Some people just naturally make their own path in life. They don’t fit neatly into the lines drawn for them, and they leave the beaten path frequently. I was definitely one of those people – and I learned some hard lessons about that life.

One of the mistakes I made, and that I’ve seen others make again and again, is believing that deviating strongly from the average means that you get to care less about selling yourself, impressing others, or “playing the game.” The total opposite is true.

Now, if you’re a true misanthrope and your idea of “leaving the beaten path” is to go off the grid and live in a cabin in the woods – more power to you, and there are days where I’ll be a little jealous. This advice doesn’t apply to you. Live your best life, and let no one stop you.

But a lot of people want to shirk society’s conventions and still be successful within that society. In other words, they want to march to the beat of their own drum, but still get all the money, fame, respect, power, or other rewards (whatever they may be) from being a successful member of the main band.

You can do it! Not only can you, but it’s awesome when you pull it off. But the mistake is thinking that you can do all that while paying zero attention to “what anybody thinks.”

If you’re doing a weird thing, you have to sell that weird thing. Intensely, and every day of your life, if you want to succeed. You have to live and breathe it, and you have to shout it from the rooftops. People who stay in society’s easy, normal paths can do so with little friction – they can keep their heads down, punch in and punch out, and no one will question them. Those lines lead to specific places with relative certainty, and if that’s where you want to go, you can just sort of strap in and go along for the ride.

But if you step off that path, life is no longer automatic. You’ve taken manual control, and that means a lot more effort. Part of that effort, if you still want the rewards from success that your society can offer, is convincing other people to believe in you.

Once you recognize that you can’t just toil in obscurity if you want to turn your weird life into a successful weird life, there’s a second mistake that you’re likely to make. I did.

That mistake is thinking that “selling your weird” means that you have to sell it to everyone, including haters and detractors. Totally false!

The second you step off the normal paths, people will start attacking you. Not many at first, but the number will grow as you get weirder, more successful, or both. Some will be random people you don’t know, but some might be old friends, family, people close to you.

You don’t need to convince them. You shouldn’t try. For every detractor, there are literally 50 million people that don’t know you at all yet. Those are the people you sell to.

A good sales professional knows that in the time it takes you to try to argue a hard “no” into a weak “maybe,” you could have just found 20 more people who give you an enthusiastic “yes!” Good sales isn’t about convincing people who are already super negative – it’s about finding people who are positive. So as you’re out there living your amazing, weird, successful life out loud, marching to the beat of your own glorious drum, don’t spend a second on the haters. But spend a lot of time on the neutral folks, and show them how amazing your drum really is.

I’m a pretty big geek. One of the geeky hobbies I enjoy is board gaming; we’re in a tremendous time for people who love complicated, elaborate board games. Growing up I’d always play anything with a board & pieces that anyone would put in front of me, from chess to Scrabble. If that represents the extent of your familiarity with the genre, let me assure you – board game culture runs deep, and it’s a lot of fun.

I’m a big enough geek about board games that I often do more than just play the finished product; I seek out discussion forums, read play-testing material, and watch interviews with designers. Not only is it solid entertainment for me, but there’s a surprising amount of insight that’s applicable to the business world.

One particular lesson that I found interesting is about when to just give up on a certain rule. The wisdom goes like this: if you’re testing a game (and these games go through hundreds if not thousands of hours of testing) and the majority of your players forget, ignore, or break a particular rule – get rid of it. The answer isn’t to try to reinforce the rule in some other way or to write it in a bigger font in the instructions. It’s to discard it entirely. Let the natural actions of your demographic shape your structure when you can; don’t fight against it.

It reminds me of a story I heard about the parks department in some Swedish town. Every time it snowed, they’d go out to their parks and make maps of where the footprints in the snow crossing the park were. Then, the next time they needed to add walkways, that’s where they would add them.

Otherwise you end up with this:

That lesson is hugely transferable to most businesses. If you’re trying to get a group of people to act a certain way – maybe your customers, perhaps your employees, etc. – and they simply won’t stay in the lines you’ve drawn? Redraw the lines around where they are.

