1. When they bring you bread and butter and the butter is too hard to spread

2. When I call in to a customer support line for the 10th time they still have no idea who I am or what my account number is

3. If I’m disconnected from a customer support call I have to go back through the phone chain again and start over

4. If I’m looking at an ad it doesn’t have a box at the bottom that says “Is this relevant to you?”

5. Chrome opens up a new process every time I open a new tab

6. I forget 99% of the things I read

7. My weather app can’t tell that I’m going on a trip soon and show me the weather in the place I’m packing for automatically

8. It takes 4 emails back and forth to schedule a coffee meeting with someone

9. When light switches aren’t backlit so you can’t see them when it’s dark

10. When they don’t put light switches on the left side of the door so that you can easily turn them on as you walk into a dark room

11. When doors have “pull” handles and are actually “push”

12. Window latches that don’t tell you what state they’re in

13. When I’m on a train and four people have MiFi’s and I can’t pay to use one of them

14. When buildings have great comfortable seating areas for people to do work in but have forgotten to put power outlets near them

15. When a sign in form says “username” but I actually signed up with my email

16. When a sign in form says “email” but I actually signed up with a username

17. When a video player crashes before it starts playing, I refresh my page, and am subjected to the same ad I just watched

18. When a bus has wifi but it doesn’t actually work so I end up wasting 10 minutes vainly turning WiFi on and off, reconnecting, and then refreshing the page

19. When I have no more clean socks

A lot of success advice centers around the idea of “being honest with yourself about the things you’re good at, and pursuing those things relentlessly.” We’re told that all successful people can be boiled down to a paragraph which states their chosen field and the personal style they brought to it which allowed them to be successful.

Here are some examples:

Bill Gates: entrepreneur and philanthropist. intensely smart, workaholic, ruthlessly competitive.

Christopher Hitchens: master wordsmith and essayist. contrarian. known for his outspoken views on Athiesm and his pugnacious writing style.

Oprah Winfrey: media mogul. revolutionized the daytime tabloid talk show. philanthropist. known for her ability to get celebrities to open up about their lives on TV.

Woody Allen: writer/director/actor. known for raucous one liners, Marx-brothers inspired slapstick comedy, portrayal of neurotic Jewish characters in romantic comedies, and a prodigious output of films over his long career.

Because successful people can be described in this way, the common wisdom goes, if you can figure out what you’re good at in a similar way it will help you be successful.

In order to figure out what you’re good at, a common piece of advice is: “Be brutally honest with yourself about it.”

But the problem with this advice is that for most of us younger than 22, asking ourselves “What am I good at?” returns a blank response.

Most success advice doesn’t recognize this because it’s generally written by people who have spent a lifetime figuring out the answer to that question. By contrast, even the most prodigious 20-year-olds among us probably have been working successfully for five years, if that many.

When you’re 50, asking yourself “What am I good at?” probably returns at least a few responses. But the key is that those responses were developed from experience over the last 30 years. When they were 18 things weren’t so clear.

People forget that you aren’t born with an Owner’s Manual tucked under your pillow that says, “You are Joe Smith. Brown hair, blue eyes, very visual, cut out to be a painter, quiet and introspective.”

So telling an 18 year old to “figure out what you’re good at” is thoroughly non-actionable. We already know that we have to be good at something in order to be successful, the question is: how do we figure out what that something is?

Some people conclude that because they can’t come up with an answer to that question immediately, it must mean that they’re not good at anything.

But thinking like that is stupid and unproductive. More importantly, it doesn’t actually reflect the reality of the process of becoming excellent at something.

The nice thing about my position is that I’m old enough to know what I’m good at (at least partially), but I’m young enough to remember not being able to answer that question at all.

Given this unique angle, I thought it might be useful to get down a few thoughts on how to figure out exactly what you’re good at.

Emulate Successful People
A common first step in figuring out what you’re good at is emulating successful people.

For example, I read a few biographies of Bill Gates when I was a kid and remember reading that he used to rock back and forth in his chair whenever he was thinking hard about a problem. This was supposedly a sign of his intense mental concentration and intelligence.

For weeks after I read that I would try to rock in my chair as I thought about business ideas.

I used to do the same thing with writing.

When I was little my mom bought me the complete collection of Sherlock Holmes stories. For months after I read it, every time I sat down to write a story it would always feature a character called “Watson” and be written in British English.

In general, all of those assumed styles and traits tend to fade after a while. Sometimes trying them on can teach us as much about who we aren’t as who we are.

Some people don’t recognize this and they try to force themselves to adopt the traits and the persona of the person they most admire because they think it will make them successful.

This is not a good idea. Even if you do manage to force yourself to take on someone else’s characteristics, you’ll end up being inauthentic, and it won’t allow you to be your optimal self. What worked for them might not work for you. You’re a different person, in a different situation, in a different time.

“Okay,” you might say, “but if I can’t actively pick what I’m good at then what am I supposed to do?”

This is actually a tough problem because if you can’t actively pick, it seems like the only other option is to sit back and let what you’re good at come to you on its own. This feels wrong intuitively. You can’t sit around your whole life waiting for what you’re good at to show up out of the blue and change your life. You could wait your whole life for it to happen and die before anything ever does.

Now you’re stuck between a rock and a hard place. You can’t pick what you’re good at, but you can’t sit back and allow it to come to you. As it turns out though there is a third option that we haven’t yet considered.

The Explorer Mindset
The third option is what I’d like to call the Explorer Mindset. In order to illustrate it, I’ll give you a quick example.

One thing that I’m good at is blogging. To get more specific, I’m good at writing long, philosophical thought pieces about startups and entrepreneurship. Because I know that I’m good at this, I’ve developed a pretty large audience of people who read my posts on a regular basis.

Traditionally, someone in my position will tell you that in order to be a successful blogger you need to decide what you’re going to write about and what unique perspective you can bring to the table.

But when I started blogging I had no idea that my niche was going to be these long-form thought pieces about startups. I didn’t sit down and say, “Yes, I’m going to create DanShipper.com and this is what I’m going to post about and this is why people are going to like it.”

And so I wouldn’t suggest that you do that either. Just because I ended up with a niche, doesn’t mean that you should pick one.

Instead of actively picking one, what I did was adopt an explorer mindset.

I knew I wanted to blog. And throughout high school and into college I started a bunch of blogs and wrote on them. No one ever really read them, and I was a pretty bad writer.

But I kept going because I couldn’t help myself but write. I just liked to do it when I was bored.

Then one day I stumbled across Hacker News and read a few of the articles. They really resonated with a lot of things I was thinking about. Most interestingly, they all centered around the software business – the other thing that I’ve always done with my free time.

And I thought to myself, “Hey I think I could write something like that.” And so I started writing about startups.

As I kept writing I started to understand what I could talk about well and what I couldn’t. It became clear what kinds of posts I was able to write most successfully. And gradually a style, and subject matter of choice materialized.

Now, 2 years later, I can confidently tell you that I’m good at writing this type of blog post.

This might seem like pretty simplistic advice: it sounds like I just sort of stumbled across something that worked and stuck with it. But I think it’s a little more nuanced than just that.

The process is almost “lean” in the sense that you want to try a lot of different things, and develop a strong feedback loop for what works for you and what doesn’t. But what’s really key is to not be discouraged by the fact that if someone asks you what you’re good at, you can’t give them an answer right away.

You weren’t meant to be able to do that.

