Review & Rating: 8/10

I should begin with the caveat that this book, like all books, should be read when the pull becomes too great to resist. Despite being a big fan of Pressfield’s War of Art, I didn’t pick up this sequel up right away. It turned out I would wait a few years.

The book is as the title suggests. It’s for creators who want to read about turning into a professional. For me, it was specifically about writing. Given Pressfield’s career as an author, that was the primary example throughout.

Turning Pro made its way to my Amazon cart half a dozen times until the inertia was too great and I finally needed to read it. I find that’s the only way to read books. At least, if you want to enjoy it. But I don’t know why people — those pat high school English— would read book for any reason beside enjoyment. I say this because for anyone that doesn’t feel the inevitable pull to read books, particularly ones that are nuanced as this, you will feel shortchanged.

I rated this book highly because it was useful to me when I needed it. At the end of it all, this book helped me take one more step towards the adventure I was afraid to go on but felt I needed to. I don’t think this is a how to book. I think it’s a book that calls out all the things you know you are guilty of. You just won’t listen to friends and family saying it to you and your introspective sessions end in denial so you need Pressfield to point it out. For him to act as a friendly bullshit detector if you will.

I noticed from reviewing the book that it’s possible to think "turning pro" is some switch you turn on. My experience is that it’s not. Months after reading the book, I still find myself committing crimes of the amateur. That’s where I’m convinced turning pro is an iterative process. The mindset shift is a start. But everything else happens slowly as one executes. There’s no change without execution.

Book Notes:

The human condition is our disposition to hate what we see in the mirror. I am my worst boss. Until a robot is able to hate its own reflection, it won’t have achieved humanity.

The human condition that ails us isn’t an illness or moral problem. It’s the pain of living as an amateur. Becoming a professional is free. It’s a mindset shift. But it has costs.

Costs like comfort. Giving up on everyday leisures, friends and relationships. It’s free to turn pro but sacrifices must be made.

Turning pro is how we earn self-respect. We are really becoming who we always were but were just afraid to embrace publicly.

Listen to that quiet voice, the spirit that tugs at your sleeve to do the things you know you should be doing. It’s not necessarily something that’s always fun. It’s something that’s difficult to do but you can’t help feeling like you have to do it.

People will pursue shadow careers because they’re too afraid to pursue their real career. An example is the guy who wants to be a screenwriter who will choose to be a lawyer in the entertainment industry. Law is the shadow career.

Working for a business news company when what I wanted to really write about was exploring humanity through travel could be an instance of a shadow career too. Look at the metaphors for clues to your true calling. After working in four different career fields…..I’m finding a constant theme around a curiosity with people and introspection.

It’s worth thinking about how we might sabotage ourselves by pushing down deeper into our shadow career so we can tell ourselves all kinds of excuses of career capital, family obligations, etc. Such self sabotage is the same ailment of self disgust at not following through on becoming a pro at what you really should be doing.

Becoming a pro means growing up. But that requires hitting bottom. To hit bottom you need to fall and that can be a long ride. It’s not supposed to be a 3 month find yourself powwow. It can take years or decades and it can lead to losses in finances, relationships, etc. It’s supposed to be hard. That’s why most people are amateurs. They might’ve aged biologically but they are still youths who’ve run away from the truth.

Remember that life is strange and things work out in weird ways. You won’t find out though unless you take the leap to turn pro.

Forced rationalization of the apparently irrational will drag you down the shadow life as well. It’s like trying to justify a writing career in the confines of an HR position in a tech startup. Be aware of the rational mind.

The difference between the pro and amateur are his habits. A pro has professional habits. It’s all about what you do. Execution is everything.

People think artists are addicts. Addicts are amateurs. An addiction is a distraction that stops you from doing the work. Addicts and artists appear in the same grouping because they are both trying to grasp the difficult topic of humanity. I’m reminded of Stephen King who said an alcoholic writer is just an addict and nothing more. It has nothing to do with being a writer.

The amateur takes pleasure in broadcasting his life as the starving artist. The pro quietly does the work. The pro’s life is simple in he has accepted what he is doing. The pro is focused on producing for the community and not filled with an obsession with the self.

Remember that addition replaces aspiration. We are what we repeatedly do. Being an addict takes away from doing what we should be doing as pros.

Use your addiction as another guide to what your subconscious is telling you. Examine the addiction and what led to it. Not all addictions are bad. Some are metaphors to be heeded. It’s the ones that become distractions that we need to avoid. Consider how my addiction to powerlifting is what my subconscious is using to communicate with me.

It’ll be hard. It’ll be tough. It’s not for everyone. Don’t quit.

Keep in mind one can be addicted to failure. It’s another form of self-sabotage. By failing, we are off the hook. We’ll use it as an excuse to give up.

Whether it’s addiction to sex, money, trouble or failure, they are all means of distraction so we can avoid doing what we should be doing. A pro needs concentration and depth. Distractions are the antonym of deep work.

Pressfield’s moment of turning pro is a story worth reading again. At 31, he moved to a small town with no TV, radio, music, sex and sports. He ate the same thing every day, wrote in the day and read every book one should read (i.e. Tolstoy, Dostoevsky). His first book didn’t get published so he got a job in advertising to make enough money to quit and go back to a little town to write. That too didn’t work so he worked as an apple picker. The cycle continued. He also wrote nine screenplays that were never picked up. He eventually sold his first screenplay for $3,500. But it was the first year when he sat down and did the work that he turned pro.

Turning pro is scary. It requires standing up to do what you believe is your true calling. Most people can’t bear to see themselves fail at that so they’d rather be an amateur. It feels okay to fail as an amateur because you can just pass it off as something you didn’t take seriously. You can pass it off as “oh if I had the time I’d pursue it fully”. But deep down the amateur thanks god that he doesn’t have to put himself in the arena. It’s this fear of having to live up to who he is that the amateur is terrified with.