If you sell a three-pack of e-books but you field a dozen calls or emails a day from people asking if they can just buy book #2, then figure out the price of book #2 and sell it alone. (Or, even better, sell Book #2 at the same price as before, but include Books #1 and #3 for ‘free’ with it. Nothing changes, but your marketing better matches your customer demographic – you’ve redrawn the lines.) Either way, don’t just fight the tide.

Remember that the end result you want is more important than the structure that leads you there. KPIs are only as good as the progress they enable towards a goal, but I’ve had more than one manager who loudly proclaimed that we were successfully hitting every KPI even as the ship was sinking. If the rules structure is working against the goals, it’s the rules that have to give.

Imagine the following hypothetical:

You have a friend, let’s say Jill, who’s working on a difficult problem, a mathematical equation of some kind. It’s deep and complex, but Jill is good at this sort of thing. Generally, Jill’s foundation is secure – however, by a stroke of bad luck, she received some bad information somewhere and her answer is incorrect.

Now let’s say that you’re also good at this sort of thing, and you spot the point of error. You decide you’re going to let your friend know. But before you can do so, some other obnoxious person, let’s say Jack, starts screaming at them that Jack knows the right answer, because Space-Emperor Zorgnax revealed it to him in a drug-fueled fever dream. Not only is Jack obviously bananas, but in this hypothetical Jack is also being a real dingus about it – claiming not just that Jill happens to be in error, but that Jill is generally unintelligent or not fit for her work, etc.

Now, let’s complicate things further. Let’s say by some coincidence, Jack actually is right. Not about the Space-Emperor Zorgnax stuff, but his actual end answer is the correct answer to the equation. You know, because you got there using actual math. He essentially just guessed, but even a broken clock is right twice a day and he happens to have gotten this one right.

What would you do?

It’s not as simple anymore as just saying to Jill, “Hey, you know how Jack is telling you that the answer is 48, in between screaming obscenities at you and threatening your death? Well, he’s right. It actually is 48.”

Your ability to be seen as objective has been stolen by a lunatic who happens to share your viewpoint.

That happens in real life, too. Not just in hypotheticals. More often that I’d like, I find myself in a similar situation:

“On the subject of X, I hold the A view. Lots of people hold the B view; I think they’re wrong, but they’re reasonable, polite, and I can see why they’ve reached the conclusion they have. Meanwhile, there are a bunch of drooling maniacs loudly shouting the A view – in my view, they’re correct, but not only are they ridiculous, they’re right for the wrong reasons.”

Why does it matter if you’re right for the wrong reasons?

Because your methodology won’t duplicate. Let’s say you decide which of two wires to cut on a live bomb by numbering them 1 to 50 and then picking a number out of a hat. If by some miracle you’re correct (and hey, there’s a chance), you still haven’t created some miraculous new bomb-defusing technique. Your methodology won’t withstand iteration.

That’s why it’s so frustrating when that broken clock is right. It’s hard enough proving someone wrong when their bad methodology has led them to an incorrect answer. It’s downright impossible to convince someone that their thinking is flawed when it accidentally got them the right answer.

I once saw a trivia-style game show where the host asked a contestant, “If I’m drinking the penultimate beer of a six-pack, which number beer am I on?” (‘Penultimate’ is a cool word that means ‘second-to-last.’)

The contestant, who clearly didn’t know the word, uttered the following string of nonsense: “Okay, ‘penultimate,’ huh? Penultimate. Pen. Like pentagon. And a pentagon has five sides. So… five?”

Ha. Broken clocks, etc.

I have a rule of thumb that’s served me well: If I have a strong opinion and a lot of people agree with me, I check my work. I’m wary of strong consensus. I’m doubly wary if the people that agree with me seem unhinged. They might still be correct, but for all the wrong reasons. That causes me to not only double-check my results, but my methodology. If I’m still right, I can be satisfied by that – but I’ll sleep better knowing that I did my extra homework before saying anything.

