How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life
by Scott Adams
Like most folks I always thought of Scott Adams as a cartoonist. He created the iconic comic strip Dilbert, an important cultural lodestone to my generation of corporate tech people.
What I didn’t know what that he would also be the most prescient political pundit of the 2016 election cycle.
I think it’s fair to say that the Donald Trump phenomenon caught almost everyone unawares. But a few people saw it coming. One of them was Adams, who on August 5th of last year wrote, “I’m watching the Donald Trump campaign for president with the same amount of amusement as everyone else. The only difference is that I think he has a legitimate shot at becoming president. You’ll choke when I tell you why, because you’ll agree.”
Adams has personally disavowed Trump and endorsed Hillary Clinton (for his own protection). He’s still predicting Trump in a landslide.
Amongst the people who called Trump in advance, Adams is distinguished by going into great detail about why Trump is so effective. He calls Trump a “master persuader” and has a huge master persuader index of blog posts in which he breaks down point by point what Trump is doing. He says that “Trump’s successful use of persuasion will rewrite your entire understanding of reality.”
When someone is highly successful, maybe we might want to understand what he’s doing. This applies to Trump (even if you want to stop him), but in this case I want to look at Adams himself, a serial failed entrepreneur who managed to rise from corporate middle management to wealthy cartoonist plus also correctly called out what was going on with Trump.
Adams didn’t come to the pundit business by chance. He had already been looking for ways to market his insights, one of which was his memoir/self-improvement book How to Fail at Almost Everything and Still Win Big.
I gave it a read to see what lessons it might hold, and there are some interesting ones. His “book tease” is:
Goals are for losers. Your mind isn’t magic. It’s a moist computer you can program. The most important metric to track is your personal energy. Every skill you acquire doubles your odds of success. Happiness is health plus freedom. Luck can be managed, sort of. Conquer shyness by being a huge phony (in a good way). Fitness is the lever that moves the world. Simplicity transforms ordinary into amazing.
I want to briefly talk about three things from the book that are particularly useful: systems vs. goals, the “talent stack” concept, and the key early tell for whether something will be successful.
Have Systems, Not Goals or “Passion”
One of the biggest pieces of advice you often hear is to set goals, write them down, etc. Adams doesn’t like goals. For one thing, most of the time you’re in a place where you haven’t accomplished your goals. You’re still a failure, still deficient, so you feel bad about yourself. And if you achieve your goal, then what?
Adams also pooh-poohs the idea that passion leads to success. I recently did a podcast on how passion is a choice. Adams says that passion is a product of success, not its cause, and that most successful people are lying about it anyway.
Passionate people who fail don’t get a chance to offer their advice to the rest of us. But successful passionate people are writing books and answering interview questions about their secrets for success every day. Naturally those successful people want you to believe that success is a product of their awesomeness, but they also want to retain some humility. You can’t be humble and say, “I succeeded because I am far smarter than the average person.” But you can say your passion was a key to your success, because everyone can be passionate about something or other. Passion sounds more accessible. If you’re dumb, there’s not much you can do about it, but passion is something we think anyone can generate in the right circumstances. Passion feels very democratic. It is the people’s talent, available to all. It’s also mostly bulls**t.
Instead, Adams says we should concentrate on setting up a good system, because good systems create the best chance of us finding success in the long term. Good systems tend to produce the best outcomes over time.
So rather than setting a goal such as “I want to lose 15” pounds, instead you focus on creating a system whereby you have a healthy lifestyle, eat right, exercise, etc. Do that and over time you’ll probably weight less, look better, and be healthier too. (Adams is strong when he notes that health and fitness are foundational to success in all areas of life). And he notes, “I prefer simplicity whenever I’m choosing a system to use. People can follow simple systems better than complicated ones.”
The systems concept works in concert with his other ideas. For example, Adams “system” for his diet is eating whatever he wants, whenever he wants. But he has “reprogrammed” his brain to be vegetarian, so that he is eating mostly healthy. (Look at the header photo on his twitter account. I personally do not recommend vegetarianism).
Build Your Talent Stack
His other maxim is that every skill you learn doubles your chances of success. So your focus should be creating a “talent stack” of skills at which you are solid, not trying to become a world class expert at any one thing.
He uses himself as an example. He was technologist, but not world class. He’s funny, but not a professional stand up comic. He can write, but isn’t winning awards for his Great American Novel. He can draw, but isn’t a great artist. But put it all together and you get Dilbert.
