Overcoming career milestone shame

Wednesday, January 18, 2023

Women have been reflecting and personalising their individual life progression milestones in terms of marriage and motherhood over the last few decades. Since the days societal expectations designated their twenties towards finding a partner and bearing children, many more life paths have gained popularity and societal acceptance in many cultures.

Where career milestones are concerned, however, many women still feel disappointed or guilty for not self-actualising by a certain age. These milestones can include starting one’s own business, earning a particular promotion, building a strong or professional network, or establishing a certain reputation in a particular field. We look at some of the aspects that may be holding you back and how to break free from career milestone shame – whatever your age, and wherever you are in your career.

Table of contents

  • Letting go of guilt
  • Ditching career envy
  • The deadline effect and the power of starting
  • Conclusion

Letting go of guilt

When women feel like they are personally responsible for not progressing to a certain level by a certain age, they can struggle with guilt around some of the personal choices that led them to a career-limiting employer or role, believing their lack of aspirations are at the core of their inability to achieve excellence. The reality is, however, that the gender gap, societal expectations around motherhood, ingrained beliefs and stereotypes around gender roles are all contributing factors in a woman’s career trajectory. In her book, In Search of Silence, author and journalist Poorna Bell offers the following validation: “Even when it comes to your career, you can graft and work hard, but being given certain opportunities still depends on so much that may not be in your control.”

One such example of not being in control of one’s own professional destiny due to external barriers is the gender gap in tech; a 2021-report by Deloitte Global cited a 2-percentage point increase of female representation in the tech industry from 2019 as notable progress: “Moving the needle is difficult, and even aggressive campaigns to recruit, hire, retain, and promote women have been found to work slowly.”

Also of note is the phenomenon referred to as ‘The Broken Rung’, which refers to the difficulties women face at the very first steps of the corporate ladder: the initial promotion to management. According to research by McKinsey and Leanin.org, this is an even bigger obstacle to women’s progress than the glass ceiling. A more recent article by MicKinsey affirms that many leaders still acknowledge that their companies have uneven early-promotion processes that perpetuate the broken rung on the career ladder for women in technical roles.

Both examples provide a welcome relief to personal feelings of guilt for not achieving more by a certain age. It should also prompt women in STEM fields to pursue opportunities that can help elevate their individual careers and help address these systemic issues for future generations.

Ditching career envy

“To succeed in a competitive world, it’s only natural for us to benchmark our progress against the people around us,” writes executive coach and Harvard Business Review contributor, Nihar Chhaya. But in a gendered industry, there can be increased pressure to compete with other women for available positions. This phenomenon commonly referred to as ‘career envy’, can hold us back and prevent us from reaching our full potential.

A CNBC article by Mollie West Duffy and Liz Fosslien offers valuable advice for navigating career jealousy to your advantage, and a helpful tool is to ‘Piece together the footage of one’s highlight reel’. When you feel envious of a co-worker or manager's successes, ask yourself whether that person is struggling in some unseen way, reflect on what you are proud of about yourself, and what you have that others might feel envious toward.

The Rightbrains platform is passionate about sharing the stories of formidable female leaders and provides a safe space for connection with female peers in the digital technology industry. It's easy to fall into the trap of comparing ourselves to others and feeling resentful of their successes, but this negativity can only hold us back. Instead, we need to shift our focus and celebrate our own wins and accomplishments – in addition to celebrating the female role models in the digital and technology fields and reaching out to those who hold positions we aspire to. Nihar Chhaya agrees with this strategy: “To keep comparison from becoming self-defeating, get curious about why someone triggered it for you and explore how their journey may teach you something about your future path, instead of assuming that their success somehow negates your chances.”

The deadline effect and the power of starting

An enlightening article by Rachel Syme, staff writer for the New Yorker, paraphrases the gist of The Deadline Effect, by author Christopher Cox: “We often summon the will to do our best work when we think we’re down to the buzzer—but by then it’s too late to actually do it. It’s only by mentally manipulating ourselves to act early and often that we can ever do spectacular things.”

Syme’s observation is not so clear-cut when retirement is the deadline in the analogy. In a RightBrains role model story about Karine Halimi-Guez, Vice President-Head of Tax at Booking.com, she mentions that women can do their best work from their forties onwards. It’s a welcome thought to women who are raising families and bowing out due to familial pressures during a specific life phase, but it is also good to know that platforms like RightBrains, training and mentoring programmes, and coaching techniques exist to support and empower women wherever they are in their careers. Instead of giving in to the anxiety of achieving a goal by a certain age and viewing milestones as ‘deadlines’, rather assess where you are in your own life and career and utilise those tools to get started where you are right now. It's never too late to find our unique path and reach our goals. The key is to have motivation and support.


Even though society has become less pragmatic in its thinking around women’s life goals and aspirations by age, women still experience guilt and envy where their professional and career milestones are concerned. Career progress, however, is unique to every women’s circumstances, life phase and industry – and not just a reflection of their ability and ambition. In 2023, women in the digital industry should challenge themselves to reflect on their own needs and aspirations while engaging with empowering platforms like RightBrains and celebrating the successes of peers and mentors to benefit the industry as a whole.

By Carine du Pisanie

Carine du Pisanie is the Content Manager and Editor at RightBrains and has a keen interest in organizational culture and creativity in the tech sector and beyond.

Carine du Pisanie is the Content Manager and Editor at RightBrains and has a keen interest in organisational culture and creativity in the tech sector and beyond.