“It’s better to keep your mouth shut and appear stupid than open it and remove all doubt.” – Mark Twain

Sometimes I’ll mess something up, badly and repeatedly, until I finally figure it out. Often there’s a lesson to be learned in doing that, and I’m happy to learn it – but all knowledge is costly. In that case, I paid for my knowledge with an expensive and lengthy comedy of errors, and I’ll often reflect on whether or not there was a more efficient way to get the same knowledge.

Looking around at smoking ruins, lessons learned can seem pyrrhic. Sure, there’s a certain nobility in getting your lessons at the School of Hard Knocks, but sometimes it’s better to just pay the nominal fee to someone else that’s already done that and learn it the easy way. You don’t have to get ALL your information from a crucible.

But if you have, maybe you should share it. After all, there’s no real value in saying “I learned this the hard way, so you should too.” The Hard Way isn’t The Best Way. And in fact, one of the best ways to recover from a long series of missteps is to turn them into a viable product for others.

Want to hear the story of how I utterly crashed a business? It’s full of failures and mistakes. How about the worst interview performance I ever gave? Or maybe do you want to hear about time I got arrested? These are all true things. Big failures. Massive learning opportunities, and they helped sharpen me into the person I am now. But that doesn’t mean you need to repeat my mistakes in order to gain my super powers. Maybe you can get the reflexes without the painful spider-bite.

Besides, that leaves you more room to make new, exciting mistakes of your own! And you will. And you’ll pass them on, too, if you’re smart. And the whole world will get better, as we teach each other.

If I can see farther, it’s because I stand on the broken shoulders of giants. I invite you to stand on mine, if you like.

Sales is the art of equalizing the information asymmetry between a problem and a solution.

For most problems in your life, there is a solution out there somewhere that someone could provide for you. Cost isn’t the major barrier here – in many cases, a great product or service saves you money. That’s often the point; a huge percentage of your problems are that you’re paying too much for something, or paying for a bundle when you could be getting the components you want cheaper, etc. And even products you pay for, you generally did so because you valued their benefit more than their cost. In an indirect way my $2 cup of coffee might make me more than $2 more efficient at work, but even if it didn’t, I enjoy the act of drinking it more than anything else I’d spend that $2 on in as convenient a way.

So if cost isn’t the major barrier, what are the barriers that separate people from the products and services that would make their lives better? Why doesn’t everyone just buy the best stuff for them?

There are two primary barriers: awareness and skepticism.

Awareness is relatively easy to understand – no matter how good a product is, information doesn’t spread instantly to everyone on Earth. And even if it did, new people are being born all the time, so you have to always be doing some maintenance. You have to not only tell people about your product or service, but you also have to learn about your market. Your market knows a lot of stuff you don’t, and you know a lot of stuff they don’t. If all information were perfectly shared, you wouldn’t have to get out there and sell anything. But it isn’t, so you do.

Skepticism is the other piece. For every dollar I have, there is a huge myriad of things I could spend it on. I want to get the most value out of each dollar, but I don’t know what that necessarily is. I need information – and there are plenty of people willing to give me information, but they all have their own agendas. Even if we assume perfect honesty from all parties, no one bidder for my dollar has all the information available about every other bidder. You might honestly believe that the product you want to sell me in exchange for my $1 creates the best possible value for me, but you might be unaware that someone else is selling a service that would do even more for me. In the face of this much information, a healthy dose of skepticism is the barrier most people choose to put up.

I’ve trained a lot of salespeople in my time, and a very early frustration I see often is the “Honest Salesperson’s Lament.” That’s where an honest sales professional with a product or service that would be fantastic for a particular customer gets shut down and can’t figure out why. From their perspective, the product is perfect for the customer – it would cost negative dollars because it would immediately save them 2X the purchase price, it requires no contract, etc. But the customer gives a stern “no thanks” and walks off. Meanwhile the salesperson’s head is spinning.

