I’m going to tell you the story of Jane the Hiring Manager.

Jane is in charge of hiring a new Account Executive for her company. The head of the sales team that this AE will work for has certain goals for his team, and has communicated those goals to Jane, and then put Jane in charge of finding someone to fill the role. Jane does her research, comparing the resumes of the existing Account Executives on the team to their performance levels, and then factoring in things like industry average experience levels and backgrounds. Based on that, she puts together a list of requirements for the role that includes a minimum of 5 years as a Sales Development Representative and a Bachelor’s Degree or better.

Jane posts the job ad listing these requirements and starts to filter through the results. She automatically eliminates any application that doesn’t meet her requirements, since she doesn’t want to waste her time on unqualified applicants. But all the remaining resumes that she gets are unexciting and don’t seem to be good matches; the head of the sales department wants to know why the process hasn’t produced results yet, and Jane can feel the pressure on her.

Deciding that she needs more qualified applicants since the current crop isn’t meeting her company’s needs, Jane decides to add more requirements in order to improve the quality of her pool. She adds a requirement of 2 years as an Account Executive in the same industry and prior knowledge of the company’s specific CRM. The pool of new respondents to this job ad is even worse than before – no one has what she’s looking for.

Then she receives an email, not an application. The email is from Amanda, and it’s addressed to Jane directly. It reads:

“Hello Jane! I was speaking with a mutual contact of ours, John Doe who works as an Account Executive in your company’s sales department. He and I have known each other professionally for several years, and he mentioned that you were looking for a new Account Executive to handle new West Coast accounts. I just moved back from the West Coast myself, where I ran my own sales team for a startup in an industry with very similar sales challenges as yours, and my account executives closed accounts regularly under my direction that John says are very comparable to ones in your firm. I’m looking for a non-managerial role myself so I can focus on the sales process; I moved into sales leadership from operations (startup life!), so I really want to focus on being a contributing member of a team and generate revenue for the company and myself!

“I’ve attached my sales numbers for the last two years so you can see what kinds of accounts my team was working with as well as the improvements over the time I led the team. I’ve also attached a few articles I’ve written on the unique sales challenges of the West Coast, and a sample training doc I worked up for your company, converting those tips to your industry. Let’s talk soon and see how I can help contribute to your team!”

Jane very politely replies:

“Thank you Amanda, but we are looking for someone with 5 years’ experience as an SDR and 2 years’ experience as an AE in our industry, as well as a Bachelor’s Degree. Best of luck in your future career search.”

Here’s your challenge: Can you pinpoint the exact moment where Jane massively messed up?

It shouldn’t be hard!

It was the moment when Jane forgot that her “requirements” were totally not requirements at all.

You see, there’s no cosmic law that says that great Account Executives have to have five years’ experience as a Sales Development Rep. They don’t need to have been Account Executives in the same industry. They don’t need to have Bachelor’s Degrees or prior knowledge of specific software. Those things are all just clues. Indicators. Proxies for knowledge you don’t have as a hiring manager.

Imagine you wanted an apple, but the store you went to stores all their fruit in opaque boxes. They know what’s in them, but they won’t tell you. And they won’t respond if you ask for an ‘apple.’ You have to describe it. So you say you only want fruit that’s red (so no blueberries), and round (no bananas), and roughly fist-sized (no cherries). Then someone offers you a granny smith and you say, “No, it’s not red, and I asked for red only,” totally forgetting that what you actually wanted was an apple, not a “round, red, fist-sized fruit.”

That’s what Jane did. She forgot that what she actually wanted was a great Account Executive, not someone with those requirements.

Those requirements were just proxies for knowledge she didn’t have. Jane doesn’t have a super power that lets her look at people and know if they’ll be a great AE. She can’t just ask directly, because, well, people lie. Or exaggerate, or fluff, whatever. And hiring mistakes are costly. So she has to come up with reasonable filters that give her a good idea of what a good AE might look like.

She started off well! She used the current Account Executives as a baseline. She incorporated their performance. She looked at industry standards. She wasn’t wrong in the beginning.

