If you’d asked me 10 years ago to predict what my career would look like today, I’m pretty sure I would have gotten it completely wrong.
Back then, I thought I knew how careers worked. I was the quintessential corporate poster girl - working hard to climb that fabled ladder. Not afraid to move to another company when the opportunities weren’t there internally.
When I left corporate life a few years back, there was a range of reasons behind my decision. First and foremost, I wanted more time with my young son. I was also deeply burned out and knew that corporate life no longer worked for me. I wasn’t sure how successful I’d be as a self-employed consultant, nor did I have the emotional bandwidth to think about what my life would look like in five years. Even if I did, I doubt I would have conceptualised where I am.
Today, I spend my time running a content, communications and marketing agency, writing books and guides, publishing this newsletter, building digital products and occasionally designing slightly sassy coffee mugs (because work should be allowed to be fun).
There are a few different names for this sort of career, and the names seem to change week to week. At the moment I’m seeing “portfolio career” and “involuntary entrepreneur” (which makes me smile). The point is that I didn’t set out with the current destination in mind. Like many people, I adapted as the world of work changed around me.
Last week I wrote about what happened to the corporate ladder. This week I want to explore a bigger question.
If the ladder isn’t coming back, what can we build instead?
If video format is more your thing, here’s some of the content I shared on Instagram… otherwise, read on!
What career assumptions do we need to revisit?
One thing I’ve realised while researching this series is that we keep trying to solve today’s workplace problems with yesterday’s assumptions.
We ask how to create more management opportunities or improve career progression, or how to make organisations look more like they did 15 or 20 years ago.
To be frank, that’s a pointless conversation to be wasting our time on. If technology, changing business models and AI are fundamentally reshaping work, perhaps we need to ask much bigger questions about the kind of economy we’re trying to build.
Who benefits from the current system?
At the top of the list of questions is whether we've unintentionally created a system that increasingly favours people who have already finished their careers over those still trying to build theirs.
For decades, the corporate ladder was one of the primary ways people accumulated wealth. Promotions led to higher salaries, company shares and eventually retirement savings.
Many of the people who benefited from that system are now retired or approaching retirement. Their wealth sits in superannuation funds, investment portfolios and other assets that depend on companies continuing to maximise returns.
That changes incentives. When you’re building your career, you want better pay, more opportunities and greater job security. When you’ve built your wealth and left the workforce, your focus naturally moves towards protecting and growing those assets.
There’s nothing wrong with wanting a secure retirement. The problem is that those incentives don’t always align with the interests of people entering or moving through the workforce today.
Reducing management layers, outsourcing work, offshoring and now AI can all improve shareholder returns while making career progression harder for employees.
I think we’ve gradually created an economic system that overwhelmingly rewards people who have already climbed the ladder, while removing many of the opportunities for those still trying to climb it.
Who gets a seat at the table?
So how do we rebalance the system?
Assuming there’s no practical way to decouple retirement savings from the share market, I think the answer starts with who gets a seat at the table.
Corporate boards exist to represent shareholders, and for good reason. Investors take risks and deserve representation. However, we often lose sight of the fact that company outcomes don’t just affect shareholders. They also shape the lives of employees, customers and the communities they operate in.
As work changes, perhaps it’s reasonable to ask whether corporate governance should evolve too. Countries such as Germany have experimented with giving employees formal representation in corporate governance through co-determination, which is a good reminder that the way we govern companies isn’t fixed in stone.
Different voices around the board table might also help rebalance our expectations of the share market itself. Investing has always been considered a higher-risk asset class. Some years deliver exceptional returns, others don’t. That’s part of the bargain investors make in exchange for the potential of higher long-term growth.
Yet somewhere along the way, we’ve started behaving as though companies have an obligation to maximise shareholder returns every quarter, regardless of the broader consequences.
When that becomes the overriding objective, employees can start looking less like people to invest in and more like costs to reduce. Perhaps a broader mix of voices at the governance level would remind us that long-term business success isn’t measured only by shareholder returns. It also depends on developing capable people, creating opportunities and maintaining a healthy economy that gives the next generation a chance to build wealth as well.
That feels like a healthier balance than simply asking companies to keep squeezing more from fewer people.
The big AI question
Then there’s the billion-dollar question around AI. If AI allows companies to create significantly more value with fewer people, what does society expect in return?
