Why are there so many bad salespeople? It’s a statistic I see pretty often when I talk to sales leaders, that something like half of sales professionals aren’t hitting their quotas or goals. Now, I could probably write another post on accurate goal-setting (and in fact, I think I will), but for today’s post I’m going to assume that the goals are accurate reflections both of what’s possible and of what’s necessary. If that’s the case, why are so many salespeople seemingly bad at their jobs?

(Spoiler: It’s a very good thing!)

Let’s also not assume that it’s a failure of leadership. It’s not about whether they’re being trained well or managed correctly – while there are definitely systemic problems with sales leadership, that’s actually just a part of the whole “some sales professionals are bad at their jobs” phenomenon, not the cause of it. Sales leaders are very typically just sales reps that got promoted.

No, the reason that many sales professionals are bad at their jobs is because sales is a phenomenal career launch point where huge numbers of people can try out in a live setting. That’s really it, and it’s fantastic.

Think about a heart surgeon. Every heart surgeon had to have a “first time” that they were the primary (not assisting) surgeon, holding a patient’s life in their literal hands. Now think about how much background had to happen to get to that point – years of training, practice runs on cadaver hearts, assisting other surgeons, etc. You can’t just show up on day one and “try out” to be a heart surgeon. But in sales, that’s exactly what happens. Want to see if you’ll be a good sales person? Go sell something today. It’s awesome.

The result is that, naturally, a lot of people try out and aren’t any good. But that same system also produces a lot of people who are great. The stakes in heart surgery are too high to have a similar system, but if we could, we’d end up with more great heart surgeons.

The more things people can try with low risk, the better off we are. There’s no substitute for a tryout, both as an individual (to discover your talents) or as a society (to help people sort themselves into their most productive and joyous roles). The more we take risks and let others do the same, the better off we are.

You can make your own tryouts, any time you like. There are tons of things you can do for a living that you could just start doing for yourself right now, to see if you can. I don’t recommend heart surgery, but there are vast reaches of things you can do for yourself just to see if you’ll like it and be any good at it before someone else offers you the opportunity.

So if you see someone who appears bad at what they’re doing, be happy. Be happy they had the opportunity to try, be respectful of the fact that they’re improving, and be grateful that you live in a society that encourages so many people to test the waters. Try them out yourself.

Endeavor to live a proactive life, not a reactive one.

There are two types of events: those that happen to you, and those you make happen. Life is better when its events are predominantly of the latter variety. The more things you’re actively choosing to do rather than reacting to, the more control you have over your life.

Symptoms of a reactive life are constantly putting out fires or spinning plates. Nothing is ever done. You never have time. You’re always fulfilling requests. You start every day with a to-do list a mile long, all stuff being demanded of you instead of things you want to do.

Have you ever heard someone lament that their paycheck is “spent before they even get it?” That means that before they even have their hands on the money they’ve earned, it’s already been earmarked for various bills, debts, and so on. This isn’t a post about financial health, but consider the analogy as it relates to time.

Every day is like a paycheck. You wake up in the morning with X amount of minutes deposited into your account, depending on when you wake up and when you want to sleep again. A reactive life is one in which most or even all of those minutes are already accounted for, paid towards debts and obligations. A proactive life is one in which most or all of those minutes are yours, to do with as you see fit.

A proactive life can easily become a reactive one. Even if you own all of that time, if you don’t spend it wisely you can quickly find yourself a slave to the demands of others instead of serving your own future self. It’s much harder for a reactive life to become a proactive one. You find yourself dependent on those debts, and it’s difficult to extract yourself.

Be careful what demands you let others make of your time. Like with money, you want to get into the habit of putting a good amount of it away as savings, and that’s true with time. You can’t bank it like you can with money, but you can make sure at least some of it is “reserved” each day for you. The more the better. Spend your time on things you choose, and your life will be better for it.

