HeyJaredCareer Happiness with Jenny Holliday
Jenny Holliday, Career Happiness Coach, shares her thoughts and experiences of career, business, work/life balance and all the things in between. This Substack began as Freelance Feels. Insta: @jennyhollidaycareercoach
- Indexed issues, last 90 days
- 11
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- Sep 30, 2026
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- Jul 22, 2026
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Iced coffee and interviews (opens the original)
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Way before the days of easy apply and Zoom interviews with AI recruiters, we used to send off our CV and cover letters in envelopes and all interviews were in person. I had a friend who used to staple a packet of mini chocolate buttons to her CV when she sent it off with a job application. Turning up IRL, you would often be offered at least a glass of water, more often than not a tea or coffee. The person interviewing you would even make it - or you’d say ‘no thanks’ if you didn’t want the faff
The ‘algo’ isn’t just targeting teens: I talked about depression then got shown related content (opens the original)
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It’s a common joke between friends that ‘the algo is listening’. For example, at the weekend, a group of friends and I were talking about an actor/presenter. The next day, that very presenter’s Instagram came up on my feed. The phone knew. We know the phone knows. I have my microphone settings on for Instagram, so I am aware that it picks up on things I say and feeds me related content. The same goes for when I’ve searched for something and then get ads for the same stuff. (Not so great when you
The word I’m phasing out of my work vocabulary (opens the original)
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“I'm just following up”“Just popping on to say…”“I just wanted to check back in…”“I’m emailing just in case…”JUST. One little word, lots of impact. And it’s one I’m phasing out of my vocabulary.This epiphany has come to me after two days at ‘Glastonbury for Business’ AKA Ideas Fest. It was advice from a panelist called Matt Elwell, as part of a discussion on words they’d ban from sales. He’s there on the far left of the stage.<a class="image-link im
Dealing with the back to work feelings (opens the original)
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A lot of us right now are having the back to school feelings, and I know for some people, that is joy. Getting the kids back into a routine, having your time, your space, your brain power, back - right? I don't have children, so I don't know truly how that feels, but what I hear from friends is “Hooray! They're out the house. I can focus again!”During this back to school time what also happens for many of us is that we get the back to school feelings - but with ‘back to work’. We might have had
Freelance communities: Finding the right one for you (opens the original)
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As I begin to onboard new members of The Freelance Media Network, I’ve been pondering more and more on freelance communities and what they offer. Every day there are new Facebook groups suggested to me in my two niches, and others have popped up on my LinkedIn feed. There are so many to join in with - everywhere from FB and Whatsapp to Slack and Circle.One thing I’m sure of is that one of the biggest things that can keep you feeling focused and balanced as a freelancer is community. Whether it’s
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