You’ve been relentless in your climb up the corporate ladder, but now you’re nearing the top, the view isn’t quite what you expected and you’ve no idea what to do about it…

You’ve never known quite where you’re going and you’ve been rerouted more times than you can count, and you can’t quite shake the idea that that’s a problem…

You’re thinking about starting to think about making your next move. You know what you want but need a dose of courage; or don’t and need a dose of clarity…

🎵Follow the yellow brick road. Follow the yellow brick road. Follow follow follow follow– 

Oh do shut up Dorothy! 

It’s a classic film, a wondrous thing (one of my Top 10 of ALL TIME!), but a girl should only ever do so much following, don’t you think?? 

What if you don’t want to follow the yellow brick road? What if you tried to be a good little follower and now you feel like a terrible failure? What if you’re more of a leader than a follower? What if the yellow brick road is totally (wait for it) MAKE BELIEVE? 

When it comes to careers, there simply is no yellow brick road (neither is there a happy band of misfits to help you follow it). There are options everywhere. Options squared. And incredible things can happen when you start – dare I say it – paving your own road. Stick with me and I’ll show you.

How to use this guide

Not gonna lie: this is a biggie, full to bursting with advice. I reckon if you’re already sold on the squiggly career (thanks to the wonderful Helen Tupper for coining that phrase!), you could skip straight to ‘Seven career moves’. If you’re feeling a bit janky about it, start from the start. You won’t regret it.

Contents:

The BS of linear career paths
Know this: other roads exist 
Seven career moves: which is right for you? 
Follow the joy
WorkJoy community story: From long haul ladder to active adventure
Next steps: Making moves 

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The BS of linear career paths

Let’s play guess who? 

• She was editor of her school newspaper then became a journalist
• She was told she couldn’t work at the same newspaper as her husband, and to find a new career (OMG to the 1950s 🤦‍♀️)
• She got a job as a picture editor at Encyclopaedia Britannica, went to graduate school then worked as a volunteer 
• At 30, she got a job as chief legislative assistant to a senator, then, eventually, at the White House
• She became an academic at Georgetown University
• She was appointed by Bill Clinton as U.S. ambassador to the United Nations 
• Aged 60, she became the first female U.S. Secretary of State

The woman behind this impressive non-linear career (and this isn’t even the half of it) is Madeleine Albright. She continued to work almost up until her death in 2002, making literal history. No wonder she got a London members club named after her. 

Looking at this list of her career milestones, I’m struck by one question:

What if the key to her success wasn’t in spite of her non-linear career, but because of it?

We all know, kind of theoretically/hypothetically/academically, that non-linear careers are just as valuable as the straight-up-the-ladder kind, but I do think many of us secretly harbour a belief that they’re also kind of…hippy-ish. That the people who follow their curiosity, wiggle around a bit, dabble here and then there, lack direction or staying power. That they’re kind of…floopy? 

Tell me honestly – how have you judged those with non-linear careers? And if you’re the owner of one of these careers, how have you judged yourself? And I’m not immune, I spent over a decade berating myself for not becoming a ‘deep specialist’ or pushing myself hard enough ‘to the top’. So my advice here comes from doing the hard yards! 

In my business, I have the pleasure of employing many excellent freelancers. One of them had this to say about her own non-linear career: 

“I would never judge anyone else’s roundabout career journey, in fact I find them fascinating. But I do seem to have this internalised voice in my head – perhaps unconsciously put there by one of my parents who had the ultimate linear career – that being able to bounce around speaks to some kind of distasteful privilege or even a character flaw.” 

That’s so interesting isn’t it? When there are so many women out there whose very success relies on the fact that they came to their current career later in life, and after doing something else – if not many other things – first, why do so many of us look down on it, either in others or in ourselves?

We learned from the Wizard of Oz that the yellow brick road – well trodden, well paved and helpfully painted an eye catching shade SO YOU CAN’T LOSE SIGHT OF IT EVEN IF YOU TRY, that the prize at the end was simply the revelation that there is no external prize. 

We learned that success is never that simple. 

We learned that it was the journey itself that mattered, all along. 

Another question to ponder: if someone had asked a young Madeleine Albright to plot a 40-year career path that led to Secretary of State, would she have plotted this one? Unlikely. And yet, Secretary of State she became. 

I wonder what you’ll become.