Where she went wrong was turning her list of clues into a hard-coded list of requirements that she’d never deviate from. Your requirements are educated guesses, so you should always leave room to be wrong – especially if you’re not an industry expert yourself, as in this case. And more importantly, you need to leave room to actually consider the corner cases and exceptions.

If someone meets none of your requirements and applies anyway, it’s probably a smart move statistically to discard them – your time isn’t infinite. But that’s only if they don’t offer you alternative proof! Amanda had tons of evidence that she would be excellent at the role despite not meeting the specific “requirements,” but Jane didn’t consider it.

I know why Jane rejected it. Jane did her initial homework well – she gathered her data, knowing what backgrounds her existing Account Executives had. But she didn’t analyze the data. She knew facts about her successful AEs, but she didn’t have an understanding of why those facts correlated with their success. That deeper knowledge is what held her back.

If you pinned Jane down and said “Can you explain to me exactly why your list of requirements adds up to a great AE, but Amanda’s qualifications wouldn’t?” She wouldn’t know. She doesn’t know what makes a great AE, she only knows what the great AEs have. That’s not the same. That’s why, when she didn’t find anyone the first time, Jane went back and added more requirements, instead of realizing she was taking the completely wrong approach.

I wish this was an apocryphal tale; that I was using this as a hypothetical. But sadly, not only have I actually seen this exact scenario play out multiple times, but usually when I hear about it, I’m hearing about it from the hiring manager, who is complaining about how there are “no good candidates,” and they “can’t believe who had the nerve to apply, as if the requirements aren’t listed on the job ad.”

Fortunately, lots of hiring managers post job ads using the “requirements” language, but then are open to unique pitches. They’re smart, and know a good thing when they spot it. But even then, you may be chasing away amazing talent simply because they’re sure they’ll get rejected even though they would be great because they’re intimidated by the phrasing!

So here’s my challenge to everyone in position to write a job ad or execute a search based on one:

STOP USING THE WORD “REQUIREMENTS!”

Instead, phrase it like this:

“We have a team of amazing Account Executives, and we want to add to it! On average, our existing, successful AEs have:

• 5 years’ experience as a Sales Development Rep before becoming an Account Executive.
• 2 years’ experience handling accounts in the industry before joining our elite team.
• A Bachelor’s degree in communications, marketing, or a similar field.

So if you have those things, we’d love to talk to you! But we’d equally love to talk to you if you can demonstrate you’d make a great Account Executive in some other way. The burden is on you to prove it to us, but we’re all ears!”

Then, work with your department heads! You don’t have to be an expert on the role or industry yourself to be a great recruiter or hiring manager. You just have to be humble about the limits of your own knowledge and be an amazing collaborator! I’ve built incredible teams in areas I had little to no prior knowledge in because I was able to leverage the knowledge of my department heads and combine it with my skill at managing this process. You can do it too. When you get those unique pitches for the role, gather more info and then take that report to your department heads. Watch them light up like a kid at Christmas!

If you do this, I guarantee you’ll have better results in every way. A better candidate experience, better hires, more satisfied department heads and clients, and more personal satisfaction in your work.

There’s an image that’s been floating around the internet for several years in one of a dozen different variations. I think it’s a very helpful thing to think about, so I’m going to share it and analyze it a little with you. They’re all the same with different phrasing, so here’s one I like:

Those circles represent various things you can do with your time. I think it’s great, but it warrants some explanation, and then we’re going to see how we can make this concept work for you.

So first, let’s look at each of the three main circles.

Things People Get Paid To Do: People get paid for all sorts of stuff, from bio-chemical engineering to early childhood intervention. People make each other coffee and shoes, they tell each other about Egypt and meditation, they take each other places and give each other tools. Human wants are infinite, so there are a whole lot of things you can get paid for.

What You Really Enjoy Doing: I love playing with my kids. I love singing, despite my utter lack of proficiency and frequent requests that I stop. I love helping others succeed. I love driving and listening to music – I love each of those things separately, but I especially love them together. I love movies and writing and designing organizational systems. Hopefully you have quite a few things you love, too – there are more things to love than there are stars in the heavens.