Figuring out the answer to that question is an organic process that unfolds over a long period of time. Expecting anything else is unrealistic: no one’s power’s of introspection are so strong that they can plumb the depths of their head and find an answer immediately.

The whole thing reminds me of sailors traveling uncharted waters during the Renaissance.

Just like you can’t actively decide what you’re good at,
Christopher Columbus didn’t sit around in his Spanish villa, point to a map and say, “This is where America is!”, and then claim that he discovered the New World.

Just like you can’t say, “I’ll wait for what I’m good at to find me,” Christopher Columbus didn’t decide that the location of the New World would just pop into his head some day and sit around waiting for it.

Instead what he did was get on his ship and point it in a direction that looked promising. And every day he would look out across the horizon and say to himself, “Do I see land?” And eventually after doing that for enough days in a row with no result, he got up one morning and saw a shoreline in the distance.

And he sailed his ship straight for it.

That’s what it’s like to figure out what you’re good at – it’s like discovering land in uncharted waters. You have to travel long distances, and constantly be on the lookout for land. And if you see land, you have to head straight for it and chart every inch of it.

——

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Conrad looked at the floor. He crossed his arms, standing lazily in the center of the stage. Subtle murmurs from the audience gradually died down. Slowly they focused their attention on him, waiting.

As he stood there, they looked more closely, drawing in their breath. Perhaps they were missing something. They moved their eyes slowly over his jeans and t-shirt. Why was he just standing there?

A few stray coughs echoed through the back of the auditorium.

The seconds ticked by.

Conrad could hear the audience’s breathing stop. Silence crescended through each row as they waited for him to say something – anything.

He looked up.

“How many of you are not where you want to be in your lives?” Conrad said. A few hands crept into the air.

“How many of you have started a business but are having a hard time making it a success?”

More hands.

“How many of you want more users, or more revenue? How many of you want to raise money?”

“How many of you want to be independently wealthy?”

More hands raised. Conrad smiled knowingly.

“I can help you with those problems. You see, I was once where you were. Broke, fresh out of school with no money. Working on a few business ideas on the side.”

“In 15 years I’ve built and sold two businesses, both for more than 100 million dollars.” Conrad spaced out the words ‘million dollars’ for emphasis as he walked to the left side of the stage.

“I’ve been featured in pretty much every publication you can think of. I’ve done it all. And now I want to give it back.”

“So what I’ve tried to do is take everything that I’ve learned over the past 10 years and condense it into this talk.”

Conrad clicked the remote in his hand and How To Become a Millionaire flashed boldly onto the screen behind him.

“So in this talk what I’m going to cover is the specifics of how you can take your business, whatever stage it’s in, and bring it to the next level. I’ll talk about building something that people want, finding your first 1,000 customers, and then scaling to your next 10,000.”

“This advice has personally made me millions of dollars, and has also made millions for my friends and business partners,” Conrad strode to the center of the stage and looked down at the floor.

“Let me start with a story.”

“When I was young, stupid, and still in high school I decided to take Honors Chemistry.”

“Anyone who knows me, can tell you that this was probably a bad idea because I’m absolutely terrible at math. As in, I have trouble with basic addition. Just terrible.”

“But I wanted to go to a good college, and so I decided that this was a good idea.”

“And every night when I got home from school, I would break out my huge Honors Chemistry book and sweat over it for hours. It was grueling.”

“The way our house was set up, I would work at the kitchen table, hunched over this huge textbook trying to figure out stochastics, and chemical reactions. And my dad would be in the living room sitting on the couch.”

“Every night he’d sit with his feet up on the couch, laptop on his lap, half answering emails half watching TV, always drinking Diet Dr. Pepper.”

“For weeks we would do this. Me in the kitchen banging my head against this class, him in the living room.”

“He must have known I was struggling with it. I was working hard, and my grades were poor. But he never really said anything.”

“Then one day, between sips of Dr. Pepper, he yelled out to me something that I’ll never forget.

“‘Conrad!’” (That’s how he used to yell at me between rooms.)

“‘Conrad, my boy. The greatest instinct a person can have is knowing when he needs help.’”

“And that’s something that’s stuck with me all of these years. You see, there are a lot of people who think that business is done in a vacuum. That a great businessman (or woman) makes decisions on instinct alone. That they don’t need advice.”

“Let me tell you something. That’s fucking dumb. That’s a recipe for disaster.”

“Are you going to avoid every mistake with advice? Absolutely not. But you will avoid at least a few of them. And you’ll be able to better contextualize and understand what’s happening in your life and in your business if you talk about it with people who have done it before.”

Conrad paused and looked out at the audience.

“Luckily for you, if you’re in the audience you already know that you need help. That’s step one. So congratulations on that.”

Members of the audience looked around at eachother, enjoying their place among the elite few.

“But blindly following advice is a recipe for disaster,” Conrad continued. “Let’s talk about why.”

“The first problem, is where people tend to get advice. The most obvious places are the things they interact with every day: movies, books, TV, and the press. You would be completely shocked how many young people build their business in a certain way because that’s how they saw it done in a movie.”

“So the first most obvious thing I can tell you is don’t do things because that’s how you ‘heard’ it was done. Don’t be a dick because you ‘heard’ Steve Jobs was a dick. Don’t drop out because X tech billionaire dropped out. The situation is far more complicated than the press and the biographers make it seem. And you should never make decisions based on this kind of oversimplification.”

“That brings me to my next point: successful people do something with their stories that make them difficult to emulate. They connect the dots backward.”

“When they give advice they tell you about all the time they wasted and all the wrong moves they made in the early days of their company, and recommend that you try the one or two things that seemed to work for them in order to build your business.”

“Many of the people who offer to help you will assume that if you just skip to The Things That Worked you’ll experience the same success that they did. But they don’t factor in the journey they took to become successful as much as they should.”

“For example, you’ll meet a lot of successful software entrepreneurs who will tell you that at first their prices were too low. And that immediately when they raised their prices things started to take off. And so you should do that too.”

“But what they forget, is that often times having a new product in the market at a low price allows you to learn things that you might not otherwise. And that while you may have to start charging more money in order to build a big business, jumping right to high prices at the beginning deprives you of what could be a valuable experience. Sometimes the journey to the decision is just as important as the decision itself.”

“So try not to take advice from people who encourage you to skip directly to The Things That Worked.”

“But by far the biggest problem that most people face with advice involves trying to parse conflicting opinions. This is so hard, and so relevant, because anyone who has gotten help before knows that if you ask 10 people for advice about a situation you’ll get 10 different answers.”

“And what I see with a lot of young people is that their opinion tends to align with the opinion of the person who most recently gave them advice.”

“They flip-flop between decisions and ways of thinking every time they talk to someone new.”

“How many people in here do this?” A quarter of the audience raised their hands sheepishly.

“For everyone that didn’t raise their hands, either you’re lying or you could have skipped this talk.”

“For everyone else: Don’t do this. This is a terrible way to run your life.”

“In order to stop doing this, you have to understand what advice is.”

Conrad looked out at the audience expectantly. “Have you guys ever heard of the story of the blind men and the elephant?” He asked.

A few people raised their hands, a few people looked confused.

“Oh, you’ve definitely heard of it even if you don’t know what I’m talking about right now. It’s really quick,” Conrad continued.

“So basically, there are these 5 blind men and they’re all put into a room with an elephant. Don’t ask me why.”

“But these blind men are all asked to describe the elephant.”

