OK Gen X,
Now What?

OK Gen X,
Now What?

13-minute read

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At this point of our lives, Gen Xers like me are asking: “So, what do I do with the rest of my life? What does the next phase of my career look like? Do I:

  1. Keep doing what I’ve been doing; or
  2. Try something different?”

You don’t need to look far to start hearing conflicting advice. Some say, “Never quit. I stuck to it when everyone told me not to…” versus, “Life is about taking risks. I had the courage to start over…”

Advice of this kind hurts my head because both sentences share the same ending:
“…and that has made all the difference in my life.”

So which is right? We know deep down that advice like this from so-called experts is not going to be tailored for us, but that doesn’t stop Gen Xers like you and I from listening to it. It is, after all, the second half of our lives at stake!

Instead of telling you what to do with your life, let me frame the question in a way that will help you come to your own, better decision.

Now What?

“Now what?” is a question that is more pertinent now than any other time of our lives, because a lot of us Gen Xers have become masters of our domain. We know our shit. We know people. We know how to get things done. We are in control. We are well on our way to financial stability.

I had this dilemma when I was 38 years old. At the time, the company I was working for suddenly shut down. It was the height of the global financial crisis, and I was well aware that finding another job might take a while.

I was thrown a lifeline by my a colleague who lined up jobs for everyone at a prestigious global consulting firm. I wasn’t as grateful as I should have been because by then I had had enough of consulting. After a decade of working with CIOs and COOs, seeing how things work in over fifty companies across four continents, I felt I had well and truly ticked that box.

The problem with being masters of our domain is that there isn’t much domain left to master. Promotions are harder to come by. And there aren’t big strides of learning left to gain. I mean, does your boss really know that much more than you?

Sure, no two days are the same, we face new challenges all the time, but broadly speaking, we’ve been solving the same types of problems, and working with the same types of people for 10-20 years. Project managers might tackle new projects every 6-24 months, but they’re following the same processes and using the same tools. Journalists might cover a different story everyday, but they’re relying on a formula honed over many years.

People with apparently interesting jobs aren’t immune to the hard slog that comes with years of repetition. Anyone can see that towards the end of his 33 years on the Late Show, David Letterman was bored out of his mind telling jokes and interviewing celebrities. And do Paul McCartney, Billy Joel, and Elton John look as if they’re having as much fun as they did when they were first starting out?

Do I keep going? Do I follow the lure of power and money? Do I endure the politics? Is it wise to keep going against what you are feeling?


I wanted to follow my urge to do something completely different. To venture out into the open seas. To learn something completely new, to reinvent myself, and to land on undiscovered shores.

The Case For Staying

I ended up taking the job. Back to the safety and comfort of doing what I know best.

You have to understand that at the time my eldest son was a baby, and my wife was still at medical school. We had just taken out a large mortgage. I felt that my 30s and 40s were my best years, and I should be building a nest egg for later life. Besides, nobody quits when they’re at the cusp of reaching partner status at a prestigious consulting firm. Hold down a partner position for 3-5 years, and I would have been set for life.

Up to this point, Gen Xers like me spend so much of our lives building up our resume. To go “off road” jeopardises our track record. Head hunters looking for a track record will find it hard to overlook a “black hole” in our resume.

So I went along with it.

A year later when bonuses were paid, I was thrilled with the financial stability I’d been able to provide, and my wife and I felt that we had made the right decision. The amount was more than an entire year’s salary just a few years earlier.

It wasn’t just the money. I was doing some of the best work of my life with the least amount of effort. That’s the benefit of sticking to what you’re good at: you get to see the patterns, know which shortcuts to take, and draw on your bag of tricks. It got to a point when I was showing up with a thirty-page report when others were producing three hundred pages. Clients valued my work and I was pulling in as much business as anyone else at my level. I let it go to my head that I had fulfilled my father’s wisdom: “Make your job your slave, not the other way around.” I got to pick which projects to work on, said “no” to those that took me away from home, and rarely worked on weekends. I found joy in helping younger consultants, developing original insight, and was quick to put my hand up for pro bono work.

Every gunslinger knows that there is a bullet out there with their name on it. Mine came in the form of a project that didn’t go well. After three years at the job, I was made redundant. By then, my second child had just arrived, and my wife was still at medical school, and not yet earning. I still remember in vivid detail the room where they gave me the bad news. It’s rarely a good omen when someone from Human Resources joins your meeting with the top boss.

I should have seen the signs earlier. My apparent lackadaisical approach made me a political target: “Is he putting in the hours? Is he committed? Is he setting the right example for our people?”

