How do I know if the grass will be greener…?
I was reminded recently of something I see often in my coaching work with people who feel stuck in their careers, particularly those who have been in one role, or one organisation, for a long time. Someone I’d previously worked with had made a significant move after many years in a role that had worked well for her around raising children and family life. It was a considered decision, not an impulsive one. I caught up with her again several months into the new job. The new role is more demanding, the hours are longer, the stress is higher. Family time, which she values and has mapped her career around, is more constricted. The new job certainly isn’t perfect or ticking all her boxes.
And yet, with the career shift, something important has shifted. She isn’t bored anymore. She is engaged. She feels more alive in her work than she had for a long time. The move has unlocked something – not because it has delivered an ideal role, but because it has created momentum where things had previously felt stagnant.
This is the part of career change we don’t talk about often enough.
So much of the cultural narrative is about finding the better job – the greener grass, the upgrade, the role that resolves dissatisfaction and improves every aspect of our lives. We’re encouraged to believe that a move only makes sense if it is clearly and objectively ‘better’ across every dimension. Less stress, more money, better balance, more meaning, more certainty.
And if those boxes can’t be ticked in advance, many people default to staying put, telling themselves that “better the devil you know” is the sensible option.
“The grass isn’t really any greener but the change has been invigorating. When it’s time to move you need to listen to that voice. I have no regrets!”
Fiona, SA
Getting ‘unstuck’
The trouble is, stuckness rarely announces itself loudly. It doesn’t always come with misery or conflict or burnout. More often, it creeps up as dullness, boredom or disengagement – a quiet flattening of energy and enthusiasm. Many people put up with this, almost see it as inevitable or associated with growing older, they acknowledge that things are “fine” and try to settle the dissatisfaction by telling themselves they have a ‘good’ job that (hopefully) pays the bills. It’s enough. Unspoken in this ‘settling’ is the assumption that you’re approaching some sort of finishing line and so you may as well stick it out in the lane you’re in.
What struck me most about this particular conversation with a former coachee was not that the move had led to a perfect outcome, but that it had shifted something deeper. Having moved once – after a long period of stability – Fiona now knew something important about herself. She knew she could move. She knew she wasn’t trapped. And she knew that if, down the track, this role stopped fitting, she would be able to make another change.
That knowledge alone was profoundly empowering.
When you shift the question from ‘Is this the right thing?’ to ‘Is this a next thing that might move me out of stuckness, something often relaxes. The future doesn’t have to be solved in one decision.
Mel Lambert
Many of the people I work with, especially in the second half of their working lives, feel a pressure to choose the right thing. They’re looking for the role that will last, perhaps even their final chapter of work. The decision to move has to be justified because time feels shorter and they feel an obligation to ‘use’ their lifetime of skills. There can be a sense that experimentation is indulgent, or that taking risks later in life is somehow irresponsible.
That belief can be incredibly paralysing. And it can be based on a false premise that you only need to be doing something ‘good enough’ to get you through to the supposed finish line of ‘retirement’.
However, our lives (hopefully) are long, and they rarely move in a straight line. Most people don’t make one neat transition and settle forever. What they do instead is make a series of moves that gradually bring them closer to work that fits who they are becoming, not just who they were. What’s more, all those decisions that draw you closer to who you are becoming build your confidence that change is possible and set you up for knowing who you want to be when paid work is no longer in the frame.
When you shift the question from “Is this the right thing?” to “Is this a next thing that might move me out of stuckness?”, something often relaxes. The future doesn’t have to be solved in one decision. You’re simply allowing the next chapter to reveal more information – about what matters to you now, about what energises you, about what you’re willing to trade and what you’re not.
We’re also sold the idea that confidence should come before change – that certainty is a prerequisite for action. In practice, I see the opposite far more often. Confidence tends to grow through movement, not before it. It’s built by taking a step, discovering that you can cope, adapt, learn, and recalibrate, and realising that you have more agency than you remembered.
For people who feel stuck but hesitant to move because they’re afraid of choosing the wrong thing, this is often the reframe that matters most. The real risk is not that the next step won’t be perfect. The real risk is staying somewhere that no longer stretches or engages you because it feels safer than uncertainty.
So perhaps you can’t know for sure if the grass will be greener. Perhaps you don’t need a decision that lasts forever.
Sometimes what you need is simply enough movement to reconnect with your own sense of aliveness – and the self‑trust that comes from knowing that if something stops fitting, you’re allowed to choose again. And again. At any stage in life.