“The first blind man grabs the elephant’s tail and says, ‘Elephants are thin and long with a tuft of fur at one end.’”

The audience laughs at this a little bit.

“Obviously, as far as elephants go that’s not a very good description. But it is actually true. It’s just only true for a certain part of an elephant.”

“The next blind man gets ahold of the elephant’s trunk and says, ‘Elephants are thick cylinders with two holes at one end.’”

“Now, this blind guy is right too. But he’s only right in the same way as the first blind guy who held the elephant’s tail.”

“And so the story goes on with each blind man touching one portion of the elephant or other and each providing his own description of what this thing we call an ‘elephant’ is. The fun part of the story is that these guys are all telling the truth and they’re all right but they’re only right within a certain context.”

“Business advice is similar. Everyone is totally blind, feeling around in the dark, trying to succeed at building this thing we call a ‘business’. And everyone who has war stories about entrepreneurship is telling the truth. The problem is, that no one has perfect insight and no one knows the whole picture. No one can possibly touch the entire ‘elephant’ of business.”

“So when you get advice from a seasoned entrepreneur like me, the question you have to ask yourself is, ‘What part of the elephant is he touching?’ ‘Is it close to my part?’”

“Looking at things this way will help you avoid the mistake of treating every piece of advice you hear as immediately applicable, and flip-flopping your thinking after every conversation.”

“When you understand this, what you’ll start doing is listening to advice in a different way. You won’t think about what people are saying to you. You’ll start thinking about what people are saying about themselves and how they think.”

“From that vantage point, you’ll be able to ask yourself if what they’re saying relates to you.”

Conrad flipped back to the first slide of his talk. How To Make A Million Dollars flashed back onto the screen behind him.

“The ability to ask for advice, and assimilate it correctly is the single most important thing you’ll have to do in your business life.”

“I can tell you how I made a million dollars. The real question is: how are you going to?”

“And that, you’re going to have to figure out for yourself.”

———–

I went to meet Jason Fried so I could learn how to stop selling software by accident.

Since I started programming 10 years ago, I’ve made a fair amount of money online. But those sales were mostly coincidental.

By that I mean, I never thought deeply about how and why products were bought. I would build something, release it and drive traffic to it. Sales would almost always trickle in. But I never took the time to understand who was buying and why. I never worked on refining my sales copy, or understanding which forms of traffic brought the most customers.

Once I released a product I would do one of two things: start working on adding new features or start working on something else. I didn’t take time to understand what was working and what wasn’t. I wasn’t really interested in refining and simplifying – just seduced by the prospect of building something new.

You can learn things by doing this. I’ve learned a lot in the last 10 years. But I think getting from being good to being great requires something else. Building great products requires constant practice at the art of building understanding. It also requires getting rid of everything except what’s absolutely necessary.

With this in mind, what my co-founders and I have been working on over the past few months with Firefly is learning how to sell deliberately. When we make a sale, we want it to be because the copy addressed customer pain and offered a solution they could connect with on an emotional level. We don’t want to make a sale because a customer is smart enough to swim through a list of features he doesn’t care about, and come up with a reason to pay money on his own.

Selling deliberately requires building understanding, and Jason is probably one of the best people in the world at doing this.

In November we set up a meeting over Twitter. Three months later I was in 37signals’s office sitting across a round wood conference table from him. We spent about two hours chatting about Basecamp (his product), Firefly (mine), and a bunch of stuff in between. Here’s what I learned.

Building products creates an information problem
There are two obstacles to selling deliberately: lack of information or too much information.

When you’re just starting out with a product you don’t have very much information. Given this vacuum, most people guess at why someone might want what they’re building – but frequently those initial guesses turn out to be wrong.

So what most of us do is talk to everyone for feedback about what we’re building. I have 37 notes in my Evernote from separate conversations with people about Firefly. And those are just the ones that I bothered to write down.

But talking to everyone creates an information problem. It’s very difficult to sort the wheat from the chaff. And the information must be sorted through. If you base your copy off of the feedback you get, it’s impossible (and not helpful) to use feedback from everyone. It’s a common aphorism in sales that if you sell to everyone you sell to no one.

The information problem can be solved
Jason’s solution to this problem is simple and effective: the only two people who can give you real feedback about your product are people who just purchased it and people who just canceled.

You can certainly gather feedback from other people. But in general it’s going to be less valuable.

The customer who’s been with you for 8 years and loves everything you do isn’t going to give you useful feedback. She’ll just yes you to death. And neither is the guy who will definitely sign up and pay you Big Bucks if you just include, like, these four features. He’ll just string you along and eventually disappear.

A customer who just signed up can give good feedback for this reason: they’re only recently removed from the buying process. Because of this, it’s easier to get useful information about why they bought your product, what emotional event caused them to look for it and which part of it is actually useful for them.

If you interview your recent customers you can use their words to sell your product. It helps you get into their mindset, figure out what’s important to them, and find what it is about your product that convinced them to hand over their credit card details.

Similarly, a customer who just canceled can tell you exactly what you’re missing. They signed up and put their credit card information in because they thought you would be able to do a job for them. If they cancel, your product didn’t deliver what they expected.

Sometimes this a problem with your copy: you didn’t provide what your website promised. Sometimes this is a problem with your product: maybe it’s too slow or too buggy or doesn’t solve the problem that you intended it to solve. Either way, in-depth conversations with customers who have recently canceled can help you puzzle out these issues and fix them for the future.

Don’t have customers yet? Jason had an answer to this too. Find your competitor’s customers and talk to them.

How to ask questions that get actionable answers
Just because you know who the right person is to talk to doesn’t mean you know what to ask them or how to ask it. This is actually my biggest issue with the customer development methodology: it tells you that you need to ask questions but it doesn’t say how to ask or what to ask about.

Let’s start with how to ask.

The human brain is a tricky, messy thing. It doesn’t deal well with high-level abstractions like “what are your problems” or “how can we make this better”. If you ask someone a high-level question about problems with their job you’ll generally get nebulous answers about how they hate their nosy co-workers or are afraid of angering their bosses. These answers are useless because, in general, abstract human problems can’t be solved by software.

But the human brain is very good at talking about specifics. Questions like “can you walk me through what you do everyday” or “are there any repetitive tasks that you do day-to-day” will lead you down a much more interesting path. You’ll find problems that your software actually can solve.

Now that we know how to ask questions, let’s discuss what kind of answers are useful to have when figuring out how to sell your product.

What job does your product do?
The first thing that you need to find out is what job your product does.

On the surface it’s easy to answer this question. A shower helps you get clean. A backpack helps you carry things. A wallet keeps your money together. Firefly helps you screenshare with your customers.

But people aren’t rational. They don’t make buying decisions because of what a product does in general. They make product decisions because of what a product means to their lives.

After we had talked for a while, Jason brought a YouTube video up of Harvard Business School professor Clayton Christensen. Clayton contends that “products find a certain market only when they help their customers get done the jobs that they have already been trying to do.”

He tells a story about a fast food restaurant that was trying to understand how to sell more of its milkshakes. They did the traditional market research that any big firm does. They figured out their target demographic and brought those people in for focus groups.

In the focus groups they asked participants: “What can we do to make our milkshakes better for you?”

And they got feedback. People wanted more chunks, or more chocolate, or a new interesting flavor. The company would go back, and according to customer feedback, modify their lineup of milkshakes.

