Hills Worth Dying On

When I was young, every hill seemed worth dying on. Each step in life there are fewer.

I’ve found that the smaller the number of things I think worth fighting for to the death, the happier I am. This isn’t because I’m less resolved or passionate about my life and goals. It’s the opposite.

When you’re ready to go to battle over every single idea or opinion, you’re in a constant quagmire of squabbles and stalemates. It’s hard to be powerful and impossible to be peaceful.

When you aren’t willing to die on most hills, you get to keep your powder dry for the handful of things that matter to the point of defining you. Those things aren’t to be trifled with. You’re able to abide like The Dude through most of life, and strike like lightning when it matters.

I try to ask myself all the time, “Is this a hill worth dying on?” If the answer is no, I try hard to resist the temptation to get embroiled.

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Starting the Day on My Own Terms

I don’t have a morning routine.

Sometimes I experiment with one, other times I alter my mornings based on other larger goals. In some phases of life, I’ve slept in ’till eight or nine. In others I’ve gotten up at five or six. Sometimes I do both from day to day.

I’ve done email first thing, writing first thing, exercise first thing, mediation, walking, eating, showering, or reading first thing. I’ve smoked a cigar first thing. I’ve gone screenless and screenful.

I like them all. Mostly I like to straddle the boundary between routine and change. I don’t want complete novelty every day, but I like changes with phases and goals. I’ve had phases where never waking up to an alarm clock was a goal I worked hard to achieve. Other times the alarm is integral.

The only thing I’ve really noticed that consistently makes mornings good is starting them on my own terms. It doesn’t really matter what the terms are. The only thing I’ve really noticed that makes mornings bad is starting them on other people’s terms. It doesn’t really matter what the terms are.

Earlier in life, if I didn’t set the terms they would be set by work or classes. Now if I don’t set the terms they’re set by my kids. Since my wife and I accidentally spread out our four kids over 13 years, it feels like we’re always in a phase where somebody wakes up early (and usually someone has a hard time sleeping and wakes up in the night too). Getting enough sleep is tough enough. Getting it between the hours we’d prefer is almost impossible. So we tend to trade off who has get up in the night and get up early in the morning duty.

When I let the first kid to awake dictate the start of my day, it takes me several hours to stop feeling chaotic. But when I get up a little before the first kid normally gets up, everything changes.

Even if the activities don’t change, the mindset does. I feel like I’m tackling the day, not the other way around.

This is true of most things in life. It’s not the terms, but the feeling that you determined them that makes for a good life.

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More Love for Your Work Equals Less Fear of Failure

Say you want something to happen really bad.

You’ve put in a lot of work to try to make it happen. Then the time comes to see if it worked. Will the thing you’re trying to make happen happen as a result of the work?

And it doesn’t seem to be happening. Or not as much as you wanted.

Then you feel a bunch of knotty stress in your gut. Did your work fail? Did you fail?

Of course this is all silly. It’s too early to make such sweeping conclusions. You know the stress is only clouding your vision. You know you can keep working and adjusting. You know the feedback you’re getting about the thing not happening is exactly what you need to improve the odds that you can make the thing happen.

But you still feel the stress.

Is the problem that you just wanted the thing too bad? Is it that you put in too much work and not enough thought? Is it the world’s fault for not being different? Is it your fault for not seeing that the world is not different?

No. None of these are problems. They may or may not be true, but none of them are avoidable, and none of them would alter the best course anyway.

The problem is not that what you worked for and what happened are different. The problem is that you’re afraid of that difference.

Panic and fear when a plan isn’t turning out right might make you think you care too much. You’re too in love with the desired outcome. Maybe, because you’re so close to it and the goal is so personal, when it’s not looking right it’s just too hard to objectively assess the feedback. Maybe you need to care less in order to fearlessly take feedback.

No, that’s not it.

You need to care more.

You need to care about your work so much, so damn much, that you can fearlessly receive feedback and assess what’s not working. It takes more love, not less, to stare problems in the face and not feel beaten. It takes more love to laugh at a failure than to cry.

