Psychologist Sharon Draper and agency leader Renee Hyde agree: if you still dread work after a break, can’t face three Mondays in a row, and your values don’t align despite your best efforts to fix things, it’s probably time to move on — life’s too short for a job that drains you.
We’ve all been there — lying awake on a Sunday night, staring at the ceiling with that heavy feeling in your chest about Monday morning. Or coming back from a much-needed holiday, only to feel that sinking dread at the thought of returning to work. Knowing when it’s really time to leave your job can be one of the trickiest career calls to make, especially when you’re not sure if what you’re feeling is just a rough patch or something more permanent.
Psychologist Sharon Draper, who’s spent over 13 years helping people understand themselves better, and Renee Hyde, who leads client and agency relationships at Howatson+Company, have seen this crossroads plenty of times. Here’s their take on how to navigate it with a bit more clarity — and a lot more self-compassion.
If you’re hoping a getaway will magically solve what’s not working at work, Sharon has some honest words for you: "I think many people take holidays in the hope it would solve some problems at work. You know I need a break and then get away from it all. And I think that's important but it's not going to solve any problems at work if there are problems."
That said, a break can give you the headspace to see things more clearly: "Whenever we're out of a system or out of a relationship you can kind of see things a lot clearer. So I think that's helpful to start the process in that way."
Renee has her own down-to-earth test for knowing when it might be time to call it: "After a holiday if you still don't want to go back to work holiday then you probably know it's time to leave."
She’s got a personal rule that’s simple but telling: "I have always had a rule that if I didn't want to go to work three Mondays in a row then I probably knew that it was no longer for me."
We’re not talking about the normal ‘back to reality’ drag after a break — we’ve all had that. It’s when that feeling sticks around: "If you don't want to go back to work after a holiday apart from oh I just don't want to put pants back on again I would suggest that is a good time to think your job."
Before you pack up your desk, Sharon suggests doing what you can to fix what’s not working: "I think it's always important to try and see what you can do to try and influence whatever it is that isn't working. It's always important for that because a lot of people worry about making making the right and wrong decisions and will I regret if I do this thing and we just don't know."
Her advice is to be proactive: "It's up to you to try to communicate in the way that you need to be heard. Speak to whoever it is try and solve that problem yourself so that you can have a better experience at wherever you're working."
Quitting is a big decision, so make it with your eyes wide open. Sharon puts it plainly: "All you can know is be as informed as possible about whatever decision you're making and you've done whatever you possibly can in this moment right now. So knowing that that can help you make decisions to whether you need to leave."
It’s about doing what you can to gather real-life feedback before you leap: "It's always about trying to be as informed as possible before we make a big decision. And we do that by doing things. Try to change things in the way you as much as you possibly can. And then that can give you some more feedback. It's always just trying to get more data so that you can make a decision. That's that's the best decision for you."
Sometimes you’ve done everything you can, but the gap between you and your job is still there. Sharon says that’s when it might be time to call it: "If things are not working out and you've tried you've given it your all then maybe the values are no longer matched with yours and then it's time to find something else."
In the end, it all comes back to how you feel about spending your time. Renee sums it up: "I love my job I've always loved my job and I'm I totally accept I'm very blessed in that. But I think if you're feeling that you don't want to do something we spend so much of our lives in this kind of world that is a very good sign."
She’s right — life’s too short to give so much of yourself to something that gives you nothing back: "It's too much time and effort to not be doing something that you're enjoying."
So if you’re lying awake on those Sunday nights, listen to what that voice inside is trying to tell you. If you’ve tried to make things better but the dread doesn’t shift, if your values feel out of step with where you work, or if three Mondays in a row feel like dragging your feet through wet cement — maybe it’s time.
Do it thoughtfully. Do it with as much information as you can gather. And remember: your wellbeing matters more than any paycheck. Work takes up too much of our lives not to feel like it fits.
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Renee is responsible for client and agency leadership at Howatson+Company. She specialises in running large, integrated clients both locally (Allianz, Samsung, CBA) and globally (Marriott International, IBM, Microsoft, Google) having worked in leading agencies in Australia and New York like M&C Saatchi, CHE Proximity and Anomaly. Renee has a unique skill set having worked in various capacities including consulting, media, customer experience and communications. She has birthed, built and grown brands and is at her best with complex challenges to solve. Renee is also a mentor at the Trenches, a qualified Mental Health first aider and has been recognised by Campaign Asia as a Woman to Watch and by B&T on their Women in Media Power List. As a mother of two young girls, Renee is a passionate advocate for diversity of all forms and is constantly tired.
For the past 13 years, Sharon has worked as a Psychologist, aiming to authentically connect with people to help them feel safe and heard. She believes, if we can gain insight into why we might think, feel and behave a certain way, we can make more sense of our current lives and then, with a growth mindset of self-compassion instead of a fixed mindset of shame, we can consciously implement positive change. Sharon has a holistic approach, she is informed by Existentialism, Neuroscience, Polyvagal Theory and Attachment Science. Sharon believes if we can accept that the behaviours we developed as children were necessary for our survival and if we can understand that all the emotions we feel provide insight into our deepest values, we can live purposeful and meaningful lives. Sharon is currently working on an online program called Taking Up Space. The program empowers women who tend to default to people pleasing behaviours. The program focuses on building insight into ones behaviours, developing emotional competence (learning how to regulate and learn from all emotions we feel) as well as building courage to integrate these insights into our everyday lives so that we can live more authentically. Sharon is also a contributor to Newspaper articles (Sydney Morning Herald), Radio (ABC) and TV (Sky News, Channel 7 Sunrise), and is the Psychologist for eHarmony Australia.
Andy Wright is happiest in a well‑worn baseball cap. As founder of Never Not Creative, he rallies a worldwide community determined to make the creative industry kinder and fairer. He also steers Streamtime as CEO and co‑chairs Mentally Healthy. Different titles, same purpose: brilliant work should never cost anyone their wellbeing. Never Not Creative was born when Andy decided it was time to stand up and make the industry a better place. What started as one person calling for change has grown into a movement that shares research, sparks honest conversations, and builds practical tools that help teams thrive. Andy’s rule of thumb: protect the humans and the great work will follow. Picture a studio cat giving you a gentle nudge to stretch, breathe, and log off before the midnight oil even thinks about burning. Off the clock, Andy is dad to three energetic kids, husband to one exceptionally patient partner, and a loyal Everton supporter (character building, he insists). Whether he is championing healthier workplaces or cheering the Toffees through a tense ninety minutes, Andy believes creative success should leave everyone standing a little taller, not lying flat from exhaustion.