I can relate to this concept. I noticed about two years ago it seemed like all of the skills I had learned over my entire lifetime – consulting, finance and accounting, writing, technology and data analysis, public speaking – were finally all being applied effectively to the domain of urbanism. I was using stuff I’d learned in completely different contexts, but applying them in a new domain. And like Adams, I’m solid but not the absolutely best in any of them.
The skills Adams rates as most important (presumably targeting a business context) are:
- Public speaking
- Business writing
- Design (basic level)
- Overcoming shyness
- Second language
- Proper grammar
- Proper voice technique
He says persuasion (Trump’s forte) is the master skill.
Thinking about this, the application might be that if you are already pretty good at the current skill you are using most, maybe it’s better to add a new one to complement it than to focus on increasing your level of expertise.
I agree there’s something to this, but it helps to have something of a “calling card” skill that sets you apart. This is the idea of being “T-shaped,” or having one deeper skill complemented with breadth in lots of skills.
Things That Will Succeed Have the “X-factor” From the Beginning
Adams is a serial entrepreneur who seems to like starting and investing in businesses for its own sake. (Why else go into the restaurant business when you’re a cartoonist?) Most of them failed. He made an observation about the things that worked vs. the things that didn’t that resonated with me:
The pattern I noticed was this: Things that will someday work out well start out well. Things that will never work start out bad and stay that way. What you rarely see is a stillborn failure that transmogrifies into a stellar success. Small successes can grow into big ones, but failures rarely grow into successes….You might be tempted to think that sometimes an idea with no x factor and no enthusiastic fans can gain those qualities over time. I’m sure it’s happened, but I can’t think of an example in my life. It’s generally true that if no one is excited about your art/product/idea in the beginning, they never will be.
This has certainly been true in my experience. My blog acquired an enthusiastic core, if small, audience right out of the gate. Conversely, my Telestrian app had little initial uptake, and it never really turned into a successful business. So I shut it down over a year ago.
Looking at what I’m doing now, the podcast that I launched has been averaging over 400 listens per episode, which is actually better than I thought would happen. On the other hand, I signed up for Instagram about the same time, and have only 70 followers. This would tell me that podcasting likely has a better future for me than Instagram.
How to Fail at Almost Everything and Still Win Big is an easy read, has a lot of useful advice on how to be more successful, and also lets you learn a bit about the man behind Dilbert. (Among other things, Adams all but lost his voice for nearly three years). And since this came out a while back, there’s absolutely nothing about Donald Trump in it.
Where the book struggles in my view is that Adams throws so much stuff at us in such a short period of time, it’s tough to digest and tough to figure out how to apply it for someone who is just starting out. Just look at that list of recommended skills alone, each of which is daunting in its own right.
Still, if you set up a system that is able to incorporate new elements one at a time over time, over the long term you’ll build quite a repertoire competencies. I may in fact do a podcast on that very topic in the near future.
Filed Under: Society and Culture
Scott Adams, (born June 8, 1957, Windham, New York, U.S.), American cartoonist who captured the malaise of the modern workplace in his comic stripDilbert.
Adams was valedictorian of his high-school class (because, he said, "the other 39 people in my class couldn’t spell valedictorian") and went on to earn a B.A. in economics from Hartwick College, Oneonta, New York, in 1979 and an M.B.A. from the University of California, Berkeley, in 1986. From 1979 to 1986 he was employed at Crocker National Bank in San Francisco (while working as a teller, Adams was robbed twice at gunpoint). From 1986 until June 1995 he worked for Pacific Bell in San Ramon, California, in a number of jobs involving technology and finances.
The character Dilbert, a composite of Adams’s coworkers over the years, first appeared in Adams’s business presentations. The comic strip Dilbert was first published in 1989, and by the 21st century it had been syndicated to some 2,000 newspapers, was being read in 70 countries, and had an official Web site on the Internet. Its lead character, a computer programmer and engineer for a high-tech company with no apparent purpose, was buffeted daily by the illogical projects and business decisions of his clueless boss and the corporation’s equally inept management. Dilbert, readily recognized by his perpetually curled necktie, survived the indignities of his existence with the assistance of his pet, Dogbert, who often seemed to have his own self-serving agenda. A few years after Dilbert appeared, Adams began publishing his e-mail address in the strip. He personally read and answered each message, and he credited his correspondents with suggesting many of the situations that Dilbert encountered.
Adams published numerous books, including Dilbertcompilations and job-related works. He also wrote How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life (2013) and Win Bigly: Persuasion in a World Where Facts Don’t Matter (2017); the latter included his explanation for why Donald Trump won the 2016 presidential election.