How to Change Careers When You Can’t Afford to Quit

We all crave a fulfilling life. Having a well-fitting career, where we get to be our most authentic selves, is a huge part of it. And there are people who seem to have found theirs. The stories of how they got there are all the more inspiring.

There’s something unique about them too. When I look more closely at these stories, almost all of them seem to revolve around a very similar sequence of events.

First, they come to realise how ill-suited their current job is to them: no passion for it, difficult coworkers, low pay, demanding bosses, you name it.

So, they quit.

They take some time for themselves—a year, maybe a couple of years—to travel, pursue their hobbies, or just wander around until their minds get clearer. By the end of this phase, they have a fairly good idea what they want to do in life, and it’s actually within their reach. It just had been lost to the messiness of everyday life.

From that point on, they set out to rebuild their careers around it. And they do it passionately. Eventually, they build the career they wanted and move forward with a greater sense of fulfilment.

For anyone who’s at the beginning of this journey, these stories are incredible morale boosters. But when I hear a story like this, there’s this one step where I turn into that Leonardo DiCaprio meme.

It’s the step where they take that long break. I can see how valuable, and necessary, this break could be. In fact, it could be one of the most important phases in the whole transition.

But not everybody can afford to take a break like that, even when they really need to. What if our financial situation does not warrant a break like this? Or what if our family depends on our income? Circumstances like these could hold us back from taking such a significant step in an otherwise life-changing journey.

Figuring out what we want to do in life is hard enough. Figuring out how to realistically move towards doing it can be even harder. And yet, I don’t think this part gets enough attention in these success stories.

So, in this post, I want to look more closely at how to change careers without quitting your job, starting with the resources you already have.

Focus on what you have, not what you don’t have

In a situation where we have to find a way forward with limited resources, it’s quite natural to fixate on what we don’t have. Scarcity is a real constraint, yes, but getting hung up on it doesn’t help solve the problem at hand.

Competitive advantage is a real thing. There’s no denying that. Some people have more money, time, or support behind them. But what truly matters is how we respond to this reality and find a way forward anyways.

But how to do that?

By being strategic.

When our resources are limited, we can’t afford to wing it. We might not have the time to just wander around.¹

We need a proper plan. And we need a positive mindset, though that doesn’t mean pretending our limitations don’t exist. Then we can work out how to use those resources to build a feasible path forward.

The questions to ask ourselves are:

• Do I really have to quit what I’m doing now to start building the foundation for the career I want?
• If I do need to leave my job, do I have enough money to support myself while I work towards earning enough from the new direction?
• Do I have other resources or support available?
• Even if the finances are covered, will I have enough mental and physical energy to sustain this process?
• Who or what would I be putting at risk if the attempt doesn’t work out?

Alongside our willingness and ability to take risks, the answers to these questions help us make a more calculated decision about how to move forward.

Find your true leverage

But planning around our resources only takes us so far if we haven’t figured out where our strengths give us an advantage. We have to be useful.

A question to ask ourselves is: does what I’m passionate about help other people in some way?

It’s not just the skills you have that matter; it’s how those skills help someone else. This is one of the fundamental first steps towards building a satisfying career: finding where something we do well creates value for other people.

But it can be extremely hard to figure this out by thinking alone. It needs some doing. A useful next step, then, is to gather evidence beyond what we’re just passionate about.

Here are some questions to ask to find this out:

• Who comes to us for help? These people could become our audience, our customers, or the group we serve.
• Where do we repeatedly produce useful results?
• What kinds of things do we improve at quickly (ideally, more quickly than others)?
• What qualities do people notice about us that we don’t even see ourselves?
• Where does our effort create real value for other people?

Through this process, we begin to recognise that our self-image alone isn’t our most valuable career asset. The true leverage comes from how effectively we use our strengths to help other people, ideally through the work we enjoy doing.

Finding that overlap is a huge milestone. It gives us a strong foundation to build a dream career, and it also opens up more options as our skills and experience grow.

For example, imagine a biology teacher who loves drawing and wants to make a career of it. They could spend a year of savings creating amazing wildlife illustrations, only to discover that very few people are really interested in them. True, the work is great, and people will appreciate the artistry. But if they’re not buying, eventually all that hard work will slow down to a halt. It will not sustain itself.

But let’s say this teacher tested their idea with a real audience. For example, their students might constantly ask for copies of the diagrams they draw to explain scientific phenomena. Perhaps the ones already available are painful to look at. They’re too “sciency”.

But the ones this teacher makes are approachable.

So they keep making them for their students. In time, teachers across the school start asking for them too. Word of mouth does its job. If they keep at it, share their work on social media, and find people willing to pay for it, this could grow into a viable business.

Their interest did not change even a bit; only where they directed it did. Now, it’s directed at a “real” audience.

That’s leverage.

Test the waters before jumping in

There’s another lesson that comes out of this story: they didn’t even have to leave their job to get started.

It’s tempting—and liberating—to just quit your job and go all in on a new venture. It sounds exciting. But, as we’ve seen, it isn’t always a realistic path to take. And it’s not even necessary to begin.

A real example that always comes to mind is Lawrence Yeo, the writer and illustrator behind More To That. Lawrence worked in finance. But he also liked illustrating his ideas and writing about them. So he started a blog and began writing while still working his day job.

He describes his employer as a “patron” of his art, funding his creative work. He later left his job to spend six months with family in Korea, living on savings while his blog was still developing into a business.

As he explained in an interview with Kit:

I always knew that the money I was making there would afford me the freedom and attention to do what I wanna do creatively.

The next question that comes to mind is: how much time could we realistically give it? Let’s do some maths to find out.

A week has 168 hours. For context, U.S. workers who usually worked full time and were at work averaged 41.9 working hours a week in 2025.

Rounding that up to a 42-hour working week and allocating eight hours of sleep each night leaves 70 hours. Here are two hypothetical schedules someone could use to work towards their dream career, initially as a side project:

These schedules might not be possible for everyone. Commuting, caregiving, and other responsibilities all have to fit into the remaining time. But even 10 hours a week—if you can keep at it consistently—could be enough to get the ball rolling.

Conclusion: choices, choices, choices

This entire article has been focused on working towards one goal: freedom. A career you love will help you build it. It may also give us more time—and, most importantly, the energy to spend that time well—with our loved ones.

True, you might be working harder on a new venture than you would in a typical nine-to-five job. But it’ll sure not feel like “work” at all.

That’s freedom.

But freedom is often hard-earned. But the good news is, no matter how scarce your resources are, if you allocate them well enough, you will eventually be able to build it.

The more carefully we make our choices, the better our chances of eventually dropping the “dream” from our dream career.

1. Although that could have been lovely! ↩︎