Knowing when it’s time to go

Arts industry figures share their stories about knowing when it's time to seek the next challenge, and how to handle the process of moving on.
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Knowing when to move on from your role is an art form in itself. For some it’s an easy choice, for others it’s a struggle. Not all of us are equipped with the skills to navigate such transitions smoothly, though thankfully for most they come with time. 

If you’re having nightmares about your job​ or feel that staying any longer in a given role will not only be deleterious to you but to the organisation you work for – clearly it’s time to move on to a new position or place of employment.

The decision to go can also be a positive one. Sometimes it’s driven by a thirst for new experiences and challenges, or by a door opening unexpectedly; and fresh blood is invariably beneficial for organisations, while for individuals starting a new job can be a joy.

But just as all jobs have their peaks and troughs, sometimes we all need to stop and take stock of whether our particular job is done.

Here, an array of arts industry figures, ranging from the Artistic Director of a major company – who feels she’s timed her impending departure well – to a ​former theatre owner who in retrospect didn’t extricate himself soon enough, offer their take on staying, going, and staying fresh. (Some responses have been edited for clarity or brevity.)

Kate Cherry, Artistic Director, Black Swan State Theatre Company

‘I think the thing about running a state theatre company that’s tricky for the leader is that you’re investing it with the time and energy as if it were your own business; but as soon as your job comes to an end – you don’t own the business. You don’t have the benefit of having invested your time in a corporation because you’re not walking away with stocks and bonds. So the time that you spend at a state theatre company say, or a state institution is not your time; you don’t walk away with a golden handshake. So I think given that, it’s often tricky to know when is the right moment to go.

‘So for me, I started feeling that the conversation needed to be happening about six months ago, and I probably initiated the conversation, because I looked at the strategic plan that we had [for] the last five years – and I realised that we had completed every aspect of that plan. Those things were now in place. And so I wanted to have a conversation about what the future held for the company and how the next generation – or my generation – would take change of the company in different ways.

‘Because there’s a new Chair, Mark [Barnaba], I stayed a little longer than I otherwise probably would have because I wanted the chance to work with him and to make sure that he had the time to settle in – and that was an agreement that we had. And the General Manager was also new, so it felt like you wouldn’t want three team leaders all leaving together. But it was clear once Mark came in that my time would be transitional – and I think it’s really important to have relationships where the Artistic Director is able to talk to the Chairman about succession planning, because I think that’s part of what the Australia Council expects us to do now, as artistic leaders.

‘And of course having a child, I’m aware of the fact that if we’re going to make a big shift – whatever it might be, whether it’s within Perth, whether it’s within Australia, or America – we want that big shift to be happening before he went to high school. So it was personal planning as well as planning for the company … It’s about kind of catching the wave – I used to be a swimmer – so it was about knowing when to catch the wave.’

Jennifer Greer Holmes, Creative Producer and Communications Consultant

‘I don’t know many people who work in this field for the money, and I am certainly not one who does. For me, I need immense job satisfaction in order to stick around, so mostly, until I started working for myself or as a part time contractor for organisations, I haven’t stayed with the same job for more than about 20 months (I think that was my record and even that was overstaying). I need my work to challenge me, but in the right ways.

‘The reasons I’ve overstayed in jobs has been because I’ve thought that the obstacles might eventually be overcome with a different approach, or a change of governance or leadership. When they haven’t, despite living in hope for months, I’ve had to walk away from jobs I once loved.

‘The first sign for me to move on is that I lose motivation for the work. When I enjoy a job, I’m energised and can work at what I consider a fairly fast pace and when I’m not, it’s the opposite. And I lose confidence in myself, even if external feedback is good; I begin to doubt my abilities.

‘The ramifications of overstaying for me were exhaustion and anxiety. These roles have been leadership roles where I’ve felt the burden of responsibility has undermined my well-being and my personal relationships. On two occasions that I can recall it was a loved one who told me it was time to leave – that made me really understand how badly overstaying was damaging me, I needed someone else to tell me!

‘The reasons for overstaying have been varied. Financial stability used to be the thing that spoke the loudest, but now I care more about having joy in my life than having a regular income. And the other things were hope for the future of what the job or company could be, and nostalgia for what it was when things were better than what they are when I needed to walk away.’

Michaela Coventry, Executive Producer, Speak Percussion

‘It can be quite obvious in hindsight but the obvious sign is if you find you are just “going through the motions” – if you no longer feel challenged and you are relying on your past performances to get you through. Not being open to new ideas and regularly coming out with lines like “Oh yes we tried that, it didn’t work”.