What You Are Good At Doing: People can be good at large groupings of skills or individual tasks and everything in between. Someone can be good at “construction” or someone can be specifically good at one particular aspect of it. Someone can be very tech-savvy in a general way or be amazing at one specific program. You can be good at something very concrete like calculus, or you can be good at something harder to measure like leadership. You can be amazing at flicking paper footballs through goalposts made of pencils stuck in erasers at your desk.

So what happens when these things overlap?

“Dream.” When you have an activity that is something that (some) people get paid for and that you really enjoy, but isn’t something you’re good at, you get the Armchair Activities. If you’ve ever been called an Armchair Quarterback or Armchair Economist (or called someone else that), then you know what I mean. It’s being an amateur. I don’t love the term “dream” because something might not necessarily be your dream just because you enjoy doing it, but it works in one sense: If you don’t do anything to improve, it will definitely stay firmly in dreamland.

“Hobby.” When you combine something you enjoy with something you’re good at, but it isn’t something people get paid for, we tend to call that a “hobby.” Some things don’t really feel like hobbies – for instance, I love playing with my kids and I like to think I’m a pretty good dad, but I wouldn’t exactly call it a “hobby” – but you get the idea. These are valuable things in your life and worth embracing, but they’re generally things you’re paying for in one way or another, not things that are paying you.

“Drag.” Hahaha, I don’t love “drag” for this category, but I’ll admit that this is where most people’s jobs end up. Stuff that people pay for and that you’re good enough at for them to pay you, specifically – but that you don’t necessarily love. I don’t like “drag” because honestly I think many people can just do their job and find happiness in other areas of their life, but I’ll also admit that most people doing that don’t reach any sort of exceptional heights in their profession.

And then there’s that middle section. The fountain of youth, El Dorado, Atlantis. Except it totally doesn’t have to be fictional. So let’s look at some actionable advice for how to find a career that puts you there!

One way is the direct approach. Take those three big circles and make them into lists for yourself. Don’t do it all at once – brainstorming is a process that’s hard to force. But make a list for each of the three, put 3-5 things on each list, and then over the next week or two, keep putting stuff on them each time you think of one. Each time you get a compliment on something you’ve done, put it on the “stuff you’re good at” list. Each time you find yourself smiling or whistling, look at what you’re doing and put it on the “stuff you enjoy doing” list. And each time you meet someone cool, interesting, smart or nice – find out what they do and put it on the “stuff people get paid for” list. The lists will grow quite a bit over a few weeks.

Once you have some pretty sizable lists for each circle, look for any overlap. Any tasks that might meet in the middle. For instance, you might have found yourself smiling while you were fixing a leaky pipe under your sink, making you realize that you actually enjoy working with your hands. And someone may have thanked you for doing such a great job helping them assemble their kid’s new go-kart. And then you met someone at the bar who you had a great conversation with that turned out to be in fabrication. Those might have been separate incidents that didn’t really connect until you were looking at them in this way, but now all of a sudden the pieces fit, and maybe you really weren’t meant to be an accountant and that’s just what your parents told you would make you “successful” twenty years ago.

Beyond that, all the technical stuff is easy. Jumping in and figuring out how to go into that industry is a piece of cake compared to deciding to do it. Start with a Google search of “how do I work in fabrication” and go from there! Or heck, just talk to that friend that does it and follow the threads from there.

So that’s one way. But there’s another way that can be just as good. Take one of your existing activities in the Dream, Hobby or Drag categories and upgrade it!

How do you upgrade it? It’s different for each category, but not hard to understand:

Dream: This is pretty simple – practice! You already love this and it’s already something people pay for. You just have to get good at it. Chances are really, really good that the only things holding you back are some combination of A.) the belief that you can’t and B.) an unwillingness to pay the cost in time and effort. Well, A is complete hogwash and B is a switch you have to flip for yourself, but just know that it’s 100% possible to do this.

