Headwinds and tailwinds: A framework to build empathy

Cartoon of two cyclists going in opposite directions. Over one of them, there is a smiley sun, whereas there is a cloud blowing air in the direction the other cyclist is going.

Remember last time you were faced with strong winds against you whilst cycling or walking? Probably yes. And tailwinds, i.e. winds that helped you to progress faster? Probably not.

In their scientific article The headwinds/tailwinds asymmetry: An availability bias in assessments of barriers and blessings, Shai Davidai and Thomas Gilovich used headwinds and tailwinds as a metaphor to explain our perception of advantages and disadvantages that we face.

As any cyclist or long-distance runner will attest, combating a stiff headwind is a challenge—often an annoying one. The wind is literally in the athlete’s face, calling attention to itself, and leading to thoughts about when it will die down or when the route might change direction. There is considerable relief when that happens and the wind is at one’s back, but it’s a relief that’s short lived: One quickly adapts to the change and soon no longer notices that there’s any tailwind at all. By their very nature, headwinds are more salient than tailwinds.

What is literally true about headwinds and tailwinds in athletic pursuits is metaphorically true in countless other contexts in everyday life. Because we have to attend to the barriers we face to overcome them, they tend to stand out more than those things that give us a boost.

Based on seven different studies, the authors reported that

  • We all take disproportionate note of the barriers we face compared with the benefits we enjoy.
  • We believe that the challenges we experience are harder than those faced by others.
  • Because headwinds can be interpreted as being treated “unfairly”, we may be more prone to endorse questionable behavior.

In summary, as we remember more intensely the barriers (headwinds) we face than our blessings (tailwinds), we assume that other people have it easier than us. This may lead to resentment and make us more open to considering questionable practices for leveling the playing field.

The authors advance that the headwinds/tailwinds asymmetry may (a) explain our resistance to feel gratitude for our blessings as we focus on our challenges, (b) impact policy interventions (e.g. developed countries underestimate their historical advantages and downplay the hardships other developing nations may have faced), and (c) affects the economic discourse (e.g. highlighting U.S. as the land of opportunity often disregards the role of tailwinds such as access to education, syndicates, transportation, infrastructure, national security, subsidies).

In my opinion, the headwinds/tailwinds asymmetry also plays a key role on how we judge initiatives to address systemic and historical biases against outgroups (women, non-white, non-cis, LGBT, non-christian, etc…). For example, consider the backlash women and minority quotas receive on the premise that discrimination cannot cure discrimination, whilst the advantages enjoyed by the ingroup members such as mentors, inner networks, sponsorships, family support, and other preferential treatment are disregarded. As Nancy DiTomaso outlines in The American Non-Dilemma

the white people she spoke with tended to consider it unfair for blacks to be chosen just because they’re black (and for women to be chosen just because they’re women). Yet, she says, “in the same conversation, they revealed all the special help they had gotten in their own life stories.” Many whites, she observes, consider affirmative action a policy where minorities and women are “cutting in line.” DiTomaso adds that she listened to multiple life stories of whites indicating that “friends were essentially saving them a place in line. Somehow, they didn’t think of this as unfair. They thought of it simply as someone helping them.”

In other words, the groups that benefit from the status quo are oblivious to the advantages they have whilst they are hyperaware of the limitations they face. What’s more, they may feel so disadvantaged that fail to empathize with the adversities of the outgroups and undermine any efforts to improve their odds.

What can we do to mitigate the influence of the headwinds/tailwinds asymmetry on the lens we use to see the world? I believe we can start by critically analyzing our blessings/barriers story (individual level) and closely monitoring the progress of women and minorities (systemic level).

Assessing individual headwinds and tailwinds

Inspired by Vernā Myers’ What if I Say the Wrong Thing?: 25 Habits for Culturally Effective People and Dolly Chugh’s The Person You Mean to Be: How Good People Fight Bias, I created my own tailwinds/headwinds tally in the context of the region I live in.


   Tailwinds  (Advantages)

Headwinds (Barriers)
Gender: Woman   x
Ethnicity: Caucasian x  
Physical and mental ability: Able-bodied x  
Socioeconomic class: middle class x  
Allien status: Immigrant   x
Religion: Christian x  
Education: University level x  
Sexual orientation: Heterosexual x  
Age: 40+   x

The exercise was a revelation. To my surprise, the list of the “advantages” largely surpassed that of the “barriers”. Definitively, the conscious work of writing them down told me a different story about myself.

Did I feel resentful as some of the research above may suggest? Curiously, I felt grateful for my tailwinds and more empathic towards those experiencing more/different headwinds than me.

Monitoring women’s headwinds and tailwinds

With so many initiatives aimed to foster diversity and inclusion both in the workplace and worldwide, as well as the progress in the last century (end of segregation in U.S., women’s vote), it is tempting for advantaged groups to resource to the meritocracy narrative and disregard their “opportunity hoarding”.

My take? Let the statistics do the talk. With that aim, I’ve created the infographic It’s a girl in decades, which aims to showcase the still very strong headwinds/tailwinds asymmetry for women through their life in terms of education, health, finances, and work.

What are your headwinds and tailwinds?

What key women tailwinds and headwinds am I missing in the infographic?

Acknowledgments: Thanks to Professor Thomas Gilovich for sharing a copy of the article The headwinds/tailwinds asymmetry: An availability bias in assessments of barriers and blessings by S. Davidai and T. Gilovich. You can see an 11-min video summarizing key findings here.

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 In 2022, I coached 5 women and nonbinary people that got promoted.
 In 2023, my goal is to coach another 50 to get the promotion they deserve!
What am I doing towards achieving my goal? I’m running again the Joyful Annual Career Assessment Week in February, after the sucess of the first edition in January. This is a one-week event from February 13th to February 17th where I help women and people from underrepresented groups get a clear picture of their professional accomplishments in 2022, tell their career story in a compelling manner, and be ready to discuss their career aspirations for 2023 and beyond.

You’ll get:

  1. 20+ page workbook to walk you through the steps to write your 2022 career review.
  2. live pop-up private online community group from Monday 13th to Friday 17th February where you can get feedback on your assessment and support.
  3. Access to three one-hour group virtual coaching calls via Zoom during the week.


“Patricia talks about how to frame our accomplishments without seeming arrogant, declare our desires in the professional sphere, and get managerial support for them, and learn about how to advance, despite upbring that may teach us to downplay our skills and contributions. It is amazing!

I wish I had learned this in my 20s- my career path would have been different, and I would have known the invisible rules, so that I could advance in the way I wanted to!”

VHA, Director, Business Development

 Benefits others have gotten from working with me:
 –  Get a clear picture of your professional accomplishments in 2022 as well as the skills and experiences gained.
 –  Ability to tell your career story in a compelling manner that it’s also true to yourself.
 –  Feel ready to have meaningful conversations about your career aspirations in 2023 and beyond.
Come and join us!

5 thoughts on “Headwinds and tailwinds: A framework to build empathy

  1. Pingback: Leadership Musings – God Dammit Billa

  2. Megan

    In summary, as we remember more intensely the barriers (headwinds) we face than our blessings (tailwinds), we assume that other people have it easier than us. This may lead to resentment and make us more open to considering questionable practices for leveling the playing field.

  3. kim fogel

    Its another good tool to use just like the privilege walk to help us understand what something actually feels like

  4. Vivian Hu Adams

    Brava!Well done !Very interesting, nice personal analysis about personaldemongraphocs,  and thought provoking!I like it!Viv x Sent from my Samsung Galaxy Note 9 – Powered by Three


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