Jul 14, 2026 · 21 min · 9 segments
There was a time when getting a job often meant staying there for life. One employer, one career. Today, changing jobs is the norm, career pivots are common, and freelancing, side hustles and…
Nora CaseyGuestPaul RyderGuest
Sean MoncriefHostI'm, I'm at a stage now where, you know, I'm 39, I'm 40 next year, and I'm almost starting to think about other options and what could be next.
What's that pensionable job? What's that lovely contract look like? What does that, I'll ring HR and tell them I need three sick days.
That's a lot of people, and especially a lot of people in the freelance industry or people who work for themselves.
My husband has just recently started to work for himself, and he's the same as me, going, "Oh, God, if I'm sick, then I just can't phone anybody.
He went, he was in hospitality management, so he was in hotels, and he was in a, a lovely five-star res- resort, and he just found it was really, really tough.
And one day, he kind of came home and said, "I'm absolutely sick of it." And you can tell when something is chipping away at somebody.
I came from a, a set of parents who said, "Well, you're not leaving that job till you have another one." And that was, you were not, like, you were never, ever leaving a job until you had something else.
I'm, I'm at a stage now where, you know, I'm 39, I'm 40 next year, and I'm almost starting to think about other options and what could be next.
What's that pensionable job? What's that lovely contract look like? What does that, I'll ring HR and tell them I need three sick days.
That's a lot of people, and especially a lot of people in the freelance industry or people who work for themselves.
My husband has just recently started to work for himself, and he's the same as me, going, "Oh, God, if I'm sick, then I just can't phone anybody.
He went, he was in hospitality management, so he was in hotels, and he was in a, a lovely five-star res- resort, and he just found it was really, really tough.
And one day, he kind of came home and said, "I'm absolutely sick of it." And you can tell when something is chipping away at somebody.
I came from a, a set of parents who said, "Well, you're not leaving that job till you have another one." And that was, you were not, like, you were never, ever leaving a job until you had something else.
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