“The amateur is a narcissist. He views the world hierarchically. He continuously rates himself in relation to others, becoming self-inflated if his fortunes rise, and desperately anxious if his star should fall.”

The amateur is obsessed with living in compliance of the opinion of others. He’s obsessed with looking, thinking and behaving as others expect he should. This is no different from trying to fit what you’re trying to do into a box that makes sense for others. It feels easier but it isn’t and it’s undoubtedly the wrong path.

Becoming yourself means divulging from expectations of the tribe. Most people think they can’t survive without their tribe. But they’ll find another.

Self compassion is the first step to turning pro.

Stop living in the past. The amateur gets trapped in the highlight reel of the past that wasn’t even real. Should’ve, would’ve and could’ve are a waste of time. Move on.

“The payoff of living in the past of the future is you never have to do your work in the present.”

Now. Not Tomorrow.

“The sure sign of an amateur is he has a million plans and they all start tomorrow.”

“Only put off until tomorrow what you are willing to die having left undone.” - Pablo Picasso

When you hit bottom, there is only yourself. Don’t wait on permission. Don’t give power over to others. Don’t idly sit waiting for that email or phone call.

Self-awareness is required to turn pro. That’s how one starts to define the self. Defining the self will set you apart from the tribe. The amateur is afraid of that.

The truth is: “There is no tribe, and there never was. Our lives are entirely up to us.”

It takes courage to listen to what’s being said. To listen to what you’ve been ignoring in the name of rationality. Listening is the beginning of the iterative process.

“What happens when we turn pro is, we finally listen to that still, small voice inside our heads."

You have the same weakness and fallibilities after turning pro. You don’t achieve enlightenment. Before turning pro, you lived a life denial and avoidance. You ran towards addiction, distraction, and shadow careers. After you turn pro, you stop fleeing. It’s not that you are no longer afraid, you just decide to do the hard thing and face it. That’s the difference.

Turning pro is a decision we make every day. It’s not one and done. Every day will have the same resistance and distractions. Every new day is a new battle.

Many end up turning pro after some epiphany moment. That uncomfortable run-in with the truth that leaves one feeling exposed and naked. It’s the moment the subconscious says enough and calls out our bullshit. Then we have a choice to make. Turn pro or go back to reconstitute our bullshit.

Epiphanies bring us reality, humility and shame. There are no glories in epiphanies. But it brings us the shame that gives us the will to persevere.

What a pro does:

• Shows up every day

• Stays on the job all day

• Commits over the long haul —10 years

• His stakes are high and real

• Is patient

• Acts in the face of fear

• Accepts no excuses

• Does not show off

• Is dedicated to mastery

• Asks for help

• Endures adversity

• self-validates

• Reinvents the self

• Is recognized by other professionals.

• Isn’t distracted – “The amateur tweets. The pro works."

• Enters combat alone — courage

• Has compassion for the self — “Horses understand the whip, but I don’t want a racer that runs that way. A horse that loves to run will beat a horse that’s compelled, every day of the week….never train your horse to exhaustion. Leave him wanting more."

• Is present. That means immersed in the work today.

• Defers gratification — Remember the famous marshmallow experiment? Well, fuck the marshmallows. The waiting is its own reward (i.e. doing the work itself).

• Doesn’t wait for inspiration. You work and you anticipate it joining you as you work. As Jack London said, you have to chase after it with a club.

• Doesn’t surrender self-sovereignty. Seek wisdom from the masters but don’t worship the person. Amateurs are groupies.

• Help others professionals. Don’t waste time on dilettantes.

There is nothing romantic for the pro. One must engage in the ordinary, workmanlike task of creating and that’s how one starts to achieve flow. There is no secret sauce or divine intervention. It’s mundane and dull. You sit and write for hours on end.

Pursuing the work for itself alone is what makes it a practice. The pro practices his craft day in and day out. It’s no different from training at the gym every day. As Neil Gaiman advised, you probably won’t get paid for your work (it’s out of your control so no point worrying over it) so might as well make something you’ll be proud of. If you don’t get the money, at least you’ll have the work.

On writing…

“We bust our butts training and practicing and studying and rehearsing and nobody shows up, nobody notices, nobody even knows we exist. No wonder people quit.”

How I feel with writing….the practice that sustains me.

“Because there were no conventional rewards, I was forced to ask myself, Why am I doing this? Am I crazy? All my friends are making money and settling down and living normal lives. What the hell am I doing? Am I nuts? What’s wrong with me? In the end I answered the question by realizing that I had no choice. I couldn’t do anything else.”

Once you’ve found your practice, it’s “until death parts us”. Charlie Munger is investing well past his 90s, Picasso painted past 90s, King Agesilaus of Sparta fought in his armour until 82, etc. There is no finish line for the pro. You just keep on going.

Write, forget and write again. Don’t stop. Finish a project? Start another.

“The best pages I’ve ever written are pages I can’t remember writing."

You can write about what you don’t know. Through whatever bullshit you have on the paper. Trust the process.

When you have a bad day, remember tomorrow is a new day. A new battle. We’re in it for the long haul so we can play for tomorrow.

Remember Neil Gaiman’s Make Good Art speech. No matter the hardship, no matter the personal trauma, no matter the adversity, distractions, road blocks, make good art. There is never a perfect moment, nothing goes according to plan and everything always falls apart. So just shut up and write.

Everything seems to start with “what if”….. write it down and chase that thread before your rational mind (the one controlled by your need to be liked and conform) shuts it down with a hammer.