There’s some general advice you may have heard before: “Always under-promise and over-deliver.” The idea is that you should commit to less than you’re capable of, and then surprise people by doing more than was expected.

I disagree with the advice.

Now, some parts of that philosophy are sound. You shouldn’t over-promise. You shouldn’t commit to more than you can handle, and then fall short. And you shouldn’t deliver less than you promised in any circumstance, as long as you can avoid it.

But the “under-promise/over-deliver” strategy doesn’t sit well with me. First, it’s inherently dishonest, something I don’t like. You’re not really being an awesome performer at your job or task, you’re just tricking people into thinking you are by artificially lowering their expectations. Second, it can backfire spectacularly – without even realizing it, you can get into a sort of mental arms race with the people who you’re promising to, as they start to realize that you frequently deliver better results than you promised to they adjust their requests accordingly.

In my view, it’s far better to get really good at “calling your shot.” Being very accurate at predicting what you can deliver, how long it will take, what the budget will be, and so on will make you a real rock star. It makes you reliable, trustworthy. Someone that can be counted on. That’s much better than being an unreliable-but-occasional “miracle worker.”

I also prefer to be taken seriously whenever possible. A history of accuracy helps that. If you’ve under-promised and over-delivered a dozen times or more, then when you say you can finish a project in a week, people start pushing back on that. They challenge whether you can get it done in four days, three, two. Can you do it with fewer resources, etc. Now you’re just wasting time and effort defending your predictions instead of being able to let your history do the talking.

Promise what’s reasonable, and then deliver what you promised. Everyone’s better off.

There are no perfect solutions. Just solutions that maximize your personal values.

But everyone has different values, and that’s okay. In fact, sometimes the best clarity you can get on a problem is from someone who doesn’t care about the same solution as you.

Why? Because people who care about the same destination as you are looking at the problem from similar angles. If you’re stuck trying to get a project done and you value speed and efficiency, you might get a better perspective from someone who values taking their time, because that’s a different angle from which to view your problem.

Don’t always seek advice from people like you. Change it up!

Have you ever done one of those “Escape Rooms?” I love them. They’re super fun. I love a challenging mental puzzle and those combine that with great entertainment, immersion, and total isolation from anything outside them, which are all aspects I enjoy. I love them enough that I geeked out about their creation for a little bit and ended up doing a bunch of research on how they’re designed.

It turns out that they’re really difficult and complex to design, but not for the reason you might guess. It turns out that the most common mistake is to make them way, way too hard.

This makes sense when you hear why. When people are designing any sort of puzzle, the natural thing that happens is the creator looks at the project and thinks “this is so easy a child could do it. Look how obvious the answer is. I’ve got to make it way harder – add in more red herrings, hide the solution better, put in more obstacles, etc.” So they do, and then it’s impossible to solve.

Why did the creator think it was too easy, then? Because everything is obvious in hindsight. All puzzles look simple when you already know the solution.

The creator knew the solution to the puzzle, so the puzzle looked easy. But making something difficult enough that it looks difficult even to the person with the answers means making it so challenging that regular people won’t ever get past the first step.

Despite this being untrue in the extreme, people have a natural tendency to equate something being difficult with that thing being valuable. This leads people down all sorts of incorrect assumptions about what jobs “should” be worth money and which “shouldn’t.”

I get why people do it. People value honest effort. They want life to be fair. In the minds of many, the person who ends the day the sweatiest should be paid the most, because they’re “working harder” than the guy in the 3-piece suit and the corner office. But guess what – value isn’t about how hard it is for you to do something. It’s about how much benefit it gives to the other person.

I’m going to tell you a strange but true cautionary tale. This is the story of a graphic artist I knew. He had always wanted to be a graphic artist – designing logos, websites, marketing materials, stuff like that. He loved it. So he worked tirelessly at it to get better, taking jobs for way less money than they were worth, because he wanted to improve his portfolio and skill set. He kept saying he’d eventually charge more, but right now he didn’t feel like he was enough of an expert to justify it. I told him he was crazy, but it was his business.