What happened? Maybe the salesperson didn’t gather enough information, and there actually was a reason that the product wasn’t a good fit. But more often than not, the salesperson was actually correct and the product would have been perfect; the customer legitimately made a bad choice by not buying. But that’s not the customer’s fault – it’s the salesperson’s. The customer’s job is to protect themselves from bad buys, and that’s not a bad thing to be doing. The salesperson’s job is to overcome that skepticism and allow the customer to see the product with clear eyes, unclouded by fear.

A good salesperson undoes the bad influence of prior bad actors. Maybe a customer has been burned before by an unscrupulous person, and now you’re paying the price for it. That sucks, but it’s exactly what you should expect.

So sales isn’t really about convincing someone that they need your product. First, it’s about identifying what people do need, and figuring out how to get it to them. Then, it’s about letting people know that you’ve done that, and doing it in a way that promotes trust.

Just talking about your day is selling, if what you did during your day was valuable to other people.

Today my girls were pretty stir-crazy, so we put a blanket, two granola bars, and a banana in the pockets of our coats and walked a few blocks away to a large section of sidewalk.

It was a picnic because we said it was, detailed be damned.

Details never matter as much as concept. Go have fun.

It might not be what you thought you said.

“I didn’t steal Joe’s green pen” is a sentence that might seem to convey only a single meaning, but the reality is that it can convey many. In the traditional example, you have the following alternatives:

“I didn’t steal Joe’s green pen.” [It was Bob! He took it!]
“I didn’t steal Joe’s green pen.” [Even though you think I did.]
“I didn’t steal Joe’s green pen.” [I just, you know, borrowed it without asking.]
“I didn’t steal Joe’s green pen.” [It was Bob’s.]
“I didn’t steal Joe’s green pen.” [I took the red one.]
“I didn’t steal Joe’s green pen.” [I took his green stapler.]

That’s a powerful lesson in both speaking and listening. Be mindful of the inflection you use, and be mindful of the inflection that you observe in others. But there’s more to it.

The modern era has taken that lesson and given it about a million more dimensions. What’s the difference, in writing, between “i didnt steal joes green pen” and “I DIDN’T STEAL JOE’S GREEN PEN!!” How about if one has an emoji after it? Which emoji? What if you get it in an email versus a Slack message versus a text? What if it’s public or private? Are you bcc’ed? If you’re not, who is?

I’ve met people who somehow manage to sound incredibly hostile in every email they send, despite being incredibly pleasant people in person. And of course, a funny thing about the modern era is that I consider video chat and even a phone call to be “in person” – after all, I can hear their voice live, which is enough to qualify as far as I’m concerned.

There’s an old adage that communication happens in the mind of the reader/listener, not the words of the speaker. That’s true – which means you can sound hostile in an email even if there isn’t a hostile word in it. You don’t realize just how much heavy lifting your tone is doing for you in most “live” conversations. As soon as you remove it, words you say every day can sound totally different.

If this has been a challenge for you in the past (and it has for me!), then you probably won’t solve it overnight. You can’t perfectly anticipate the “mind of the reader” for every person you communicate with, especially if you haven’t made it a practice in the past. But what you can do, is be honest about that up front, and establish certain “rules” early on.

For instance, someone I know has in their email signature the following disclaimer: “Please assume any hostility in the tone of this email is entirely unintentional, and accept both my apology and my invitation to provide feedback.” Then there’s a little smiley face. That’s nice! It shows, at the bare minimum, that this person has thought about this concept at least once in their life and decided to make some positive effort towards improving. That’s better than a lot of people do.

No matter what, be flexible. These rules change. Some people seem hostile in emails because they came up in an era where it would be unthinkable to deliberately leave out punctuation just to soften an otherwise stern-sounding statement via text message. And people sending emojis now might not adapt well in ten more years where it turns out emojis are generally seen as super patronizing and rude. Who knows? The point is that honesty goes a long way – it’s okay to not know every informal rule, but all anyone really wants is effort. Show genuine effort and care, and you can get a pass on a whole lot of other stuff. Even in writing, a smile goes a long way.

