Imagine your weirdest friend or acquaintance. That person who has some pretty “out-there” worldviews and opinions, lots of unusual interests, and maybe grew up in a bubble that’s pretty different from yours. They’re not a bad person, but they’re definitely strange. They also have a pretty high opinion of their own importance and intelligence. Lots of people know someone like this – if you don’t, just imagine it.

Now imagine a world where all of your information about things that happen outside of your own sphere of direct observation comes from this one person. Other than what you see and hear with your own eyes and ears, all the rest of your news and information comes from your weird friend. They decide what to tell you about, and they tell you about it through the lens of their own personality, experiences, and objectives.

That would be super strange, right? They’d only tell you what they thought was important, which would probably be very different from what you’d objectively like to know. You’d be getting everything filtered through their value system, all the narratives that surround the facts would be from their perspective (even if the facts themselves were faithfully reported), and all context would be dependent on the other stories they told you. You would have no way of knowing what else was happening or other perspectives; you wouldn’t even know there were other perspectives. Since you’d have no way of knowing what anyone else was interested in, you’d be led to believe that this was what everyone was interested in. And if your weird friend presented themselves as just someone giving you information, you’d never even realize how much of your worldview was being shaped to match that of this one very odd person. They’d become neutral in your eyes for lack of any reason to believe otherwise.

So if you’re imagining your entire worldview being shaped by your one weird uncle’s Facebook feed, that’s the idea. You probably think that would be very weird, indeed! But you only think that because you have a counterfactual to consider – you’re comparing this weird hypothetical situation to the world as it actually exists. But the point I’m making is… well, that’s the point. You currently live in that weird hypothetical. You just don’t know it’s weird, for exactly the reason that you’ve always lived in it.

The weird friend isn’t necessarily malicious. They might not be lying to you deliberately or intending to manipulate you. But they don’t need to! They’re just weird, and you’re getting all your info filtered through that strangeness. That’s all it takes.

However diverse you think your sources of external information are, they are not diverse enough to avoid this. They couldn’t be, unless you were getting your information from at least a few billion sources. Lots of information can be wrong, and everyone is essentially someone else’s weird friend with their own agenda. So diversify your friends more, trust each one less, and most importantly, don’t ever let someone else become the “neutral” source in your mind. There’s no such thing.

Carrying water across the desert is a tricky proposition. You need water to live, so you have to carry some. But the more you carry, the more difficult your journey becomes – and thus, the more water you need. Rockets have the same problem; fuel is heavy, so the more fuel you’re carrying, the more you need.

You have to find the right balance between the weight you carry and what that weight gives you.

When you carry other people’s water for them, the calculation changes significantly. That’s a lot of weight to drag across the desert when that weight isn’t giving you any additional ability to do so.

Sometimes there are very good reasons to carry water for other people. But always make sure of two things: One, that the people are worth carrying water for. Two, that it actually is water – and not just rocks.

An old story about my grandfather came to my mind last night, and it made me want to write a blog post about it. Something that I’ve learned after years of writing a daily blog is that my actual memory pales in comparison to the volumes I’ve written (in fact, that’s kind of the point), so I habitually check to see if I’ve written about things before whenever I want to write about something from the past instead of a current thought. Turns out, I had written about this already (of course).

My father repeated his best stories often. Of course, he had a million stories to begin with and he was a phenomenal teller of these tales, so I never minded. In fact, I’d even get upset if someone else interrupted a story I’d heard a thousand times – I was enraptured by the telling. There was humor and wisdom in these stories. And part of me knew that there was something special about the way I was hearing them, something that couldn’t be duplicated even as we recorded his best ones.

I’m glad we did, but I don’t let those recordings replace retellings. When my own children need to hear those stories, I won’t dig through old videos to find them. Those videos are for me, for my nostalgia, for my homage to one of the greats. But for my children, I’ll retell the stories myself. I’ll say, “One time, your Pop-pop…” and go from there. Because the power of these stories is the telling, the connection, the questions they raise and the answers I’ll give. It’s in the inspiration to go make new stories, by living a life worthy of retelling.