But it never had any effect on sales.

So they brought in a consultant to help them figure out how to sell more milkshakes. The consultant approached the problem by asking a very specific question: “What job do people hire a milkshake to do for them?”

What he found was that 50% of people bought their milkshakes in the very early morning.

So he made a point to go out the next day and start talking to customers who had just purchased their milkshakes. A very interesting pattern emerged.

Nearly all of the people who buy a milkshake in the early morning are on long commutes. And while they were on these commutes they needed something to do.

It turns out a milkshake is a perfect food for a long drive to work in the morning. It’s sweet. It takes a long time to eat so it lasts for most of your drive. It’s in a cup so that it doesn’t make a mess. And it’s pretty filling.

So for these people, a milkshake wasn’t just a sugary drink. It was something to keep them occupied on their commute.

Once you figure out what job your product does, there’s another important thing to find out.

What are people switching from to use your product?
In the milkshake example, it turns out that the people who buy milkshakes in the morning had tried other things. Some had tried to eat bananas. Bananas are healthy and they taste good.

But unlike a milkshake they’re gone pretty quickly – they don’t last for your whole car ride. And they’re also not very filling.

Other people tried to eat donuts. Donuts work well because they’re sweet.

But they get the steering wheel sticky and make a mess in the car. They also don’t fill you up very well.

It turned out people were switching to milkshakes because they were the perfect solution to keep them occupied on their commute.

The same goes for any other type of product.

You say people aren’t switching from anything to use what you’ve built?

That means one of two things: either you don’t understand your product, or no one wants what you’re selling. Every product has competitors. Sometimes they’re other products and sometimes they’re human processes.

Knowing what they are switching from tells you a lot about how your product should be marketed and what problem it needs to solve.

And when you do the research, you’ll find that what people are switching from is often-times surprising.

Your competitors may not be who you think they are
In the milkshake example the fast-food restaurant initially thought that their competitors for the milkshake market were McDonalds and Burger King. But as it turned out, they also had a broader range of competiton that they had no idea existed.

This applied perfectly to my product as well.

Firefly does download-free screensharing for customer support. And one of the things that we think about a lot is how commoditized the screensharing market is. There are bunch of free screensharing products out there. So in order to charge money for our software (which we do) we need to understand our customers’s needs better than anything else on the market.

I gave Jason a demo and he seemed to like it. He called in his customer support person and we demoed it for her as well. To figure out what job it might do for her, we asked her what she does right now when she’s on the phone with a customer who needs help.

We found out that right now her process doesn’t include screensharing. It can’t, because any type of screensharing that requires a customer to download software is a nightmare for a support rep to explain.

What she does instead is she asks the customer to describe the page he’s looking at and what he wants to get done. Then she, from memory, instructs them on which buttons to press to fix their problem.

Many times they describe the page to her and she has no idea what they’re looking at. Other times, she’ll tell them to press a button she believes is on the page they’re looking at but is told that the button isn’t there.

Worst of all, she can’t tell whether there’s an actual bug in the product or the customer just isn’t looking in the right place.

Firefly fixes this problem: she can see exactly what the customer sees without interrupting their browsing experience at all. But what’s interesting is that we’re not really competing against other screensharing software in this case. We’re competing against her memory and her willingness to explain things from memory day after day to customers.

This is key to understanding how to sell it. Just because we ostensibly do the same thing (allow someone to see a customer’s screen) doesn’t mean that we do the same job as traditional screensharing.

And if we reflect this in the way we market our products it will help us find more customers and charge more money.
Think about who your real competitors are. To figure it out, find what job your product does and what people are switching from to use it.

After my meeting with Jason, my girlfriend and I spent the rest of the day in our hotel room pointing out different products and trying to decide what job they do. It’s a fun game, and some of the things you’ll find are surprising. For example, a shower doesn’t just get you clean – its job is to be a place to get away from everything and be alone with your thoughts.

You may have noticed that a lot of what I’ve said in the preceding pages seemed to apply both to product development and product marketing. This is because understanding your customers tells you what features to build and also how to pitch your offering. That brings me to my next point.

Great marketing and a great product come from the same place
Jason never explicitly told this to me, but it seems to ring true from everything else he said. If it turns out he doesn’t actually believe it, I’ll take full credit.

When a lot of people think of marketing or sales they think of tricks that fool people into buying something. But great marketing doesn’t do that. Great marketing comes from understanding exactly what the customer needs on an emotional level, and showing how your product will satisfy those needs.

A great product comes from the same understanding. When you know what your customer needs emotionally you can build something simple that fits those needs exactly.

When you understand what each UI element in your product means to your customer’s life, you’ll understand how to sell it better. What your product is and the way it is sold are completely symbiotic. And both depend on detailed understanding.

This realization is both simple and beautiful.

Doubt

I think the most important thing that I took away from all of this wasn’t necessarily the specific advice he gave, although that was certainly valuable. What was most important was how he gave the advice, and what it reveals about his approach.

The first thing that I noticed about him was that he wasn’t trying to convince me that he was right.

“This is what we’ve found works for us, and it could be wrong, but it seems to work,” he said gesturing at an image of Basecamp’s homepage being beamed to the wall by a projector wirelessly hooked into his Macbook.

I had come prepared with questions, a lot of them, and he had answers. But not quite the typical kind.

You see, when smart people give advice they tell you what you should do.

But what I’ve found over the past few years is that when the smartest people give advice they do three things:

1.     Before saying anything, they ask what you’re hoping to accomplish
2.     When they do give advice, it comes with a few caveats
3.     They don’t hesitate to say “I don’t know”

Jason was no exception. He was interested in why I was doing things just as much as what I was doing. (Aside: as a philosophy major nothing makes me more excited.) And he didn’t seem concerned with trying to appear right at all costs.

What he seems to do really well is concentrate on finding everything unnecessary about his business and removing it. That requires a deep understanding of his customers that he seems to pursue relentlessly.

It’s very easy to do things without taking the time to go back and evaluate how well they work. What’s difficult is to constantly and deliberately revise until you’ve cut to the bone of the problem.

That’s the mindset he seems to have. And that’s what I want to take with me.

——–

Thanks to Arielle Shipper, Ryan Shea, Mark Bao, Paul Singman, Joanna Weibe, Justin Mares, and Tony Diepenbrock who all read drafts of this post.

I like the holidays because they’re a chance to take my foot off the gas a little bit, get out of the car and reset the engine. They’re a chance to take a look at the map and make sure I’m headed in the right direction.

Over the years I’ve had a lot of conversations with some very smart people about what it takes to be successful. And as I get older, it’s interesting to get a chance to look back and see the parts of the conventional wisdom that turned out to be untrue.

I guess you can call these things myths, but really they’re statements that I can slip into a conversation with someone and have very little fear that they’ll do anything other than nod in agreement at their self-evident truth.

Two things have stuck out to me lately. The first is that the highest opportunity cost for an entrepreneur is when she’s in her early twenties. The second is that an entrepreneur has to drop every other interest in their lives except for business in order to be successful.

Myth #1: Your highest opportunity cost is your twenties
There are certain advantages that accrue to the young: lack of financial and social obligations and more energy to get things done.

But the problem with being in your early twenties is that in general you have very little idea of what the fuck is going on. Trust me, I’m 21.

Seriously though, the story of the young kid who comes out of nowhere to take his industry by storm has become incredibly ingrained in our collective consciousness. We take it so far that I know people who worry that if, by 25, they haven’t built a huge company they will be over the hill. I know people who think that if you don’t make it by 30 you just don’t have what it takes.