Hobby: Monetize! For almost every possible hobby, there’s a way to turn it into an enterprise. If you’re good at something and you love doing it, guess what – other people love doing that thing too, aren’t as good as you but want to be, and are willing to pay to make up the difference. Consider – for your hobby, have you ever read a blog, watched a video series, bought a book, etc.? Well, someone made those things – and in one way or another, someone is probably making money from it. Follow the threads!

Drag: This is probably the toughest one, but it’s possible. If you’re good at something and people are paying you money to do it, figure out what you hate about it and see if you can eliminate that aspect without throwing the baby out with the bathwater. Maybe you’d love what you’re doing if you had a different boss or a slightly different spread of workload. I made a lot of incremental improvements in my career by figuring out which specific aspects of my job I didn’t like and then moving into something that was really similar but with some slight tweaks. You’d be surprised how much even small tweaks can improve your enjoyment of your task. Try a transfer to a different department, a different schedule, or even the same industry but a different company within it. Then see what’s changed. If you still want to pull your hair out, you can still bail out – but at least you’ll know more.

You might not ever reach the perfect center; the apex of perfection probably doesn’t exist. But you can be constantly moving towards the center, doing more and more stuff that you enjoy, makes money, and you’re good at – and less stuff that doesn’t fall in those categories. That’s the path to a happier life.

This week, I had about a half-dozen occasions where I reached out to other people for small favors.

None of them were huge, or even things I couldn’t have done on my own. Most were information-based. Each of them represented a use of comparative advantage, though – in each case, the small favor took less than ten minutes on the part of the other person, but would have been hours upon hours of work for me, given the disparity in skill set or knowledge base.

While that alone would be a great lesson in why specialization and networking are great, that’s not actually the lesson I want to draw from the experience.

The lesson is that people are awesome.

None of those people asked for anything in return. None of them blew me off. I asked politely for a favor and made it clear I understood that they were doing one for me (in other words, I didn’t try to disguise my asking for a favor as something else; I was up-front). I offered sincere gratitude both before and after. And people came through.

This is a powerful force at your command. Master these three things:

1. Politeness
2. Gratitude
3. Character

And the world is your oyster. Politeness is a virtue I shouldn’t have to explain, but I will offer my own unique definition of it: “Politeness is treating other people’s time as a finite, precious resource that is at least as valuable, if not more so, than your own.” Time is money, money is effort, everything is juice, and so when you take up even a moment of someone’s time you’ve cost them something. The absolute least you can do is make them feel good about the expenditure, and that’s what politeness does.

I’ve already talked about gratitude, but just remember – politeness may get you the favor, but without gratitude, you’ll never get another.

And character, in this context, is simple: Be the kind of person other people are happy to do favors for. That means, among other things – do favors yourself when you can; don’t let their favors be wasted; always show that you’re putting in plenty of your own effort and not relying exclusively on the favors of others.

If you nail down those three things, I promise you that the good people of the world will fall over themselves to help you. People want to help! People want to lift up their fellow humans, do good deeds, and contribute to their society. The heart and soul of mankind is good. Give them the opportunity to make you the focus of their altruism and they will, again and again, if you meet those criteria.

Politeness, gratitude, character. And to everyone that did me a favor this week or ever: I know I thanked you directly, but I thank you here again. Profusely and sincerely. You made my life easier. If I can ever do a favor for you – or anyone – don’t hesitate to ask.

A flaw I carried around with me for many years was not being great at “checking in.” I’ve worked remotely for a long time, and while I’m good at communicating high-level strategy and giving reports when needed, I’ve often fallen into the trap of communicating only the bare minimum necessary. I’ve never liked being micro-managed (who does, right?), and I’ve often chafed under onerous reporting requirements – I preferred to just manage my own affairs and deliver on my promises. While some of those requirements have indeed been too onerous, I have to admit that good management often needs more data than I was providing, and there have been plenty of times when I should have checked in more than I did.

But not lately. Lately, in fact, I’ve gotten more than few compliments from people that I’m a great over-communicator. That I go above and beyond in keeping people in the loop and connected with what I’m doing.

