Most people will encounter a career crossroads at some point in their lives. The challenges confronting an executive or senior manager contemplating a career change can be complex and potentially perilous. The aftermath of the pandemic has only heightened these challenges, with executives having navigated their organisations through, hybrid/remote working environments, inflation, labour market shortages, and significant shifts in workforce participation following Covid-19 fiscal support measures.

The Great Resignation and Great Reshuffle

The pandemic-induced Great Resignation saw a significant number of over-50s exiting the workforce, causing widespread concern. Now, we are witnessing the Great Reshuffle, with workers of all ages job-hopping, upskilling, or returning to the workforce. In both the UK and the US, self-employment is on the rise again, with almost a million Britons aged 55-64 and nearly half a million over 65 now self-employed.

Understanding the Career Crossroads

Facing a career crossroads can be especially pressing if thrust into such a situation unexpectedly. Executives, often at the midpoint of their lives, may find their initial career path has left them feeling bored, empty, or worn out. Known as a midlife career change, this phase demands clarity, foresight, and prudence to make the best decisions.

For executives and senior managers, this calls for life-changing decisions, and the transformation can either accelerate one’s career or be the worst decision ever. Understanding how to make a career transition can help individuals achieve professional and personal objectives. How can executives, and leaders assess the options, get advice and determine a new path?

Andrew Raymond, Director of Redline Executive, shares his insights on guiding executive-level candidates through career transitions. Drawing from his extensive experience working with CEOs, COOs, Presidents, Senior Vice Presidents, and Directors in engineering and technology sectors, he outlines strategies to ensure a smoother transition.

“Over the course of my executive recruitment career, I have worked with 100s of key Executives at engineering and technology companies including – CEOs, COOs, Presidents, Senior Vice Presidents, and Directors. These top technology business professionals present special challenges to a career change.”

Andrew continues:

“Midlife career change is a scary business, fraught with obstacles—a resistant spouse, relocation, financial concerns, fear of failure. Where do you start? What should you consider? Such fears have prevented many high-achievers from reaching beyond their comfort zone, but the biggest rewards come from taking the biggest risks, otherwise, you may be filled with regret at the end of your life—and that prospect helps put steel in your spine.” 

Strategies for Executives at a Career Crossroads

1. Consider financial commitments

Evaluate the financial implications of potential new roles. Research average salary ranges and discuss your plans with colleagues and family members to ensure financial sustainability.

2. Understand your priorities, wants and needs

Reflect on your identity and desires. Identify what gives you joy and passion, essential for making a fulfilling career move.

3. Evaluate your strengths, weaknesses, and motivations

Conduct an honest self-assessment to recognise your unique skills and areas for improvement. Understanding your motivations will help align your career choices with your values and goals.

4. Time Management

Determine how much time you can dedicate to your career transition, including any necessary training or education.

5. Network effectively

Build meaningful, authentic relationships that can support your career advancement. Networking is a two-way exchange based on shared interests and mutual respect.

6. Be your own story-teller

Reflect on your past to find clues for your future. Writing an autobiography highlighting key events, relationships, and achievements can provide surprising insights. Ask yourself questions like:

• What part of leadership gives you the most happiness?
• What were the high points in your executive career that gave you a jolt of energy and pride?
• What do you want more or less of in your next executive role and can this be achieved in your existing role?

7. Think long-term

Consider how short-term career moves fit into your long-term objectives. This perspective can make the transition less daunting and more strategic.

8. Set milestones

Break down larger career goals into manageable steps. Setting milestones helps track progress and maintain motivation.

9. Explore emerging industries

Stay ahead of the curve by exploring new industries and roles. Embrace opportunities in fields that align with your interests, even if they are outside your comfort zone.

Making the Transition

Career Crossroads can be a difficult moment in any professional’s life, but for many, the biggest barrier to change is ourselves. By following these guidelines, executives can navigate their career crossroads with greater confidence and clarity.

The best way to stay informed about director, executive, and senior career opportunities in your area of expertise, along with relevant news and events, is to book mark Redline Executive.

If you are an considering a career change and would like to seek further advice, please contact Andy Raymond on 01582 878907 or email ARaymond@RedlineExecutive.com.