The Basics

It goes without saying that you need to know the essential elements of something before learning the advanced stuff. The tricky part is that this remains true even if the basics are generally wrong and you know they’re wrong – you have to learn them anyway.

For instance, my job involves me (to boil it down considerably) helping people improve their careers. The “basic” career advice that you’ve heard all your life is really, really terrible. Most people find it very frustrating and not very successful, so when they want a more advanced (and way more effective) approach, they come to me.

But almost all of the methodology I teach relies on understanding what the basic (and incorrect) approach is. My lessons lean on the frustrations you’ve already experienced as “teachable moments” to illustrate certain other topics. Every once in a while, I find someone that simply doesn’t have that background, and it’s tricky.

For instance, I once helped someone who had gone to jail before his 18th birthday (and had never held or even looked for a job before that), and wasn’t released until after his 30th. Not only did he have zero career experience, he didn’t even understand most of what people talked about when they talked about how bad some interviews were, or the frustrations of sending out countless resumes without response, etc. Heck, he didn’t know what a resume was!

Trying to teach him the correct way to do this stuff was really difficult without that foundational knowledge, even though the foundational knowledge is mostly wrong. But I actually had to find a way to teach it to him anyway, which was an interesting challenge. I’m happy to say that he landed a really great role and is once more a productive member of society, so that particular story has a happy ending.

I use my own job as an example, but I’m sure there are thousands more. People often have to “un-learn” the bad habits of basic knowledge before moving onto advanced versions, but despite that, there’s no way to skip right to the advanced stuff.

Keep that in mind the next time you’re frustrated by having to “start at square one” on some particular topic, even knowing that “square one” is mostly garbage. Learning the garbage may be essential to learning the gold.


I’m okay with people saying nice things about me. In fact, probably like most people, I really like it. I’m not above admitting the surge of pride that comes with seeing a social media post about me from someone I’ve helped. If a client, co-worker or CEO praises me in that context, I love it. It’s a big motivator for me.

Even in more private contexts, I like this. If I get to overhear one family member or friend telling another about some positive thing I’ve done, it really refuels me.

On the other hand, I’m really, really awful with people saying those same things to me.

If my boss posts on LinkedIn “John is super awesome, look at this great thing he did,” then I’m over the moon. If she says to me “John, you’re super awesome, and this thing you did was great,” then I stare blankly, as if at an oncoming truck.

Sometimes people say really, really nice things to me. Often in a professional context, people will express to me that I did a lot for them, helped them in really significant ways, changed something important in their lives for the better. This is what I live for – the act, not the compliment. All I want in the world is to do those things, but when people compliment me for it, I shake.

I feel like no amount of gratitude I could express would be equal to the compliment they’re giving me, because it really means the world to me that they’re saying it. People don’t have to say anything at all, so when they go out of their way to do so, I’m consistently blown away.

Recently, someone I’ve been working with for some time gave me such a compliment. It’s been so fantastic to work with him and I’ve enjoyed every second, and yet still in that moment I didn’t know how to properly thank him for what he was saying. Instead, I expressed this sentiment, about how I didn’t know what to say in exactly that scenario.

And he said, “Dude, you just say ‘thank you.'” He said it isn’t about justifying their opinion or matching their emotion with my own. It’s just about giving them the space to say what they want to say, because they need to express their emotion. That was incredibly good advice.

Gratitude is important, but that doesn’t mean it has to be complex. Thank you.

Push & Pull

Change is a journey between two points – Here and There.

Change doesn’t come without motivation. You need a catalyst; a reason to alter whatever it is you’re altering. But there are two distinct kinds of such motivation, which we’ll call “Push” motivations and “Pull” motivations.

