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

  - The Achievers Paradox

• The Nature of Leadership + Career

  - Sarah’s story

  - 6 reasons we fall into the Achievers’’ Paradox

  - 7 ways to leapfrog the Achievers Paradox

Illustration of the week

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The Nature of Leadership + Career

Sarah worked at a cutting-edge tech company, whose software is adored by everyone globally. She feels lucky and proud to be part of the company.  

When Sarah first started at her company, she got two big assignments. She poured her heart and soul into work, shelving her well-being, friendships, and family to impress her boss and coworkers with her high-quality output and pace of delivery.

Sarah was promoted within 6 months and was widely recognized as a high achiever.

Sarah loved the validation and the status. She felt she was invaluable to the company.

Yet, after some time, she began to struggle.

The more she impressed, the more people leaned on her for help. Her two projects morphed into 4 projects, running an Employee Resource Group, and leading a design community of practice.

At first, she went above and beyond, juggling it all. She sacrificed personal time and relationships to keep up her quality and pace.

Then, her health began to crumble, along with her ability to excel at any task, let alone keep up.

She stopped being invited out by her friends to social events because they knew she would say no. Her relationship with her family and partner were also strained.

Sarah started dreading going to work every Monday and she regularly dreamed about ways to escape.

Sarah might be a fictional character, but her story rings true for many. It was once mine in my early career, and I've heard it from countless readers and the women I've coached.

This often results in one or more of:

• Burnout

• Feeling stuck

• Impostor Syndrome

• Heightened self-doubt

• Increased depression / anxiety.

The question is why did Sarah / why do we let it get to this stage?

6 reasons we fall prey to the Achievers’ Paradox

1. Unclear ambition or definition of achievement

It’s funny how high achievers like Sarah have never clearly defined what success or achievement means to them. Sarah assumed it to be title, salary, and financial flexibility/purchasing power. So she strived for more and more but was not quite sure to what end. Ambition and achievement are not dirty words. They are, however, murky words if you haven’t taken time to define what they mean for you.

2. People Pleasing / Fear of saying no

When we aim to please others, we give more of ourselves because we are afraid of losing something; respect or a reputation for fear we will be seen as uncooperative or unhelpful, opportunities for career advancement or even our job security, the approval and validation from our boss and colleagues. This drives people pleasers to be eager to please, even if it means overcommitting themselves.  

3. Shiny object syndrome

I raise my hand for this. For me being around new innovative projects, ideas, and possibilities is like being a kid at a candy store. I want to do it all. Many of us have this personality type / working style preference. We love variety and having fingers in many pies. We take on more than we can deliver without trading off other important parts of our lives.

4. Pitfall of self-doubt: Overachievement

Ironically individuals who excel the most also tend to have elevated levels of fear of failure. They try to “cover up” their perceived lack of competence by putting in extra effort to ensure success. Ironically this strategy also perpetuates self-doubt as they may attribute our success to our extraordinary effort rather than our inherent abilities.

5. An organizational culture of “up or out”-high achievers

When I worked in management consulting, the “up or out” model was an unwritten law. If you weren’t striving to be promoted and achieve, you were either managed out or put on mundane projects.

These cultures can exacerbate toxic competitive behaviors and fear-based motivation to keep climbing the ladder. This environment prioritized the longevity of the organization’s profit over the longevity of your career and wellbeing.

6. Diversity and Inclusion imbalance

In her book “Becoming” Michelle Obama highlights the familiar adage within communities of color: "Work twice as hard to get half as far." This saying resonates with individuals identifying as female, gender-neutral, people of color, and those who are neurodivergent for two key reasons:

a) They often contend with unconscious biases and organizational structures that require them to exert extra effort to gain recognition.

b) Even in organizations without explicit bias, the perception of needing to work harder due to their identity can motivate them to put in additional effort.

7 ways to leapfrog Achievers’ Paradox

1. Design your ideal work and lifestyle goals / north star for a given period of time (e.g. 1 – 2 years). Use these as a litmus test to also accept or deny new opportunities which you feel tempted or obligated to achieve in.

2. Identify your top 3 personal values, then use them as a way to guide whether you will accept or deny new opportunities.

3. Practice saying “no” in different ways

This includes practicing saying no to yourself for shiny object syndrome.  Often, we fear saying no because we don’t know how, or worse we have tried saying no to someone by saying “No I can’t do this” and they react badly, especially if they are in positions of power.  

4. Consider each hour of your time is billable to yourself

Typically, in a job, you allocate 8 hours a day of your time in exchange for your salary and benefits. However, when your organization requires an additional unit of your time or someone in your personal life asks for a favor, consider the following:

1. Ask yourself whether you're doing it to satisfy your own desire or to prove something to others.

2. Reflect on what you gain from this action, whether it's monetary compensation, personal satisfaction from helping, or nothing at all.

3. Evaluate what you're sacrificing by giving up this unit of time, such as your personal time, time spent with loved ones, sleep, or your mental and physical well-being.

4. Finally, determine whether the trade-off is worth it, answering with a clear "Yes" or "No." If you're uncertain, return to the first point.

I acknowledge that this approach may seem overly transactional when considering your time for yourself, for work, and with loved ones. However, it's a method that helped me value each hour of my time as much as I did when billing hours to clients as a consultant. Ultimately, the end result is anything but transactional; it's about making conscious choices that align with your priorities and well-being.

5. List your top five work boundaries related to time and effort.

More importantly, outline a plan for how you will uphold these boundaries, especially when faced with irrational thoughts and fear that may entice you to disregard them.

6. Understand your organizational system 

Are you being lured into pushing yourself harder and aiming for greater achievements within the confines of a golden cage?In the tech sector, this may manifest as intensifying efforts and focusing on accumulating equity before a company goes public. In different industries like consulting, it might involve rapid promotion cycles and bonus structures.

Choose if and how you play the game.

7. Understand the Diversity, Equity, and Inclusion imbalances in your organization.

Distinguish between the actual imbalances that exist and those rooted in fear or past experiences. Gain a clear understanding of what success entails for someone in your diversity demographic.

Then, ask yourself if you are willing to exchange your billable hours for this pursuit. If your answer is yes, revisit point 1. If not, it may be a good time to explore organizations that provide a more conducive environment for your growth and well-being.

❓️ Have you experienced the Achievers Paradox in your own journey? Reach out and let me know.

If you are going through a career or leadership transition and would like to discuss coaching support.

Find out more about me here.

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

• Can a little self doubt be useful?

• Part 1: Why we don’t like going backwards in our careers

• Part 2: Backwards or Backloop - Why we don;t like going backwards in our careers

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