My reaction was… huh? Me?

Since I’ve always known that was a flaw of mine, and it remained stubbornly so despite my attempts at correcting it, I’d mostly abandoned the idea of improving that metric (I know, shame on me!). Instead, I’ve tried to just be so valuable in other ways that it washes out; I’d made peace with the idea that my idea of ‘sufficient check-ins’ was going to be different than others’. So what suddenly changed that after years of trying to improve and then giving up, would I suddenly be great at it with no deliberate effort?

Oh yeah. I started blogging every day.

Put another item on the list of benefits that this blog has generated for me. Without even realizing it, I’d been training myself to talk about what I’m doing in a public way, every day. I don’t do a “recap” blog once a week or twice a month. I blog every day. That habit is strong. And it cleared the road to doing that in other ways, like making sure to send frequent updates to the rest of my team.

You can train yourself like this for anything. You can give yourself small, daily tasks that have similar skill requirements to things you want to improve on. It’s one of the reasons I say “When in doubt, work.” You never know what other skills you’re teaching yourself that you didn’t even realize.

I’m a big believer in visualization.

In the same way that the hardest stage of a rocket is the first, the hardest part of the trajectory of an idea is the stage where it leaves your brain and makes the jump into the world. The brain cleanses itself; it forgets things, rewrites them, convinces you that ideas weren’t good.

Once it’s on paper, the brain can’t do those things to it anymore. It’s escaped the brain’s gravitational pull.

There is a distance between “an goal in my mind” and “a goal I wrote down;” call that Distance A. There is also a distance between “a goal I wrote down” and “a goal I accomplished.” Call that Distance B.

I’m telling you that Distance A is way, way, way greater than Distance B.

Is your self-esteem lower than it should be, given objective facts about you? Have people told you to “tell yourself that you’re great!” Well, that’s hogwash. You’re the one telling yourself that you aren’t great, so at best you’re evening the scales.

Instead, write down that you’re great. Every day. And hang it up where you can see it.

Because unless you’re writing down that you’re a loser every day and hanging THAT up (and if you are, you know, stop), you’ve not put the good thoughts in a tremendously advantageous position over the bad ones. (By the way, this includes words you post on social media or anywhere else.)

You can say “I want to lose weight.” But another part of your brain is saying “sitting on the couch is easier.” Those scales are even, so inertia breaks the tie and you do nothing. Instead, write down your goals. Make a plan on paper. Commit to it publicly. Take the good thoughts and ideas and barricade them outside of your brain, where they’re vulnerable to all the biases and flaws of our psyche.

Outside of your brain, somewhere you can see them, these thoughts will gather power and momentum. A wall will slowly fill with pieces of paper you’ve taped to it with goals and positive words. A word document or excel spreadsheet will grow and grow with things you’ve accomplished or wisdom you’ve gained.

Maybe a blog will gather entries like a snowball rolling downhill.

And before you know it, you’ll have a combined sum that is far greater and more powerful than any passing, fleeting negative thought. “Man, I feel like such a loser today. Oh wait, here’s this list of 547 things I’ve accomplished in the last two years. Never mind, I’m cool.”

Write down something today. Anything good. A thing you did, a thing you learned, a thing you want to do that’s positive. It doesn’t matter, just write it down, right now. Comment on this post if you want, and you’ll have an instant cheering section. But wherever you write it, write it where you’ll see it, and do it right this second.

Then do it again tomorrow.

This past weekend, I had the opportunity to meet an artist whose work I’ve followed and enjoyed for more than a decade. He’s brilliant, and he’s given me tremendous insights into the world over the years, as well as more than few Darmoks that I’ve been able to use with friends. In fact, I’ve even met new friends due to shared appreciation of his work, so you could definitely say he’s had an influence on my life.

The bulk of his work has been in serial comics, but he’s done tons of other stuff, from novelty items to sketch comedy to pop science publishing and even a new political book. Because of his sketch comedy, I’m not only familiar with his work, I know what he looks like, sounds like, etc. We’ve also interacted in a friendly way online a few times within the fan/creator dynamic, but that further pushed him into the part of my brain that registers “friend” rather than “public figure.”

