The most profound life and career advice I’ve ever come across was an obscure letter written by Hunter S. Thompson to a friend asking him for life advice. Career advice is tricky because many people give tactical advice on how to navigate the future. If you’ve never heard of Thompson, he was a famous writer and journalist who was known for being unconventional throughout his life.

What follows are some thoughts from 22 year old Thompson who was responding to a friends request for life advice (you can read the full letter here). At the beginning he questions whether or not anyone is even qualified to give advice:

For to give advice to a man who asks what to do with his life implies something very close to egomania.

Thompson argues that all life advice boils down to swimming or floating:

And indeed, that IS the question: whether to float with the tide, or to swim for a goal. It is a choice we must all make consciously or unconsciously at one time in our lives. So few people understand this!

Ignore Goals & Design A Life That Aligns With Who You Are

He meanders a little and reflects on the fact that many people seem to get caught up in pursuing goals and re-shaping themselves to fit those aspirations without figuring out who they are and who they want to be at an essential level:

In every man, heredity and environment have combined to produce a creature of certain abilities and desires— including a deeply ingrained need to function in such a way that his life will be MEANINGFUL. A man has to BE something; he has to matter.

Put more simple, one must design a life they actually want to live:

In short, he has not dedicated his life to reaching a pre-defined goal, but he has rather chosen a way of life he KNOWS he will enjoy.

How should one do that? They should actively choose a path to follow. Instead of “swimming” they should find a path and follow it and learn from it. If they aren’t happy with the paths presented before them, they need to dream bigger:

Let’s assume that you think you have a choice of eight paths to follow (all pre-defined paths, of course). And let’s assume that you can’t see any real purpose in any of the eight. THEN— and here is the essence of all I’ve said— you MUST FIND A NINTH PATH.

Thompson says to “beware of looking for goals: look for a way of life” and I believe at its core, any career advice worth a lick start with advice on how to navigate life. Here are some advice I think is worth revisiting throughout your journey:

They don’t overly prescribe but identify things to avoid, systems to develop and highlights patterns to be aware of.

Scott Adams Talent Stack

Scott Adams argues that trying to be the “best” at one specific thing is a terrible career strategy. Being in the top 1% of a certain domain is incredibly challenging.

Instead, a better strategy is to try to become the top 25% in a number of areas of domain knowledge and expertise.

He uses the example of his own career where he doesn’t think he is the best at anything, but a certain combination of skills has led him to be a successful successful cartoonist.

Everyone has at least a few areas in which they could be in the top 25% with some effort. In my case, I can draw better than most people, but I’m hardly an artist. And I’m not any funnier than the average standup comedian who never makes it big, but I’m funnier than most people. The magic is that few people can draw well and write jokes. It’s the combination of the two that makes what I do so rare. And when you add in my business background, suddenly I had a topic that few cartoonists could hope to understand without living it.

One of the skills he believes everyone should develop is public speaking. Since so few people are good at public speaking, its pretty easy after some practice to be in the top 25%.

If you were trying to become one of the best coders in the world, it is going to be pretty hard and you’ll probably come up short. If you, instead, you focused on becoming a top 25% coder who can also work well with others, understand design thinking and knows how to build good PowerPoint presentations, you’ll probably have a lot of opportunities.

For Adams, the key is to always be adding to your stack to become less competitive with others and become one of a kind:

Capitalism rewards things that are both rare and valuable. You make yourself rare by combining two or more “pretty goods” until no one else has your mix.

Debbie Millman On Taking Leaps

Debbie Millman is a successful designer, lecturer, author and podcaster and has had a fascinating career which she detailed in an amazing interview with Tim Ferriss.

She shares how her whole life she had this dream of taking a more creative path in her career:

And here it was. This was the big decision of a life. Do I become the CEO and have this amazing continuation of money and career and security and everything else that is conventionally approved of, or do I say no, actually, I am not going to double down; I’m going to live the way in which I have been saying I wanted to with more freedom and more opportunity to do more personal projects, and pro bono projects, and give back.