But we forget that the young kid with no experience striking it rich is the exception to the rule, not the rule itself. According to The Anatomy of an Entrepreneur, a research study conducted on over 500 successful companies by the Kauffman Foundation, “the average and median age for [successful founders] when they started their current companies was 40.”

Another study by SV Angel shows that 33% of founders with big (500 million +) exits were over the age of 30. 90% of founders with big exits were repeat founders.

Anecdotal evidence abounds as well.

Take Workday for example which was started in 2005 and IPOed this year. It was founded by David Duffield who is a sprightly 70 years old.

Even Paul Graham himself, champion-in-chief of the young entrepreneur, was 30 when he started ViaWeb.

Don’t get me wrong, there’s something to be said for young entrepreneurs. I’ve been the beneficiary of that stereotype as much as anyone else. But in this particular case, the truth of the “over the hill” entrepreneur is all made up.

Myth #2: To be a successful entrepreneur you must not do anything but focus on the business.

I was having coffee with someone a few months ago when they asked me why I blog. “Most successful entrepreneurs don’t have time to spare from their business to write,” he continued. I was a bit taken aback by this, and despite the volume of evidence that says otherwise, I resolved to think about it.

After all, if I had to pick between writing and having a successful business I should pick the business, right?

Well that’s something that I’ve thought about for a long time. I’ve been programming for 10 years, but I’ve been writing for even longer. When I was in elementary school I wanted to be a professional novelist. I wrote a 90 page story in 4th grade. But I decided at the tender age of 9, that I hadn’t experienced enough to really write things of substance. And so I started programming instead.

Yes I was an over-intellectual dweeb back then too.

But that choice has stuck with me, and it’s one that I’ve come back to think about a lot. There’s a lot of pressure to pick one. I have this image of a great writer who does nothing but sit in his room all day and churn out scintillating sentence after scintillating sentence. And then I have this image of a great entrepreneur who does nothing all day but build product, sell to customers, and rake in the revenues. Sometimes I feel like I have to pick one.

After all, isn’t intense focus on one area the hallmark of someone who’s great at anything?

But if I really sit down and think about it, if I spent all day sitting alone in my room I wouldn’t have very much to write about.

The truth is that being in business has made me a more interesting writer. And likewise being a writer has made me a better businessman. It gives me a platform to build an audience to market my products to and reach interesting people that I ordinarily wouldn’t be able to get a hold of.

This sentiment isn’t unique to me. I read an article a while ago that featured a letter written by Teller (of Penn and Teller) giving career advice to a young magician.

“Love something besides magic, in the arts. Get inspired by a particular poet, film-maker, sculptor, composer. You will never be the first Brian Allen Brushwood of magic if you want to be Penn & Teller. But if you want to be, say, the Salvador Dali of magic, well THERE’S an opening.

I should be a film editor. I’m a magician. And if I’m good, it’s because I should be a film editor. Bach should have written opera or plays. But instead, he worked in eighteenth-century counterpoint. That’s why his counterpoints have so much more point than other contrapuntalists. They have passion and plot. Shakespeare, on the other hand, should have been a musician, writing counterpoint. That’s why his plays stand out from the others through their plot and music.”

This isn’t to say that you should try to go and find two things to love so that you can merge them. That’s ridiculous. But it is to say that, in a way, the total agony of loving two things can help you be better at both. The choice between one or the other is fake. In fact, I’d venture to say that the choice is fake any time you feel forced to decide between two things that are important to you in your life. Non-obvious solutions exist for the intellectually curious.

I think the thing to take away from this is that unless you live in a hole you’re going to get advice from a lot of people. Some of it sounds true, and is completely false. Some of it sounds ridiculous and turns out to be true. But the only thing that you can do is honestly evaluate what’s been said (even if you don’t like it) and try to decide whether it makes sense. Sometimes the answer won’t be obvious right away. But time has a habit of making most of these things more clear.

George Bernard Shaw wrote, “The reasonable man adapts himself to the world: the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man.”

Don’t be stubborn for the sake of it. But next time you feel like you HAVE to make a decision, or you’re running out of time to do something with your life remember this:

The choices are fake and the truth is all made up.

———–

By the way, if you have a website and you want to do great customer support check out my startup Firefly.

From: Scott Carleton

Subject: just refactored your find_art.js that you did over a year ago

Part of me is thinking: in some ways, you were a terrible programmer

Other part is, well shit, it’s worked perfectly for the last 20 months and I’ve never had to touch it.

Scott is absolutely right: I am a terrible programmer. I don’t comment my code very well. Sometimes I ignore the DRY principle. I tend not to use fancy ternary statements, or worry too much about whitespace. My data structures can get ugly sometimes.

But in other ways, I (dare I say it) am a pretty good programmer. For example, Artsicle is a Rails shop and prior to working for them I had only had very limited experience in Rails or any true MVC framework. After a few weeks, I had mostly picked up the codebase and was building features without inordinate trouble.

I also ship stuff. A lot of stuff. I’ve probably built and released 20 apps over the past two years in a variety of languages and frameworks from Python to Rails to Node to Backbone.

42 Floors even publicly offered me a job to become a programmer for them. You can argue that it may have be undeserved, but either way given my ability to produce products with code, it seems that we have a dilemma on our hands.

Am I a terrible coder, or a good one?

I think it’s clear that we have definitional problem: what makes a good programmer?

In general, my priority since I started coding 10 years ago has been speed. How do I get this built as quickly as possible?

And there’s a very specific reason for that: when you’re working for yourself (and you’re young) it’s very unlikely that any one particular project that you build will be around for very long. So for me, it was more worthwhile to spend less time creating beautiful code so that I could spend more time testing out my minimal products. I always approached programming from a very practical perspective.

For me, the beauty in programming was the fact that it allowed me to build businesses where the only cost was my time.

I always coded with a product in mind; never just for the hell of it.

But when I got to college something interesting happened. Even though I’m a philosophy major, I began to take computer science courses. And approaching programming from a theoretical instead of a practical perspective really opened my eyes. Not only was programming a way for me to build businesses, it also became engrossing as something to study.

Real theoretical computer science (things dealing with complexity theory) actual becomes a lot like philosophy. And what’s funny is that a lot of the supposedly theoretical things that I was learning, actually made me better at building products.

It turns out there are problems that you face every day building an app like Firefly that having a grounding in the principles of computer science can help you with (who’d a thunk it?). If you understand algorithms and data structures you’ll be much better prepared to face a lot of the challenges that crop up building more complex web apps.

So a good coder is someone who has a theoretical understanding of the tenets of computer science, right?

Wrong.

Just because you graduated with a degree in computer science from Penn does not make you the next Jason Cohen or Patrick McKenzie.  You have to do more than just finish your homework to become a good coder.

Like most things in life, the answer to what a good coder is, is somewhere in between the guy who wants to get it out fast and the guy who wants to make it beautiful.

The answer is: a good coder knows when something should be quick and dirty, and when something should be thorough and clean. You learn to ask: is this really necessary? And sometimes taking a extra few hours to plan out how you’re going to build something is necessary. As time goes on that’s certainly becoming true for me.

The stuff I build today is much more likely to used than the stuff I built 5 years ago was. Which means that I have to shift my thinking a little bit. Instead of focusing purely on speed, I’m starting to look for elegance as well (if I didn’t my exasperated co-founders would probably kill me).