“Push” motivations are all the reasons why Point A sucks. You hate Point A. Point A is uncomfortable, miserable, and unpleasant. You want to leave Point A as quickly as possible and never look back. Or do you? That’s the thing – sometimes change is involuntary. It can still be very good (and we’ll get to how to ensure it is in a minute!), but certainly you’ve encountered unwanted changes in your life. When you do, sometimes your “Push” motivation isn’t so much a motivation as an actual push. Quitting because you hate your job is a “Push” motivation. So is getting fired, even if you liked your job. In both cases, something is pushing you away from Point A.

“Pull” motivations, on the other hand, are the things you like about Point B. A “Pull” motivation might motivate change even if there isn’t a thing wrong with Point A. Maybe you’re perfectly comfortable in your current house, but a fantastic deal on a beautiful place opens up and you have to jump on it. Having a heart attack is a “Push” motivation to get in better shape, but deciding that you want the thrill of finishing a marathon is a “Pull” motivation, even if you’re otherwise in average (and comfortable) shape.

“Push” motivations are just as valid as “Pull” ones as far as initiating needed change. But “Pull” motivations help ensure that the change is healthier and more positive. If you quit your job because you hate it, that’s well and good – but you might end up in an even worse one because you were only motivated by getting out of your current situation. Meanwhile, quitting because you’ve found something you’d rather be doing is more likely to initiate a positive result.

You can combine these! If you find yourself on the verge of unwanted change due to an involuntary “Push,” you can always find the right “Pull” and add it to the mix. Just because your car was totaled in an accident doesn’t mean you can’t shop for a new one with the motivation to find your dream car. Focus on that Point B, not just putting distance between you and Point A.

Life will push you. But you have to pull yourself up.

Money Grows On Trees

There’s a whole series of folksy parent-isms that range from irrelevant to the point of being actively misleading (like “life isn’t fair” – maybe true, but very bad advice) to being the exact opposite of the truth. I love thinking about them, and one of my absolute favorite from the latter category is “money doesn’t grow on trees.”

Because… of course it does.

But let’s take this apart, shall we? First off, trees grow a ton of stuff that’s worth money. Heck, trees are worth money. But that’s surface-level insight that I think most people figure out by the time they’re adults (or much younger in some cases), so let’s go a little deeper.

Let’s say money – as in actual currency – did grow on trees. That wouldn’t be any more helpful to you, for a whole host of reasons. One of those reasons is that “growing on trees” is not the same thing as “effortlessly appearing before you.” I mean, oranges grow on trees, but you don’t have an infinite supply of oranges appearing in your kitchen on demand and for free, right? Even abundant resources that grow in nature without our help still require us to put in effort to go and get them.

In fact, interesting story – a few cities have tried to help their homeless population by planting only fruit-bearing trees in public spaces, as opposed to typical shade trees. The idea being that having some free food just literally growing in public spaces would be great for those that might have difficulty getting their next meal ordinarily. Sounds good in theory, but it didn’t help. Why? Because those public spaces are frequented by lots of people that aren’t part of the homeless population, and nothing was stopping or discouraging them from picking the fruit for themselves.

Which brings up another point – even if money did grow on trees, that neither means there’s an infinite supply of money nor that you would be the one to get the limited crop that did exist.

Now, let’s take the phrase in the spirit of its intent – usually, this is a parent’s way of saying “we don’t have infinite money, so whatever expensive and ludicrous thing you just asked for, the answer is no.” But think about the message that sends on a deeper level. It says: I have to work for my money, which is inherently harder than it would be if money grew on trees. Money growing on trees is a Utopian fantasy.

But which is easier – buying corn or growing it yourself?

Working for your money is actually much easier – in the short term. If you had to actually plant “money trees” and then wait for them to grow and start yielding little pennies when they were very small and eventually ten- and twenty-dollar bills at maturity, you’d be waiting a long time for any sort of income. Which of course is what you would have to do – so called “wild” money trees would be picked clean long before you ever got there, unless you were willing to camp day and night by the money forest until the first bills started to unfurl in the Spring, and even that would be a lot of work.