She realized three things:

#1 Anything that takes months to decide probably is something you don’t want to do:

And I had to decide. It took me four months to decide. Simon Williams finally said to me, “Debbie, anything that takes you four months to decide probably means you don’t want to do it.” And it was the hardest decision of my life but I turned it down. I turned the CEO job down. And then, two things happened.

#2 There is never a “right time” to do something

if you’re waiting for something to feel right before you do it, if you’re waiting for a sense of security or confidence, that those things are sort of like being on a hedonistic treadmill. If you think you need enough of this before you do that, when you achieve whatever that is you think you need, you’re going to then up the ante and you’re never, ever going to be satisfied with whatever it is you think you need before you do something, if it’s not something that is real.

#3 Courage is more important than confidence

But in order to take that first step you need courage, and that’s much more important than confidence. So, for anybody who’s waiting for the confidence to show up, take the first step in a moment of courage, even if it’s aberrant courage, to come full circle in this conversation.

Marc Andreessen Guide To Career Planning

Published in 2007, he immediately argues against the notion of planning. with the warning that you can’t predict the future:

The first rule of career planning: Do not plan your career. You can’t plan your career because you have no idea what’s going to happen in the future.

Here are six takeaways from his guide

#1 Develop Skills & Pursue Opportunities: Similar to Adams, he suggests that people focus on “developing skills and pursuing opportunities” and that they should look at their career as a portfolio of different skills and experiences over a long time horizon:

Once you start thinking this way, you can think strategically about your career over its likely 50+ year timespan.

#2 Take Risks If You Have Big Goals: He also argues that people need to take risk and that if you have big goals, you probably shouldn’t prioritize a comfortable life:

The issue is that without taking risk, you can’t exploit any opportunities. You can live a quiet and reasonably happy life, but you are unlikely to create something new, and you are unlikely to make your mark on the world.

#3 Surround Yourself With “The Best”: One of the interesting arguments he makes is that you shouldn’t worry about being a “small fish in a big pond” – something Malcolm Gladwell argues against in his book Outliers. Andreessen feels you want to be in the “best pond possible” so you are surrounded by other curious humans:

Don’t worry about being a small fish in a big pond — you want to always be in the best pond possible, because that’s how you will get exposed to the best people and the best opportunities in your field.

He echoes the same advice for identifying which industry, city and companies to target in your job search:

Optimize at all times for being in the most dynamic and exciting pond you can find

#4 Learn How To Mess Up (Especially if you’re from an elite background): A bit of a warning for the types of people that were “tracked” from top school to top school and have learned how to be achieve and be successful by performing well in school, he advises getting exposed to “real world” environments where you can fail and learn.

If you have lived an orchestated existence, gone to great schools, participated in lots of extracurricular activities, had parents who really concentrated hard on developing you broadly and exposing you to lots of cultural experiences, and graduated from an elite university in the first 22 or more years of your life, you are in danger of entering the real world, being smacked hard across the face by reality, and never recovering.

#5 Work in industries where the founders are still engaged: If you want to be on the cutting edge, avoid companies that are run by 3rd or 4th generation managers

If not — if the industry’s founders are dead, or old and out of touch — beware. That industry is now dominated by companies that are being run by second or third or even fourth generation managers who inherited their companies pre-built, and are serving as caretakers.

#6 Target younger, higher-growth startups: These companies will offer more opportunities, challenges and autonomy early in your career and give you a strong reputation which you can bring with your to other companies.

Paul Graham’s “Do What You Love”

Paul Graham has an incredible collection of essays he has been writing for years that offer career, life and business wisdom. His essay “How To Do What You Love” is great for becoming more aware of some of the traps of career thinking and still offers a lot of wisdom more than a decade later.

His central message is:

To do something well you have to like it. That idea is not exactly novel. We’ve got it down to four words: “Do what you love.” But it’s not enough just to tell people that. Doing what you love is complicated.