So next time you’re working on a project, give some thought to what’s most important: speed or elegance. Learning to answer that question correctly is half the battle.

P.S. In my defense, the find_art.js file that Scott was referencing was supposed to be a prototype. They weren’t sure if people would actually use the feature and wanted to test it. It ended up being so popular that they left it in!

I  write shitty code for my startup called Firefly. If you’re interested in doing better customer support and you have a SaaS business – we can help you.

The thing that stuck out the most is a passage where he describes how bias works. He talks about a study in which pairs of research subjects are given a real legal case to read. One is assigned to play the defendant and one is assigned to be the plaintiff, and they are given real money to negotiate with. He says:

When both players knew which role each was to play from the start, each read the case materials differently, made different guesses about what settlement the judge in the real case had imposed, and argued in a biased way. More than a quarter of all pairs failed to reach an agreement.

However, when players didn’t know which role they were to play until after they had read all the materials, they became much more reasonable and only 6 percent of pairs failed to settle.

What he’s saying here is that when players knew their roles in advance, they genuinely read the information differently and came to different conclusions about what a reasonable outcome from the case was. This reminds me of how people evaluate their own startup ideas. Here’s how it works:

1. They come up with an idea

2. They get very excited about it

3. They avoid doing real research on competitors.

4. If they happen to come across information that indicates that there might be problems with their idea they dismiss it immediately.

5. If they come across ANY positive sign that what they’re working on might be valuable they get incredibly excited about it, and cite it as a reason why their idea will work.

6. They think that their blind insistence that their idea is The Next Big Thing is why their vision will come to reality

Conversations with these people tend to have a very similar script.

Founder: “We allow companies to view their support requests from customers as threads and then post those threads publicly to avoid answering the same questions over and over again.”

Me: “What about Zendesk? Doesn’t that do the same thing?”

Founder: “Yes, but Zendesk only allows you to submit requests as text. We’re going to allow customers to submit videos of themselves describing the problem. I read an article in TechCrunch last week that said video is the future of online communication, and we’re super passionate about videos so that’s why we think we can win.”

There are a few problems with this approach.

Blind insistence that you’re right is not vision, it’s dangerous

If your goal is to spin all facts that come your way in a positive light for your startup you’ll very quickly find yourself removed from reality. Doing so is deadly. It’s lonely out there. And it’s very hard to make money in a fantasy.

Jason Fried wrote an article a few days ago where he talks about the advice that Jeff Bezos gave to his team recently. His key takeaway was that people who are right a lot, change their minds often. In the Hacker News comments on the article someone shared this quote:

As Keynes said, “When my information changes, I alter my conclusions. What do you do, sir?”

I think that abiding by that quote is a critical part of creating a successful startup. When you’re in love with your idea it’s very easy to stay in a bubble and disregard or rationalize information that you don’t want to hear. Most of the time you don’t even realize you’re doing it.

For me, a large part of my growth process over the last year has been to try and get rid of the tendency to explain away flaws in my plans without giving them deeper thought. Starting to get over that tendency has really helped me move more quickly and adapt the product that I’m building to real customer needs.

Don’t get me wrong, it’s great to be excited about your idea. But you should be excited about it for the right reasons, and interested in exploring why it’s exciting.

Which brings me to my next point:

It’s not about different features, it’s about different understanding

The founder we discussed above who is making a Zendesk competitor is making a critical mistake: he assumes that different features automatically means a better product. The reality is that it’s very easy to take a product and change around its features or add new ones. Doing so is like saying, “Look I just made a better house! I took all of the windows and replaced them with doors. That way people can get in and out of it more quickly.”

Clearly this is not an example of a better house.

The way to build a better house is to do this: understand how a specific group of people are currently using houses, understand how the way current houses are built is not conducive to the way that specific group wants to use them, find ways to build the house that satisfies those needs.

If you want to build a Zendesk competitor, the solution is not to go and add video ticketing to their list of features and try to get on TechCrunch. The solution is:

1. Understand Zendesk completely. Do this by talking to people who use Zendesk, both companies and customers

2. Understand Zendesk’s current competition

3. Figure out how customers and companies use Zendesk to interact with eachother.

4. Then find a specific set of companies that has a specific type of interaction that Zendesk doesn’t do well.

5. Then build a product that helps them to do it more easily.

Most people skip right to step 5 in this process. That’s why the products they come up with generally don’t do things better than Zendesk. There’s a reason why on the Y-Combinator application one of the questions is: What do you understand about your business that other companies in it just don’t get?

If you have competition (which if you’re building something with an existing market you will) then this is the key question to building your business. If you can nail that, the features will come and so will the customers. Without it you’re sunk.

But the funny thing is, you can’t see any of this unless you take those goddamn glasses off.

I have a startup called Firefly. If you’re interested in doing better customer support I’d love to talk to you about it some time.

But I got this in an email from them this morning:

Given that they were nice enough to credit me 100 bucks I decided to put aside my misgivings and give it a shot. We’ve been thinking a lot about online advertising recently at my startup, and so I thought it would be interesting in comparison to Adwords and LinkedIn Ads.

I set aside $50 to spend on a “Promoted Account” and $50 to spend on “Promoted Tweets”.

The Promoted Tweets function allows you to pick a few of your tweets and have them show up in other peoples’ stream. I selected a few of my most scintillating 140-character tidbits and let ‘er rip.

Those are pretty cool results! An 8% CTR is rather astoundingly high by online advertising standards.

The next thing that I noticed is that promoted accounts don’t seem to work too well:

They tell you to optimize your bio so people can connect with you more readily. I neglected to do so and forged ahead with all of my current settings. The result was that for $11 I got 6 followers.

My first thought was “this is dumb”. The ROI on something like this has to be very low. For the Promoted Tweets, I did get 130 clicks, but I couldn’t target those clicks at all beyond geographic region. And as far as the followers, I already have 3,000. How valuable could 6 extra really be?

For a total of $61.81 spent it didn’t seem like I was getting very much.

But as I thought about it more, I realized that what made that money seem like such a bad deal, was tied to the reason that advertising on Twitter feels icky to me: when you throw ads onto Twitter, you start treating it in the same way that you would Google. You begin to start measuring things like CTR, conversion rate and ROI.

But the way people interact with Twitter is fundamentally different from the way people interact with Google. And so measuring things like CTR and conversion rate on Twitter is completely missing the point.

Let me give you an example.

If you’re ever in New York and it begins to rain, a stunning and incredible ritual occurs. As soon as the clouds begin to form, a bunch of guys suddenly materialize toting umbrellas. They walk around the whole time it’s raining selling them for 5 bucks a pop.

I’ve been in at least a few rainstorms and have thought to myself “hey, what the hell?” and just bought one. After the rain goes away, the vendors just disappear into thin air.

The guys selling the umbrellas are filling an expressed need. When it’s raining out and people are walking around and getting wet, they need umbrellas. The vendors conveniently swoop in because they see that need and fill it.

The same thing happens on Google: people are already searching for things that they want. They’re like people getting wet in a rainstorm. They’ve expressed need, and they have the oft-quoted “purchase intent”. So putting an ad next to search results makes perfect sense. The ad is just like the guy hawking umbrellas.

But Twitter is not like Google. And selling things on Twitter is not like selling things on Google. Twitter is not like a rainy Manhattan avenue.