If you’re after some additional thinking on this subject of careers for your ears (see what I did there) then let me point you towards this conversation I had with Kathryn Bishop – author of Make Your Own Career Map (I highly recommend it as a read!). Here’s a little snippet of the delights on offer: 

KNOW THIS: OTHER ROADS EXIST

In their book, The Squiggly Career, authors Helen Tupper and Sarah Ellis ask readers whether they might be, ‘Holding onto a version of success that needs to be redefined.’

Hands up, now. 

I’ve always admired people who know exactly what they want to do with their lives and run headlong towards it, working their asses off lower down the ladder to accelerate their climb, and all but crushing obstacles in their way. But the notion that this is the only way to do things or that it’s the only kind of career that has value, is complete fallacy. 

The yellow brick road was the only road leading to Oz because that notion was fundamental to that narrative. But out here in the real world, there are yellow roads and blue roads and pink sparkly roads. There are brick roads and paved roads and hellish dirt roads with potholes every two metres that only the hardiest of us can navigate. There are roads that go from A to B and then roads with diversions and roundabouts and no damn signs at all. 

To step off the yellow brick road onto any of these others is to choose an entirely new adventure. Sometimes you’ll have an idea of where you want to get to, sometimes you’re totally winging it. 

It’s all valid.

SEVEN CAREER MOVES: WHICH IS RIGHT FOR YOU?

As careers are rarely linear, it may be worth considering what different types of career moves are possible. This approach looks at the shape of your career and these seven examples are possible in many organisations. When you read them, you’ll likely recognize some moves that you have made so far and perhaps be inspired to consider alternative options. They can stand alone, and some can be combined. It’s not intended to be an exhaustive list and there will be nuances associated with your own career, different organisations, and industries. Take it as broad thinking and see if it could help you to explore options. Over a working lifetime, some people may only make one type of career move. Others may try all the options out.

FREE DOWNLOAD It’s helpful to see where you’ve been, so you can better plan where you’re going. My ‘Mapping your career moves’ template is printable, scribblable (that’s totally a word) and should give you some clarity. Download it here.

1. Selectively sideways

These moves are some of the most valuable moves you can make. Often taken up within the same subject matter, area of expertise, or profession, these sideways(ish) moves enable you to build your knowledge, skills, and breadth of experience. They allow for gradual development over time and can expand your horizons by exposing you to different people, skills, and challenges. There are often plenty of opportunities to move in a zig-zag pattern.

These moves can happen within your immediate team, or sometimes beyond into another part of your organisation. As you experience new things, your capabilities and self-belief grow, as does your ability to see things from different angles. This comes with a side order of wisdom, a wider network, and institutional knowledge, which can be career gold dust. Perhaps you’ll want to move upwards at some point, and you will be just the rounded candidate needed. Or you’ll be able to spot an opportunity to create camaraderie between different parts of the business, creating a new process that makes things more efficient. Maybe you’ll build comradery between teams and create a more collaborative culture. All these things are what great reputations are made from and that is a foundation of career success.

The breadth of experience garnered sets you up for career adventures outside of your current organisation. That might be a move to another firm, expanding your horizons with different people, products, or services. Or maybe it allows you to develop into a new specialism or industry, having developed new knowledge and skills. You may even discover a gap in the market and set up your own thing to fill that gap.

2. Tactical trip

In a tactical trip, you apply your skills in a new context, broadening your experience and deepening your understanding of how you ‘do your thing’ when the environment has changed. Internally, this could mean moving between a specialist function and a customer function or moving from managing a small project team to a big operation. If you’re considering moving organisations, perhaps you’ll move from a corporate to the third sector, or from a corporate to a cool new start up. The options for tactical trips are plentiful.

In the new environment, you’ll build a wider network and be able to explore a whole new world of opportunities. These are some of the most common of career moves and are often taken up by people with a transferable set of skills. If your skills are in demand, you may also be able to secure a role with increased salary/benefits. In fact, it is sometimes easier to gain a pay rise through a tactical trip than it is to do so by growing within your existing role. Plenty of organisations value breadth of experience in different organisations and industries, yet some have not yet seen the value in this, so don’t be surprised if some (rightly or wrongly) ask for you to have industry-specific experience.