‘Once you start wanting accolades or praise for your work and have lost satisfaction in just doing the job as well as you know you can (I don’t mean you should be a martyr, but you need to be thriving on a job well done). Basically it is if you have lost the “passion” – sometimes that can just mean you need a break or holiday but in my experience it means it’s time to move on.

‘This relates to employment in an arts organisation but also for board members. Boards that are not refreshed and re-evaluated regularly can potentially ruin an arts organisation.’

Cameron Stewart, Freelance Producer

‘I think it’s very much kind of a gut instinct as to when to break off relationships. For me there was a turning point a couple of weeks ago; I had this moment of once again being in the position of waking up, or not being able to sleep so much, going into a project and going “Okay this isn’t healthy.” And if this is going to be a long-term career, this can’t be something that I have hovering over my head every time, this sense of anxiety or dread on some level.

‘So for me, I kind of went “this isn’t healthy for me to be doing this” … And I think it’s important to take that step back and not necessarily say yes to the next project … but making sure that you’re saying yes to projects because it’s something that you believe in, and something that you truly believe you have the skills and capabilities to undertake to the full extent that it needs to be undertaken.’

Jason Cavanagh, former owner & operator, The Owl & Cat Theatre

‘I remember precisely when I decided to leave the Owl. I was having a particularly challenging conversation with one of the artists who had a show coming up in the theatre and at some point during that conversation I just snapped. I ended the call and said out loud to myself, “That’s it. I’m done”. It was long overdue. I had gotten to the point where everything seemed like hard work; all the things that used to bring me joy now just brought me aggravation … I started to get annoyed at people for coming to the theatre because it just meant more work for me. That’s the time to leave. 

‘After I left I felt 10 years younger. It literally felt like a weight had been lifted from my shoulders and I could now stop stooping. I started smiling and laughing again and I had that all too precious commodity, time.

‘I think it’s really hard to know sometimes when you’re in the middle of a situation how much it’s impacting on your life. I battered away at that space for so long, I didn’t notice that I wasn’t enjoying it anymore, and it was just making me ill. Mentally and physically.

‘All I can say about avoiding that kind of situation is to make sure to look up every now and again and check yourself. If you feel a burden and you don’t know where it’s coming from, it could be because it’s coming from something you used to love that has now turned toxic. That’s a really hard thing to admit sometimes, I think.’

Overstaying in a small organisation by Anonymous

‘I stayed in my job for six years in a small arts company, and now that I have moved on, I feel like I should have either left earlier or made better use of my time by upskilling and training. It was a small office of five people which had worked well in the past, but the workload increased dramatically with no change on the amount of resources available, be they time, money or staff.

‘I recognise that this was a brilliant learning opportunity as I had to step up and take on responsibilities I most likely wouldn’t in a larger company, but I feel now that the benefits were outweighed by the disadvantages.

‘Due to the lack of resources I felt stretched thin and spent each day just trying to do my best to keep each project moving. This required prioritising of course, but it also meant that some projects were neglected and I never got to make up the time as I had to move on to the next thing. Feeling like you are just trying to keep your head above water is not conducive to creativity in the workplace or anywhere; in the end you stop taking risks and just stick with what works. It’s also very stressful and I had little energy for anything outside of my work life. I had always wanted to pursue a Master’s degree, but the intense nature of my work made that impossible.

‘A regret I hold now is not having opportunities for training and up-skilling during those years, due to the fact that they were not offered to me (the company had no budget or interest in this) and that I failed to seek them out for myself (I felt I had no time or energy in or outside of the workplace).

‘My advice would be if you aren’t ready to leave a place of work for whatever reason, that you make the most of opportunities for training, and if they are not offered to you to seek them out, because when you are ready to leave, these skills will be invaluable in your search for a new position.’

Next week: Keeping fresh and focused in a long term role

Richard Watts OAM is ArtsHub's National Performing Arts Editor; he also presents the weekly program SmartArts on Three Triple R FM. Richard is a life member of the Melbourne Queer Film Festival, a Melbourne Fringe Festival Living Legend, and was awarded the Sidney Myer Performing Arts Awards' Facilitator's Prize in 2020. In 2021 he received a Lifetime Achievement Award from the Green Room Awards Association. Most recently, Richard received a Medal of the Order of Australia (OAM) in June 2024. Follow him on Twitter: @richardthewatts