How to Fail at Almost Everything and Still Win Big

I was lucky enough to be given some time to interview Scott Adams for WSO about his new book: How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life. His book covers an enormous amount of topics relevant to our readership. It’s a tremendously good book and I would highly recommend getting a copy with one of those Amazon gift cards I know you received over the holidays. You will enjoy its humor all while learning important lessons that will serve you well throughout your career.

If you think your odds of solving your problem are bad, don’t rule out the possibility that what is really happening is that you are bad at estimating odds.

Scott Adams – How to Fail at Almost Everything and Still Win Big

Goals are for losers.

Passion is bullshit.

These are two of the early lessons found in Scott Adams’ new book. At first glance, this seems a bit counter-intuitive. Surely the denizens of Wall Street had well thought out goals that got them there. Surely they are passionate about finance. Intuition and experience with myriad self-help success stories suggests this is the case but, those of you who are more seasoned in the world of Wall Street know better. Goals are for losers, systems are for winners.

[A] goal is a specific objective that you either achieve or don’t sometime in the future. A system is something you don a regular basis that increases your odds of happiness in the long run. If you do something every day, it’s a system. If you’re waiting to achieve it someday in the future, it’s a goal.

I’ve heard of many systems being utilized by my fellow monkeys to accomplish any number of tasks, the most popular being those surrounding getting a job. For example, sending out X cold emails per week, following up successful cold emails with requests for informational interviews, and writing a thank you note is a popular system for networking. Successful monkeys don’t have the goal of “get a job” or “network with bankers” they have a system which, if practiced regularly, will get them in front of decision makers and eventually, a position.

The biggest component of luck is timing. When the universe and I have been on a compatible schedule – entirely by chance – things have worked out swimmingly. When my timing has been off, no amount of hard work or talent has mattered. Dilbert was the best example of lucky timing you will ever see. It wasn’t a complete accident that luck found me; I put myself in a position where luck was more likely to happen.

The timing component of luck is a big reason why systems beat goals. Having a system in place to network your way into a job is substantially more likely to work out in the long run than a goal to work in the bulge bracket. At best, the latter puts you in a position of constant failure until some ill-defined stroke of luck occurs to make you successful. The former, the system, keeps your mind in the right place, you’re successful if you put out those emails, you’re successful if you meet people for coffee, you’re successful every step of the way, and so long as those steps will reasonably get you in the door, you’ll be successful in the long run.

What about passion? Surely passion is something every successful person has in spades. If you spend enough time here on WSO, the passion every analyst has for working +100 hour weeks building models and painting decks comes into clear view. Maybe I haven’t been around long enough, but I don’t see many monkeys declaring their undying love and Viagra-esque sensations after staying at the office until 4am scrubbing a model. That’s because passion is bullshit. Our readership is full of smart, successful young people yet “passion” isn’t something that’s regularly touted. This isn’t surprising. Adams, a former commercial banker, tells the story of his old boss, a commercial lender of over 30 years:

[My boss] said the best loan customer is one who has no passion whatsoever, just a desire to work hard at something that looks good on a spreadsheet. Maybe the loan customer wants to start a dry-cleaning store or invest in a fast-food franchise – boring stuff. That’s the person you bet on. You want the grinder, not the guy who loves his job.

I’m sure many of you are quietly nodding your heads after reading the last sentence. WSO is home to the grinders of the world – the ones you bet on. Now, this isn’t to say that passion isn’t something that’s bad or anathema to your success; it’s just better viewed as a proxy for talent rather than a prerequisite for success.

How to Fail at Almost Everything and Still Win Big is not exclusively about systems and passion and other success dos and don’ts. It has a bevy of hilarious stories from Adams’ myriad failures in the technology world (how Ninja Closet failed is beyond me – that was genius), as a restaurateur, and in the always volatile microwavable burrito market. But, reading about these failures tells you about how Adams was able to take something that didn’t work out well and turn it into something useful, leading him to the conclusion that failure is what gives us the tools we need to be successful. In short, How to Fail at Almost Everything and Still Win Big tells the reader the lessons Adams learned that have led him, in the words of Winston Churchill, to stumble from failure to failure with no loss of enthusiasm. Or, put another way, to success.

Let me take a quick moment to say thank you to Scott Adams for speaking with me and sharing his thoughts with WSO. Adams was able to put together terrific answers touching on his unified field theory of success, public speaking, being a proper asshole, hamming it up with your MD, and of course, golf.

How would you guide the readers of WSO in digesting the information found in your book?

While every person is going to be different, in How to Fail at Almost Everything and Still Win Big I wanted to describe a unified field theory of success. It appears that WSO readers are people who have figured out how to excel at something, so I would focus on the “Happiness” section that I have simplified into:

Happiness = Health + Freedom

The health part is simple: exercise and diet. You need to make sure you’re active every day. That part is non-negotiable. Over the course of your life, you learn a lot about exercise, and in the book I talk about how you can use boredom to lead you into variety; and let it happen how it’ll happen. And on the diet side, I talk about how willpower is finite, and how to build a diet system that doesn’t draw upon your limited supply of willpower that you may need later for something more substantial.