3. Long haul ladder

A ladder career move is associated with a traditional career structure. It involves applying for and/or being promoted into a new role at a more senior level. They can happen within your current workplace or be a part of a move to a new organisation. These types of moves most often exist in organisations with more traditional, hierarchical structures. The rungs of the ladder are often easier to navigate and climb in your early career. It’s often at the mid-levels where the ladder becomes more challenging and the requirements of what is needed to ‘make it’ become opaquer.

A ladder move often relies on there being a vacancy to fill. If you’re looking in a place with lots of different roles and high levels of people movement, these opportunities can regularly present themselves. If you’re in a niche area, a smaller organisation, or one with higher retention, it can feel like you’re stuck in a waiting room. Perhaps you’re ready to take on your boss’s job, but they’re making no sign of moving? Maybe there’s an opportunity at the next level, yet there are 17 of you in the team all vying for the same role. Or one of the most annoying examples: the next role you want has a requirement of management experience. You don’t have it (yet) and you can’t get it until you get a job which requires it, and you’re stuck because there’s missing rungs thwarting your ascent.

There are also the ladder moves you craft for yourself – they are a lesser-spotted opportunity, yet they can be a brilliant thing. Perhaps you’ve noticed a role that’s really needed in your team. Maybe there’s an opportunity to expand the level and scope of what you do now. Or there’s a project role or secondment that could act as a temporary rung on your ladder, getting you that experience you require to turn it from a stop gap to a solid step.

A single-organisation, fully ladder-based career is becoming less common as the world of work continues to evolve, organisations get flatter and less hierarchical in structure, and more movement between different organisations becomes the norm.

4. Executive escalator

In a limited number of industries, the pathway from junior team member to executive leader is still clear, very structured, and in-built as part of the organisational structure. In law, accountancy, some medical careers, and academia, time- and skills-based progression are still the norm. In these cases, the routes are planned for you. You’re likely to have to put in the hours in both learning and delivering results at each level. You may have to pitch yourself, present your story, and prove that you are worthy of the next promotion, with each stage becoming more challenging.

A word of caution – Executive escalators and long-haul ladders Hierarchical structures are built as pyramids. There are more roles and more opportunities at the entry- to mid-level than at the mid-senior level, and the pinnacle of the pyramid is reserved for a very small set of leaders. As you ascend, there is usually a combination of increasing responsibilities and demands placed on you. Additional hours become the norm and expectations change. They sometimes come laden with the lure of more money and benefits, of status within the organisation and fancy-sounding job titles, but also with the requirement to manage and lead people. It is rare (yet not impossible) to find a series of ladder moves that allows you to become more and more senior within your specialism, without having increased management and leadership responsibility. Yet managing people is not a guaranteed joy maker. As anyone who’s managed people will tell you, it’s not all fun and games! These career moves hook you in and keep you firmly on a predefined path. If you’re in one of these careers, take a moment occasionally to check in with yourself and challenge whether the outcome is still what you really want.

5. Deep dive

There are some roles and industries where depth is the most important feature. Being a specialist on a specific subject matter and being the expert is highly valued. Whether it’s your skills or technical prowess, you will know it upside down and back to front. It’s likely that your work will be at the core of the business or a key enabler to business success. People will rely heavily on you to apply your expertise effectively and efficiently. Many people who enjoy the experience of deep dives find themselves gainfully employed in this way throughout their careers.

A challenge can be around the traditional progression view of career, and you may not feel that sense of career growth. Some forward-thinking organisations are now finding ways to enable people to develop in these careers (many of them in the tech industry). They’re investing in the depth of skill in their organisation and rewarding growth within roles, rather than asking them to step out of these roles into management or generalist roles. Let’s hope that this type of career path becomes more recognized and rewarded across more industries over the coming years.

Make sure you keep your eyes on the horizon, as being in a specialism or an industry that is changing (and which industries aren’t being disrupted?) can leave you desperately catching up. Imagine being a specialist in a specific programming language. You’ve spent years becoming the best you can be at it, your skills are highly valued, you can take your pick of career opportunities. Then a new language comes along (as they always do) and you were so busy being brilliant at what you do now, you didn’t see it coming and wham, you’re not ready for the future. So, keep an eye out, keep Learning (see chapter 6) and re-specialize yourself before the market forces you to!

6. Active adventure

If you want to mix up what you do, the active adventure may be the right move for you, as you step out of your current role, specialism, or profession. You step in and discover new things, work with different people, in new environments – a fresh challenge. You’ll need to learn new skills, develop your strengths, and be ready to throw yourself in at the deep end. There’ll be a new language to learn (there’s always new lingo and acronyms and shortcuts that leave you wondering if you’ve landed on an alien planet) and a new culture to investigate.