You have to love the actual success of your efforts more than you love the feeling of succeeding. You have to love the desired outcome more than you love people thinking you caused it. You have to love your work more than you love your reputation.

If you do, you can find even signs of failure as delightfully interesting and useful as a mad scientist who creates an unexpected lab fire.

At least I think so. I’m still aspiring to a level of love for my work that conquers all stress over negative feedback.

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The Insane Advantage of Being Insanely Fast on the Job Market

We recently had an entry level opening at Crash. We put the word out to some people, and we had six excellent value propositions come in.  But one of them had a massive advantage over all the rest.

She was fast. Insanely fast.

We got her pitch within 12 hours of making the opportunity known. We put out the word in the early afternoon and she turned around a well-researched and written email with a one-page value prop by late morning.

Her stuff was good, but so were some of the others that came in over the next several days. The problem they all faced was that they were playing from behind. She was so fast that she instantly took the lead, and every hour that went by during which another applicant did not send something made us wonder why. If she could, why couldn’t they?

This isn’t some weird obsession with speed for its own sake. Nor is it an objective measure of ability to do the job. Working fast does matter, and not going dark on comms is important. But the reason she took a huge lead for being so quick was more personal and subjective.

Hirers are humans too.

Humans like it when people are interested in them.

I often compare the job hunt process to the dating market, because I think it helps people understand the employer side better. Feeling like someone is interested in you, and excited about the idea of working with you, matters a lot! Speed is one of the best ways to generate that feeling.

When someone replies lightning quick to an opportunity, they signal how much they genuinely are excited to work with the company. Like, can’t sleep excited. That is an awesome person to work with!

Speed isn’t everything of course. If she’d sent a sloppy pitch, her enthusiasm wouldn’t have been enough. But in a field of similarly skilled peers, as entry level roles often are, the differentiator of being insanely fast is insanely powerful.

Show you care. Be fast.

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Me and Goals Have a Love Hate Thing

I don’t like goals.

Kind of blasphemous from a company founder who’s trying to build massive, world-changing stuff.

I’ve written about how I prefer small, daily challenges and daily accretion of value to lofty goals. But I’ve never had a super clear point of view on goals. Just some vague discomfort.

On an episode of the Office Hours podcast a listener asked a question about goals. It forced me to think a little more about what I do and don’t like about goals. I tend to do my best thinking when I have to articulate something. What came out seems directionally correct.

I like really short term goals (“publish a blog post today”), and I like really long term goals (make the world freer when I leave it than it was when I entered). I don’t like mid-term goals. They feel constraining, and unnatural. Why aim for a made-up halfway target instead of just aiming for the true, big giant end target?

“I want to do one thing today to make my company more valuable” feels awesome. “Here’s my list of ten things to knock out this week” does too. So does, “We want to help launch 10 million careers by 2024”. What feels weird and annoying is, “What metric should we aim at in the next 6-18 months?” Which is exactly the kind of goal and time scale that matters to investors, and investors are a key part of success for the company we’re now building. But I chafe at this stuff. It feels made up just for the sake of having something to go into a board deck, or to put other people at ease.

We could pick a reasonable metric (and we have, and we will continue to), but it’s guaranteed to be the wrong one. Maybe not wrong enough to cause major trouble, but it will be sort of off by a little. Yes, we’ll learn that and adjust accordingly. But I struggle to convince myself (though everyone else seems convinced) that we need intermediate goals. We know what we have to accomplish today and this week and (mostly) this month to make the company more valuable to customers. We know what we’re trying to do in the world and the magnitude of impact we’re seeking.

Do we need to define what the halfway point, or quarter way point, or tenth of the way point is? Do we need to aim for that? Does it help?

I know it does in some ways. It definitely helps me talk to investors and others who are outside the company and pop in every month or so to see what’s up. The daily is too granular for them, and the big vision too abstract. They want to know what we’re aiming for on a time scale relevant to their checkins.