Natural resources are abundant. And useless – until you do some kind of work to make them useful to you. Even if you had a backyard full of fully-mature, blooming Money Trees – that does nothing until you go out and harvest the crop. You still have to work somehow.

And of course, you absolutely can plant money trees. I mean, they’re called trees. You could plant something that yields something else that someone will pay for, harvest it, and sell it – it’s called farming and it’s pretty much the first invention. Even in a more modern and less literal sense, you can plant seeds now – investments, small businesses, etc. – that will return passive income for years to come, after a ramp-up period that’s slower than simply getting a job. In fact, it’s a pretty good idea.

Money grows on trees. Go plant some.

The Cliff

Over this past weekend my oldest daughter and I went camping.

What fun! This was her first backpacking trip and we had such a blast. She’s such an amazing adventurer. We hiked for five hours, covering roughly nine miles total. She scaled cliffs and trees, bounded along rocks in a riverbed, collected samples of mud and bark and fungus. The phrase “Daddy, watch this!” was uttered about a bajillion times, and I watched every one.

During one of her climbs… she fell. Head over heels, tumbled right down to the bottom. As a matter of practical skill, the karate lessons have paid off in terms of self-awareness and resilience; she tucked and rolled, landed extremely well, and bounced right back up. But then more importantly – she attacked that cliff.

Not once or twice, but a dozen more times – up and down, sideways, different paths. She wanted to let that cliff know who was boss. It had taken a bite out of her and she was determined not to allow that to pass. She aggressively attacked her weakness and in its place she made herself strong.

Something that kids obviously take for granted is the ability to be single-minded. When you’re 7 (nearly 8!), there aren’t dozens of other responsibilities and worries and stresses and deadlines pulling at your brain, so when you decide I am conquering this cliff it can be the single focus of your entire existence. That lets you summon all of your powers to the task, and very little can stand against that.

The thing to remember as an adult is that even with all the deadlines and all the responsibilities – they don’t own you. It’s the other way around. When you’re at the base of the cliff, none of those things have a physical ounce of weight if you don’t let them. Leave them at the bottom, be free, and climb.

Show that cliff who’s boss.

A Day Without

Some things are unhealthy but we think about them every day. Usually we call those “addictions,” but they could just be bad habits. Either way, they’re dangerous. They’re not only unhealthy actions, but they’re eating away at your thoughts even when you’re not engaged in them directly. Thoughts aren’t infinite; you only get so many each day, and wasting them thinking about things you’d rather be doing isn’t productive.

Some things are healthy to engage in every day but they aren’t things we’re passionate about. I’ll fully admit that only every once in a while do I really “look forward” to my workout. I almost never wake up and think about it first thing. 99% of the time I’m happy about it after I’ve done it, when the endorphins are high and I have a sense of satisfaction, but the act itself is something I’ve had to incorporate into my routine because I believe in it, not because I’m obsessed with it.

But there are some things that are both healthy for you, and obsessively occupy your thoughts. Things that would be beneficial if you completed or engaged in, and are also things you can’t go a day without thinking about.

When you find something like that, fight like hell for it.

Passion will get you through hard days. Long-term motivation can overcome short-term hardship. Being passionate about something isn’t sufficient on its own, but it’s a heck of a booster for your work ethic. So something like that – a great goal that you’re legitimately obsessed with – is a Golden Target.

And yet, people let Golden Targets go to waste all the time. It’s amazing how often humans will pick comfort over meaning. How often we’ll pick not rocking the boat over standing for virtue. We’ll let the hardship involved in pursuing a worthwhile goal convince us that the goal isn’t worthwhile.

It is.

Because if you’re that obsessed, you have two options – chase that dream for all your worth, or don’t. But if you don’t, those obsessive thoughts aren’t going anywhere. Instead of being your best friend, they’ll be your worst enemy. Instead of motivating you to amazing success, they’ll poison all your other efforts and keep you from meaningfully caring about or engaging with anything else.