My own benchmark for whether or not I was living a good life was always whether or not that life generated things I’d want to tell my father about. If something happened and I immediately thought “I can’t wait to tell this to Dad…” then I knew things were going– well, not always well, but at least According To Plan, in some sense. The way of the world was as it should be.

Now, that same benchmark still exists, but it’s whether or not I’d want to tell my kids. They’re old enough for real stories now, and I love telling as much as they love listening. My dad’s own father passed away before my dad had any kids himself, so for him, that threshold was forced. He never got to make the decision whether or not a story should go up the generational chain or down it. My transition had more overlap – all of my children got to meet their grandfather, got to know him, got to build an understanding of the power of those stories. He trained them to listen to old stories, to hang on those words waiting for a punchline or a moral or just the joy of hearing. Now they listen to me like they listened to him. Like I listened to him.

Power in the old stories. Never stop telling them. I write mine here just like I tell them, but don’t ever let this be the only way they exist. If you’re (somehow) reading this fifty years from now, don’t just read it. Go find my kids, and their kids, and maybe their kids – and listen to the stories yourself. They’ll be better, I promise.

It really is good to have productive, professional work that you do because you’re passionate about it. And to be clear, I’m talking about work that you’re purposely being under-compensated for.

Why is that good? Well, because it’s a different kind of work. Different work means different results, and it’s good to know what your own work is like when viewed from different angles. Your ability to work is like a particular kind of machine, and it will produce different outputs with different inputs. One kind of input is “being paid to do this,” and another kind is “you want to do this enough that not being paid for it is okay.”

That’s also different than hobbies or things like that, though. I’m still talking about work. Just a different kind. Like, this blog doesn’t count – this is passion work, for sure, but this is by me and for me. I’m talking about if I was writing content like this for someone else’s website, and either not getting paid, or getting paid less than what I could command.

So… why do that? Well, because for one – it can help you discover what things you care about enough to do that. And two, it can help you command the process of discovering and utilizing that process.

You see, lots of other people want to convince you that their passion should be your passion, and thus that you should use your skills on their project because of that passion. Instead of, you know, for money. Sometimes you should! But it should be because you genuinely do have a great desire to do that work and see its results. But if you’ve never engaged with a passion project before – how will you know what it looks like? How will you avoid being conned?

So do a little bit of passion work. Do it on your terms. Seek it out. Don’t let someone else sell it to you. Find it yourself, and play with it. You can even find some other ways to get compensated, while you’re at it. But learn what it looks and feels like to work on something you believe in, because it really is great to do when it works.

Sometimes, the world conspires to prevent you from accomplishing your tasks. Sometimes, random events just change the calculus a little.

You could plan to mow the lawn on Saturday, but then it rains. Technically, you still could mow the lawn… but it’s certainly a lot less appealing. But what you probably shouldn’t do is stand around looking at the lawnmower.

There are only three jobs. In any industry, in any organization – there are only three jobs. Everyone that works has a variation on one of these three, and understanding this concept can be of incredible value to you.

Here’s what they are:

1. Some people Bring Money In. Every business needs resources, even charities and non-profits. There is always someone whose job it is to bring that money in. Salespeople, marketers, fundraisers, and everyone like them or part of their ecosystem. They have the job of bringing money in the front door.
2. Some people Keep Money In. Money is constantly trying to escape the organization. If too much of it does, the venture fails. And so some people have the job of preventing that escape. Lawyers do this when they prevent lawsuits. HR people do this when they prevent turnover of employees. Cybersecurity people do this when they prevent security hacks. Procurement people do this when they negotiate lower prices for raw materials. Customer service people do this when they keep clients from leaving due to bad experiences. Accountants do this… well, pretty much always. But all these people are really just using different tools to do the same job: keep money.
3. Lastly, some people Fix Things That Break. Most businesses are doing things that are actually really simple, except fires keep starting and someone has to put them out. This one sometimes confuses people, because they think: “Wait, my job is to load blank postcards into the postcard printer so that printed ones come out the other side. I’m not fixing anything!” Oh, but you are. Imagine what would happen if you didn’t show up to work: the postcard machine wouldn’t have blank cards, so nothing would get printed, and nothing would get shipped. That’s a major problem – and you solve it. And you probably solve a thousand little problems along the way, like when the machine jams or when the shipment of blank cards is late or when they were cut incorrectly and don’t fit or whatever. But the point is that every business ever was perfect on day one, except for all the problems that keep cropping up – machines breaking, industries shifting, competitors cropping up, etc. Someone has to fix those problems.