Years passed and lo and behold, the dude actually became absolutely amazing. His skills were honestly unparalleled. He was not only an amazing designer, but he knew every tool, every piece of software, every technical skill that was complimentary to his design. And do you know what happened when the people in his network, family and friends and friends-of-friends, came to him with work?

He did it for free.

I was gobsmacked. Why wasn’t he charging? Do you know what his excuse was now?

“I don’t feel right about charging them, because it’s so easy for me to do. If anyone brought me a challenge, something that was difficult, I’d charge them of course – but I don’t feel right charging a thousand bucks for something it takes me 20 minutes to do.”

I nearly strangled him. One of the best graphic artists I’ve ever seen and he was working in a bank to pay the bills.

Nothing was ever going to be a challenge for him because he’d spent all his time and effort becoming a master – and he didn’t charge when he wasn’t because he wasn’t. In his mind, the only things it was “right” to charge for were things where you gained no benefit personally (so he couldn’t charge while he was learning) and were also difficult to do (so he couldn’t charge when he wasn’t). See the problem?

He still works in a bank. Don’t be him.

If something is obvious to you, then you might instinctively devalue it. You might think that it would be wrong to offer it to the world in exchange for money, because it isn’t that hard for you. Just like the puzzle-maker, you think that because you see the solution immediately that it must not be that difficult for anyone else.

But someone out there desperately needs that solution and can’t find it on their own. They need you, but you don’t think you’re valuable.

Each thing that comes easily to you – think to yourself, “Who doesn’t find this easy?” That’s the person you need to help. That’s your client base.

Obviously.

I was having a conversation with someone today, and they mentioned a really interesting question – what four albums were your biggest influence in high school?

That’s a neat question for a few reasons. First, four is a more interesting number than five in this context; having to pare the number down is more challenging. But more importantly, the question isn’t what albums you thought were good, or even what albums you like now. It’s about what influenced you.

I have five tattoos (as of this writing; I have plans for more); all of them are book quotes. They’re specifically from books that were hugely influential in my development. They aren’t all from books that I would even recommend to someone today (though one remains my favorite), but all of them had a dramatic impact on me as a young man. Whether because I embraced them or rejected their ideas, whether because I found shared solace in other readers or protection from a callous world in their pages (as so many young men do), these books changed me. The tattoos are a mark of that.

That’s why I’m comfortable with them as tattoos. Even if I eventually grow to hate every single one of those books, they will still always have been the books that helped shape me. Since that will always have been true, a permanent mark is appropriate.

So how about those albums? What would be my four?

Dookie, Green Day. Honestly my first real exposure to modern, popular music. Everything else I liked before that was from my parents’ generation (and their influence); this was the first album I ever bought that was actually targeted at me. I wore out multiple copies of this CD with my friends, and it was the soundtrack to a lot of my best memories of that time.

Bad Hair Day, Weird Al Yankovic. A long-standing nerd icon, Weird Al was a major Darmok for “my people.” This was the album that introduced me (and probably many others) to his genius.

The Wall, Pink Floyd. Still one of my favorite albums of all time, this album was shown to me by the coolest person I’d ever met (besides my dad), and I think I’ll forever associate this music with aspirational coolness.

Flood, They Might Be Giants. TMBG are absolute geniuses, and every… single… song on this album contained elements of that brilliance. I listened to this album a million times and shared it with everyone I could. I sing songs from this album as lullabies to my kids. I know the whole thing by heart.

Those albums range from things I think are fantastic even today, to stuff I don’t even listen to any more. But I can see where one thing led to another thing, how each new passion grew from an older one. Whether it’s what entertains us or inspires us, threatens us or propels us forward, it’s worthwhile to do a little personal archaeology and uncover the building blocks we stood on to become who we are.

It can sometimes be an excellent idea to work for free. But you should never work for nothing.

