You know you want to make a career change, but you have a mortgage, a family, and a retirement to think about—how do you even begin?
Many mid-career professionals are longing for change. Maybe you‘ve reached a point in your career where you’ve achieved everything you set out to achieve 15-20 years ago: the status, the recognition, the associated compensation – yet you’re not feeling as fulfilled as you once did. Maybe you have big ambitions but have been thwarted over and over again by corporate politics. Or maybe you‘ve never found satisfaction in your career, instead pursuing other people’s definitions of success without pausing to consider what it is that would make you happy.
Whatever the cause, many people I know are trying to find a way to feel inspired and alive again at work, and like they are making a difference in the world.
However, once we reach middle age, career transitions can feel much more risky. By a career transition, I mean more than changing jobs from one company to another. I mean making a transition to work that you find more meaningful, more fulfilling, more rewarding. Or finding the confidence to transition into a new role in your current company that is more in line with your own aspirations. There is more at stake – families to support, mortgages to pay, and retirements to plan for. All sorts of natural cognitive biases, such as loss aversion, the status quo bias and the endowment effect kick into gear, effectively locking us in a place of indecision where our heart longs for one thing, but our minds hold us back. (For a great book about the psychology of quitting, check out Quit, by Annie Duke).
So what does it take to truly make that transition?
Most of my clients come to me asking for support with defining their purpose and identifying potential future roles. They want feedback on their CVs and advice on the best way to find a job in a market that is characterised by LinkedIn job posts with thousands of applicants and AI recruitment bots that auto-screen resumes.
And while we can work on those topics, I find this is not usually what makes career transitions so hard.
The four steps for a successful career transition
One of my favourite thought leaders on change once said: “Change only happens when the dream is big enough or the pain is real enough.” In my experience, I’ve found that to be true. Changing careers is hard because it’s about more than finding a new job. It’s about actually giving yourself the permission to dream, and freeing yourself from limiting beliefs that make it hard to move forward, so that you can step into a new identity.
In the past five years that I’ve worked with clients on these topics, I’ve boiled down my work to four essential steps:
- Make space
- Dream big
- Address barriers
- Take action
Make space
We need to be in the right mental and emotional space to make a change. Neurologically, when we are stressed, burned out, or even just too busy to think, our brain and body are in a state of fight or flight, or even complete shutdown. When we are in these states, we are focused on survival. We literally can’t access the higher executive functioning of our brain or our ability to think creatively.
If we try to contemplate a career transition from this mental space, our options will seem limited. Often, the first step in a career transition is about managing your energy and creating some space where you can take stock and reflect on what’s important to you – whether it’s taking a week of holiday, going on a longer sabbatical, or even carving out regular time to go for a walk or run without headphones, where you can let your thoughts wander.
If you’re properly burned out, beyond just creating space, it’s important to find ways to reconnect with things that bring you joy. For one client, that meant reconnecting with her love of singing by joining a local choir. For another, it was learning to ride a motorcycle. While these activities may seem frivolous, they do wonders for getting us out of the “fight or flight” state into a place where we see more possibilities.
Dream big
Once you are in a more centred, grounded state, we can start dreaming.
The first thing I do is ask my clients to write three stories: one ‘should’ story and two ‘dream’ stories. I find that, most times, they already know more than they think they do – they just haven’t given themselves the space to put it on paper.
Once they’ve written out these alternatives, I read the stories back, one at a time, and ask my client to notice their reaction to each. Usually, the ‘should’ story makes them feel contracted, and the ‘dream’ stories make them feel more excited or expansive. That is our intuition telling us which direction we should explore further – which direction makes us feel most alive.
Sometimes my clients have a hard time writing their dream stories. So we take a step back. We reflect on what they enjoy doing most, when they have felt most engaged at work, what topics they have always cared about. We might explore who their role models are, and why. We move beyond job titles and discuss the types of people they want to work for, the size of organisation they prefer, what defines the organisational culture. And then we come up with a few hypotheses for them to explore further.
This is enough for now. Many people get stuck here, wanting to know the end destination before they take a single step along the path. But actually, as you start walking the path, your view changes. You meet new people and gain new perspectives. That’s why it’s not about having the final answer at this stage. It’s about having a few vectors you are keen to explore more.