And then this past weekend, I met him in person, in a format that was pretty casual and familiar. And I had this very strange moment of experience when I first went to shake his hand where I realized that he felt like an old friend to me, but I was more or less completely unknown to him.

To be honest, it wasn’t a pleasant feeling. It felt creepy, like I was a stalker. I knew so much more about him than he knew about me, but then we were just chatting about parenting and board games and stuff. I felt dishonest. Normally one of two things is true about another person. Either:

1. You know roughly the same amount of information about each other in terms of volume, OR
2. You don’t ever actually interact.

It’s one or the other. I know way more about Donald J. Trump than he knows about me, but we also never talk so it doesn’t matter. I talk to my sister all the time, but she knows about as much about me as I know about her so I don’t feel weird in our interactions. This was a new experience for me. I started to even use this idea as a conversation-starter, but even that felt creepy. Saying, “Isn’t it weird how you don’t know anything about me but I know so much stuff about you,” felt like a line from a horror movie. Thankfully there were lots of other things to talk about. Also thankfully, he was a super cool guy and really great to interact with, which lessened the awkwardness considerably.

The whole experience made me reflect on all the different levels of information asymmetry we encounter every day. How much more you might know about some subject than someone else. I think we mostly walk around thinking that human knowledge is spread pretty evenly, and that even expertise only represents a small increase over the norm. In reality, you probably have many orders of magnitude more knowledge than the median within a few areas, and virtually none in most others. It’s a yawning chasm, and it can give you some vertigo to look over the edge.

I love hearing about other people’s experiences. I love the everyday minutiae, and I love the big formative events. I love culture, down to the individual level. Many times, I dive in – if someone starts telling me about things I’ve never experienced myself, I’m very drawn to try those things out. It’s very easy to convince me to try a new book, restaurant, musician, etc. Just suggest it and I’m practically there.

Sometimes, however, I’ll learn about experiences that I don’t have any interest in trying first hand. I don’t want to smoke meth. I don’t want to kill a person. Things like that. That means, though, that when I hear someone has done something like that and is willing to talk about it, I’m all ears.

I will hopefully never learn about the experience of meth smoking, person killing, or similar unpleasant things directly. And the people who have done them are probably not as likely to cross my path naturally as someone who hasn’t, simply because of the common consequences of those things. So they represent “rare information” to me. I can read about meth addiction and the criminal justice system from the safety of my office, but that isn’t the same at all.

I also, however, don’t want to seek out murderers and meth heads and strike up conversations with them. But that’s because I have a preconceived notion of what a “murderer” or a “meth head” looks like. I have no idea if those stereotypes are true.

Quick aside: I’ve interacted with – in fact worked with – at least one person I know to be a murderer. They served jail time for it. They paid their debt to society and rehabilitated. Then they were my awesome co-worker. But apart from knowledge that the event occurred, it was never really appropriate to discuss it, so I didn’t learn much. Except, perhaps, to challenge my assumptions.

Quick aside #2: I’m not some morbid person obsessed with locating killers to talk to. That’s just an example.

My point is, humans have a strong tendency to pre-judge and form opinions on what people must naturally be like based on certain criteria, and then if we miss that window to pre-judge we can be really weirded out by it.

Let’s say you’ve formed the opinion that everyone from HokeyTown is a brain-dead jerk, stupid and mean no matter what. Low-brow, no culture, etc. All things you dislike. Then you meat some wonderful person named Sam, and Sam is the love of your life. Erudite, sophisticated, kind and nurturing. You fall in love together and have plans to get married, and Sam says they’d love to have the ceremony in HokeyTown, because it’s their home town.

Blam, ton of bricks. You’ve got to reconcile these two ideas. “Everyone from HokeyTown is an idiot jerk” and “The most wonderful person I’ve ever met is from HokeyTown” don’t jive; the ideas can’t coexist.

