How to Ditch The Ladder (and Design a Career You Love)

  • Archived
  • May 25th, 2021

In this class with Amazing If CEO Helen Tupper, we explored the changing nature of careers and why you need to take ownership of yours. After holding leadership roles at companies such as Microsoft, Virgin, and BP, Helen created The Squiggly Careers podcast to help people make better choices about the future.


We’ve all been taught the quickest path on any important journey is a straight line. Helen Tupper would like to offer you a slightly different perspective.

Tupper is CEO of Amazing If, a consulting and coaching firm, author of the best-selling The Squiggly Career and host of an exceedingly popular podcast of the same name. As the name of her book and podcast suggests, Tupper has committed her life to showing working people the path to career success and happiness definitely does not follow a straight line.

“This notion of a career ladder was developed over a hundred years ago when the world of work looked much different than the one we are seeing today,” Tupper said in a Ezra webinar, How to Ditch the Ladder. “When work was more predictable, when people were in similar roles in similar places and doing them in similar ways, the career ladder was right for that moment in time. But the world of work that we are all experiencing – it’s not linear, it’s not predictable, it’s not certain. It’s ambiguous, it’s full of change, it’s full of challenge.”

Enter the “squiggly career,” a reimagination of the traditional career path where “people can develop in different directions,” Tupper said. While most people think of upward or forward as the only directions a career can develop, increasingly people are finding that there are a number of different tacks that can define career progress.

However, as much as the “squiggly” career suggests an almost careening approach, it actually requires individuals to do some intense spadework to figure out who they are and what they really want out of their working lives. 

What makes you, you and other acts of self-discovery

Tupper said one of the reasons why so many people are unhappy in their jobs is that they have not taken the time to reflect on their specific values and strengths. 

To define our values, Tupper recommends a self-assessment where we review the good and bad times in our working lives to identify the common threads. When things went well, what were we doing at the time, who were we working with? Conversely, when things turned sour at work, what specific tasks were you performing at that time and what was the state of your relationships with colleagues and managers? This process can help you identify the things most likely to make you happy and fulfilled.

This allows individuals to build a list of “must haves,” the things that most often have made us happy and satisfied at work, and “must nots,” those things that are almost always present when we struggle to find our purpose or motivation at work.

“Next time you’re faced with a career decision, stop and pause and think: how does this reflect on my ‘must haves’ and my ‘must nots?’” Tupper said. “All I’m trying to do is make sure that the things that make me, me, are going to be present in this job.”

I’m good at it, but does it make me happy?

A similar act of self-assessment is needed to identify our true strengths. Tupper said that too often, individuals get trapped doing things that they are really good at but which don’t make them happy. Just as we can find meaning in an examination of our successes and failures, so too can we find significance by dividing the things we do well into two categories: things that drain your energy and things that give you energy.

“I have seen in my career and in the people who have worked with me … what I now think of as a strength trap,” Tupper said. “That is where people have something that they’re good at – which I think we traditionally call a strength – but every time they do it, it takes away their energy. The problem here is that when you have something that you can do, you’re good at, that other people see you doing, they kindly find other opportunities for you to use that skill you’re good at. The problem is, every time you do it, it takes your energy away.”

The myths and realities of confidence

Tupper acknowledged there is a plethora of advice from self-help gurus on how to build confidence. However, much of what these gurus are offering are really just “tips and tricks” that don’t really build a long-term, sustainable sense of confidence, something that Tupper says can build a belief in yourself.

“A lot of the work around confidence focuses on tips and tricks,” she said. “Are you wearing your lucky blue top, or how you stand or minimizing your ‘ums’ and ‘uhs.’ (These) tips and tricks can help them in the moment … but they don’t help you to build your belief. Belief is below the surface, it is about me feeling confident in my work and my worth. And you don’t sort that out with tips and tricks about your lucky top.”

After self-discovery, applying the tools of the modern career path

Tupper said she preaches four major tools that can be used to forge a career path that anyone can utilize at almost any time of their working lives:

  • There is the “obvious” career move, a variation on the traditional upward mobility approach where you follow a path with a series of fairly well-defined stages. 
  • Then, there is the “ambitious” move, where you focus on something completely new, a much more different or senior role, perhaps without knowing exactly how to get there. 
  • The “pivot,” where an individual chooses to move sideways within the same organization, or even back to a job or organization where you were previously employed. 
  • And the “dream” job, where we identify our ultimate career goals and start plotting a path to achieve them.

The key theme that connects all of these career plotting tools is “to be as open as possible,” Tupper said. 

“Careers are squiggly and that means they’re full of change, challenge, uncertainty, ambiguity,” she adds. “But, good news: they’re also full of opportunity and possibility. You can have a squiggly career that is individual as you are, where you don’t have to follow a ladder in somebody else’s footsteps. You can do you in your squiggly career.”

Ezra has redesigned leadership coaching for the digital age to transform your company’s workforce through affordable, scalable and high-impact solutions that promote equitable access through our world-class coaching app. Find out today how everyone can benefit from digital coaching.

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