Changing Jobs Over 40? Do This First.

A Pattern of Professional Frustration

In my two decades as a corporate lawyer, I experienced a pattern that many successful professionals might find familiar: despite achieving my career goals by my early 40s, each job change felt like a case of “different place, same frustrations.” This pattern finally led me to a profound realization about career transitions that I now share with the executives and business owners I coach.

The Current State of Workplace Engagement

Recent data from Gallup reveals that U.S. employee engagement dropped to 31% in 2024, with over half of workers actively seeking new opportunities. The reasons cited are familiar: inadequate raises, limited advancement opportunities, increased office presence requirements, and widespread cost-cutting measures. For professionals in their 40s and beyond, this dissatisfaction often creates a sense of urgency—a feeling that this might be their “last chance” to make a meaningful career change.

Common but Ineffective Approaches

However, the conventional approaches to addressing career dissatisfaction often fall short:

First, there’s the pursuit of higher-paying positions without addressing underlying dissatisfaction. While this might temporarily boost motivation, it rarely leads to lasting fulfillment. Then there’s the “wait and see” approach, hoping things will naturally improve. Finally, many try to force passion into their current role through seminars or motivational courses.

Understanding the Root Causes

The fundamental issue with these approaches is that they don’t address the root causes of professional dissatisfaction:

Lack of Alignment

When your work doesn’t align with your purpose, frustration deepens, motivation wanes, and opportunities slip away. This misalignment often manifests as a persistent feeling that something’s missing, even in objectively successful careers.

Unsustainable Focus

The pursuit of financial rewards without meaningful engagement inevitably leads to burnout. Many professionals I’ve worked with achieved their income goals but found themselves feeling empty and questioning their choices.

Disconnect from Personal Vision

The frustration of building someone else’s dream rather than your own can be profound. This disconnect often signals that your work isn’t aligned with your personal vision, even if you haven’t fully articulated that vision yet.

Feeling Undervalued

The basic economics of employment means companies must profit from your work, which can leave even well-compensated professionals feeling they’re giving more than they receive.

A Strategic Approach to Career Fulfillment

The solution isn’t necessarily changing jobs or forcing passion into your current role—it’s about creating alignment between your work and your core values. Before making any career moves, consider this strategic approach:

1. Begin with purposeful self-reflection. Dedicate time to understanding what truly matters to you through targeted exercises and deep introspection. This foundation is crucial for making meaningful career decisions.

2. Explore how your existing skills and interests could generate income streams that align with your values. Often, the solution isn’t abandoning your current career but complementing it with purposeful initiatives.

3. Consider developing multiple income streams through low-risk, manageable ventures. Whether it’s rental property, dividend investments, or automated business models, the key is choosing options that don’t add unnecessary stress to your life.

4. Leverage modern tools like AI and automation to create space for higher-impact opportunities. This approach helped me transition from corporate law to a more purposeful career without sacrificing income.

5. Reassess your current role through the lens of purpose. Sometimes, this process reveals that your existing position actually aligns well with your values. In such cases, the goal becomes building sufficient passive income to work from choice rather than necessity.

Why This Approach Works

What makes this approach particularly effective is its focus on three key elements:

Clarity and Alignment

By starting with purpose, you ensure that any career changes or income initiatives truly reflect what matters to you.

Efficiency

Using proven systems and tools prevents overwhelm and allows for sustainable progress alongside your existing commitments.

Strategic Scalability

A structured approach to building additional income creates steady progress without the stress of trying to master everything at once.

The Surprising Truth About Career Transitions

The most surprising insight I’ve gained from working with clients is that many discover they don’t actually need to leave their current roles. Once they build sufficient passive income and align their work with their purpose, they often choose to stay—but with a transformed relationship to their work. They continue not because they must, but because they want to.

Building a Stable Foundation

For those who do decide to transition, the key is building passive income to cover core expenses before making any moves. This approach might take longer than the “burn the boats” strategy often advocated by others, but it creates a much more stable foundation for lasting change.

Conclusion

Remember, the goal isn’t just to change your job—it’s to transform your relationship with work itself. By focusing on purpose first and building financial freedom second, you create the conditions for sustained professional fulfillment, regardless of where your career journey leads.