The Nature of Leadership and Career

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The Nature of Leadership and Career is a weekly newsletter where I provide 1 illustration and ~3 ideas to help you connect to your career, leadership, or work journey more naturally.

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Today at a glance

• Illustration of the week

  - Let go of this career mental model

• The Nature of Career

  - 5 cognitive biases that explain why we don’t like going backward

  - What does going backward in your career actually mean?

  - How has society and organizational culture shaped our thinking about career trajectory?

Illustration of the week

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The Nature of Career

“I don’t want to go backwards.”

If you have thought this, you’re not alone. It is one of the most common phrases I hear from coaching clients, friends, and family members.

I too used to feel like this and sometimes I can still slip into this thinking, from time to time.

For the most part, I have reframed my uni-directional thinking about career progress by thinking through the following questions:

❓️ What does backward even mean to me?

❓️ Why don’t I want to go backward?

❓️ Why do I view career progress as forwards or backwards?

What does going backwards in my career mean to me?

Take a few moments to think about it now.

*

*

No really.

*  

What did you come up with?

Most likely these were part of your top reasons:

Loss of momentum/status in:

• Title

• Salary

• Prestige and work/lifestyle opportunities this affords us

• The admiration or respect from friends, family, and randoms.

Why are these reasons for avoiding career regression so common?

5 cognitive biases that explain why we don’t like to go backwards in our careers

1️⃣ Sunk Cost Fallacy

We are reluctant to abandon our current career trajectory (even if we don’t love it) due to the time, effort, and resources we've already invested, even when changing course is more beneficial.

2️⃣ Aversion to Loss

I write about this bias nearly every two newsletters because it is so deeply ingrained into career transitions. We fear the pain associated with losing twice as much as the pleasure of gaining.

3️⃣ Ambiguity effect

We avoid career options where we don’t have all the information or that seem ambiguous. We are more likely to select an option where the probability of achieving a certain favorable outcome is known.

4️⃣ Status Quo Bias

We've achieved a certain level of success or recognition in our careers, going back to a previous stage can feel like a loss of prestige and comfort.

5️⃣ Fear of Judgement

We're afraid of what others will think when they see us taking a different path or reevaluating our choices. This fear of judgment often holds us back from making brave career adjustments.

💡 None of these cognitive biases are “right” or “wrong”.

❣️ There is no need to feel shame, guilt, or self-judgment.

✅ They are useful to be aware of as a checklist to see what might be lurking beneath the surface of your consciousness informing your decisions.

🧠 For psychology nerds this is one of my favorite websites on cognitive bias and decision-making: The Decision Lab

How do organizational culture and society shape our thinking about career trajectory?

Our inner world is often shaped by our outer world and the norms we have learned from our families, countries, and societal structures at large.

Here are 2 obvious + 1 non-obvious reason for the ways our thinking on career has been shaped:

1️⃣ The Careers Ladder mental model – the idea is something that we need to continually climb up.

The idea of the career ladder rose in the 1950s – 1960s when you joined a company at an early age and progressed up the ladder until retirement. This slowed down in 1980 with the trend of organizational downsizing. Unfortunately, the prevalence of mental models and outdated HR practices remain in a lot of companies.

2️⃣ Organizational cultures that marry progression with promotion.

In larger cutthroat companies this is known as the up or out model. If you not working hard enough to move up – you know where the door is.

In smaller tech scale-ups, especially in hypergrowth, it’s the fear of not working hard enough or quick enough that you will be leveled by someone more senior.

3️⃣ Games

The world of work is much like a game. The board and video games that were prevalent in society before the 2000s were largely 2D and uni-directional. e.g. Super Mario Brothers, The Game of Life.

Any time they were bi-direction you were penalized for going backwards e.g. Snakes and Ladders, Monopoly “go directly to jail, do not pass go, do not collect $200.”

Games these days are often non-linear. You choose your adventure, there are multiple pathways and non-linear endings based on the decisions you make e.g. Fallout.

If you have any more ideas, I would love to hear from you as I continue to explore this intriguing topic.

So what now?

I leave you with this quote and the promise that next edition we will look at practical ways to reframe and address multi-directional movement in your career.

🤝 If you would like to explore how you confidently navigate your career path

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Catch up on recent issues of The Nature of Leadership + Career

• What bold career moves are you avoiding?

• Leader As Gardener. 2 Steps To Help Employees Find Their Roots And Thrive

• "It's not me, it's you". Gaslighting - the corrosive organizational disease

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