Cowboys grow eyes on the back of their heads and sleep with one eye open. I don’t think that would have saved me from getting the bullet. I didn’t know it at the time, but it is clear to me now that the rot began the day I took a job when my heart wasn’t in it. I can’t blame anyone but myself.

The Case For Status Quo

There are times in our lives when we have to work on things that we’re not that passionate about. Entire civilisations are built this way, and I am thankful for the billions of people who find the motivation to show up everyday to grease the wheels that keeps the world turning.

There are a lot of good reasons to stay. If you have a great boss who will accelerate your career; if you have a chronic health condition and your job offers an excellent health plan; if you’re facing financial ruin and have people who depend on you; if you have no better alternatives; if you are working on a mission like feeding the poor; if you’re at the cusp of greatness ‒ then for goodness sake, don’t quit!

There are some vocations where you have to persist for many decades in order to reap the benefits. Like becoming a heart surgeon or building a global empire. Persistence pays off because over the years people quit or are forced out, and so you get the entire field to yourself. If you’re one of these people, then don’t quit.

Our Bias For Status Quo

The thing to recognise is that we have a bias to keep things the way they are. Psychologists say that we are prone to seeking evidence to confirm our biases, and inclined to dismiss contrary signals1. For example, fans of competing football teams will watch the same slow-motion replay, and come to a conclusion that favours their side.

The point is that we can be misled by our own instincts. We’ve all received poor service from people who have lost passion for what they do. It’s easy to spot it in other people, much harder to see it in ourselves, and even harder to do something about it.

I created the following table to help Gen Xers like myself get to the truth: to examine both sides of the argument, and judge for themselves what is the best course of action.

Reasons we use to justify staying:Questions we should ask:
I have nurtured strong relationships, I’d be more effective here.How valuable is my existing network? Would it be valuable to expand my network? Would it be good for my career longevity if I practised building new relationships? How long would it take for me to build a network somewhere else?
I am at the cusp of promotion, maybe 1-3 years.What is the opportunity cost? What will I achieve with the 1-3 years if I did something else?
A few more years and I will achieve financial stability.Researchers found that regardless of the amount of money we already have, we tend to think that we need three times more to be happy2. How much do I actually need?
I have a mortgage and a family to feed. I need to be saving up for my kids’ education, and to build up a nest egg for my retirementCould I halve my expenses? If I did, how much income would I need? What if there isn’t a need to build up a large nest egg? What if I assumed that I will be working on something I loved for the rest of my life?
It has taken me years to get to this position. I have built a great reputation. I can’t afford to throw it all away.To what extent have I fallen for the sunk cost trap? Am I worried that quitting looks like defeat? At the end of my life, what do I want to be known for? Are there other dreams and passions yet to be fulfilled?
I am comfortable. I’ve been here so long, I’m part of the furniture.Am I in a rut? Have I stopped growing? If my job were to be taken away from me tomorrow, would I be able to fall back on other opportunities or other skills? What would it take to double my value?
I’m happy where I am. I don’t need the stress. People should learn to accept that not everyone is destined for great things.Do I complain about my work more than I should (e.g. about colleagues, work conditions, customers, politics etc.)? Is this fear speaking? How secure is my position?
They need me.Is this my ego speaking?
These are the prime years of my life. I need to make the most of it.What if I assumed that I have another 30-50 good working years left? Would I want to keep doing this or use my “prime” years to build towards something else?

We have a tendency to overestimate our ability to stay motivated, to keep doing the things that don’t excite us. Conversely, we have a tendency to underestimate our capacity to come alive when we take on new challenges.

Getting good at change is in itself valuable. It builds resilience, gives us confidence and sets us up to be more agile as we age.

Us Gen Xers already know that change is good for us. So what holds us back?

One of the reasons people avoid change is because of the “up only” mindset prevalent in our society. We can’t go backwards in our careers; we are reluctant to take time out and come back to the same position; we’d rather not go backwards in lifestyle; and saying “I’m taking a different direction” sounds awkward because, well, maybe it’s actually a euphemism for being unemployed. People expect our resumes to reflect a steady career incline, not a hodge-podge of sideways movements.

The trick is to know ahead of time when a change is due, to tune into the early signs of discontent, rather than ignoring them. In my previous article, I outlined how forcing ourselves to “keep going” can come at a price that is paid in multiple ways. It’s worth repeating here: “some of us overeat, some become lazy, or act out by bullying, being territorial, obstructing progress, grandstanding, complaining, backstabbing, gossiping, and having marital affairs.” None of us want to work with people like that, given a choice.

The Answer?

After a long discussion, a mentee will ask me, “So James, should I stay or should I go?”

