Stay or Leave Your Job? 5 Books to Help You Decide

Some mornings, the hardest part of going to work isn't getting out of bed.

It's knowing exactly what's waiting for you when you arrive.

The same responsibilities. The same frustrations. Perhaps the same people or problems that have been wearing you down for months.

You've probably imagined handing in your resignation more than once.

But then you remember the bills, the mortgage, your financial commitments and the years you've spent building your career.

And suddenly, leaving doesn't seem quite so simple.

You find yourself asking, Should I quit?

It's an uncomfortable position to be in, especially when you're no longer happy at work but aren't convinced that leaving will make everything better.

The difficulty is that staying and leaving can both feel risky.

Stay, and you might spend another five years feeling frustrated.

Leave, and you could discover that your next job comes with a completely different set of problems.

So how do you decide?

These five books offer different perspectives on career dissatisfaction, difficult decisions and finding a better way forward.

Why Staying Can Feel Wrong — Even When Leaving Feels Risky

After spending years in a profession, your job becomes more than a source of income.

It provides routine, familiarity, professional relationships and often a sense of identity.

You know the systems, understand the expectations and have developed the experience to handle difficult situations.

Walking away from all that can feel intimidating.

But familiarity doesn't necessarily mean satisfaction.

Perhaps the work has become repetitive. Maybe the responsibilities have increased without a corresponding improvement in your working conditions.

Or perhaps you've reached a point where the things you once valued about your career no longer matter as much.

The important question isn't simply whether you're unhappy.

It's understanding why.

And that's where these five books can help.

1. The Good Enough Job — Simone Stolzoff

When Your Job Has Become Too Important

For years, many of us have been encouraged to find work we're passionate about.

We're told to pursue ambitious goals, build successful careers and find fulfilment through professional achievement.

But what happens when work begins consuming the energy you need for everything else?

In The Good Enough Job, Simone Stolzoff questions the expectation that our careers should provide our entire sense of purpose and identity.

The book encourages readers to consider whether a job can be valuable without becoming the centre of their lives.

Perhaps you don't need a more exciting profession.

Perhaps you need reasonable working hours, financial stability and enough energy left to enjoy your relationships, interests and personal life.

That shift in perspective can be particularly useful when you're considering resignation because work has become overwhelming.

Before deciding to leave your career entirely, it may be worth asking whether a healthier relationship with work could make a difference.

Why read it? It helps you reconsider what you actually need from your job and whether professional achievement has become too closely connected to your personal happiness.

2. Quit — Annie Duke

Knowing When Persistence Is No Longer Helping

There's a familiar message attached to success.

Keep going. Don't give up. Push through difficulties.

And sometimes that's exactly the right approach.

But persistence isn't automatically a good decision simply because you've already invested years in something.

Quit: The Power of Knowing When to Walk Away by Annie Duke explores how people make decisions about continuing or stopping.

One particularly relevant issue is our tendency to remain committed because of what we've already invested.

Imagine spending twenty-five years building a career.

You've worked hard, earned promotions and developed valuable expertise.

The thought of leaving can feel like admitting that all those years were wasted.

But your experience doesn't disappear because you decide to do something different.

You still have the skills, knowledge and judgement you've developed.

The real question is whether continuing along the same path makes sense for your future.

Why read it? It offers a thoughtful perspective on when perseverance is worthwhile and when changing direction deserves serious consideration.

3. Designing Your Life — Bill Burnett and Dave Evans

Exploring Alternatives Before Making a Major Decision

Sometimes people remain in unhappy jobs because they can't imagine what they'd do instead.

They know they want something different, but they don't have a clear destination.

And when the alternative is uncertain, staying can feel safer.

Designing Your Life by Bill Burnett and Dave Evans offers a practical approach to exploring different possibilities.

Rather than expecting yourself to discover one perfect career, the authors encourage experimentation and learning through experience.

For example, perhaps you've considered moving into training or mentoring.

You could begin by exploring opportunities within your current workplace or speaking with people who already work in those roles.

Maybe you've thought about changing industries.

You could investigate job requirements, transferable skills and realistic opportunities before making a commitment.

These steps won't guarantee success.