🙂

I’ve noticed that there tends to be a pretty big divide between the “builder” personality and the “fixer” personality.

When I picture all the people I think of as “builders,” I think of really creative people. Innovators and idea generators. Visionaries.

When I picture all the people I think of as “fixers,” I think of really intelligent, observant people. The people who can make things work, who can deliver, who can improve.

Those two circles don’t overlap. No one came to mind who I couldn’t decide which category to put them in.

I think it’s honestly really hard to iterate on your own big ideas. I think when you have an awesome, big, amazing idea it can be very difficult to see its flaws, because you’re really emotionally invested in it. Likewise, I think when you’re someone who’s really good at visualizing all the moving parts of something, it can be hard to step back and see a macro version of it.

Some people are at their happiest dreaming big dreams. And some people are at their happiest tinkering. (And plenty of people aren’t happy doing either – this isn’t a “everyone in the world falls in one of these two categories” kinds of things.)

A lot of magic can happen when a great example of each of these get together. If you’re a builder, find a fixer. If you’re a fixer, find a builder. Work together. Make something amazing.

Imagine I told you: “Elon Musk stood on his head and recited poetry in Latin every morning.” You might think, “wow, no wonder he’s successful – he’s truly different than most people. His weirdness is a sign of the type of intelligence and creativity that led to his success.” I know that’s the reaction most people have when they learn a weird fact about a successful person.

Now imagine I told you: “Ted Bundy stood on his head and recited poetry in Latin every morning.” Many people might have an understandable response: “Wow, what a weirdo. No wonder he killed people – with other strange behaviors like that, people should have seen it coming. The guy was obviously nuts.”

Okay, so standing on your head and reciting Latin poetry: which is it? Sign of genius and sign of mental instability?

In a vacuum, you’d have no idea. If I told you that “someone” did that, but didn’t tell you who, and then asked you to guess if they were more likely to be an eccentric genius or a serial killer, you wouldn’t have a clue. But boy do we love those stories!

(By the way – neither person actually did that, at least to my knowledge. But you never know, I guess.)

The lesson here is to be careful about what stories about someone’s past you take as having been obvious evidence about their future. If you hear that a famous NFL quarterback played with toy cars as a kid, that neither means that all famous quarterbacks probably played with toy cars, nor that all kids that play with toy cars will become famous quarterbacks. But there’s always someone who will craft such a story, with confident-sounding nonsense like “Well, it’s obvious he had a predilection for accuracy and leadership right from his youth, because he admired racing, which requires both accuracy and sharp decision-making,” etc. Utter hogwash, but someone always says it.

The fact is, you can take anyone’s current situation and then find random anecdotes about their past and decide those anecdotes are reasons for their current circumstances. But not all of them are. People aren’t forged by single data points, and it’s extremely rare that the world turns on them. Your life evolves due to consistent actions, over and over again. Patterns of behavior, not weird single incidences.

Remember that as you try to draw life lessons from the success stories of others. Success comes from putting the work in, not from intriguing stories. Those anecdotes are interesting to us because stories are fun and interesting, but they only make sense as part of a larger context of that person’s life. You can’t just take that story and drop it into your own life and expect that it will be some sort of magical formula for your own success. You are your own context, and the stories we someday tell about you will be unique.

So take those stories for what they are – interesting, thought-provoking maybe, entertaining often. But they’re not an instruction manual. You have to do the work.

One year ago today I started this blog.

Since then, I have written in it every day. Plus an extra post here and there, so I have almost 400 posts. And maybe 80 good ones! I’ve experimented with recurring monthly themes, different writing styles, and a variety of topics. I’ve shared stories from my childhood and stories from the day I wrote the post.

I did not have a goal in mind when I started this blog. I wasn’t trying to sell anything or build an audience or sway people’s opinions on a particular topic. I targeted no particular demographic and spent no money on advertising. Other than trying to make sure every post was valuable enough to read, I had no immediate agenda.