So that’s it. If you work, then you do one of those things. Why is this incredible oversimplification both true and helpful?

Because most people are really bad at understanding, and thus even worse at talking about their own value.

Most people think of their job in its exact, literal terms. They think of their job as what they do, where they do it, what industry it’s in, what tools they use, etc. They think in such ultra-specific terms that the thing they’re currently doing starts to feel like the only thing they can do. They think, even unconsciously, that their only value is in being a very, very specific cog and that they could only change maybe one tiny aspect to do something very adjacent.

Not true! First, realize that you have one of the three jobs listed above (you actually might have more than one – if you’re a solopreneur, you have all three!). Figure out which it is. Do you bring money in, keep money in, or fix something that breaks? Okay, now how does what you do specifically help further that goal – or to put it another way, how would achieving that goal be hindered if you just stopped working? Now you have a much clearer picture of the value you add to an organization!

Understanding the value you add in broader terms helps you advocate for yourself. It helps you grow. It helps you learn and improve. In just about every way imaginable, it’s better for you to look at things this way – so take some time and think about it!

Very few words make me laugh as much as “permanent.”

There’s no such thing! The best you can do is “indefinite,” meaning “this will absolutely end, but I have no idea when.” I like that word better because it’s honest. If someone offers you a “permanent solution” to your problem, or a “permanent role with our company,” or some such – you’re thrilled! Woo hoo, my days of ever having to worry about this thing are over!

Bah!

Imagine instead, someone was honest about offering you an “indefinite role with our company.” That sounds… bad. It sounds like they’re saying that the job could end literally at any moment, and you’d be back to searching for your next opportunity.

Yes. Yes, that is exactly what they’re saying. They’re just, intentionally or not, lying through their teeth about it by saying “permanent.”

Personally, I’d rather know when something is going to end. In fact, I plan for it even if the other party doesn’t. I feel more secure in a two-year contract than in a “permanent” role because at least I have a pretty reasonable assumption that some thought went into the “two-year” part. If you’re in a permanent role, imagine cornering your boss and saying: “Are you 100% certain that I’ll still be working here in 50 years?”

In between sweating bullets, they’ll probably hedge a little – but the hedging will be honest. They’ll say things like “it depends on your performance, how the business is doing, on industry trends as a whole, on your continued desire to even work here, and a thousand other factors we can’t predict. But as long as those conditions continue to be favorable, then yes, you’ll still work here.”

But that was always true. That’s true for everything, all the time! If you own your house, it’s your permanent home… as long as you decide you still want to live there, and it doesn’t burn down, and you don’t lose your job and stop being able to afford the mortgage, taxes, etc. It’s permanent, until it isn’t.

So be honest with yourself, even if no one else is. Say: “This thing is indefinite. Here’s what could cause it to end. Here’s how long I’ll plan to stay, and then I’ll check in again. I will never let myself assume that it’s safe. That doesn’t mean I have to panic and worry all the time, but it means I will always be honest with myself about what it takes to maintain it, and want to maintain it, and what the alternatives might be.”

Nothing causes as much pain, strife, stress, and damage as when a “permanent” thing goes away. Don’t let the world trick you, and don’t trade away things you care deeply about for “permanence.”

If you really want a happier life, here is simple (though not easy) advice:

If something is a bigger priority in the “long term,” the big picture, your whole life – then make sure it’s a bigger priority in the day-to-day, too.

“Priority alignment” will make you happier. If you care more about being healthy than about being wealthy, then don’t skip the gym to work overtime. If you care more about your family than your video games, then don’t skip the reunion to shoot zombies.