These moves offer you the opportunity to explore how your skills can be expanded and applied in different settings. They often appeal to people who favour trying new things over deep expertise. Some may say they are riskier moves, as you’ll need to push out of your comfort zone. There is also the risk that you could become a Jack/Jackie of all trades, but that’s more about how you sell your expedition to future employers. In many places, breadth and diversity of experience is becoming highly valued.

Structured adventures may come in the form of graduate or management development programmes. Often these happen early on in your career, working through different specialisms, developing a breadth of understanding across a business before finding your niche. They can also be in the form of secondments, cover roles, or fixed term opportunities. At the self-led end, they can step you out of employment into the work of self-employment and/or entrepreneurship. There are almost unlimited opportunities if you’re prepared to pack your rucksack and head out on an adventure – the world really is your oyster.

7. Grounded growth

Contrary to popular belief, having a great career is not all about moving role or organisation with intense frequency. Great careers can still be made from staying rooted in one type of role and/or in one organisation, adding strings to your bow as you grow.

Some people spend their whole careers in grounded growth. Those who value deep relationships that are formed when you stay rooted for a period thrive here. The approach requires commitment to staying up to date, developing skills and expertise – so it’s not a stop and stick. It’s planting yourself and feeding your roots, allowing yourself to expand into the organisational space.

To make this (un)move work well, you’ll need to feel really connected to your role and your organisation. Your value to the business will expand as your institutional understanding increases over time and people will be lost without you (although it’s important to remember that, often, no role is indispensable). There is huge value to having grounded people in organisations and much joy to be had within these roles. You don’t always have to be chasing the next big thing.

COACHING OFFER Making career moves is tough. I’ve done it many (many!) times myself and supported loads of clients through it. If you need to weigh up your options, figure out your next steps or just have someone on your side, book a quick chat with me.

FOLLOW THE JOY

If you’re looking to make any kind of career move, here are some ways to make it happen while making it more likely that you’ll find and maintain the WorkJoy!

Build your career on solid foundations

There are some things that can have a lasting impact whatever shape your career takes:

• Deliver great work in the job you’re currently in
• Do more than the bare minimum
• Display that you can do bigger or different things
• Demonstrate your commitment by doing ‘beyond-the-day-job’ stuff
• Dedicate yourself to your personal development
• Dare to work like you’re already in the job you want

Rest your ladder against the right wall

Consider whether the organisation and boss you’re resting your career on can provide you with the developmental support you need for your next move. This doesn’t mean it’s their responsibility to provide you with everything, as your development is always your personal responsibility. Make sure they can enable you and advocate for your career goals. If they can’t, you may need to consider resting your ladder on a different wall!

Build your pathway

Being able to define what is needed for a career move and then having it provided to you in a nice, neat bundle is likely to be a pipe dream. Going through the challenge of things like lack of clarity and having to make big leaps is just part of the process. Rather than being annoyed that the provision of career development advice, options, or opportunities isn’t offered to you, take that energy, and DIY it. For example:

Whatever you’re lacking, find a way to fill the gap – your future self will be grateful you didn’t wait around for someone to do it for you.

Internal vs external moves

Some internal moves are notoriously challenging to make, so it may feel easier stepping into a different organisation. Internally, people often have set expectations of you. If you started as a junior member of the team and are now a leader, their stories about you may be out of date. Others may still come to you to do the work you did before. This is normal but niggly. In a new workplace, you can start a new story, with fewer preconceptions.

Moving organisations comes with challenges. It can take months or even years to learn a new role. Building a new network takes time. Navigating different processes, policies, systems, and politics as well as a new culture can be as draining as it is exciting. You will need to weigh up what the right decision is and that’s part exploration, part intuition, and part taking a gamble. You will never know for sure, and remember, no career decision is ever final – you can always choose to change it.

Do your due diligence

When another organisation wants you, they will put on a show for you. From the shiny recruitment website showing wonderfully happy, well-rested people, to the interviews and offers of free breakfast and flexible culture. The smoke and mirrors may have you signing on the dotted line before you can say ‘due diligence!’. Don’t be fooled by the flash, look under the hood of the new organisation before you sign on the dotted line!

