Dating tips from grandpa: Why it's past time to scrap the ladder

"AS YOU gain experience and proficiency in all these duties, you will grow in confidence. You will be able to take more responsibility, and in time take advantage of any opportunities for promotion that may arise.
"There are many chances of promotion for the capable girl."
– "A Career with Woolworth," distributed 1950s-1960s
The career ladder promise is long past its expiration date.
It wasn't always this way. At one time, believing that strong performers would simply earn promotions over the course of their working lives, following a preordained track, made sense. Obey the rules, learn the ropes, and you'll climb the ranks until you retire with a gold watch (or for a Woolworth's "girl," probably until you get married). But that time has come and gone.
Hearing traditional advice based on the idea that career paths are predictable feels like getting dating tips from your grandpa – it might have worked decades ago, but the world is different now.
The reason is simple: the only guarantee today is change. Finding your way forward requires constantly adapting to your circumstances, committing to exploration and understanding that where you head next can only come from your internal compass.
Once upon a time, employees could reasonably expect that they could simply follow a sequence toward success over the course of their working lives. This historical blip has outlived its relevance. The pace of change has increased to the point where it's tough to predict what jobs will even exist a few years from now, which companies and industries will survive seismic changes, and what skills will be prized in the future.
That's why professionals today aren't climbing ladders. We're riding rivers. Our circumstances – in work and in life – are constantly changing. We can adapt, or risk getting swept away.
Moving up – or on?
"Every encouragement will be given you to progress rapidly, but naturally much depends on your ability, interest, initiative and determination to become a valued member of your team."
– "A Career with Woolworth," distributed 1950s-1960s

I'm a survivor of the early twenty-first century media industry. Somehow, I've been employed in journalism for nearly 20 years (!), despite being told early on that "there were no jobs in journalism" (inspiring stuff from my college advisor). Take a quick scan of the first four companies on my resumé and you may notice some themes:
- Community newspaper (founded 1852): 7 years.
- Reporter
- Assistant Editor
- Online Editor *new role
- Local Editor
- Magazine publisher (founded 1934): 3 years.
- Digital Content Specialist
- Audience Development Specialist
- Consultancy (founded 2015): 3 years.
- Engagement Strategist
- Editorial and Community Manager *new role
- Engagement Manager *new role
- Nonprofit membership association (founded 2009): 3 years.
- Member Collaborations Editor *new role
- Director of Collaborations *new role
Roughly half of the roles I've had did not exist before I did them. And two of the four places I've worked at did not exist when I started working. My tenure at a company is measured in years, not decades.
This is the new reality: people switch companies regularly, build skills and craft new roles, because promises of stability and success for simply sticking around no longer work. And yet, we haven't updated the way we talk about our careers from the laughably outdated ladder model (seriously, it's way older than you'd expect).
Does the ladder work sometimes? Sure! At my first job I definitely had the support I needed to grow my career and move up the hierarchy. But the world is shifting too rapidly to expect that every move has already been mapped out for us. Trying to balance on a ladder in a rushing river won’t work for long. It’s just not built to handle change.
Progress for the whole person
"You have begun a job in which your personal appearance is important, and you will enjoy keeping up the standard of smartness which we ask of you."
– "A Career with Woolworth," distributed 1950s-1960s
Imagine visiting a clothing store selling only one suit in one size. Since you don’t have any other options, you buy the suit and you have to pretend it fits, maybe try having it tailored to you.
But what if you didn’t even want a suit in the first place?
The ladder was only ever designed for the comfort and success of employers, not employees. It incentivized employees to act in the ways employers wanted – good behavior would be rewarded by promotions. They were expected to buy the suit.
Clearly, this does not account for how a job could be rewarding outside of the purely transactional rubric of gaining more pay and responsibilities for meeting the company's expectations. And it doesn't at all consider the many ways work interacts with one’s personal life.
I’ve heard from many people who found that as they moved up, they also moved away from the work that really mattered to them. And let’s be real, we’ve all met managers and executives who exemplify the Peter principle (“in a hierarchy, every employee tends to rise to their level of incompetence”).
Outside of work, the relentless pursuit of success on the company’s terms can directly conflict with your personal priorities. This was made painfully clear to me when I became a parent. I was running a 10-person team at the newsroom, and the news cycle never stopped. I hated getting pulled away from my young son for work at all hours, and this was a major reason I decided to move on. Finding additional stability between my responsibilities at work and at home was the driving force for choosing my next role, even if I didn't see it at the time.
I've heard this desire for work that supports our personal lives called work-life chemistry, or harmony, instead of balance. But whatever you call it, it's clear that our careers are just one factor in how we pursue meaning in our lives. Sometimes, work might be your primary focus. And at other moments, personal priorities can – and should – take the spotlight.
Our sense of purpose cannot be reduced to a checklist for a promotion. Finding what fuels you, in work and in life, is a process of discovery.
A model for modern work
"Your STORE MANAGER is responsible for the general operation and control of your store. He relies on the conscientious service of each employee to enable him to operate with maximum efficiency. Needless to say, he is also very interested in your personal progress and at all times is ready to offer help and advice.
– "A Career with Woolworth," distributed 1950s-1960s
I’m not here to tell you to simply “follow your dreams.” You’ve got real life to worry about, which could include a mortgage, saving for retirement, health insurance, kids … there’s too much at stake to simply chase a shiny new horizon. And frankly, I’m not convinced that there’s any such thing as a “dream job.” I’ve heard too many people say they thought they found their dream role – only to find reality fell short of their expectations, or to wake up realizing their dream had changed.
Instead, I’m offering a powerful new narrative that captures what it’s really like to navigate the shifting world of work today, one centered on what you need, not what your company wants from you. Will it be perfect? No. Real life never is. But it’s better to move toward fulfillment than be crushed by the weight of impossible expectations.
I am more than my job, and you are too. Purpose and fulfillment don’t only come from what we do to earn a paycheck. It’s past time that we stopped holding ourselves to the standards of a bygone era and recognize our career journeys are just one component of a meaningful life.
If you’re ready to:
- Move toward goals you define
- Confidently navigate change
- Embrace discovery, even with uncertainty
Then I’d like to welcome you to your Career River.
Happy navigating,
Bridget
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