Will You Still Have A Job After 50? (Probably Not, But Here’s What You Can Do)

Will You Still Have A Job After 50? (Probably Not, But Here's What You Can Do)

A 42-year old IT Leader came up to me last week with a worried look on his face.

He asked me pensively…

“I’ve had a great career for the past 2 decades and am making very good money now… but after seeing so many of my colleagues/friends in their 50s getting retrenched, I’m beginning to ask myself, will I still be employed in my 50s?”

Surprisingly, he wasn’t the first person to ask me this question as the sudden realisation that there might be a ‘Career Cliff’ rushing towards us as our 50s draw nearer.

And we’ve all known friends who have been retrenched at this stage who are struggling to land similar (or even smaller) roles…and then a thought crosses our minds – “that could be me years down the road”.

But why is this happening? Let’s explore some Uncomfortable Truths.


A) It’s All About The Money (*TriggerWarning*)

Unless you’re a SuperStar Like Tom Cruise, nobody’s gonna show you any money

When you get rejected for even the screening call by the Junior Recruiter for being “too senior for this role“, you will soon realise that this is an HR Code for “You’re too Old/ Expensive/ Experienced for us, go somewhere else.”

But honestly, of the too old/expensive/experienced mix, it’s the MONEY part that they’re most uncomfortable with.

In your early 50s, you should be at the peak of your earning capacity and if they brought you on board, you just might jolly well be the biggest cost-item on their payroll! And if they can’t see you bringing at least 5x that amount, you’re a non-starter.

And if you think “haha, I won’t have that problem because I’m cheap”, you’re in for a rude shock as well.

Cos she’s smarter and better looking than you?

Because if you’re 52 and your salary is in the $7,000 range, it only takes a few wags of a bunny’s tail for someone in HR to realise that cost-wise, some younger graduate with a few years under his belt could be trained (ironically, even by you) to do your job, and you will be replaced/upgraded by this younger version.

So, moving into your 50s will present challenges in terms of holding on to your job or even looking for one if you are laid off.


B) Are You Skills-Inspired, or Skills-Expired?

The Struggle to Stay Relevant is Real.
Just Ask Robert De Niro’s Character in the movie, “The Intern”.

Now, I’m not going to harp on the need for acquiring new skills to stay up to date, or to lament the lack of modern capabilities like Data-analytics, coding or Prompt Engineering with our seniors.

It’s not so much that your skills are expired and out of date.

It’s that many in their 40-50s never realised that as they grow older, their skills need to move up the value chain towards higher value-creation activities instead of simply doing the low-value activities better.

e.g. A young salesman can knock on doors and sell, a Sales Manager knows how to manage his team to optimise sales effectiveness, a Sales Director knows how to segment the market and uncover new opportunities, and the Chief Revenue Officer needs to create Blue-Ocean Strategies and innovate new solutions to address yet-untapped markets.

Unfortunately, as many of us grow older, we focus on ‘getting better at the low-value-creation activities’, e.g, becoming better sales-men and pushing more boxes to customers – and this unfortunately puts us squarely in the same boxing weight-class as the younger and more energetic turks who are after our jobs.


C) Do You Still Want To Chase The Rainbow?

One of my favourite movies is Lethal Weapon (1987) and the best line ever said by Detective Murtaugh was:

To be honest, there are days I feel this way too

Many of us don’t realise that whilst we are in our 30-40s, the drive to succeed was evenly matched by our energy levels and health. We were able to pull all-nighters, travel 3 weeks out of 4 for extended periods of time, and even take a red-eye from New York to Singapore and turn up fresh for work the next morning.

But to Detective Murtaugh’s point, we’ll all eventually hit our physical limits and something will have to give (hopefully, our will, not our heart valves), and we will need to slow down.

Moreover, at this stage, our focus and priorities would have changed and suddenly, the thought of getting promoted to a global role and its attendant 2am Zoom calls with US doesn’t sound too appealing anymore.

As we approach a different season in our life, we might just realise that a smaller, less painful role would suit us better, but often, Employers would beg to differ, and landing these opportunties can be very difficult.


What can you do about it?

1. Build Your War Chest

The last thing you want to have in your precarious 50s is a huge debt obligation for your private yacht, sprawling mansion or Bugatti Veyron.

Instead, start building your War Chest of savings, or what we call, your ‘Freedom Fund’ so that you will have more financial freedom to make bolder career choices (like starting a Business, Downshifting or even Retiring early!)

You’d be surprised at how a healthy War-chest can change your perspective on that job you hates – and how liberating that can feel.


2. Play the Long Game – Work towards Longevity, not Advancement

In the classic movie Highlander (1986), a bunch of Immortals fight it out to outlast and outlive each other because in the end, “There can be only ONE!”.

Their strategy was not to win every fight as soon as possible, but to outlive and outplay the competition over centuries if need be, making use of that time to train and get better.

Sometimes, we are inclined towards ramping up our salariess or climbing the corporate ladder too quickly, neglecting our longer term viability in the company. (Remember, the air is thinner at the top, and so are the opportunities!)

And also, keep upgrading your skills to stay relevant and in demand! Predict what future capabilities are needed and be the Subject Matter Expert in it!

Pace yourself with a Sustainable Career Strategy (come talk to us if you want to know what this is) and make sure you stay relevant until you’re into your 60s!


3. Plan for a Gig – Any Gig

Always have a backup plan – preferably one that does not involve a Corporate Employer.

Lots of great ideas here – if you can stomach them!

Should a time come where you feel it’s time to walk away from the Corporate Life, you will need some ideas which can keep you sufficiently challenged and decently funded. These could include

  • Real Estate (or any kind of) Sales
  • Teaching/Lecturing
  • Coaching/Consulting
  • Starting a Business
  • Going into a Trade – Plumbing/Carpentry/Locksmithing
  • Volunteering at a local charity

I have solid examples of people in their 50s and 60s who have embarked on their ‘Second Half’ of their Careers with these ideas and are enjoying themselves tremendously!


Ultimately, we all need to recognise the possibility of a ‘Career Cliff’ heading in our direction that we will need to address – and no matter how old you are, now is probably the best time to do it.

Come talk to us if you’d like a professional assessment on your Risk Profile and your Possible Options now!