I watched a man say his dream out loud and apologise for it in the same breath.

The question was: “If you had a shot of courage, what career would you choose?” He thought carefully, then said: “I’d work on my app.”

It was an idea he’d been carrying for years, but he quickly shut it down. “But I haven’t started on it because I feel stuck in my current job. Trapped by the salary.”

His fear of public speaking was loud, but the shame of being trapped by a pay check was louder.

It was heartbreaking and familiar.

The elephant in the room

Finances are the number one concern when it comes to making a career change or starting a business. Understandably so, when the job market is brutal. Mass layoffs, shrinking industries, and precarious contracts are leaving people clinging to their jobs for dear life. Even those in “safe” corporate roles can feel the ground shifting beneath them.

As Rosie Spinks reflects in her piece, Everyone I know is worried about work, there’s a widening gap between the work people expected and the work they’re actually living. Jobs and companies that were meant to provide both meaning and security haven’t held up their end of the bargain…

What Do We Do Now That We're Here? Everyone I know is worried about work Almost everyone I

…Or perhaps we were naïve to think they ever could.

This disconnect isn’t limited to freelancers or creatives. It’s everywhere.

We put all our stock in the idea that specializing in one field, industry, or competency — one that almost always occurs within the confines of a screen — in exchange for a steadily-increasing paycheck was the smart move to make. We accepted that we better get really, really good at it if we wanted to command the kinds of salaries that keep us afloat in this system, so we worked until the point of burnout to deliver to companies we thought would love us back. Or at the very least, not fire us the very moment there was a marginally cheaper way of doing things.

And so, people find themselves in a bind.

It isn’t only about the money. It’s about the status a job carries, the identity it gives you, and the sense of belonging to a certain peer group. It’s about retirement contributions, health insurance, school fees and the mortgage. These aren’t trivial concerns. They’re the scaffolding of modern life.

The problem is, many people assume the choice is binary: cling to their career (and all the security it provides) or start over from scratch. This kind of black-and-white thinking is exactly what keeps them stuck.

A true shot of courage is often found in the grey: in the experiments, the gradual shifts and the creative solutions that allow you to move forward without losing everything you’ve built.

There are practical ways to support yourself as you transition into meaningful work. It takes planning and a clear-eyed view of the risks you’re willing to tolerate. And of course, everyone’s circumstances will be different.

Here are some of the most common strategies people use to fund a career change—without blowing up their lives. My hope is that this cracks open a sliver of possibility for you.

Stay put, build on the side

One of the safest ways to begin is to keep your full-time job while experimenting with something new on the side. It’s the old adage: use your 9-5 to fund your 5-9.

This path isn’t without challenges. It often means giving up evenings or weekends, and sacrificing free time. In return, you give yourself the chance to learn, make new connections, build confidence and even start earning, without letting go of the security of your salary.

In his essay, The Death of the Corporate Job, Alex McCann argues that traditional jobs are no longer forever homes. Instead, they’ve become funding mechanisms—a way for people to maintain a corporate persona while quietly building their escape route.

They're using the corporate infrastructure—the steady salary, the laptop, the stability—as a platform for building something real. The corporate role hasn't died; it's become a funding mechanism for actual work.

Still Wandering The death of the corporate job. Last week, I had coffee with someone who w

I’ve seen this play out in clients and friends of mine who’ve kept one foot in the corporate world while carving out space to build their own thing. It’s not about splitting your energy forever; it’s about creating a bridge until your new path can stand on its own.

And yet, I personally found this strategy difficult. I tried to treat my job as “just a job,” but it’s not in me to coast. My free time has always been sacred. By the end of the workday, I needed space to decompress. Staring at a computer for 12+ hours didn’t energise me and switching gears into my own project after work wasn’t sustainable.

So while this is the safest route, and perhaps the most ideal on paper, it doesn’t work for everyone.

Re-negotiate your hours

A second, often overlooked option, is to re-negotiate your hours. Most people assume their employer would never agree to fewer days or flexible hours, so they don’t even ask. But in reality, this strategy is often more accessible than it seems.

Reducing your hours, even by a single day a week, can free up headspace and energy for exploration, networking, or building your business, while still keeping income flowing. Some choose to go part-time. Others compress their hours, working four longer days instead of five.

One of my clients was a global brand director at a multinational company. Her role was demanding: back-to-back meetings, no time to think and by the end of the day, she was depleted. Outside of work, she was training as a coach and longed to give more time to it. But her reality was complicated: bills to pay, little savings and even a company-provided car. Walking away from her salary would have been reckless.