Check your obsession and make sure it’s healthy. But if it is, listen to it. It would be unhealthy not to.

Middle Ground

I often have trouble with balancing a middle ground. When I have the boundary provided by professional distance I communicate well, and I’m fine with people that I’m very close to. But when there’s a middle ground I often falter.

I’m never sure how much to ask, how much to share. I have a lot of switches and not a lot of dials. I tend to view trust and openness as binary; complete or absent.

I know there’s a middle. I’m exploring it. Slowly, but nonetheless.

Shock or Dread?

Would you rather be surprised by bad news, or know it was coming in advance?

Many people would instinctively say they’d rather have time to plan, but what if you couldn’t plan? If it were simply something that was going to happen, would you still rather know in advance, having to live with the dread?

Or is even dread something you can plan for?

Roll with the punches or be prepared?

The Escalator

I had to take a flight early this morning, leaving during a particularly busy time from a particularly busy airport.

I was approaching the escalator that went down towards the gate, and I saw a young boy, looked about 4, terrified of the machine that everyone else was hopping on so easily. He had his little Spider-man roller suitcase clutched tightly and was trembling and crying about the prospect of leaping onto a machine seemingly made (from his perspective) of perpetually-gnashing metal teeth.

His dad looked to be a guy my age, and was not impatient or unkind about this. He leaned down and said, “Okay, I know it looks pretty scary! But we can do it together, okay? Hold my hand, and on three we’ll jump together.” He counted three and they jumped, and the kid giggled at the stairs moving beneath his feet, but dad held him steady. “Ha ha, it moves pretty fast, huh?” he said cheerily, turning it into a fun ride instead of a scary danger.

I watched this moment happily and stepped onto the escalator behind them. They got to the bottom, and there was an older couple half-frantic waiting. They immediately seemed relieved when they saw the two, and profusely offered up their gratitude.

“Oh thank you thank you! It was so crowded and busy we hadn’t even noticed that he didn’t follow us down the escalator and then we couldn’t see where he was. We were starting to panic when we saw you coming down. Thank you so much for helping our grandson, it’s his first time ever flying.”

And this guy, who was not the kids’s dad, didn’t even know the kid, just said, “Oh, no problem. Have a good flight, little guy!” And the kid smiled and waved and dragged his little Spider-man roller suitcase with his grandparents off to their destination.

Humans are good. Humans are so good.

Go Around

I once read an interesting “true crime” story about thieves that wanted to rob a particular hotel room. Apparently there was someone very wealthy staying in that room, with a large assortment of valuable things like jewelry, and the thieves wanted to get at it. This being a high-class hotel, the security was very good – all the doors were basically unbreakable and had all sorts of high-tech locking mechanisms and such. There was virtually no way to bypass these doors.

Except… to bypass them. Entirely.

The thieves just booked the adjacent room under a false name and cut through the drywall. Because that’s all it was: ordinary drywall, the same as would be between any two rooms that aren’t bank vaults.

I often see problems of this nature absolutely confound people. Even very smart people. Because society in general does a good job of herding us towards the doors. But if a particular door is incredibly secure – locked, bolted, sealed, onerous – then maybe look at going through the wall.

A classic example I see a lot in my line of work is submitting a job application. People are often nervous about everything from applicant tracking systems and keyword filters and hiring manager bias and competition and all those other barriers. But those are locks on the door. That machine is horrible – I’ve lived in it for years and years. Skip the door. Go through the wall, the window, the skylight.

That can mean a lot of things. In one instance an old client of mine just found out who the head of the department he wanted to work for was, recorded a video of himself making a pitch for the job, and then sent that video on a USB drive via FedEx direct to the manager at his desk. The manager had to sign for the package, which contained a USB drive and a hand-written letter from the applicant explaining why he sent it. The manager watched the video and hired the man the next day.

That’s going through the wall.