How to Break Free from the Perfect on Paper Job and Find Fulfilling Work

Do you have a perfect on paper job? It’s prestigious, you’re highly paid, you’re doing well and climbing the corporate ladder, your bosses love you. Yet… something is missing? Have you achieved society’s definition of success yet feel hollow and empty inside? You want work that’s more fulfilling but not sure what that looks like or how to get there? In this article, I’ll be sharing how to move away from jobs that may look great on the outside but feel unfulfilling, and share some strategies to help you find more satisfaction in your career.

Understanding the Perfect on Paper Job Trap

It’s easy to get drawn into the allure of a job that promises financial rewards, status, and security and end up people pleasing your way into a perfect on paper job. These positions often come with external recognition that can boost your self-esteem, at least temporarily. However, many professionals in such roles realise that their work doesn't align with their personal values or passions. Despite the outward success, they may feel disconnected, unmotivated, and, over time, trapped by their golden handcuffs. This is why finding strategies for improving job satisfaction becomes increasingly important for personal well-being.

Why Prestige and High Pay Often Do Not Bring Satisfaction

While prestigious jobs may seem appealing at first, they often fail to provide lasting happiness for many professionals.

  • Initial satisfaction vs. long-term happiness

While high salaries and impressive titles can bring short-term gratification, they rarely sustain long-term fulfilment. Over time, professionals may find themselves questioning their true sense of purpose at work.

  • High pressure with little personal growth

These roles often come with demanding hours and immense pressure, leaving little room for personal growth. As a result, many individuals feel stuck despite outward success.

  • Frustration from lack of meaning

External success and building a career that only looks good on paper doesn't always align with internal satisfaction, leading to feelings of frustration. Many professionals start searching for roles that resonate more with their values and passions.

Common Signs You Are Stuck in an Unfulfilling Career

1. Constantly feeling anxious, burnt out and have no energy for anything outside of work

Feeling drained at the end of the workday or dreading going to work each morning are strong signs of an unfulfilling career.

2. Lack of interest and accomplishment

If you find yourself losing interest in your job and no longer feel a sense of achievement, it’s a clear indicator that your career might not be fulfilling. These feelings can sometimes lead to physical symptoms such as stress or even burnout.

3. Underutilised skills and passions

When your work no longer aligns with your passions or utilises your skills, you may feel disconnected. This can contribute to ongoing dissatisfaction and a desire for more meaningful engagement.

2. You don’t see yourself becoming your boss

If you don’t see a long term career path for yourself here that’s usually a telling sign that this might not be the place for you.

3. Lack of career upside
If there’s no growth for you from both a learning and earning perspective, why are you still here?  

Acknowledging these signs is the first step in exploring strategies for improving job satisfaction and considering a more fulfilling career path.

Steps to Identify What Truly Fulfils You

Breaking free from an unfulfilling career begins with understanding what you truly want from your work. It requires self-reflection and a willingness to explore new possibilities that better align with your values and passions. While it may seem daunting, knowing how to find fulfilling work that makes you feel truly engaged is essential for long-term job satisfaction.

Reflecting on Your Values, Purpose, Passions and Strengths

1. Take time to think about your core values and what drives you. 

At this stage of your career, what are you optimising your career for? Is it money? Learning? Purpose? Making a difference? Power? Prestige? Once you’ve identified 4-5 core values, prioritise them and figure out what you’re willing to give and take. 

2. Define your North Star
What are some causes or missions you feel strongly about? What were some personal struggles you’ve experienced that you’d love to help others with? 

3. Identify your passions
Don’t know what you’re interested in? Here are a few questions you can ask yourself. What activities make you feel energised and purposeful? What were some things you’ve always loved as a kid? Still stuck? Leverage social media’s algorithm - what type of content is Youtube, TikTok, Instagram pushing you? 

4. Consider your strengths
What do you do well, and what skills come naturally to you? Don’t know what you’re good at? Take a look at your performance reviews and ask people around you to tell you what they think you’re good at! 

You can begin to pinpoint career paths that are not just about external success, but about aligning your work with what brings you joy and satisfaction by understanding these aspects. This is a key component of how to find fulfilling work.

Exploring Career Options That Align With Your Goals

Once you've identified your core values, purpose, interests and strengths, it's time to explore career paths that match them.

  • Research and professional networking

Start by researching new industries or connecting with professionals in fields that interest you. The best way to understand the role is to talk to people who do the job day in and day out. This is also a great way for you to successfully pivot into a new industry.

  • Test drive different career paths before you commit

Take your career out for a test drive to see if this really is the right career path for you. And if it is now you have a portfolio to showcase to future employers that you do have what it takes to do the job!

How to Overcome Fear and Take Action

One of the biggest barriers to pursuing more fulfilling work is the fear of the unknown. Whether it's fear of financial instability, societal expectations, or the risk of failure, these concerns often prevent individuals from taking the necessary steps towards change. Understanding and overcoming these fears is essential to making progress and discovering how to find fulfilling work.

Addressing Common Fears Like Financial Instability and Societal Judgement

Fears surrounding financial instability and societal judgement are common obstacles when considering a career change.

1. Managing financial instability

Create a financial safety net or transition gradually into a new role to alleviate financial concerns. This allows for a smoother shift without the immediate pressure of financial loss.

2. Handling societal judgement

Concerns about how others view your career change can be overwhelming, particularly if the move is unconventional. Remember that personal fulfilment is far more important than meeting societal expectations.

3. Long-term benefits

Career changes, though challenging, often lead to greater satisfaction. This is why strategies for improving job satisfaction are essential during this transition.

Building Confidence Through Small Changes

Building confidence doesn’t require drastic, immediate action. Instead, start with small adjustments that better align your current role or personal life with your core values.

  • Small steps towards alignment

You can begin by taking on new projects that genuinely excite you or building a side hustle related to your passions. Maybe it’s helping to consult for a startup pro bono, or starting a business selling a product you’re interested in. Or perhaps starting a podcast deep diving into a topic you’ve always been passionate about. The key is to take action - no matter how small and even if it doesn’t make money at the beginning. 

  • Gradual confidence building

These incremental steps help you gain confidence, making the idea of a larger career change feel less overwhelming and help you build up a portfolio of work to show you have the relevant experience to successfully pivot. As you build momentum through smaller changes, the larger leap towards a fulfilling career becomes more achievable.

  • Long-term transition

Over time, these gradual adjustments can ease your transition into a role that aligns with your personal goals and passions. This method embodies the core principles of understanding how to find fulfilling work while reducing the fear of immediate, sweeping changes.

Take the First Step Toward a Fulfilling Career

For more personalised guidance on how to execute and build a fulfilling career? Sign up for a free discovery call and join hundreds of high achievers from Google, McKinsey, Goldman Sachs, and more who have worked with me and my team of career coaches. We’d love to help you build a “perfect for you” career. 

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Identifying Your Life’s Calling: A Guide for High Achievers Unhappy with Their Perfect on Paper Job