildly different career change but told yourself it’s not “realistic” or possible?

Our minds place all sorts of limits on what we can and can’t do, and what’s permissible, so in this episode I invite Samantha Day to share her story and insights on how she made the seemingly impossible shift from accounting to stand-up comedy.

In her inimitable style, you’ll hear about how Samantha made the decision to leave her 30-year career for something new and incomparable; the thought-provoking psychological approaches she uses to deal with fear and doubt; and the practical steps she took to get started and build her profile.

In this episode we discuss

  • The push and pull factors that drove Samantha to make a career change
  • How she sanity checked her choice to move into comedy so that she could feel confident she was making the right decision
  • Two powerful psychological perspectives Samantha uses for developing courage, one of which she got from Michael Macintyre’s director! 
  • The steps and approach she took to build her new career from scratch
  • How Samantha’s old job made her ill and the physical signs to look out for that suggest real change is needed
  • How Samantha feels doing a job that’s in alignment mentally, physically and emotionally

A bit more about Samantha Day

EP002 Guest Samantha Day 2

Samantha Day spent 30 years working as a tax accountant in the city of London, before making a career change that couldn’t be more polarised.

In her early 50s she embarked on a transition from accounting to stand-up comedy, turning a very new hobby into a real job that she earns a living from.

She’s won numerous comedy awards, is regularly gigging around the country, and she’s (at the time of recording) had two really successful runs at the Edinburgh Fringe Festival.

Find out more about her on her website at or follow her on Instagram.

Questioning your options to change careers?

In this episode I quickly talk about my Work Wonderland™ Course, which is what Samantha completed before I got to actually meet her. She used this as a temperature check to make sure that when she was thinking of changing her job, she wasn’t making a jump to something else that she wouldn’t be happy with.

The course and web application is a low investment to help you to determine the right career path (even if you have no idea what the right direction is at the start), or to confirm that what you are already thinking is the right choice. Read all about it here.

There is a community with this show

If you enjoy this podcast show, then you will definitely enjoy being part of the Dream Chasers Unite community.

Come and meet, learn from and be inspired by awesome, like-minded people who are on their own Dream Chaser journeys (at various stages).

Find out what’s possible, by seeing what other people are doing to determine and go after their ideal careers and lives.

Join the group here.

Ways to watch and listen

Listen on the go, on your mobile phone:

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All full episodes are recorded in video as well, and are uploaded to the show’s playlist on my YouTube channel. (Click here to quickly subscribe to my channel to see future episodes).

If you want to watch with auto-generated captions – click the captions icon on the YouTube play bar menu at the bottom of the video.