Together, we explored her options: moving to another department, becoming an independent consultant, finding a new job, or reducing her hours.

Her top choice was a four-day week. The idea of asking filled her with anxiety. She caught herself thinking: “I don’t want to know, in case it’s a no.” We prepared by clarifying her boss’s likely concerns, identifying compromises, and building the courage to have the conversation.

In the end, her boss said yes without hesitation, and that one shot of courage gave her the breathing room she needed to build her coaching practice, while still holding onto stability.

The lesson? The fear of asking is often bigger than the reality.

Save for a rainy day

This isn’t just a strategy for career change. It’s basic financial hygiene.

Without savings, every setback feels like a crisis. With a buffer, you can approach the transition with calm and focus instead of panic.

If you’re serious about a career change, give yourself a buffer that’s bigger than you think you’ll need. Especially if you’re building a business, it will take time before income is consistent. The runway you create can be the difference between giving up too early and seeing your new path through.

Small, creative income streams can help you top up savings too: renting out a spare room, selling unused items, or freelancing. They may not replace your salary overnight, but together they add days, weeks or maybe even months to your runway.

Streamline

As our salaries increase, so too does our spending. It’s almost automatic: the nicer apartment, the gym membership we rarely use, the extra streaming subscriptions, the daily coffees, the expensive holidays to recover from the stress of the job.

Some of this spending is intentional, but sometimes, it’s a coping mechanism for a reality we don’t love. When the workweek feels draining, we justify the €25 lunches, the €300 outfits for a job we secretly hate, or the wine that takes the edge off.

The problem is, these habits quietly raise the bar on the lifestyle we feel we “need” to maintain. Which makes stepping away from a steady salary feel impossible.

Streamlining is about breaking that cycle. Go through your outgoings with a fine-tooth comb and ask: Do I really need this, or am I spending to soothe myself?

By lowering your baseline expenses, you create freedom. Every euro not spent on coping can be redirected into savings that support your transition. The sooner you do it, the less dependent you become on keeping a salary that no longer serves you.

Downsize

If trimming small luxuries isn’t enough, bigger shifts may be necessary. Housing is often the biggest lever: moving to a more affordable home, taking in a flatmate, or even going home for a while.

Most of us accumulate more than we actually need. I’ve downsized multiple times. I left a relationship and moved back in with my parents. Later, I sold most of what I owned to move overseas. In Lisbon, I sold everything again when I decided to take a year-long sabbatical. Downsizing wasn’t deprivation. It was an investment in buying myself time and space.

Every time I let go, I felt closer to the life I wanted.

Re-engineer

Sometimes the money is already there, you just need to restructure it. Refinancing a mortgage, transferring high-interest debt to a 0% card, or renegotiating big bills can free up cash. That extra breathing room can fund classes, childcare, or tide you over during a slower income period.

I’ve seen friends make bold moves by unlocking assets, such as selling a shared apartment with an ex, which gave them the peace of mind to start fresh.

Not everyone will have the same financial flexibility. If you’re living paycheck to paycheck, the road is harder. But even then, resourcefulness can create a buffer, whether through salary negotiations, side income, or restructuring expenses.

Career change is not easy, but saving, streamlining, downsizing, and re-engineering your finances are all levers you can pull. Together, they buy you the most precious resource of all: time.

Ask for support

For many, the idea of asking for help feels uncomfortable. We don’t want to be a burden, or admit we can’t do it all on our own. But no one makes a big transition without support. Sometimes the most overlooked resource in a career change isn’t money. It’s people.

Support can take many forms:

Financial

Changing the breadwinner dynamics, reaching out to family or arranging temporary living situations. Even short-term help can create enough breathing room to make choices from a place of calm rather than desperation.

As with most things in career change, starting small helps. For example, if your partner is open to it, you might experiment with living on one salary for a set period of time. That way, when the time comes to step into something new, it doesn’t feel so drastic.

Practical

Support doesn’t always involve money, but it can be a game-changer. It’s about redesigning how you live and with whom. Examples include:

• Childcare swaps with friends

• Batch-cooking circles to free up time and energy

• Sharing a car, splitting groceries, or rotating school pick-ups

Though not directly related to career change, I love the idea of mommunes: shared living arrangements where single mothers (or mothers who crave more community) live together under one roof. They pool resources, share childcare, and offer one another the emotional scaffolding often missing in isolated, nuclear-family living.

While not for everyone, mommunes show what becomes possible when people decide they don’t have to “go it alone.” These models aren’t just cost-saving, they’re life-giving. They create space for single mothers to pursue study, work, or entrepreneurial projects they might otherwise have shelved.