What’s the difference? Well, “free” generally just means “not for money.” But there are tons and tons of valuable things you can get in exchange for your efforts that aren’t money.

One of the first rules you should adhere to is this: When working for free, you set the terms. Don’t let someone tell you that designing their website for them pro bono would be “an honor” or “great exposure.” There are plenty of great reasons to work for free, but unless you’re specifically doing it as charity for someone who needs it, you should be aiming to get something for your free work.

What are some of the things you can get in exchange?

1. Barter. Sometimes you have a service you can provide, and the person or organization who wants that service has something you need directly. Instead of charging each other your standard rates, you can each get a little discount by trading.
2. A head start. If you’re trying to compete with others for a permanent role, especially early in your career (or early in a new vocation) where you don’t have a large established body of work, it can really put you at the front of the pack to provide a sample of what you can do. Exchanging a little free work for the best shot at a great gig can be an awesome trade.
3. Reputation/”street cred.” Even later in your career, you can get a lot of benefit out of doing free work by making sure you’re getting the proper accolades. Letters of recommendation, great reviews, even official titles can all open new doors. Make sure you’re actually getting all of that!
4. Connections. Doing free work as a way of getting face time with people that can make a big difference in your life can be the sort of exchange that pays huge dividends. If a person or organization is really a big deal in the sphere you want to work in, it can absolutely be worth it.
5. Experience. The classic “I can’t get this job without experience, but I can’t get the experience without a job” is totally untrue. There are TONS of ways to get experience without having a job first. This is one of those ways. I’ve met people who have been echoing that same lament for 2 years, but balk at the idea of doing a month’s worth of work for free to get their foot in the door.

There’s a ton of stuff you can get for your work that isn’t money – at least, isn’t money directly. All of those things are steps on the road to greater income from your work. There are intangible things too, like just satisfaction or enjoyment, but those are their own rewards. If you like painting fences for the sake of it, then you don’t need my advice.

Be careful when doing free work, though. First, like I said, make sure you’re setting the terms. Going out and volunteering your work for free is actually one of the best ways to avoid being taken advantage of; if someone seeks you out, they might just be trying to get one over on you – and if you’re good enough for them to seek you, you’re also good enough for them to pay you. But if you’re hitting the proverbial pavement actively looking to give your work away in exchange for one of those things above, you’re more likely to find a great opportunity. People love moxie.

Don’t ever let anyone – including you! – treat your work as less valuable just because you aren’t charging money for it. Respect the contract no matter what the terms are. If someone promises you a title, or a service, or anything else – collect on that as surely as if you were chasing a dollar.

One last thing – if you really want to gain the maximum benefit of doing free work, you have to really lean into it. You can’t do it begrudgingly. You have to be eager to provide value, show off the confidence in what you can offer, and demonstrate that you aren’t being pushed around – you’re setting the terms. It can be a difficult hill to defend sometimes, but the people that do it well get a huge advantage from it.

How can you tell if something is important?

It’s not as easy as it may seem. I’ve met plenty of people that either think everything is important or nothing is. Have you ever had that co-worker that marks every email “urgent?” Or known that friend that gets a call from a family member in the hospital and lets it go to voice mail?

I’ve had both. Lots of people just aren’t great at prioritizing.

Many of us aren’t quite so extreme, but think we’re doing a good job deciding what’s important on a day-to-day basis while actually still getting pulled into the weeds. Emails come in, phone calls, people knocking on your door. Meanwhile you have projects, priorities, things on your to-do list. And that’s just your responsibilities! What about your ambitions, your goals, the things you do to improve yourself and move beyond just treading water? How do you figure out which of those things need to happen, and in what order?