But they can help you make decisions based on information rather than assumptions.

Why read it? It encourages you to explore alternatives before making a potentially expensive or disruptive career change.

4. The Squiggly Career — Helen Tupper and Sarah Ellis

A Better Career Doesn't Always Mean Moving Up

For many people, career success has traditionally meant climbing the ladder.

More responsibility. A higher salary. A better job title.

But what if you no longer want to climb?

Perhaps you've reached a stage where flexibility matters more than promotion.

Maybe you'd prefer less responsibility, more independence or work that leaves you with greater energy for life outside the office.

In The Squiggly Career, Helen Tupper and Sarah Ellis explore a more flexible approach to career development.

Their ideas challenge the assumption that progress must always follow a straight line.

You might move sideways into a role that suits you better.

You could develop a different set of skills, explore another area of your organisation or rethink what professional success means to you.

A career move doesn't have to look impressive to everyone else to be worthwhile for you.

Why read it? It encourages you to think beyond traditional promotions and explore career choices that better reflect your current priorities.

5. I Can't Do This Job for Another 20 Years — Julian Merren

Finding Out What Needs to Change Before You Leave

Sometimes the thought of resigning isn't about wanting an entirely new career.

It's about no longer wanting the working life you currently have.

Perhaps you're exhausted by the hours, frustrated with management or tired of responsibilities that no longer interest you.

But after spending decades building your career, walking away isn't necessarily straightforward.

I Can't Do This Job for Another 20 Years by Julian Merren explores this situation from the perspective of experienced workers who want change without unnecessarily starting over.

The book encourages readers to identify what's actually making them unhappy before deciding how much needs to change.

Perhaps another employer would provide a better working environment.

Maybe a different role could allow you to use your experience without the same pressures.

Or perhaps a gradual transition towards another career would be more practical than resigning immediately.

The book also includes exercises and a 30-day challenge designed to help readers examine their circumstances and explore manageable next steps.

Why read it? It offers a realistic approach to improving your working life while considering your experience, financial responsibilities and future options.

If you're wondering what the next stage of your career could look like, you can explore I Can't Do This Job for Another 20 Years by Julian Merren.

Three Signs You May Need a Change — But Not Necessarily a New Career

Before deciding to resign, it's worth looking for patterns in your dissatisfaction.

1. You Still Enjoy the Work, but Not the Environment

Perhaps you find your profession interesting but struggle with poor management, difficult colleagues or unrealistic expectations.

A change of employer or team may address some of those problems without requiring a completely new career.

2. Your Responsibilities No Longer Suit Your Life

You might have enjoyed managing people or working long hours earlier in your career.

But your priorities may have changed.

A different role, more flexible schedule or reduced responsibilities could be worth investigating.

3. You Want Something Different but Haven't Explored Your Options

Sometimes the desire to leave is genuine, but the next step remains unclear.

Before making a permanent decision, investigate related roles, speak with people in other industries and consider which of your skills could transfer elsewhere.

The aim isn't to delay change indefinitely.

It's to understand what you're moving towards.

A Better Question to Ask Yourself

When you're unhappy at work, it's easy to focus entirely on whether you should resign.

But perhaps a more useful question is:

What would need to change for my working life to feel better?

That question creates more possibilities.

Maybe the answer is a different employer.

Perhaps it's fewer hours, a new role or greater independence.

Or perhaps you've genuinely reached the end of your current career path and need to begin planning something new.

If you keep returning to the question Should I quit?, try writing down three things:

What you're unhappy about in your current job.
What you'd like your working life to look like instead.
One realistic step you could take towards that change.

You may discover that the solution is closer than you expected.

Or you may realise that leaving really is the right decision.

Either way, you'll have a clearer understanding of why.

Final Thoughts: Your Next Step Doesn't Have to Be Dramatic

Feeling unhappy at work doesn't mean you've failed.

And choosing to explore other opportunities doesn't mean the years you've invested in your career were wasted.

Sometimes people outgrow their roles.

Sometimes working environments change.

And sometimes our priorities simply become different as we get older.

The important thing is to make a decision that reflects your current circumstances rather than remaining stuck because of fear or resigning purely out of frustration.