Address barriers
Usually, as soon as we start having the courage to name our dreams, all our inner barriers start coming up – the voices in our head that tell us why our dreams aren’t realistic.
We all have inner ‘operating systems’ that were coded when we were young. Our parents lived in a world where the social contract between employers and employees was much stronger, where if you were good to the company, they would be good to you. They perhaps sacrificed their hopes and dreams in service of earning a good living and providing a future for their families.
As a result, we often internalise career advice from well-meaning adults that may have worked for them but isn’t appealing to us – especially not when the social contract between organisations and employees has changed so much. We learned that success means working long hours, climbing the career ladder, and retiring in your 60s. We are told that if we get off the corporate ladder, we’ll never get back on, that quitters never win and winners never quit. One client of mine, who was content just to stay where he is for now, was told by his father that this was a bad plan because “he would become too expensive” (which presumes that pursuing those annual raises is the #1 priority). I once gave my own father some heartburn when I told him my career goal was to maintain my current level of income while minimising my working hours.
To make it even harder on ourselves, we also compare ourselves to our peers, saying to ourselves: Look how far he has gone in his career – I should be there too, I’m smart enough. She has just bought a holiday home, why can’t I afford one yet? That couple is already retired in their early 40s – what am I doing wrong?
With all these voices in our heads, no wonder it can be so hard to find the courage to leave our current path and find a new one.
Addressing our inner barriers has two components: (1) identifying the assumptions and limiting beliefs that are holding us back; and (2) re-writing our definition of success. This work can run deep – one of my clients described it like a fortnightly “deep tissue massage” where we dig in and really work the muscles. It is often very uncomfortable, but the benefits last far beyond a coaching session.
Take action
This is where the rubber hits the road – when you have enough of a spark of a dream, and a bit of space from your inner skeptics – to start exploring how to make the transition work in practice. While there are lots of different practical actions that you can take to start exploring your transition, the two actions that I mainly encourage clients to do are to (1) start talking to people and (2) try on your new identity.
(1) Start talking to people.
I have lots of clients who say “I think I want to do something related to X. But how do I do it in practice?” Honestly, I have no clue (unless you want to become a coach and a facilitator). It’s because I haven’t walked that path. But others have. And if you can find them and talk to them, they will help you craft your path.
Begin to breathe life into your dream by sharing it with others. Get their perspective: who else do they know who does this type of work? What is it like in practice? Let them know you’re looking for encouragement about what it would take to make it work – not all the reasons why it won’t. If your dream is still fuzzy, this is a great way to clarify what you want. One of my clients knew he wanted to work more in org analytics, but wasn’t sure how. So he started speaking with people about the different types of roles that are available, and then narrowed it down to two different roles that felt like they might be a good fit for him.
As you refine your dream, start getting tactical in your conversations: What does it take to find a role like this? What do I need to show I’ve already done? What courses do I need to take to upskill myself? Through these conversations, you’ll start to see new opportunities that you wouldn’t have seen by thinking through this on your own and get clarity on what the right next step is for you. Over time, these conversations often leads to job opportunities.
(2) Try on a new identity
Ultimately, career transitions are tricky because it’s not fundamentally about changing what we do – it’s about changing who we are. It’s about disentangling from our identity as a consultant, lawyer, banker, tech person, or however you professionally define yourself, so that there is space for a new identity to emerge.
But we don’t have to go from 0 to 60 in adopting a new identity. A more measured sequence is to first experiment with it in private, before going public. Ultimately, it might become part of your new profession. So for now, ask yourself: what is the smallest step I can take to “try on” the new identity of who I want to be? Maybe you introduce yourself as a writer, or a musician, or an aspiring chef, just to see how it feels. Maybe you take a course that lets you see if it’s something you like, or shadow someone for a day at work. I encouraged a client who had a dream of opening up a small daycare center in her town to first volunteer at one to see if she liked it in reality.
Properly changing careers isn’t for the faint of heart. It takes real courage to let ourselves dream big, explore some of the patterns that have been holding us back, and take steps – no matter how big or small – towards change.
This change also doesn’t happen overnight. It can take a few years to successfully transition careers, as well as a few interim moves. The most important thing is to identify where it is that you’re getting stuck – whether it’s a need for more space, lack of a clear dream, or a really strong inner critic – so that you can slowly but surely find a way to move forward.