The freedom side sounds like the biggest problem for your readers. In this context, I define freedom as not just work freedom, which is nice, but being able to do what you want, when you want to do it. The when is just as important as the what. Take the typical schedule of most people with a job, a boss, and customers: they end up working when they’d rather have a nap and eating when they’re not hungry. Your schedule can be a mess and that can take a big bite out of your happiness. Even if you look around and say “I have all these things that make me happy”, I have a nice car and all that, or I have a family, or I have kids (if that’s what you’re looking for); you’re still going to be miserable if everything you do is on someone else’s schedule. So, getting control of your schedule over the long run (this is almost impossible to do in the short run) can be as simple as eating when you’re hungry and napping when you’re tired. I would say that’s the thing to keep in mind, try to get a flexible schedule over the long run, otherwise nothing else is going to matter.

You talk at length about key skills everyone should have. What skills in particular do you think would benefit the readers on WSO?

There’s no one in the business world that wouldn’t benefit from learning how to give a more professional public presentation. If your coworkers were good at their job but you could speak to a crowd, chances are that you would be the one who would be chosen as the next boss. I’d say communication in all its forms is #1, and public speaking would be at the top of that list. I would also say that psychology is something that you should pick away at your entire life. Read the internet sites that continually have stories on new studies and articles on psychological subjects. In particular, understanding that willpower is a finite resource (this is a gigantic deal), understanding that you can form habits in yourself in the same way you can train a dog with a treat, and understanding how to persuade people to buy things are three key areas of psychology to focus on. Those are like super powers! But, it’s just knowledge, and once you have the knowledge, you have the power.

In your book, you warn about being an asshole. But, if you believe half of what you hear about Wall Street bankers, this is a seemingly impossible task. How would you recommend our readers approach this seemingly difficult aspect of life in finance?

You know, I’ll tell you, in my experience, I’ve never met someone who was an asshole and wasn’t completely aware of it. There are a lot of defects that one can have where everyone knows it but you, but this isn’t one of them. People tend to use it as a lifestyle. I actually had lunch with somebody, an employee of mine (I won’t name names), where at one point I said, “What’s the deal with being an asshole all the time?” He explained, in very clear terms, that it was a lifestyle choice, and he knew that there was a cost to it and he was willing to take that cost. But I hear about people who flip in and out of it because they weren’t paying attention. I’m just trying to raise the issue if you’re one of those people who flips in and out of it; someone who could avoid it. Because whatever payoff an asshole gets by being an asshole, if you’re flipping in and out of it, you’re probably not getting that payoff.

You get into great detail about effective conversations, storytelling, and humor. How would you recommend young bankers approach these issues in their professional lives?

Storytelling can be dangerous if you’re not good at it, which is why I included a section on constructing a good story. I would say the more important thing to do is what’s found in the Dale Carnegie question stack (if I can call it that) which, is how to talk to anybody by simply showing interest in them by asking questions whose answers you don’t already know. If you already know their name and where they work, ask them where they are going to take a vacation or what’s up with the kids. Show a larger interest in their life and everybody will respond positively. Nobody will take that the wrong way. It may feel like you’re being nosy and intrusive, but it won’t be viewed that way from the other side. The other person is happy to talk about themselves! Because, well, that’s always fun to do!

As for humor, the first thing I’d say is that it isn’t for everybody. If you think that you have some talent, then maybe you should look at some of the tips in the book and do a little bit of practice. But, I would guess that more than half of the public isn’t really going to get there and they should probably leave the humor to others. That being said, here’s what I suggest in the book, you don’t have to be the joke teller because sometimes, the straight person is even more valuable. If you’re talking to your boss and you know the boss likes being a ham and likes to tell a joke, you would get further by simply bringing up a topic that you know your boss could be funny about. There are some topics that are naturally funny and by letting your boss tell the jokes while you are the straight person you’ll get further than you would if you tried making your own story. Bosses always like to hear themselves talk more than they like to hear you talking. Remember, if the result is that you both have a laugh, it doesn’t matter who told the joke because you’re both enjoying the same moment.

You also talk about the importance of golf, what advice can you give to people who are probably already predisposed to golf?

I’d simply recommend that everybody do it. If you’re in the business world, plan to be in the business world, or just want to get out of the house, I don’t think I know anybody who golfs, gave it a good try, and worked at it for a while and didn’t like it! I just haven’t met that person. There’s something universal about it. If you factor in the business benefits to the fact that it’s seems to be fun for almost anybody, you can play at any level, you don’t have to be great at it; it’s kind of a no-brainer. It’s like coffee! You know, if you don’t drink coffee, you really ought to.

I would like to say thank you once again to Scott Adams for allowing me to interview him for WSO and I can’t recommend enough that you monkeys out there buy his book and give it a good read. It’s a fantastic read and it will help you in whatever future endeavors you take on.