But is that a good enough reason to create team goals? For non-team members and non-customers? It might be, because allies, business partners, and investors are key customers, just behind the end user in importance. They matter. A lot.

And common startup advice is common for a reason. It tends to work. If everyone else has found those kinds of goals necessary, it’s more likely I’m missing the point than that everyone else is.

Then again, I don’t really get excited by arguments for following the crowd.

I need to either find a better reason that I genuinely value to follow mid-term goals, or find an alternative to setting them that still gets us what we need with the relevant audiences.

I’m still searching.

Here are some other posts I’ve written about goals:

Don’t Have and End Goal

Tiny Daily Challenges Over Big Lofty Goals

You’re Never Done

When Goals Don’t Cut It, Focus on Obstacles

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Public Compliments as a Recruiting Tool

The other day I saw that a prominent venture capitalist had just joined a VC firm as a new partner. It was kind of a big deal in the startup world for this guy to join this firm.

But what hit me was the fact that, in the month or so prior to this move, I had heard on at least three occasions at least two different people from this firm publicly compliment this guy. He was mentioned in Tweets about the best VCs to follow, complimented in a podcast episode, etc.

I have no idea how it actually went down, but I thought it would be a pretty good strategy to publicly praise someone you wanted to work with on a regular basis and in a genuine way. If someone tried to recruit you to join their company, you’d be a lot more inclined if there was an established track record of them saying nice things about you over the years on social media, etc. You’d know you were known and respected there already.

I’m incredibly fascinated by talent recruitment. I’m always trying to build the best team in the world, and I like to keep a list of A players I would love to work with if and when possible. I like the idea of tipping those people off in some way to the high opinion I have of them to help lay the groundwork for potential future recruitment.

ABC. Always Be Cultivating.

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Career Leverage and the Structure of Production

One way to think about careers is leverage.

It’s not something that gets talked about much, but it’s sneaky powerful. Most people think in terms of titles and salary when they think about success. This leads many to pursue jobs as doctors, lawyers, and managers at large firms.

Others think more in terms of control over schedule and more creative autonomy, so they might become freelancers, consultants, etc.

As different as those career paths are, they share a key constraint. Neither is highly leveraged.

Lawyers and freelance designers both charge by the hour. Doctors and corporate consultants both make money only when they’re working directly with customers.

There is nothing wrong with that. It’s probably preferable for most people, as there’s something clean and simple about earning directly for your work. These jobs are highly specialized and relatively high value, but it’s just as much a direct labor for pay model as pumping gas or digging ditches.

All those roles hit a ceiling: the amount of work you can put in. It caps out pretty fast.

But a highly leveraged career doesn’t have a cap. A leveraged career is more about what activity is being done, not how long and hard and how many times you’re doing it. The activity itself does not directly generate income. The activity generates something else that generates many times more of something else that generates many multiples of yet another thing that generates income from tons of people at once.

It’s not give a man a fish. It’s not teach a man to fish. Giving and teaching aren’t leveraged. It’s raise the money to buy the land to build the factory to make the rope that goes into the nets that help millions of people catch billions of fish. Leverage.

Most of us have to begin our careers in an unleveraged role. Maybe you bag groceries. Or maybe you become a lawyer. You can transition into a leveraged career if you train your brain to see it. The leverage-seeking lawyer might think, “OK, I’ve mastered creating this kind of legal document for this kind of client. Now can I build a franchise or a software product that does this repeatedly at scale?” Then you get stuff like LegalZoom. Leveraged activity springing out of mastery of a non-leveraged activity and some insight and investment.

I’m a big fan of the Austrian School of Economics, which focuses a lot on the structure of production, which is a fancy way of saying the long process of how stuff gets made. It’s the process of going from products (Here’s an apple), to tools (Here’s a ladder to reach more apples), to tools for making tools (Here’s a saw to cut wood for ladders), and on and on.  The deepening of the structure of production requires insight and foresight, since it adds ’roundaboutness’ to a straightforward task like apple picking. But it also adds massive leverage.

