Micro guide to seeking tailwinds

How can I increase my chances of experiencing good fortune and avoid making my life harder than it has to be?

Micro guide to seeking tailwinds
NY sailor / Kodak Portra 120mm

Focus on the tailwinds you already have

Tailwinds vs headwinds:

  1. Dwelling on headwinds – life's problems – is easy, but doing so can produce feelings of resentment
  2. Focusing on tailwinds – things that make your life easier and better – is hard, but doing so can foster a sense of gratitude

Why it feels hard to focus on tailwinds:

Focusing on existing tailwinds will likely feel difficult, because there exists what Davidai and Gilovich describe as a "headwinds/tailwinds asymmetry" in the way humans perceive life. Due to an availability bias, people tend to focus on their headwinds. "Barriers and hindrances command attention because they have to be overcome; benefits and resources can often be simply enjoyed and largely ignored" (Davidai and Gilovich, 2016).

How to focus more on tailwinds:

  • Routinely ask yourself questions like, "How have I been lucky in life?" and "What happened recently that made my life easier or more enjoyable?"
  • Keep a gratitude journal – this can be paper or the notes app on your phone

Recommended reading:

The headwinds/tailwinds asymmetry: An availability bias in assessments of barriers and blessings - PubMed
Seven studies provide evidence of an availability bias in people’s assessments of the benefits they’ve enjoyed and the barriers they’ve faced. Barriers and hindrances command attention because they have to be overcome; benefits and resources can often be simply enjoyed and largely ignored. As a resu…

Universities can provide tailwinds

Before you apply to a university, ask yourself if the school can provide you with meaningful personal and professional tailwinds.

Is the university's brand nationally or internationally recognized and respected?

The benefits of attending and graduating from a well-known and well-respected university are similar to those of working at a well-known and well-respected company.

  1. You get a brand name that can lead to valuable opportunities
  2. You get the chance to form relationships with smart, high-achieving people who can support you

The doors that can open for people with an elite degree range from landing a job that you are excited about to connecting with the potential life partner of your dreams. This happens, because the brand of the university you graduate from is a common cultural filter. "Harvard" will serve you much better than "Little known state school" on your résumé and your dating app profile. In a society with a lot of assortative dating, school brand matters.

Recommend reading:

"Assortative (online) dating: Insights into partner choice from an experimental dating app"

Pedigree
How social class determines who lands the best jobs

"Culture" can provide tailwinds

Before you select the socio-economic status and "culture" of your parents, ask yourself if either can provide you with meaningful personal and professional tailwinds. ...This is obviously a joke, but it is important to recognize the role "culture" plays in many competitive professional fields. Dr. Lauren Rivera explains this phenomenon in "Hiring as Cultural Matching: The Case of Elite Professional Service Firms":

"The fate of students with similar credentials in the competition for elite jobs was linked to their display of cultural signals; applicants whose experiences, leisure pursuits, and self-presentation styles matched those of employers could cash in these cultural similarities for jobs offering double to quadruple the salaries earned by other graduates from the same schools and for admission to a prestigious occupational group that serves as a gateway to the contemporary U.S. economic elite"

Cities can provide tailwinds

Before you move to a city, ask yourself if the city can provide you with meaningful tailwinds.

Is the city full of people who have achieved and people who are attempting to achieve the type of thing that I want to achieve?

Want an amazing career in tech or design? Move to SF. You can work at startups that succeed in other cities – I joined a bootstrapped startup in Washington, DC that grew to $100M in annual revenue over 10 years – but you won't benefit from tailwinds. My professional network and net worth are both smaller than they likely would have been had I lived in SF over the last decade.

Want to write, direct or star in feature films? Move to LA. You can possibly "make it" in New York, Atlanta or other cities, but you won't benefit from tailwinds.

Success stories like Michael Arndt, the screenwriter behind Toy Story 3 who stayed in New York after going to film school at NYU, are rare. Arndt points this out in an interview with Writer’s Guild of America East:

"It’s all out in Los Angeles, and I think I was lucky that everything was so cheap back then in Williamsburg. (...) I also went to film school in NYU and when I got out I was like, “Should I move to LA or should I stay in New York?” I chose to stay in New York in a weird way. I probably could have broken in a lot more quickly if I’ve gone to LA, but I don’t think I would’ve ever written Little Miss Sunshine."

Always keep in mind that people who succeed, despite strong headwinds, are extreme outliers.

Survivorship meme. Originally created for a web design presentation by Cameron Moll

Recommend reading:

Cities and Ambition
Essay by Paul Graham
Why Startup Hubs Work
Essay by Paul Graham

Companies can provide tailwinds

Before you join a company, ask yourself if the organization can provide you with meaningful tailwinds.

Is the company's brand nationally or internationally recognized and respected? If not, is it highly likely that it will be in the future?

The benefits of working at a well-known and well-respected company are similar to those of attending an Ivy League school.

  1. You get a brand name that can lead to valuable opportunities
  2. You get the chance to form relationships with smart, high-achieving people who can support you

The doors that can open for people that work for a widely-recognized company range from landing future jobs that you are excited about to connecting with the potential life partner of your dreams. This happens, because the brand of the company you work at is a common cultural filter. "Apple" will serve you much better than "Little known local business" on your résumé and your dating app profile. In a society with a lot of assortative dating, company brand matters.

Is the company growing quickly and significantly?

A growing company offers many tailwinds. The two that matter most:

  1. Professional challenges from which you can learn
  2. Opportunities to make more money, in the form of an increasing salary and rising equity value

The company growth tailwind is most important if a company is not yet very large or does not yet have a nationally or internationally recognized brand. Be wary of working for a growing company that lacks a widely-recognized brand, especially if equity is not part of your comp.

People can provide tailwinds

Before you continue to invest a significant amount of time in a relationship, ask yourself if the relationship provides you with meaningful tailwinds.

People who tend to provide great tailwinds:

  • A supportive partner
  • Supportive friends
  • People who are in the same phase of life as you who are doing similar things (aka friends and potential friends)

People who tend to create headwinds:

  • A cynical partner who is always critical and ridicules you
  • Cynical and critical "friends"
  • People who are not in the same phase of life as you who are not doing similar things

Not having a partner or friends also creates headwinds.

There are obviously exceptions to all of these examples. Use this information as a compass, not a strict guide.

Recommended reading:

Micro guide to making friends as an adult
How can I identify environments that are conducive to finding new friends? How many hours does it take to form a close friendship?

Good personal health can provide tailwinds

It is hard to improve your lot in life if you are unhealthy!

The guide below covers strategies to stay healthy and recover from illness using modern tools and knowledge.

Recommend reading:

Micro guide to health and longevity
“A healthy man wants a thousand things, a sick man only wants one.” – Confucius. How can I live a healthy life as long as possible? What modern services and tools are available to help me?