Emotional

When you’re in the middle of a career change, you’ll inevitably hit moments of doubt:

What if I fail?
What if this was a terrible idea?
Maybe I should just go back to what I know.

Those are the moments when who you have in your corner matters most. You need people who remind you of your vision when you lose sight of it. People who cheer for you on the hard days and celebrate the tiny wins.

Surround yourself with expanders: people who’ve successfully made bold changes themselves. Their stories make your own feel possible and you can borrow courage from their path until you find your own footing.

Be discerning about who you share your goals with. Not everyone will understand why you’re stepping off the beaten path, and some will project their own fears onto you. Find the people who pull you up, not the ones who quietly tug you down.

Even the best financial plan can crumble under the weight of self-doubt. That’s why people in transition often seek out niche communities and group coaching to feel less alone, and to keep going when things get hard.

Institutional

Depending on where you live, government benefits, retraining grants, or business incubator programmes can all act as a temporary bridge.

Some organisations go further: On Purpose runs year-long associate programs in purpose-driven companies, providing training, coaching and a modest salary. ivee helps women return to work after a career break, with flexible roles, upskilling and community support. These kind of programs give you community and a softer landing as you transition.

Proof that you don’t always have to bootstrap your way through change completely on your own.

Build bridges, don’t burn boats

The truth is, there isn’t a single best way to fund a career change. The most resilient path usually combines several of these strategies.

What matters is that you don’t leave your job as an emotional reaction. As one person I interviewed wisely put it:

“Don’t leave your job. It’s tempting, but it’s also destabilising. Career change isn’t an easy threshold to cross. You want to be sober when you make that decision. Make sure it’s coming from the right place. A clean place.”

Of course, sometimes staying isn’t possible. I know that feeling too. There was a point when I couldn’t force myself to stay any longer. I needed space and time away to figure out what I wanted.

I was fortunate: I asked for support from family when I moved back home. I downsized my life. I took a four-day-a-week job, then I freelanced for a few years. I had enough savings to carry me for years. Piece by piece, I stitched together different strategies. And almost by accident, I ended up with what I now call a portfolio career.

Why portfolio careers matter

The new model of security is about diversification. Instead of putting all your security into one employer, one paycheck, one identity, a portfolio career blends multiple streams of income. It creates resilience. If one piece falls away, you still have others.

Think of a portfolio career as having one foot in what you already know, and one foot in the future you want to create. It’s the bridge that offers the stability of a regular salary while you experiment, learn and take measured risks.

In practice, it might look like:

• Consulting two days a week in your old field while you develop your coaching practice

• Taking a fractional role with a startup while you work on your book

• Freelancing with former employers while building a new skill set

But here’s the catch: a portfolio career relies on people knowing who you are and what you offer. Opportunities don’t appear out of thin air, they come through reputation, relationships, and visibility.

That’s why your personal brand matters: the act of being recognisable for your ideas, skills and perspective. Visibility isn’t vanity. It’s leverage. It’s what allows opportunities, collaborations, and clients to find you. A personal brand is your body of work (essays, talks, projects, collaborations) that signal: this is what I do, this is what I stand for and this is the value I create.

My hope here is simply to open the door: to show you that something more fulfilling is available beyond the confines of a full-time 9–5 job.

When you step into this liminal space between employment and entrepreneurship, you begin picking up invaluable skills that no one can take away from you: how to create an offer, how to market yourself, how to sell, how to communicate.

I can’t tell you how many times I’ve met professionals who’ve held director or VP-level roles and, when they finally decide to start their own business, realise they have no idea where to begin. Even seasoned marketing executives often stumble when it comes to marketing themselves.

That’s the hidden gift of a portfolio career: it teaches you how to stand on your own two feet, develop skills that travel with you, and build a body of work that belongs to you, not to an employer.

Maybe this is what a true shot of courage looks like. Not blowing up your life overnight, but daring to take one step into the grey space, where security and possibility can coexist. You can value financial security and still take bold steps.

Portfolio careers may be the answer to the transition problem. For many of us, this is the grey space we’ve been looking for. Not clinging to the old model, not leaping recklessly into the unknown, but building a career that’s flexible and truly our own.

About Work Worth Doing

Work Worth Doing is a space for people who’ve outgrown a professional career they’ve spent years building, and aren’t sure about what comes next. You’ll find essays on identity, purpose and finding fulfilment outside of work too.

I work 1:1 with people transitioning from a professional career into meaningful work. To learn more about how coaching can support you, book a consultation or learn more below.