This is how you become massively wealthy and have a massive impact on the world. The best manager in the world can only manage so many people. Maybe a few hundred. But the person who builds the best tools for helping more managers do their jobs better can touch millions.

That’s leverage. If it appeals to you, chase it. Focus on tools, products, and processes that are very far back in the production process. So far back most people can’t see how they connect to the final act of consumption.

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We Need a Substitute for the Word ‘Support’

I support good things because I’m good!

Almost every time someone uses the word ‘support’ it sounds nice but means something nasty.

When people say they support something, it usually means they want governments to make laws that will advance that thing. Legislation is not like business, or family, or society. Those institutions require persuasion and value creation to get the thing you support to win. Legislation is a different beast. The single feature that distinguishes governments from every other institution is that they initiate violence to back everything they do.

So when someone supports something by wishing there were government action, ‘support’ has a very different meaning from the nice one we give it. The nice kind of support might mean you invest your money in or say nice things about something. ‘Support’ as most often used, however, means desire for government action.

To bring clarity and prudence, we should use a more accurate phrase. Try this out with yourself and others, and see if it changes the way you think about things.

Every time you see the word ‘support’, replace it with the phrase, ‘advocate violence on behalf of’. That’s what it usually means.

That’s why supporters of things tend to be regressive and uncivilized. To advocate violence on behalf of something is the approach of very bad children and animals. Humans can do better in 99 out of 100 situations.

In fact, if you modified the statement to ‘advocate the initiation of violence on behalf of’, you could do better 100 times out of 100. Violence sucks, but as a defense against violence may be the least bad approach. Initiating violence never is.

It’s also interesting when you consider the fact that most ‘supporters’ – of wars, drug bans, wage mandates, border walls, land use restrictions, etc. – would find it unthinkable to initiate violence directly on behalf of these things. How many, when they say they support bans on fossil fuels, head to their neighbor’s house with a gun and promise to cage or kill them if they don’t destroy their car and buy a Prius?

But those same people happily vote for people to vote for bills to fund other people to hire others to order others to send threats to their neighbors, the ultimate end of which is the same should they refuse to comply.

The state is that great obfuscating abstraction where we hide our violence in a fog of procedure and collectivism.

It is the most dangerous institution in human history.

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A Fun Little Project About Brutally Honest Feedback

I woke up super early for some reason one day last week.

I decided to see what Squarespace was all about and spin up a website for a little project a few friends and I have joked about.

It’s called Brutally Honest Coach.

The idea is that any kind of life or career guidance or advice is usually given in the context of a friendship, family, colleague, or customer relationship. This can be just the thing, since those people have some reasons to care about you and give you advice in line with your long term well-being.  This can also be just the thing to keep you blinded by your own bullshit, because nobody who knows you personally wants to be the one to give you uncomfortable feedback, and you may not want to ask uncomfortable questions.

It’s the reason confessionals are done behind a veil. Anonymity or pseudonymity can be powerful forces, like wearing masks, that allow us to access truths and see things too hard to see or hear as our normal selves.

So anyway, I thought it would be fun to see if I could get the site up. Amazingly, it took me under and hour to set it up.

I even got a cadre of experienced advisors and coaches to agree to respond to queries from a shared inbox under the BHC moniker. So no, it’s not me. (At least not just me.;-)

It’s kind of a fun experiment. I may or may not keep it live, but I’ve wondered if there’s a demand for this kind of thing. I actually envisioned a more open forum type experience, like an anonymous Quora, where everyone could see answers and questions but no real names were involved, but I didn’t want to spend the time to mess with that. Plus quality control sounds like a lot of work.

The number of little ideas like this floating in my brain is too great to spend real time on any of them while I’m building a company, but I think it’s been important for me to not shut down this kind of stuff entirely. It’s the non-techie equivalent of doing open source stuff on the side.

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The Time Element in Alchemy

“Everything he touches turns to gold.”