Titles, levels, and remuneration

If you get hung up on job titles, you forget that the joy is in the doing of the job, not in what it’s called. A title ‘bump’ will make you feel good for a day or (if you’re in a very title-focused organisation) perhaps a week. Getting excited about what you get to do every day because you’re learning, growing, and being increasingly more valued has so much more potential joy to be squeezed out of it. That’s months, if not years, of WorkJoy waiting for you to grab. In a world where more and more job titles sound like they were made up by an alien playing with a thesaurus, getting hung up on what the name is rather than what you do may be a misuse of your energy.

In some organisations things like grades and levels seem like they’re important – a badge of honour. They’re used to define what you do and how you can do it and who you can play with at work. That’s just the way it is. In others, they wouldn’t know what a hierarchy was if it slapped them in the face. It may be very important to other people and not to you. It may be important to you and not others, and it may be important to you and others. Whether it is or isn’t, don’t limit your potential because you don’t get the badge.

Your rank does not define your worth or worthiness. The value of your role in society also doesn’t equate to your salary (if it did, nurses and teachers and sanitation workers would surely be paid the most?). We exist in a capitalist society and the market sets the monetary value for your role. That value will be different in different industries – almost unlimited in some and very defined in others. If you’re waiting for what you offer to be valued more only in terms of rank or remuneration, you’re surely on a path to more gloom. Be the person who acts like a leader and doesn’t need a number, letter, or badge on their shoulder to be brilliant.

Of course, everyone wants more money. It would be wonderful if there were a magic wand to give everyone the pay rises. There are budgets and limitations. Sometimes a career move comes with additional salary or benefits. Sometimes it doesn’t. Sometimes, the best career move you make, the one that sets you up and defines the amazing next steps, the one that brings you regular, consistent joy in your work, is the move where you take a pay cut. One thing to always understand is the market rate for your set of skills, in the industry you work in.

Do the maths

Before you embark on your next career move, make sure the maths adds up in your life. Will the job itself give you the joy you crave in a role – will there be enough of what brings you joy?

REFLECTION QUESTIONS:  Are any additional money, status, or benefits going to be enough to offset the extra hours and responsibilities placed on you? Will the job allow enough space for your balloon of life to invest in other areas?

WORKJOY COMMUNITY STORY: FROM LONG HAUL LADDER TO ACTIVE ADVENTURE

I’d worked in football for almost 15 years when I was informed that my job was going to be made redundant. It was a really intense and stressful time (I was also moving house!) but I was lucky to have a four-month period in which to work things out. I loved my work, but I’d been shoe-horned into management and really disliked it, so I decided not to apply for any of the positions within my organisation. Instead, I wanted to make a change and go after something I wanted to do. The WorkJoy toolkit helped me work out what I was passionate about. I spotted a history of writing throughout my life; never for a sustained period, but I kept coming back to it in various guises. That was it: I wanted a career in writing, but it never dawned on me that I was capable of setting up on my own. I saw other people starting businesses, and I thought, Nope, that’s not me. I thought I was destined to work for other people. But the more I thought about it, the more I realized I had nothing to lose. I had no dependants; it was only me and my cat so I thought, If I don’t do it now, I’m never going to do it. Through WorkJoy, I found the courage to set up on my own. Within a few months I had a writing business and my first two clients, who I still have today (plus, many more of course!).

REFLECTION QUESTIONS:  Which type/s of career moves have you taken so far? What did they give you? What might you be considering for your next move?

NEXT STEPS: MAKING MOVES

Maybe your next move is imminent. Maybe you’re only thinking about making a move. And maybe you’re just thinking about when to start thinking about making a move. It’s all good. It’s all valid. And I’ve got something for everyone.

Follow me on Linkedin for tidbits of interesting worky things.

Dive into the WorkJoy Jam podcast archive for interviews with experts on all aspects of WorkJoy.

Grab my 21-day GloomBusters audio guide ( a five-minute audio pops into your WhatsApp every day for three weeks) and start working your way out of WorkGloom.

Pick a chapter of my book, WorkJoy: a toolkit for a better working life to read each week.  

Book a 1-1 chat with me for an instant hit of strategy, courage or confidence. 

SPREAD THE WORKJOY

We all know people poised on the precipice, perhaps wanting to move but frozen, or knowing where they’d like to go, but scared. Why not send them this article, and check in with them next week?