Career Transitions Past 50: From mid-life empty nest to Embracing New Beginnings

Embarking on a new career journey can be both exciting and daunting, especially when it comes later in life. As someone who recently transitioned into a new role as Head of Strategic Partnerships for Nanyang Executive Education - Nanyang Business School at 新加坡南洋理工大学 , I understand the unique challenges and opportunities that come with making such a significant change past the age of 50.

What is the path of least resistance?

As I headed into my mid-50s, I observed many peers and friends wanting to semi-retire and expressing a desire to become either a coach, Advisor or Board Member. I chose to be honest and shared brutal truth with them that if they seriously thought coaching was going to help meet their basic financial needs while they fed a seemingly insatiable need to pay it forward, “forget it”. This would be different if you already have a strong passive income stream or inherited wealth or enough liquidity to last you till 100 years.

This bitter truth was hard for some to swallow but many thanked me months or years later. Almost everyone I know who wants to retire after decades of HR or business experience wants to be a coach. However, the sheer dearth of over supply of coaches versus the demand for coaches today is simply a gross mismatch. Fees are coming down rapidly and coach platform companies with Ai capabilities and ability to scale and provide efficiency simply added further substitution effect. The huge influence of the entire global machinery of monetisation of coach training and credentialing with yearly renewal fees may have distorted some of this decision makings for them.

The Motivation Behind the Move

After decades in the corporate sector, focusing on Talent, Leadership Development, Organizational Development, and doing various roles in HR and business, I felt a strong pull towards making a broader societal impact. The education sector, particularly the Executive Education arm at NBS, presented the perfect opportunity to fulfill this purpose. Developing Custom Programs for senior executives allows me to leverage my experience and passion for developing leaders on a much larger scale. But you see, this wasn’t by chance. I was already an adjunct faculty with NTU before, as well as at other universities in the past, conducting and facilitating various HR and Leadership development courses for executives and at Masters level. My purpose ‘cup’ was already being ‘filled’ way back so it was not an overnight awakening. The bridge to transition my career now became easier as I was not starting out totally raw into something new.

Why Consider a Career Transition Past 50?

1. From Purpose to Renewed Purpose and Clarity of Purpose: A career change can reignite your passion and provide a renewed sense of purpose but you need absolute clarity and live by this purpose earnestly. It must show in your energy and actions outside of work in your daily life.
2. Broader Impact: Moving to a sector like education can amplify your influence, allowing you to make a difference in more people's lives. Paying it forward does not have to mean doing work pro-bono or for lower fees which demean your years of valuable experiences. Be intentional about broadening your impact.
3. Continued Growth: Embracing new challenges is essential at any stage of life. Ensure your new career path offers opportunities for continuous learning and growth. Being an independent contractor could potentially limit your network and knowledge updates unless you are extremely resourceful. With the rapid pace of AI, staying current is crucial. Therefor for me, choosing the education sector, especially at a renowned university, provides endless access to new research and knowledge. So be intentional about your career transition especially from full time to part time roles.

Challenges to Overcome in Late Career Transitions

1. Age Perceptions: Overcoming stereotypes and biases about age in the workplace can be challenging. Demonstrating your value and experience is key. Don’t just try to look young. Feel young and act young. And do not at any stage allow the mindset of ‘ageism’ to deflate your confidence. Continue fighting age biases to stay relevant. Stand tall, walk tall. Your spine has years to keep you going.
2. Networking: Building new professional relationships takes time, especially past 50. I planned a deliberate 12-month career pause to re-establish old ties and networks, ensuring my next role aligned with my purpose and passion. I was intentional on not giving myself internal pressure with a shorter waiting period. The more dots you join (meet) and further away, the larger your circle of network. Hence, Patience is key when reconnecting with your network.
3. Seek Support: Don’t try to do all by yourself. Connect with mentors and peers who can offer guidance and support during the transition. Be transparent with them about your situation and where you eventually want to be. Then wait, be patient. You are in your 50s after all so no need to rush. Be in your stride.

Past 50s career role transition strategy for stability. My two step Career rule.

1. Importance of Skip Manager: Aim to understand the relationship between your potential manager and their reporting manager. Why? You probably hear this most often "People leave their managers, not the company". Yes, that's true. However, some of these good people are managers themselves who have an awful work relationship with their own bosses and are mot respected by them. If your boss and their boss (your skip manager) get along really well, most budget submissions get through easier, headcount approvals easier, promotions easier and much more. If your skip manager does well and moves up, your boss also moves up and so could you potentially. Else you are stuck with rotating managers who keep leaving their bosses and you have to proof yourself all over again to a new boss which can be very tiring. This is another reason when you get into your 50s, you want more stability.
2. Importance of Next Two Career Steps: Think two steps ahead. Ensure your next role serves as a bridge to your ultimate career goal. Don’t allow yourself to be caught in a career transition stage only to regret you did not have anything to justify value of skills and experiences which could have been the “bridge” to get you into a new role later.

Final Thoughts

Transitioning careers past 50 is not just possible; it can be incredibly rewarding. By leveraging your experience, embracing continuous learning, and seeking opportunities to make a broader impact, you can find renewed purpose and fulfilment in your career. And there is no such thing as “I want to retire”. Human beings are not designed to sit down and do nothing to ‘retire’ themselves out. Semi-retirement and continued career, community or societal engagement makes more sense. These days some call it having “career portfolios”. Whatever it's called, take that word ‘retire’ out of your head. Stay continuously engaged, paid or unpaid, as that is the only sanity you get with sense of goals and purpose to live by and make it count.

I am grateful for the opportunity to join Nanyang Executive Education - Nanyang Business School and look forward to making a meaningful impact alongside an amazing team. To anyone considering a similar transition, I encourage you to embrace the journey and believe in the potential for new beginnings.