The Midas idea, or Rumpelstiltskin, or alchemy in general brings to my mind an instant transformation from cheap material to gold. It’s a useful analogy, but it lacks something.

On the way to the office this morning, a thought popped into my head. Everything I touch turns to gold. It was a weird thought, because it doesn’t seem true. I’ve had tons of failures, and many more long, slow slogs through the shit-trenches to get success.

But it struck me that, if I collapse my life into a single set of before/after descriptions, the Midas idea may appear true. I have made some valuable stuff I’m proud of. If you look at the resources used before I mixed my labor with them, then look at the final outcome, it’s like alchemy. If you add one missing element: time.

What if Midas had to touch something, and keep touching it, working it, adjusting it, sweating over it for years before it turned to gold? What if alchemy is as much about time and work as it is magic?

Even the great wizard Gandalf had to labor and sweat to transform the world with magic. Witches need rare, difficult to obtain ingredients and hard to learn spells and rituals to perform their feats.

If viewed outside of time, most human lives and activities resemble alchemy. We are masters at transforming lower order inputs into higher order goods. Adding time doesn’t make it less magical.

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Career Crashers with Chuck Grimmett

Be Generous with Your Work with Chuck Grimmett

Chuck Grimmett is the product manager at Crash. He joins Isaac to talk about how he launched his career through photography, internships, and a willingness to share his work.

Topics:

  • How Chuck used photography to land an internship with the Foundation for Economic Education and then transition to his first full-time role out of college
  • The power of being an engaged customer for creating career opportunities
  • How free work pays off in the future Creating opportunities with photography
  • Doing more than just applying for an opportunity

Links:

Visit Foundation for Economic Education

Chuck Grimmett’s Personal Website


Seizing Opportunity Before You’re Ready with Chuck Grimmett

In the last episode Chuck shared his story of launching his career with the Foundation for Economic Education, and in this episode, Chuck talks about how he transitioned from his first job into his career working in tech.

Topics:

  • Saying yes to projects before you are 100% ready
  • Just in time learning instead of just in case learning
  • Using side-projects to build trust and create opportunities
  • How consistently creating leads to opportunities

You can stay up-to-date on every Career Crasher episode as it launches here. Plus, if you’ve got a story or know someone who we should feature, don’t forget to email me!

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Introducing Crash

We’ve learned a lot in the five years since creating the Praxis apprenticeship program.

We’ve seen the world change rapidly too. It’s not so unusual anymore for people to understand that chasing degrees doesn’t equal life and career success. There’s a lot more buzz about self-directed living and learning.

As TK Coleman put it way back at the beginning, “We are pioneers of the inevitable”.

Praxis provides one tangible way for mold-breakers to get started: an intensive bootcamp and apprenticeship. But we’ve encountered thousands (probably more like tens of thousands) of people who want to launch (or re-launch) their careers and who for whatever reason aren’t a good fit for a startup apprenticeship. This thing is big. There are a lot of people blazing trails out there.

So the question is, if you choose to go your own way, do you have to go it alone?

We say no. We’re building a platform for career-launchers of all stripes. It’s called Crash.

We’ll start with regular blog posts, a new podcast featuring stories of unconventional careers, a weekly newsletter, tools, resources, and a whole lot more coming soon.

Check out the first blog post to get a little more of the flavor, and be a part of the career revolution!

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No, It’s Not the Degree

I often see people say things like, “Sure, they say you don’t need a fancy degree to get the job, but then they hire people with fancy degrees.”

It’s not because companies are lying about not needing a degree. It’s because candidates are totally lame and uninteresting.

In a pool of generic, flat, 2D resumes and applications, the better formal credential will get more attention, because there’s nothing else to go on. In such a pool it’s also true that anyone who can show anything more interesting than a paper credential will also get more attention. That is a really low bar.

Degrees are incredibly weak, flabby signals. Anyone with average or above intelligence, drive, or ambition is undersold by the signal of a degree, since they are already capable of proving more with just a tiny bit of creativity and work.

Don’t blame the credential. Be more interesting.

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