You don’t have to go 100% – you can still shoot zombies and work overtime. Just make sure you’re doing those things less, and the important stuff more.

And hey – do both! Play Super Mario with your nephew. Work from home on the treadmill. Harmony is good.

But don’t work against yourself. If you say something is important, believe yourself.

I want you to brag more. And I want to show you how bragging can be a force for positive good in the world.

Sometimes, when you’re hiking through difficult territory for the first time, you plant flags along the way. These aren’t just trophies designed to make you feel good about yourself. They’re also markers so that others can find their way more easily. They’re helpful.

When you talk about good things that you’ve done, that’s the key. Do it in a way that plants flags, that brings attention to things that deserve attention. If you donate to a charity, say so! Then you give not only your money, but your voice – you amplify awareness of that charity.

If we’re discussing status and awareness, there are sort of four categories of commentary: you can put yourself down; you can build yourself up; you can put someone else down; you can build someone else up. Here’s the secret: only do that last one.

Don’t talk about yourself at all, because you don’t need to. Every word you say is “talking about yourself” already because words are a reflection of the speaker. So you don’t ever need to say a word about yourself. Most of the time when we see off-putting “bragging,” we’re reacting to someone speaking too directly about themselves. “I’m the greatest person in the world because I donated to charity, and I donated more than anyone else!” Even though they did an objectively good thing, we scowl.

Compare: “My local food bank had a wonderful fundraiser this weekend and they raised more than double their goal! Congratulations to everyone that helped organize this event, your hard work and dedication are an inspiration to everyone. Kudos!”

If you read that, you’re more likely to smile than scowl. You elevated someone else, and you did it without putting anyone else down. But here’s the thing: you still bragged!

You bragged because anyone who reads that understands that you were a part of those fundraising efforts. They understand that you also did something good. But they also see that you spoke with humility, that you used your voice to amplify others, and that you inspired others to give without admonishing any who didn’t. You invited people in, rather than pushing them away.

That’s a flag for others to follow. If you can wrap your head around that as a force of good, then you’ll feel better about bragging. That will, in turn, motivate you to find more things to brag about. We are social creatures, and if the desire for social status can be harnessed to encourage us to noble deeds, then that’s a wonderful thing!

Plant your brag flag, and plant it high!

There are no universal defaults. There are only decisions that other people made, and which you accept blindly without consideration.

Each time you do this, you yield power over your life to someone who didn’t earn it, doesn’t deserve it, and probably is using it poorly.

“Oh, this task showed up in my inbox, so I guess I have to do it.” No, not necessarily! You might choose to do it because it’s the best option. But you also might delegate it. You might email your boss and have a discussion about priorities and responsibilities. You might flip your desk and jump out the window. But all of those decisions are yours.

In the above example, just doing the thing in your inbox might actually be the best call. But there are great and mighty swaths of defaults that totally aren’t. You don’t have to accept them.

Develop a little healthy belligerence. A little resistance to the natural flow. Remember that “natural flow” leads to the lowest point, always. Sometimes that’s where you want to be; often it isn’t.

This is a true story: I once watched a man approach a city intersection and press the little button that (in theory) summons the “safe to walk” sign. Perhaps the button was broken, or perhaps the button doesn’t do anything anyway. But this man stood at that intersection, staring at the red glowing hand telling him not to walk, for three full traffic cycles. During this entire time, not a single car drove by. This was at a time that was far from peak traffic at an intersection that wasn’t that busy to begin with. Three full traffic cycles of… nothing. And then, then, the little glowing “safe to walk” man showed up. And only then did the man cross the street.

He didn’t even look both ways.

(I don’t wish anyone ill, so I’m glad he was okay, but wouldn’t it have been perfect if he’d gotten clipped anyway?)

Anyway, that guy had totally yielded his power. He’d given over the decision of when to cross the road to poorly-maintained and foolishly-deployed equipment instead of recognizing that his own eyes and brain had the power to make his life better. You have a voice, and it can make your life better.

Don’t be herded. Be heard.