How To Fail At Almost Everything And Still Win Big Summary5 min read

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How To Fail At Almost Everything And Still Win Big is the memoir of Dilbert cartoonist Scott Adams, in which he shares how he learned to take care of himself, so he could go from loss to loss, until eventually winning big.

We all have the occasional episode of “I should be much further along in life.” We look back at the past few months, maybe even a year or two, and wonder what went wrong. Often, it’s nothing. We’re just not patient enough. Even lots of young people are kicking themselves, but who ever ‘made it’ before they turned 30?

By that age, most of us haven’t even begun working on our real career. When he was 30, Harrison Ford was still a carpenter, not an actor. Andrea Bocelli only played the piano in bars until 33. And the founder of Mary Kay sold books door-to-door until she was 45.

For Scott Adams, the creator of the world-famous Dilbert office cartoon, life’s path wound just the same. Through many jobs, failed startups, and useless patents, he eventually an outlet that made his failures accessible to the world. Now, Dilbert has been in circulation for almost 30 years. In How To Fail At Almost Everything And Still Win Big, Adams shares his story, along with the lessons he learned about keeping himself motivated, healthy, and happy while racking up all the failures that ultimately led to his success.

Here are my favorite 3:

  • Goals have two inherent flaws, so build systems instead.
  • Wherever you’re most comfortable taking risks, that’s where you should apply for jobs.
  • To find your own energy schedule, think of activities in terms of space and time.

On the way to success, failure is inevitable, but how much you hate it? That’s up to you. Let’s make sure you don’t lose hope!

Lesson 1: Build your life around systems, not goals.

Adams first learned about systems from a man he sat next to on a flight. The man said systems had helped him go from employee to CEO, one in particular: going from job to job, always trying to find something better. It was simple enough and the more Adams thought about it, the more he preferred systems over goals in general. He says goals have two problems:

They’re in the future. To get an outcome on an unknown day far out, you have to put in work today. That’s depressing.

They’re specific. Unless you get exactly what you set out to get, you’ll be disappointed, even if you end up with something that’s pretty close or even better.

For example, if Scott had focused on trying to publish 365 comics in a year, each day would have been a potential failure until he had actually drawn something and no individual day would really have felt like a win, because it’s just 1/365th of the mission.

Systems, however, leave room to adjust your plans and make timing irrelevant. When you just focus on, say, publishing a blog post each day, every day when you do it feels like a win, the others are just rest days. And even if it takes 500 days until your work takes off, that won’t matter, because you never set a deadline.

Goofs use goals, winners use systems.

Lesson 2: Sample jobs in which you’re comfortable taking risks to find the best one.

We all have specific skills we’re good and bad at, but identifying those isn’t always easy. If you can’t think of certain hobbies from your past that you were obsessed with, and thus likely good at, Adams has an interesting question that might help you find them:

Which areas in life are you comfortable taking risks in?

For example, public speaking is a big fear for most people, but maybe it’s easy for you to start talking in front of a crowd. That’s something you can work with, whether it means leading a group at work or starting a stand up comedy show on the side. With this guideline in mind, you can then start job sampling, which is just trying different things, until you find something that sticks.

Lesson 3: Use space and time to manage your energy.

Adams doesn’t believe in finding your passion. He believes in finding your energy. It makes sense. As long as you stay energetic and motivated, it doesn’t matter how many iterations of failure you have to go through until you figure out what works, because you’ll enjoy life along the way.

Scott suggests three specific angles, from which you can look at your energy levels:

Activities. What’s exciting and what’s draining? I, like Adams, hate shopping, for example, but love listening to music.

Space. I need to go to an office in the morning, whether it’s a coffee shop or a library. To me, home is relaxing. When you’re used to doing certain things in distinct places, don’t mix them with others.

Time. Some people are early risers, like me, others like sleeping in and kick into gear late in the day. The more you can adjust your work day to your internal clock, the better.

Don’t worry if you can’t switch to your perfect schedule right away. It takes some time to find and even more to implement, especially if you find you’ll need a different or no regular job to make it happen. But that doesn’t mean it’s not worth trying.

If you can manage your energy well for long enough, you can fail at almost everything and still win big.

My personal take-aways

Scott Adams is a fascinating man, definitely listen to a podcast with him some time. His most recent work is a book about Trump’s persuasion skills, he tweets a lot, and is an interesting thinker to bounce ideas back and forth with, even if you just do it on your own time.

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