Why write at all, then? I wrote because of my belief that it’s always a good idea to be moving forward. To be developing a skill, preparing in some way even though you may not know what you’re preparing for. Because movement, any movement, is good.

Inaction is the source of most regret.

And in that year, I’ve thoroughly enjoyed putting an entry into this blog every day. It’s given me a place to be productive when I want to be, and it’s forced me to be productive when I didn’t. An early commitment to keeping a public blog (as opposed to privately journaling or something) and shipping something every day has challenged me in very healthy ways. I’ve learned tremendous lessons about what I’m capable of during different moods, while different things are happening in my life, and so on.

I maintained a few rules for myself when writing this blog, too. With only rare exception, I actually wrote the same day I posted – I didn’t create a backlog except in the case where I knew in advance I wouldn’t be able to access my computer for more than a full day (such as going on a backpacking trip where I wanted to unplug specifically, things like that). Otherwise, I made myself actually sit down and write every day. Another rule I made for myself was that this would be a place of positivity. I would dig down even on the darkest days and find something, anything, that was uplifting, thought-provoking, or represented learning.

Pessimism is not an input in the Opportunity Machine.

There have been many, many side benefits that have come unexpectedly as a result of me writing this blog. I’ve been able to use it as a teaching and coaching tool in my work. I’ve been able to showcase my other writing and create a portfolio of sorts. I’ve had people reach out to me privately and tell me that one particular post or another was tremendously influential. People I’ve never met.

That one was a wild experience. Imagine you’re just doing a thing for you, like gardening or something, and someone comes to you one day and tells you that looking at your flowers as they walked by one day made a dramatic, tangible impact on their life. It’s not what I set out to do. But if any random two words I put together can lessen someone’s pain, their anxiety – can provide even a moment of clarity or inspiration, then I’ll write forever.

I hope I do, in fact.

Thank you, dear friend, for coming along on this journey. Whatever small good it may have done for you, it has done a thousand times more good for me. It’s made me a better thinker, a clearer writer, a more focused person in general. It’s made me more deliberate. It’s given me something to hold onto when things weren’t great. It’s been the space I feel most at home, and it’s been an honor to welcome you into it, as often as you’d like to come.

What will I try to do in the coming year? Maybe I’ll make a newsletter. Maybe I’ll experiment with discussion forums. Maybe I’ll do some videos. Who knows? What matters is that once you have a sandbox, you can build whatever you want in it.

Here are my top 5 lessons from writing a daily blog for a year:

1. Shipping something every day has tremendous value. It gives you more room to experiment, removes “perfection anxiety,” and creates momentum in your growth. Whatever you want to get better at, you have to do every day.
2. You can’t objectively evaluate your own work as well as you think you can. Posts I thought were brilliant collected dust, and posts I thought were just okay got shared a bunch. Everyone is different, so don’t be afraid to experiment with different stuff.
3. You can’t wear a mask 365 days a year. No matter what persona you want to display, if someone looks your way all year they’ll eventually spot the man behind the curtain. In other words, if you write every day, you’ll write authentically. You’ll be real.
4. People actually do care. I massively struggled with the “who the heck would want to read anything I wrote” thing, and I got around it by saying I was only writing for myself. But people did care, they did read, they still do. Ideas build bridges, and people cross them.
5. Positive action in one area begets more positive action elsewhere. I’ve done a lot for myself in this last year, and being able to write about it gave me extra motivation. Plus I’d been building the habits of daily action, which carry over elsewhere.

My favorite thing about April 14th, apart from it now being my blogiversary, is that it isn’t any sort of significant day for me otherwise. It wasn’t auspicious. I didn’t wait until the start of a year or even a month. I didn’t time it with any other event. It was just the day I decided “today I’m going to start a blog.” Now it gets to always be that day – and the day I stuck with it for (at least) a year.

What thing can be the thing you just decide to do today? What can April 14th, 2021 be the anniversary of for you?

Whatever it is, I’m with you. You can do it!