There’s a pretty simple method that I really love – though don’t confuse “simple” with “easy,” by any stretch. It’s called the Eisenhower Method, because ol’ Ike had a pretty efficient time management system (though he didn’t claim to actually invent this one, it’s just inspired by him). It basically divides all possible tasks into one of 4 categories, based on where that task falls in relation to two binary descriptors. Any given task is either time-sensitive or it isn’t (Urgent/Not Urgent), and it either has big consequences or it doesn’t (Important/Unimportant). That gives us four possible combinations, arranged like this:

That means for any task that comes in, you just have to ask two questions, and then you can put that task in the appropriate box. After that, you can have pre-set ways you treat each box.

The first question is, “Is this time-sensitive?” The definition of that term can be different for different people – different things are time-sensitive for a surgeon than for an accountant. But whatever time means to you, you should define “sensitive” in terms of regular intervals, and update your matrix at those intervals. For instance, you could update your matrix once a day, each morning when you get to work. In that case, a task whose outcome won’t change whether you do it today or tomorrow isn’t time-sensitive according to the scale you’ve set. Note that just because it isn’t time-sensitive doesn’t mean it isn’t important! But it’s a good idea to separate the two, and you’ll see why.

The next question is whether or not the task has big consequences. Again, you have to define this, but there are plenty of solid ways to do so. One way is simply a monetary question – how much money do you stand to make or lose based on this task? Anything above a certain threshold gets marked “important.” But there are plenty of other measurements – just be honest with yourself. How many other people get screwed if I don’t do this thing? How many days do we lose? How much cookie dough gets wasted? Whatever threshold you pick, be honest about it.

Okay, now based on the answers to those questions, you have a box for each task. Lots of people just default to putting everything in that top left box, but if everything is critical then nothing is, and you’ve done nothing to prioritize your day. Meanwhile, if tasks are actually in their proper boxes, you can do what you need to:

• Important & Urgent: Do first.
• Important & Not Urgent: Do next. Each [time increment], move things to first box.
• Unimportant & Urgent: KILL IT WITH FIRE (or delegate, you know).
• Unimportant & Not Urgent: Give to other people to train on.

See the trick? The trick is to just not do the stuff in the bottom two boxes. This whole matrix is just a way to help you clarify what belongs there.

The things that are “unimportant but urgent” are the things you should avoid doing as much as possible. Delegate, outsource, automate. Turn your phone off, or close your email tab for a few hours. Install a chat bot, hire an assistant. Whatever the solution is, find it – because that quadrant will kill you otherwise.

The things that are neither urgent nor important are dead weight. If they don’t matter, don’t put the same resources towards them as you to towards the things that do. That doesn’t mean they’re completely useless – they’re great training fodder. If you want to duplicate yourself, that’s a great bank of tasks to give someone to train on, because the stakes are low and they have time to figure it out.

(Pro tip: If you’re a parent, these are great tasks for your kids.)

One last tip: If you’re dividing up your tasks, every box should have something in it. If you don’t think you have any tasks that are neither urgent nor important, you’re calibrated incorrectly. Something goes in every box – or you’re ignoring something important about your life.

You’ve probably heard the phrase “you’re the hero of your own story” before. For plenty of people, you’re your own villain, too.

One of my favorite movies is a completely underrated masterpiece called Stranger Than Fiction, starring Will Ferrell. Ferrell’s character, Harold Crick, discovers that he’s a fictional character in a novel when he suddenly gains the ability to hear the voice of the narrator and book’s author. Since no mental health professionals will take him seriously, he seeks out a literary expert, Dr. Jules Hilbert (played by Dustin Hoffman). Dr. Hilbert approaches the problem with a literary eye, telling Harold that he needs to look for clues as to whether the story he’s in is a comedy or a tragedy, in order to predict Harold’s ultimate fate. The same events can happen in either story, but the lens through which you view them changes the nature of the tale significantly.

I won’t spoil any more for you (it’s such a good story and so absolutely worth a watch), but the element I want to draw out is that this is also true about you. Hopefully you’re not hearing any disembodied voices describing your life, but the point is that you’re life is only partially defined by your actions. The rest is defined by the story those actions become a part of.