To which my answer is: “Let’s frame the question differently. Imagine we are able to rewind the clock and be 20 again. Let’s assume we’d have a 70-year working life ahead of us3. As a 20-year-old, what would we want to accomplish in our lifetime?”

The biggest reason why people avoid change is because of a lack of viable alternatives. If we’ve spent the last 25 years working as a doctor, we’re not going to give it all up to become a plumber. And curiously, the reverse is true. If we’re a general manager at a bank, it’s too big a leap to start a musical career, or move to the country to become a writer. If we’re an actor, producers aren’t going to entice us with bags of money to direct their next film.

This logic rings true at age 45, when we’ve done so much to get where we are, and starting over is painful and risky. Our 20-year-old selves might have answered the question differently. They might ask, “Isn’t 70 years a long time to be focussed on one thing only? Why can’t I spend 10 years in marketing, work 30 years as a doctor to look after people, 15 years building houses and 15 years writing books?” Our 20-year-old selves might have a point. Would we be better people as a result of this experience?

The late Dr Catherine Hamlin AC, who passed away at age 96, had the kind of career that 20 year-olds might describe if you asked them what they’d like to accomplish in their lifetime. After 13 years working as a doctor at hospitals in Sydney and Adelaide, Dr Hamlin moved to Ethiopia to work as a gynaecologist (at age 34). At the age of 50, she established the Addis Ababa Fistula Hospital, treating women who suffered obstetric fistula (for free). At age 70, she embarked on a mission to expand her medical team opening five rural hospitals. At age 83, she established a midwifery school.

Clint Eastwood, aged 90, has worked as a pool digger, a swimming coach, an actor, a director, a producer, and a mayor. He is an accomplished pianist, singer, and stuntman. He has owned and operated a restaurant and a film production company. He has written and scored the music for his films. When asked why he did certain things in his career, he said, “I’m always up for a challenge”.

I use celebrities here because they’re easy to identify with, and you can verify the facts yourself. Ordinary people have varied and interesting careers too. In fact, there are likely to be people in your circle of friends that fit this description. I don’t have to look far: my best friend, Roman Sisa, has worked as a fireman, a pool manager, a lifesaver, a fitness instructor, a gemologist, an opal miner, a photographer, a caravan park owner, a story boarder – to name a few. He has fixed cars, operated heavy machinery, built houses, made sourdough bread, repaired smartphones, and stripped at a hen’s party. He’s one of the most graceful agers I know. Always in demand, I’ve never known him to feel insecure about his job, nor have I seen him grandstand, bully, backstab, or feel the need to boast about himself (except to make you laugh).

To be clear, I’m not advocating career diversity for the sake of diversity. Management gurus have a point when they say that it is better to focus on a single mission rather than to spread ourselves too thinly. My goal is to liberate those who feel stuck. If you don’t enjoy what you do, if you have other aspirations, then feeding these aspirations might come at a short term cost, but they may help you age more gracefully over the long run.

Some readers will be wondering how people like Dr Hamlin, Clint, and Roman are able to have such a varied and interesting career. And some might feel that it is beyond their capability. Or perhaps it’s too late now to start? “I could have done it 10 years ago, but not now.”

The good news is this: if you have made it this far into this story, then you’re likely to be the kind of person who can do anything of your choosing. In future editions of this blog, I plan to explore how people like Dr Hamlin and Client Eastwood stay motivated for decades; how they transition from one career to another with little risk; and how we can all breath life into unfulfilled desires, curiosities, pipe dreams and side ambitions. If you’re as excited as I am about “What’s Next?” for us Gen Xers, please feel free to subscribe.

Back in 2012, when I got made redundant, my wife was midway through her medical studies and not yet earning. Our second child had just arrived. I had no idea what the next phase of my career would look like, I just knew I didn’t enjoy being a consultant anymore. I asked my wife, “Is it OK if I did something else for a while? I’m not sure what though.” I felt the guilt of being a bad provider, the ground beneath me softened like quicksand. Facing financial stress, and suffering from a lack of sleep on account of our newborn, she said, without even a wobble in her voice, “Isn’t this what you’ve been working towards? If not now, then when?” And that has made all the difference in my life.

Thank you

Thanks to Jocelyn Rikard-Bell for the lesson on tone control, and thanks to Jermir Punthakey for reviewing early drafts.

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© James Lau  May 14, 2020

  1. Confirmation Bias
  2. Norton, Mike. 2014. Harvard Business School. Cited in Dan Ariely in his WSJ article: https://www.wsj.com/articles/can-money-buy-happiness-1499447773
  3. Why 70 years? See my previous article “Why You Were Never Meant to Retire”.

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