For generations, businesses earned their social licence in more ways than simply generating profits. They created jobs and helped people build careers, buy homes, support families and participate in the economy.
AI has the potential to change that equation. If organisations can continue growing while employing fewer people, we need to ask whether the old social contract still works.
I’m not suggesting companies should avoid AI or artificially preserve jobs that no longer make sense. Technological progress has always reshaped work, and in the long run it has often created new industries and opportunities.
The difference is the speed and scale of what we’re seeing right now. If productivity increases dramatically while employment opportunities become more concentrated, who benefits from those gains?
Do they primarily flow to shareholders through higher profits?
To consumers through lower prices?
Or should some of that value be reinvested into the workforce and the communities affected by the transition, for example through adjusted rates of taxation based on human participation in the workforce?
These are questions for governments, business leaders, investors and all of us as citizens. Unfortunately, right now, it seems to be the technology companies making these decisions for us, and that’s not going to result in a balanced outcome.
Stop measuring yourself against yesterday’s career model
None of those “big picture” debates will be resolved any time soon. That doesn’t help you if you’re wondering what to do with your own career right now.
I’m not a career coach, and I don’t position myself as one. I share what I’ve learned as someone who successfully transitioned out of corporate life, and on that basis here’s the advice I’d give.
First, stop assuming you’ve failed. I speak to so many capable people who feel like they’re falling behind because they haven’t reached the role they expected by now. Maybe you’re measuring yourself against a career model that no longer exists.
The old corporate ladder rewarded depth within a single organisation or industry. Today’s environment increasingly rewards adaptability. That doesn’t mean everyone should quit their job and start a business, but it does mean thinking differently about security.
Maybe security isn’t one employer anymore. It might be transferable skills, multiple income streams or investments. Perhaps you need to go back to the fundamentals of building your professional relationships and reputation.
What that looks like will be different for everyone, but I suspect very few of us mid-career professionals are going to close out the second half of our careers inside a single organisation.
One day, it will be our turn
A final thought on this topic. It’s a little nebulous, but I wanted to put it out there.
Many of us who feel frustrated by today’s corporate system will eventually become the people making the decisions.
We’ll become business owners, executives, investors and business owners. Over the next decade or so, we’ll inherit wealth. We’ll be the ones in charge.
When that happens, we’ll face exactly the same choice every generation faces. Do we recreate the system that benefited us? Or do we build something better for the people coming after us?
It’s easy to criticise a system when you don’t hold the power. The real test is what you do when you finally have it.
I hope our generation remembers what it felt like to build a career at a time when the old rules no longer seemed to apply. If we’re serious about creating a better future of work, we won’t achieve it by rebuilding yesterday’s corporate ladder or focusing on maximising our own comfortable retirements at the expense of younger generations.
Perhaps we should start thinking now about designing something that gives the next generation the opportunities we never had.
One thing I’m thinking about this week
My son turned 10 a few days ago. It’s one of those milestones that makes you stop and wonder where the time went.
When I left corporate life more than five years ago, he was a big part of that decision. I wanted more control over how I spent my time and more freedom to be present during the years that matter most.
Financially, it wasn’t the obvious choice. Professionally, it certainly wasn’t the conventional one. Looking back now, I’d make the same decision again.
One of the themes running through this two-part series has been that many of us are still measuring ourselves against an old definition of career success. Promotions, titles and climbing the ladder became the benchmark, because that’s the world we inherited.
However it’s easy to forget that careers are only one part of life. As I’ve watched my son grow up over the past decade, I’ve realised that some of the biggest returns on the decisions we make never appear on a payslip or a LinkedIn profile. Things like time, flexibility and being there for the moments that don’t come around twice.
Those things are harder to measure than a promotion, but they’re just as valuable when you’re measuring the success of your career - if not more so.
Things I’ve made (and you can buy)
If you enjoy my content and would like to support my work, here are a few things I’ve created.
🛒 Track Changes On Shop - Coffee mugs for corporate rebels
📖 Do Give Up Your Day Job - Guide to corporate exits and transitions to self-employment
After years on the corporate ladder, I finally stepped off.
I don’t want rungs anymore. I want room. I want sky.
Life after the ladder feels like drifting into my own constellation, where direction isn’t vertical but expansive.