Here’s another phrase you’ve probably heard: “History gets written by the winners.” While that’s a cynical look at geopolitics, there’s a powerful lesson for the individual there. The meaning of events is often open to interpretation. Let’s say you’ve decided to take up rock-climbing. One day you have a pretty bad fall and you break your arm, resulting in you being in a cast for a few months. Those are the events, but that’s not the story. The story is up to you – is that the story of why you decided to quit rock-climbing, or is that the story of how you learned a valuable lesson about both safety and perseverance, and got back on the mountain and became great?

That’s up to you.

No event exists in a vacuum, good or bad. A story is created by connecting different events together – and the meaning of an event can change years later when something new happens or new facts come to light. There’s always time to write a new chapter, which means even the past is not set in stone. You can’t change what happened, but you can absolutely change what it means.

So often we let our personal narratives define us, instead of the other way around. We often use the power of these stories to shield us from uncomfortable truths – to shift blame away from ourselves, or to explain away our failures as inevitable, or to define ourselves as deserving of something we haven’t earned. It’s natural, but it’s dangerous. Once we start to tell our story this way, it becomes difficult to change. You can’t tell the story of how you overcame a failing in order to rise to great heights if your story doesn’t include acceptance of that flaw to begin with.

Even worse is when we write the ending of the story far in advance, and yet use that power to write a bad one! You’re literally taking a third-person omniscient view of your own life and using that to predict failure. If you’re going to pretend that you can predict or even manifest the future’s events flawlessly, you might as well write incredible success! At least then you’ll be striving for something, giving yourself a road map, and inspiring yourself. But what’s the point of writing an inevitable failure?

Of course, I know the point. You write a future failure as inevitable because you’re more afraid of the “failure” part than the results of that failure. People want to avoid blame more than they want to avoid disaster. As long as you couldn’t have been expected to do better, you can at least be comfortable in the knowledge that the failure wasn’t your fault. So we decide in advance that the failure was inevitable. And then of course, it becomes so.

So few of us ever realize that the exact reverse of that power is also true. You can just write an inevitable success, and writing it will make it so. Failure is a choice – as long as you choose not to quit, you’ve only got two states of existence you can occupy: Success, or Still Trying. You don’t fail until you quit.

It’s an adventure story. Your adventure story. And it has a happy ending.

You need other people to succeed in life, but they’re also your greatest impediment.

All the good we do in this world we do for, and because of, other humans. We care for them, raise them, feed them, motivate them, help them, protect them. Simultaneously, all of these efforts are impeded by other other people – they will distract you, attack you, hinder you and rob you.

They’re worth it regardless, but we have to be vigilant.

If you don’t think crab pot mentality is real – then go out to the bar with people you knew in high school, but tell them you don’t drink. Or go to a family gathering for the holidays but tell them you’re on a diet. Or decline an invitation to an event you could afford because you’re being frugal. You’ll see.

The socially-safe route through life is one of sloth and dependence. The lower the bar of your ambitions, the easier it is to find “your people” and have a lazy river carry you through life. The path of greater virtue and reward is harder and more rapid, but perhaps the hardest thing about it is how many people don’t want you to do it.

The best thing to do is to avoid the crab pots altogether. Instead of trying to tell a bunch of alcoholics that you don’t drink, don’t go out with them in the first place. If your co-workers are telling you not to “stick your neck out,” then rather than try to convince them otherwise, you should quit and find a better environment.

Some people will read this and interpret it as me advocating for a radical autonomy, but quite the opposite. I think it’s vital to find your tribe. To have your friends, your circle, your people, your society. I just advocate being selective as heck about it.

Some great advice I once heard: “If you find you’re the smartest person in the room, find a better room.” That’s true, and you can replace “smartest” with any other positive attribute – hardest working, most creative, etc.

The world is too full of amazing people to waste time with crabs.