Ep. 384 Career Options After Corporate: The Full Menu of Alternatives

Why the stay-or-go binary keeps you stuck

Most people frame career decisions as binary. You’re employed or self-employed. It’s safe or it’s risky. You’re in or you’re out. But that framing is what keeps people stuck – because they stay in something that isn’t working, because the only alternative they can see feels too big a leap. Or they leap, and then create the same problems in a different container.

My first book, Leaving the Corporate 9 to 5, mapped five different paths – changing sector, going freelance, starting your own business, having a portfolio career, and taking a leap of faith when you’re not quite sure what you want yet.

Today I’m going to walk through an even more nuanced and complete menu, with some honest trade-offs for each. Because everything has an advantage and a disadvantage. The question is always: what kind of business or career are you building for you and your life?

One big distinction I’ve experienced: a lot of business advice is aimed at people building a company as a product to sell one day. For most of my clients – and for me – the business is a container for your best work and your actual life. You’re the expert, you want to do fulfilling work, you’re not building something anonymous to exit from. That question alone can help you know which options are going to be relevant.

Variations on employment – the options most people overlook

Let’s start with variations on employment – the options most people overlook before even going independent. You can move from high-pressure corporate into social enterprise, B Corp, public sector, or academia, using the same transferable skills in a completely different culture and values fit. This is often underestimated as a genuine alternative. You don’t have to throw it all in. You can change the container. Especially if you have a pull towards a particular sector.

There’s also moving to part-time or compressed weeks. The four-day week, a nine-day fortnight, job-sharing at senior levels – you’re still employed, but you have structural flexibility built in. The hashtag #parttimeworks on LinkedIn is a great community if you’re exploring this. And remote-first or async-heavy roles can give you de facto autonomy without changing your employment status at all.

Then there’s intrapreneurship – carving out a semi-autonomous unit or new product inside a large organisation. Some big FMCG companies have created internal incubators for startup-style ventures. If you can work on one of those within a larger framework, you get the entrepreneurial challenge with a corporate safety net. It’s an underused option for people who want to build but aren’t quite ready to be fully on their own.

These options obviously depend on the organisation being willing – and many aren’t – but they’re worth exploring before assuming the only exit is the full binary leap.

Freelance, independent expert, and fractional – what’s the difference?

Now, most of us sit somewhere on the independent expert spectrum. And there’s far more nuance here than people tend to realise. Classic freelancing means selling time and deliverables on short contracts, often embedded in client teams, on a day rate or project basis. The danger is it can drift towards being an employee without the benefits. You’re busy, but you’re still beholden to clients, there’s often a cap on what you charge, and you’re not necessarily building anything that compounds.

There are brilliant freelancers doing brilliant work – it’s absolutely still an option. But independent expert, as I’d describe it, means narrower positioning and higher leverage. You have your own IP, frameworks, group programmes, facilitation, speaking, advisory work. More control over your calendar and your model.

Fractional is something else again – being a fractional CFO, CMO, or COO, sitting inside a leadership team one, two, or three days a week across several clients, with clear accountability for particular outcomes. The company gets senior expertise without a full-time salary. You get stability and end-to-end involvement without being fully employed. Demand for fractional executives grew 46% year on year in 2024, and it’s only growing as scale-ups realise what they can access.

The key distinction: freelancing is traditionally time for money. Independent expert is expertise and IP for money. Fractional is leadership accountability in slices of time. They’re genuinely different models, with different ceilings on earnings, different lifestyles, and different sustainability profiles.

Portfolio and hybrid careers

Portfolio and hybrid careers are probably where more people land than realise it. Several job titles at once – mixing employment, freelance, a side business, or other income streams simultaneously. In practice, it might look like a part-time functional role plus consulting, or teaching alongside client work, or speaking and advisory work plus a programme. The seasons of life matter here too – a school-hours portfolio looks different from a big-push portfolio when family load is lighter, or a sabbatical portfolio when you need to recover and recalibrate.

The freedom is real, but so is the complexity. It doesn’t run itself. And if you’re running B2B and B2C simultaneously, you can end up with two different targets, two different messages, and effectively two businesses on top of each other. The key is a coherent umbrella message that makes it all work together, rather than doubling your workload.

Startup paths – what actually suits most people

On the startup side, there’s an important distinction that often gets conflated. A VC-backed startup is hyper-growth, exit-focused, board oversight, aggressive targets – you trade equity and control for capital. Most of my audience, if I’m honest, probably doesn’t want that. But it’s worth naming so you can consciously rule it out. A lot of entrepreneurship advice is aimed directly at that model.

Angel investor-funded is slightly different – smaller cheques, more flexibility, less pressure around control. Bootstrap means you fund through savings and revenue, keep the control, optimise for profit and values, and scale more slowly. The personal financial risk is higher, but you have genuine autonomy.

And then there’s the solopreneur or micro-firm model – bootstrapped but not a startup. Expertise-led, built around a life and not an exit. Success metrics become income per hour, depth of work, autonomy – not headcount or valuation. Most of us are building this, often without having a clear name for it.

Less obvious options worth knowing about

Then there are less obvious options worth knowing about. A deliberate sabbatical isn’t an undefined void – it’s a structured experiment. Take six months to test three career hypotheses, shadow someone, do short stints, take a course. It’s underused and under-respected as a path, but it’s a smart way to test whether you actually want to go out on your own before you burn bridges. I’ve spoken to people for my book and podcast who tried this, found it didn’t work for them, realised they missed the team and the safety of a corporate umbrella – and they learned that without too much risk.

Returnships – structured re-entry programmes for people who’ve taken a break – are more available now, particularly in finance, tech, and professional services. Co-founding with a complementary partner, whether that’s expert and operator or strategist and techie, is somewhere between solo and startup. It works really well when skills and values genuinely complement each other. I’ve also seen it go sour many times, so it needs real care and honesty going in.

And there are productised, asset-based paths – books, courses, templates, tools – that try to decouple earning from hours. These can supplement any of the above models. They’re not quite the passive income dream some people sell, but done well, they’re a meaningful part of a sustainable portfolio.

How to decide which model is right for you

If you’re deciding which of these feels right, a few questions help. Do you want investors in your calendar – if not, rule out the VC and angel paths. Do you enjoy managing people, or do you want to stay close to the work yourself? Do you need income stability immediately, or do you have runway to build? What does your life actually look like right now – kids, health, location, energy? And are you building something to sell one day, or building a container for your work and your life? That last question is probably the most clarifying of all.

As for my own path – I left corporate in 2013 and landed in digital marketing consulting, which was something between contracting and consulting, essentially coming in almost like a temporary employee without the benefits. Then I discovered coaching and went through what I call my hippie phase, leaning into flexibility and passion without earning much. A few years later I restructured around my partner’s hours, took the financial side more seriously, and then came children, COVID, moving to the sea, and the model has shifted with each season.

It’s not a linear leap. These were models and nuances I wasn’t even aware existed when I first left. They’ve been a series of choices in response to what life demanded. You don’t have to know the whole path. You have to know the next right move, given who you are and what your life looks like right now.

If you’re already out of corporate and building something of your own, the free Solopreneur Diagnostic shows you in five minutes where your business model is strong and where it’s quietly holding you back.

And if you want to work through these questions alongside a small group of established independents, Off Script is the community built for exactly that.

If you’re still mapping your options and want to hear fifty real stories of people who’ve made the transition across all these different paths, Leaving the Corporate 9 to 5 is the place to start.