The best case scenario is that you say, “Wow, I guess I was wrong about my very strong opinions on the residents of HokeyTown – and in fact, maybe my deeply-held priors could all use a little review.” The worst case scenario is that you conclude that Sam has somehow tricked you, hiding their true nature as a malicious moron in a deliberate attempt to deceive you, and in fact this itself serves as further evidence for your bias.

Most people land somewhere in the middle, unfortunately. They keep their opinions on HokeyTown in general, but come up with some excuse or exemption for Sam that makes them “no true HokeyTownie.” Of course, that won’t solve the problem for long – Sam probably doesn’t share your dismal view of the residents of their home town, and if you insist on holding fast to your bigotry then the relationship is unlikely to persist.

Which, unfortunately, is what often happens. The story of star-crossed lovers who cast aside their societal prejudices in order to be with someone they’ve evaluated on their merits to be wonderful is a great tale, but it plays out less frequently in real life than I would like.

So in my head, I have this sort of mental encyclopedia entry on “meth” that says “Everyone who has ever done meth now looks like this, and no one who looks like this has ever done meth.” So if I meet a bunch of professional-looking folks at a networking event or something, my natural assumption is that none of them have smoked meth before. That’s probably true, statistically, and the assumption by itself isn’t the problem.

The problem come up in the unlikely scenario that one of the professionals A.) has in fact smoked meth in the past and B.) I find this information out somehow. Maybe they tried it once in their teens, thirty years ago, and learned to avoid it ever afterwards?

Because I have this pathological desire to learn everything about people, I’m likely to be the tactless guy that says, “Wow, you’ve done meth?! That must have been crazy! Tell me all about it!” That’s not the standard reaction, though.

The standard reaction is your brain starts sounding alarms, because if given the choice between revising an entire mental model of how you perceive the world versus throwing this one person under the proverbial bus, your brain will probably try to convince you that this person isn’t worth talking to – no matter what “disguise” they’re wearing now, they’re obviously a deranged, drug-addicted meth head. Forget about the fact that they were just telling you about their 30-year career investing in charities that help crippled children, that’s just a cover for the dangerous scum they really are… right?

The lesson here is complex. It’s not “never judge anyone, ever.” Past behavior remains the best indicator of future behavior. Contrary to folksy truisms, the cover of a book tells you a lot about the contents. The lesson also isn’t “people can always dip their toes in the pool of bad behavior or immorality and come back from it.” Sometimes they can’t – or at least they don’t.

I think my lessons here are: don’t hardline, and try to get first-hand data when you can. Don’t hardline, meaning don’t let your mental encyclopedia define things in terms of “never” or “always.” Leave a little room for exceptions. Leave room to be wrong. People are complex, and rarely entirely good or bad. Leaving yourself room to be wrong about them also leaves them the room to improve. There’s no surer way to make sure someone never gets better than to build a society that tells them they never can.

Get first-hand data when you can, because everyone is biased. You’re biased, and the person you’re getting even first-hand data from is biased, too. So it’s best, whenever you can, to not play whisper-down-the-lane and introduce a bunch of extra biases as well. Don’t let too many editors get their hands on your mental encyclopedia, and screen them well.

I’ve never murdered anyone and I’ve never done meth. But I’ve done plenty that would fall into other people’s unpleasant mental categories. And sadly, I’ve personally experienced the rapid change in opinion when someone learns of one of those things that happened twenty years ago. It makes me less likely to write someone off for the red in their own ledger, and maybe that’s enough for it to have been worth it.

When my oldest daughter was about 4 years old, I showed her a picture. It was an actual photograph, not electronic. She wanted a closer look, so she intuitively placed her thumb and index finger on the photo close together, and then spread them apart while in contact with it. She then tried a few more times and was frustrated that it didn’t change.

She was zooming in. She’d literally never seen a photograph that wasn’t on a screen before, and so she was confused that it didn’t respond to the input. At first I laughed in the way old people laugh about kids that can’t use a rotary phone, but then I realized how impressive it was. She was four years old, and her level of interaction with these devices was nearly innate. Things that adults struggle to learn will be second-nature to her.