#1 Beware of the fact that many people pretend to hate their jobs and not know why they do what they do: Graham shares a belief with me that many people seem to pretend to tolerate or enjoy what they do:

The main reason they all acted as if they enjoyed their work was presumably the upper-middle class convention that you’re supposed to.

He places part of the blame on the fact that our work beliefs are derivative – they are hand-me-down beliefs from decades, if not centuries ago:

Just as houses all over America are full of chairs that are, without the owners even knowing it, nth-degree imitations of chairs designed 250 years ago for French kings, conventional attitudes about work are, without the owners even knowing it, nth-degree imitations of the attitudes of people who’ve done great things.

#2 Beware of Prestige Warping Your Thinking: One of the things he calls out and one of the things I’ve grappled with personally is chasing prestige. I believe that we need to be more aware of the prestige hierarchies we play in and if we really want to be good at the things we get prestige from. For many, including me, prestige warps your brain early in your life as the fast path to social approval and sometimes riches.

Prestige is like a powerful magnet that warps even your beliefs about what you enjoy

#3 Would you do it if you weren’t paid?: Many people would likely not keep doing their work if they were not getting paid:

“The test of whether people love what they do is whether they’d do it even if they weren’t paid for it—even if they had to work at another job to make a living. How many corporate lawyers would do their current work if they had to do it for free…

#4 Your parents tell you to make money because they love you: Many people get frustrated by the narrow career advice they get from their parents (“be a doctor or lawyer”), but parents are likely on the hook if you go broke and don’t experience a lot of the upside (or misery) if you are making enough money to support yourself.

The advice of parents will tend to err on the side of money. It seems safe to say there are more undergrads who want to be novelists and whose parents want them to be doctors than who want to be doctors and whose parents want them to be novelists. The kids think their parents are “materialistic.” Not necessarily. All parents tend to be more conservative for their kids than they would for themselves, simply because, as parents, they share risks more than rewards. If your eight year old son decides to climb a tall tree, or your teenage daughter decides to date the local bad boy, you won’t get a share in the excitement, but if your son falls, or your daughter gets pregnant, you’ll have to deal with the consequences.

#5 There are two good strategies to molding work to fit your jobs: I love how he frames these two routes because they mesh well with how many people end up creating a life they actually want to live

1. The organic route: as you become more eminent, gradually to increase the parts of your job that you like at the expense of those you don’t.

2. The two-job route: to work at things you don’t like to get money to work on things you do.”

In addition to these, I’d probably add a third way which is to experiment with creating your own business after several years in the working world and embracing living cost arbitrage by living abroad or embracing minimalism.

#6 Find Jobs Where You Can Work On Many Things: While we may be pushed to pick “one thing” it can be beneficial to work in environments where you can work on many things:

to seek jobs that let you do many different things, so you can learn faster what various kinds of work are like

Overall, Paul Graham thinking finding work you love is damn hard:

It’s hard to find work you love; it must be, if so few do. So don’t underestimate this task. And don’t feel bad if you haven’t succeeded yet. In fact, if you admit to yourself that you’re discontented, you’re a step ahead of most people, who are still in denial. If you’re surrounded by colleagues who claim to enjoy work that you find contemptible, odds are they’re lying to themselves. Not necessarily, but probably.

Barry Ritholtz – The Learner

I’ve been reading Barry Ritholtz’s blog for over ten years and I love how he’s succeeded in a traditional field (finance) while following an extremely unconventional path. You can read his whole story here, but here is his

#1 Be multi-talented; Be genuinely interested in many things, including those that may not be related to your career;



#2 Work harder than everybody else (Coaches know that hard work beats talent most of the time).



#3 Find something you are good at, then hone that skill until its razor sharp;



#4 Read voraciously. Build a library, learn from the masters.



#5 Your academic background matters less and less the longer you are out of school.



#6 Create something of value that others want — and are even willing to pay for;



#7 Meet as many people in your field as you can. Learn from them, and when possible, be genuinely helpful.



#8 Develop a specialty.



#9 “Once in a lifetime” opportunities come along more frequently than you imagine; Be prepared for when those opportunities presents themselves;



#10 Be lucky.



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