Twitter is like a synagogue.

Every Saturday at a synagogue a bunch of people get together. The relationship is social, and it’s communal. They go to synagogue for the services and then the schmoozing afterward.

Twitter is similar. Their tagline is, “Find out what’s happening, right now, with the people and organizations you care about.” Twitter is social. Twitter is communal.

And so, selling things on Twitter is like taking our Manhattan umbrella vendor, and having him go try to sell umbrellas in synagogue.

Imagine the scene. A bunch of hungry people are eating bagels and lox after services and chatting amongst themselves. Suddenly some guy comes up toting a bunch of umbrellas.

“Hey I know you’re busy talking with your friends but can I interest you in an umbrella? It only costs $5. It’s a great deal!”

I shiver even thinking of having to do something like that. It’s grotesque. And most importantly, it’s very unlikely to work.

What’s interesting to note is that the people that the vendor is talking to are the same people that minutes earlier may have bought an umbrella from him on the street on their way to temple. But now that the context is shifted, it completely changes the way the sales pitch is perceived.

In advertising, context is everything. And an umbrella vendor in a synagogue misses that entirely. As Gary Vaynerchuk might say, he’s like a teenage boy with his first girlfriend. He’s trying to close too fast!

So how you sell umbrellas in a synagogue?

Well, let’s say you’re Moses Goldstein of Goldstein Umbrellas. You go to services every Saturday. And then you go eat with the community. You share advice, and expertise. You trade stories with people in other industries.

It may seem like you’re just idly wasting your time. If you go and measure the ROI of what you’re doing it will stand at zero. It looks like it’s a very bad idea for you to pay your yearly dues at the synagogue.

But what you’re really doing is a primitive non-scalable version of content marketing. With every person you talk to, and every story you swap you’re establishing yourself as a trustworthy, reliable and well-liked authority on umbrellas.

Still, you won’t see any ROI.

Then one day a member of congregation comes up to you and says, “Hey Moses, my company is looking for an umbrella vendor. Of course the first person I thought of is you!”

And you suddenly have a new customer.
What this says to me is that there are a lot of companies that are going to get on to Twitter’s advertising platform, throw a few thousands dollars at it, see a low conversion rate and conclude “This sucks!” These are the guys that are selling umbrellas in a synagogue.

But as people understand the social web more they’ll begin to realize that on social sites the advertising context is shifted in much the same as the context is shifted between the street and the synagogue. In the street, the relationship is all about immediate need. You have a need, I’m the most convenient way to fill it.

By contrast, in a synagogue, the relationship is all about connection. It’s about developing and cultivating bonds between people in a genuine fashion. And then once those bonds have been formed, they’ll be utilized when need arises i.e. when someone is looking for an umbrella vendor. The arc on the relationship is many times longer than the arc on the relationship with a street vendor. The upshot of it is that Twitter allows you to build those relationships in a scalable way.

So am I going to continue using Promoted Tweets? Nah, but I do have a startup called Firefly. If you’re interested in doing better customer support I’d love to talk to you about it some time.

Despite the recent success of this blog over the past year (250,000 uniques, hundreds of new subscribers, republished in Lifehacker and others) the truth is that I’ve been a failed blogger for far more time than I’ve been a successful one.

The other day I got curious and went back to look through sites I had written on before I started my current blog. I found a two: one primarily written in 2005 called Techcast (I used it to promote my tech podcast) and one written in 2007 called Sanity for Dummies. Side note: I was 14 in 2005.

Go take a look at them. They’re horrible. Nobody read them. Frankly, I don’t even know why I bothered to link them up.

But really I think it’s a good example of how something that looks like a very fast road to a big readership really took a long time to build. If you visit my blog today it looks like I’m some kid who threw up a couple of blog posts on the default Posterous template and started raking in the traffic. In reality though, it took a long time for my writing and my experiences to catch up with my ambitions and begin producing returns.

I get asked a lot to give advice on how to blog. Having gone back and read through my old posts (this one is by far the best – seriously I was a lot funnier when I was younger) I thought this might be a good time formalize a few of my thoughts on how beginners can approach improving their blogging skills. There are a lot of patterns to be found in poor blog posts, and I’ve done my best to formalize a list of them and discuss how they can be avoided. So without further ado here are a few tips for aspiring bloggers.

Don’t blog

Seriously. It’s not for everyone. It’s really, really hard to do well in a consistent fashion. And no one will care about what you write for a long time. If you don’t like it, and you’re doing it because you think it’s good for your “brand” I think it’s unlikely that you’ll stick with it long enough to see results from it. 

The primary reason that I blog is simply because I can’t help myself. Writing things down is an instinct for me. Putting them on the internet is learned next step.

But here’s the good news: blogging is just one means to an end; it’s not the only means. All the benefits that you accrue from good blogging, can be accrued from other types of content creation. Maybe you enjoy talking more than writing? Host a podcast. Maybe you’re more effective when people can see your face? Start a video blog. 

Do whatever makes the most sense to you. You don’t need to fit into the blogging mold to start creating things that people want to consume. 

Stop writing a school report

A lot of the posts that get sent to me, especially by younger writers, are written like school reports. The school report format is this:

1. Do some research on your given topic

2. Pretending to be a subject matter expert, write an impersonal take on the facts you’ve gathered

It’s not your fault you write this way. We’re taught by teachers to write like this because they imagine that by the time we start writing things that someone else will see, we’ll be enough of an authority that this style will be effective. Unfortunately that’s not the case in the real world. And in the real world, writing like this is banal and forgettable.

Good writing has the essence of its author in every sentence. If you’re some kid in Iowa writing about venture capital, you can’t be writing posts in the style of Chris Dixon. If you’re a bootstrapped student in Pittsburgh you can’t write posts like Jason Cohen. Not only is doing so not believable, it’s also boring. 

Some people (my younger self included) want their writing to be read devoid of the context of its authorship because they think that their ideas won’t be taken seriously if people know they’re young, or inexperienced. They think that context will hold them back. But that couldn’t be further from the truth.

Context will set you free. 

If you remove the bland, impersonal filter that we’re all taught to adopt in school and replace it with more of yourself a few things happen.

1. Your writing will gain a personality and a unique perspective

2. It will instantly become more interesting and engaging

If you recognize your limitations, and your inexperience but also show how limited experience (or a different experience) leads to different perspectives, you’ll suddenly have things to say that are just as interesting as someone who has been in business for 20 years. Embracing your context, and framing your writing within who you actually are is the first step to writing interesting things that people want to read.

It’s also a lot more honest.

Decide who you’re writing it for

Are you writing for yourself? Or are you writing to be read?

I meet a lot of people who ask me to critique their writing, and when I point things out like: “Well people aren’t going to believe this” or “This is isn’t expressed clearly enough for someone to follow” I hear a lot of, “Oh, well I mostly wrote it for myself anyway.”

In a lot of cases this is a cop-out. It’s an easy way to excuse mediocre writing. In some cases it’s true though. Some people are genuinely uninterested in writing things that people want to read – as an example try reading some Hegel. 

And there’s nothing wrong with that.

For me at least, part of my measure for whether my writing is good is whether people want to read it. Don’t get me wrong, I’ll write blog posts even if no one reads them and I’ve done it for a long time. But if I can get someone to feel something when I’m writing; if I can get them to learn something, that’s what’s most satisfying to me.

You also hear this sentiment echoed by people other than lowly internet bloggers, like musicians. Here’s an excerpt from a John Mayer interview.

