Headwinds, tailwinds



By Caitlin Kelly

As an official #avgeek, who thrills to the sight of any aircraft and loves the smell of JP4, aka jet fuel, I often think in/use aviation metaphors.

Last week I had a long heart-to-heart with a dear friend, a much younger woman still in her 20s. She’s feeling stuck and frustrated, and has had a family tragedy hit her as well. It’s a lot!

When all those around you look like they’re making much faster progress towards personal and professional goals — marriage, kids, buying a home, getting a job or a promotion — it’s so easy and so demoralizing to feel left behind. Even at my age, decades into a good journalism career, I still gnash my teeth and rend my garments when I see other writers winning big awards and fellowships and fancy book and movie and TV deals.

Envy is also a fairly human emotion.


I also subscribe to the belief that, just as some flights go much more quickly thanks to a tailwind and some more slowly thanks to a headwind, so do our lives.

And many of the obstacles and many of the privileges (head/tailwinds) also remain invisible. 

And in American can-do, individual, no-social-safety-net culture, it’s completely normal — and really bad for your psyche — to blame only yourself. If only you had done X! Or didn’t do Y! So and so did Z and look at their success!


We just don’t know, unless someone is completely candid with us, what tremendous advantages or disadvantages they have had to overcome or enjoy. It’s rare that we compete on a level playing field.


Headwinds can include:


Chronic illness

Mental illness

Serious illness

Acute illness/recovery — or any of these for a loved one








Lack of skills

Lack of access/income for training

Solo parenting


Poor access, or none,  to transit/transportation

No medical care


Lack of education and access to same

Race, gender, ethnicity, religious prejudice


Becoming a crime victim

Emotional or physical or sexual abuse



Luxury itself is a tailwind



Inherited money

A high-earning spouse or partner

A safe, green and attractive home and neighborhood

Wealthy parents or grandparents offering money

Excellent health

Excellent education

Fluent English

Excellent work skills

Successful legal role models

Wise, kind, reliable people to turn to for help and advice

Secure housing

Secure employment

Secure non-work income, like a pension or other solid investments

Social capital, i.e. knowing people with power who will help you

A sense of self-confidence

A safe and reliable vehicle or ready access to safe, affordable, reliable public transit

People who actively love and check in on you

Solid, strong friendships


So I told my younger friend it was necessary to see her life differently, even though the tragedy is permanent and life-altering and no one seems to understand its effects, which also leaves her isolated.

I know the choices she’s made were risky and unconventional — and I admire all of them, for her guts and sense of adventure and all the skill and wisdom they have brought her.

And I told her how much I admire her.



malled cover LOW


I worked retail for 2.5 years, a day a week for The North Face, and made $11/hour, from 2007 to 2009. It was a tiring, poorly-paid, emotionally-taxing and unrewarding job in most ways.

We needed cash. It offered steady, reliable cash. And I was not a teenager, far from it — in fact the oldest person of our 15-member staff.

How I felt about it was irrelevant to getting the damn job done.

It ended up becoming my second book, but none of that appeared likely to me until September 9, 2009 when we had a major publisher committed.

The 2008 crash was very much a headwind, and a shared one.

Now, 12 years later, we’re all screwed thanks to the pandemic — with only the wealthiest and healthiest feeling no/few headwinds.


The rest of us will have to fly onwards as best we can.



9 thoughts on “Headwinds, tailwinds

  1. Oh, this is lovely. Spot on. And I think you’ve helped me identify what I still struggle against. It’s always odd to me how some people seem to glide through, with very few challenges. And others of us signed up for the Masters class, replete with obstacles. That young woman is lucky to have you. One of these days, we have to have our own virtual chat with a cocktail. I have a feeling we’d have much to share . . .

    1. Let’s!

      For sure.

      What social media has much exacerbated is the crowing and bragging about success — when we never see what underpins it and eases it. Americans are taught that ONLY individual effort counts — and don’t ask for help!!! — which really hurts a lot of people who then just assume they’ve screwed up when the system itself (plus others’ invisible tailwinds) may have much sped their competitors’ trajectory instead.

      I arrived in NYC w no U.S. — even NYC!– job or American education on my resume in recession. I had NO idea how hard it would be without those two things to start with.

  2. it is always so good to stop, take stock of things, and consider them from the perspectives of others. you gave your friend excellent advice, and you are lucky to have had a bit of life and experience behind what you say. the older i’ve become, the more aware i am of this, and wish someone had clued me in when i was younger, but i may not have listened. each of us has a story, with ups, downs, shortcuts and blockades, which lead us one way or another. we cannot presume to know what a person has walked through unless they offer it, so it’s important to consider things before judging, comparing, or jumping to conclusions.

    1. In our industry, especially, there are people whose career takes off like a rocket and you think….why? Yes, some of it is envy but some people are massively connected and get a lot of breaks and opportunities we never even know about.

      So you have to just enjoy your journey and keep making course corrections.

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