A few days ago when she sat down with me to add a few words to this very blog, I didn’t even have to give her any instruction. She knew how to operate the keyboard – how to hold shift to capitalize letters or generate an exclamation point. When I was 7, I certainly didn’t – but I didn’t grow up around keyboards in the same way that she will.

If you’re young, never ever underestimate just how much value you can bring to the table simply because of stuff you grew up doing that older folks are clueless about. Don’t fall into the trap of thinking you can’t compete with more experienced people solely on that basis. I might have decades more experience than you in certain things, but there are other things that are literally second-nature to you that I have to struggle to learn. Find areas where those skills are in demand and use that to your advantage.

When Microsoft Office Suite was first being introduced, it was all the rage to be able to use it. It was a hugely in-demand skill that impressed employers and moved you along in the application process swiftly. So people caught up and pretty much every white-collar professional learned how to not only use it, but learned to indicate that they knew how on their resumes. For many people of that generation, the learning was formalized – classes or certifications, etc.

Now, I hear younger people laughing about the question. Not knowing it would be the strange departure, so it seems silly to even ask. Imagine there was a 6-week certification course in smartphone use. It covered things like downloading and using apps, text message communication skills, WiFi versus 4G, etc. There’s a segment of the older population that might think that was useful, but for a young person that would be laughable.

Older people and younger people bring different strengths to the table when it comes to value-add for employers. I see both populations struggle with naming that value sometimes. There’s plenty of ageism in both directions among hiring managers, but in general I think the older folks are better at knowing the positives they carry. They know the value of their experiences, their wisdom, and their maturity.

Young people, on the other hand, often struggle to realize just how many things are second-nature to them that would represent massive investments to learn for older people. Heck, I’m 36 and the whole reason I’m writing this post is because I started researching how to make short instructional videos that don’t look like garbage and people who are 15 are cranking out stuff that would have gotten you on national television when I was their age.

If someone grew up on a horse farm, then they know more about horses than someone who never saw one in their life before they went to college and got their degree in “equestrian studies.” But the degree gives you a certain sense of confidence that you know what you’re talking about (whether you actually do or don’t). So many young people have essentially a decade or more experience in complex skills simply by virtue of their generation, but there’s no “official” or socially-accepted category for that kind of knowledge. It’s not a degree, it’s not work experience, etc. But it would be insane to discount knowledge you gained because you literally grew up around a particular subject.

Take honest stock of your skills. Pay attention to things that you do well. If you’re thinking, “this can’t possibly be a valuable skill, because it’s so easy for me” – you’re exactly 180 degrees wrong. The fact that it’s so easy for you is exactly why you can use it to add value.

I’ve never been good at sleeping.

Somehow I just never mastered the elementary skill of shutting my brain down for a few hours. I exercise and eat well, but I’ve got very persistent insomnia.

I drink way too much caffeine, but even when I was completely caffeine-free this would happen. I drink caffeine now to combat the fatigue that results from not sleeping.

Years ago I took some time off to try to concentrate on doing nothing but getting a regular sleep pattern going. No work or other responsibilities for a few weeks. I used the time to get a lot of exercise outdoors, read books, avoided electronics, and avoided stress. The closest thing I got to a natural rhythm was a stable pattern of 30 hours awake followed by about 6 hours of sleep. The only way I can sleep for 8 uninterrupted hours is if it’s preceded by at least 48 hours awake straight, or at least a week of 3 hours or less per night.

I don’t like the idea of things like sleeping pills, because I always worry that I’ll need to wake up for some emergency and be unable to. I have three young children and don’t want to be unresponsive if they need something.

As always, I’m interested in your thoughts! If you’ve got any good advice, I’m all ears.

Here’s how to improve your writing: Be more direct. Use fewer words.

I struggle with this. I like to build strong visual analogies. But when you hand your work to an editor, they almost never say “you should make this longer.”

Look at your sentences. Highlight every word you could remove and still have the sentence make sense. Then remove them.

People’s attention is a finite resource. You’ll only have it for so long. Use it well.