[You have to] define your expectations. Life is so much easier when you do that.

Otherwise you don’t know when you’ve hit the mark…I knew that I wanted to be a listenable artist. I wanted to be the guy that the best guitar players…wanted to hear when all the music in their heads was driving them nuts. I wanted them to come to my room and let me play them a song. That was when I figured out that writing songs was my calling.

I don’t concentrate full-time on my writing – I would call myself more entrepreneur than writer. And I don’t have nearly the same level of skill, talent or depth of experience at writing blog posts as John Mayer does at writing songs but I feel the same way. I want to be read. 

And if you make the decision to write to be read, that requires you to take care to express things in simple terms, to put your personality into the piece, and to contextualize everything you’re saying. It’s a lot harder to write things that people want to read. But that’s just part of the challenge.

You only get better by writing more. And reading more.

Apply the Lean Startup to your blog posts

I know a lot of people who have a file of finished blog posts sitting on their hard drives, or that they quietly post on their blog but make sure not to publicize in any way. They spend hours and hours combing through their posts trying to make them as perfect as possible and end up never publishing anything.

If you do this then stop. Please.

A big part of perfectionism is fear of failure. It’s an ego thing. Or it’s fear of being misunderstood. But seriously, no one is going to remember your crappy first few blog posts. Unless you’re an idiot like me, and you relink to them after people start to read what you have to say.

But really, the only way to learn how to be a better writer is to have as many people read what you have to say as possible. Over-editing your work is not helpful at the beginning. 

I’ve written over 100 posts on this blog since I started it. I can honestly tell you that every single post on this blog was published in first draft form. Every. Single. One. I read it as I’m writing it, and I give it a once over for errors. Once in a while I’ll send it to someone for a sanity check to make sure what I’m saying isn’t totally dumb. But beyond that I don’t do any real editing.

I’m not advocating that you don’t edit your work. I am advocating that you don’t overedit it. Just get it out there. It’s ok if it’s not perfect.

Don’t pay attention to things that don’t matter

Things like picking just the right template to capture your “feel”. Or finding the perfect blog title and matching domain name. Or getting the right tag line. Or crafting your bio page. Those are nice optimizations to make once you have traffic coming in. And honestly I would probably have a much higher subscriber count if I paid attention to any of it.

Maybe one day I’ll put enough time into this site to take it off of the default Posterous theme and start converting some more of my traffic into sustainable eyeballs. But the first step is to consistently generate high quality content that’s interesting, informative and most of all personal.

If I’ve done my job right, after you read a couple of posts on my blog you’ll feel like you know a little piece of me. And that’s the only way, if you’re writing without an exceptional degree of experience in your subject area, to generate content that’s exciting enough to get people to read it. 

Anything else is boring.

If you liked this post you should check out my startup Firefly. We do download-free screensharing for websites. If your company uses GoToMeeting, or cares abut customer support we can help you get better.

Even though I’m in college I still take a class with my old high school history teacher. No grades are given, and class takes place sporadically on the weeks when I’m back home in Princeton. 

Many teachers dislike when students bring food to their classrooms and eat while they lecture. In this class, food is a requirement and lectures are held at the Panera by my house. Most classes become unbearable to sit through after about an hour and a half. Students start wriggling around in their seats, and coughing loudly. The clock starts to move more slowly and the view outside the window suddenly becomes captivating. In this class, though, the hours seem to melt away almost imperceptibly. 

This is a class I hope I never graduate from. 

Mr. Figueroa is probably the smartest person in any room he walks into. He’s also the type of person that doesn’t seem to know it. Or if he does, he doesn’t let it on. 

He’s 40ish and married with two kids. He grew up in Puerto Rico, and moved to the US after he was accepted to Princeton for college. Eventually he ended up staying at Princeton as a professor. 

Back in those days, his students probably called him Professor Figueroa. These days he teaches high school history. Everyone calls him Fig. And that’s the way he likes it.

Most of his classes center around religion, or philosophy, politics or history. Today’s class, however, is on regret.  

.  .  .

“The older I get the more consequences each decision seems to have. It feels like everything has more weight. Like staying in school. What if by staying in school instead of dropping out I missed my opportunity to build a big company?” I begin. Fig is listening intently, hands folded in his lap. “How do I live with myself if that’s what happens?”

“Do you feel like you regret staying in school?” The thing about Fig is that no question is innocent. One question leads to another, which leads to another, until he’s asked you so many questions that the answer becomes clear to you. Very rarely does he need to do any explaining himself.

“Most days I don’t. But at least for me it’s sometimes easy get stuck on ‘what ifs’. And sometimes it’s difficult to get rid of. I read somewhere that you end regretting the things that you don’t do, rather than the things that you do. That kind of stuck with me.”

“Let’s think about that. You end up regretting the things that you don’t do, rather than the things that you do. Explain that to me a little more.” Fig replies leaning back in his chair. 

“Well the idea is if you go and ask senior citizens what they regret, most of the regrets start with ‘I wish had pursued my music career’ or ‘Or I really missed out on hanging out with my kids’. So most of their regrets come from times when they decided not do to do something.”

“But isn’t every decision not to do something, also a decision to do something else in disguise? So when the senior citizen said ‘I wish I had pursued my music career’ couldn’t that just as easily have been rephrased as ‘I wish I hadn’t become an accountant’?”

“I guess,” I say thinking hard.

“So ‘You regret the decisions you don’t make’ seems like a pretty vacuous distinction doesn’t it?”

“Well when you put it that way it does, I guess. But if it is a meaningless distinction then there’s no easy way to figure out which decision to make when you’re faced with one.”

“Sounds about right,” he replies with a wry smile. 

“This is not helpful,” I say shaking me head and laughing to myself.

“Every single person that has regrets, has them with the benefit of hindsight. But you don’t have the benefit of hindsight when you’re making your decision do you?”

I shake my head, no.

“So it makes no sense to judge a decision you made without the benefit of hindsight and let it affect your emotional state. When you make these types of decisions, and you make them carefully, sometimes you’ll choose right and sometimes you’ll choose wrong. All you can do is always make the best decision given the facts at hand. If you’re lucky you’ll learn your lesson from the wrong decisions and correct them. But other than that you can’t beat yourself up about these kinds of things. It’s just not useful.” Fig takes a bite of his sandwich. “The other thing is, regretting a pivotal decision basically means you want an entirely new life.”

“What do you mean?” I say.

“Well let’s say you regret going to Penn instead of Princeton,” he starts.

“That’s one thing I definitely don’t regret.”

“Alright, well for the sake of argument let’s say you do. In your imagination you’re thinking, if I went to Princeton my life would be exactly the same except that at the top of all my resumes I could write ‘Princeton Class of 2014’ and I could go to Princeton reunions and hang out with all of the high fliers.” Another pause for a bite of his sandwich.

“But what you’re not thinking about is that if you went to Princeton instead of Penn, by doing so you’d have to give up every single moment from the time you decided to go to Penn until now. Everything. Every friend you’ve made, every class you’ve taken, every website you’ve worked on, every lesson you’ve learned. You’re a completely different person if you choose differently on a decision like that.” 

“Ok, I see that.”

“And so the only time you ever regret a decision, is if you’d rather give up every single part of your life from then until now. Now, thinking about it that way, do you regret not leaving school?

“No.”

“And that, my friend, is the regret fallacy.”