When You Know What To Do, Don't Change Course For No Reason Cover

When You Know What To Do, Don’t Change Course For No Reason

For the past three years, I’ve been chasing the same vision: sustaining an entire human life with nothing but a laptop and an internet connection.

My life.

Work anytime, anywhere. No boss, no boundaries. All expenses and safety paranoia considered, that adds up to a $10,000/month goal. If you asked me how to accomplish such a goal, I would give you a simple, rational answer:

  1. Find a way — any way — to make $10,000 in a single month online.
  2. See if you like it.
  3. If you don’t, adjust until you do.

I knew that answer three years ago. But when I look back on my past choices, that’s not what I see.

I see a young man who’s passionate and motivated, but whose hotheaded ambition often dissipates into thin air. His heart is in the right place, but his thinking is erratic. And so after three years of hard work, he yet has to make $10,000 in a single month.

I learned a lot, but I could have reached my goal a long time ago. Why is that?

For one, I dealt with a lot of crises. Most of which were fickle, because I made them up entirely. The breakup with the girl I was never meant to be with. The artificial overwhelm I forced upon myself. The routines I used to paint myself into a corner. Collapse was always imminent, but rarely necessary.

We all do this. The old adage is old for a reason:

“I’ve had a lot of worries in my life, most of which never happened.”

 ― Mark Twain

But beyond an opportunity to examine your own capacity for imaginary drama, there lies a lesson. A lesson about the double-edged nature of imagination itself.

Adversity is real. A loved one dies. The global economy tanks. Your thrift shop is foreclosed. Imagination is our greatest shield against it. A springboard we can use to recover from any setback.

It’s the backbone of humankind’s accomplishments. The Dark Ages made way for the Renaissance. The European Union emerged from the ashes of WWII. All because people imagined something better.

Necessity is the mother of invention. We all face different necessities at different times, and so we all imagine different solutions. It’s this collective, creative power that civilization is built upon. And it’s nothing shy of awe-inspiring.

At the same time, when we leave necessity behind, we begin to overindulge in our imagination. Soon, it bears poisonous fruit. What if our hard-earned prosperity was taken from us? How could that happen? And off we go, into the dark corners of our mind.

The path ahead may still be clear, but our vision isn’t. We get busy preserving the status quo from imaginary demons. We fight windmills while treading water. Life happens, we say. And it does. But just as often, we happen to ourselves.

We dream up a crisis for a lack of drama, not a lack of real-world problems. We get hung up on past adversity instead of focusing on future aspirations. Because we let go of the reigns. And our imagination darts way too far across the finish line. Right into the wrong direction.

Imaginary problems are a fairly obvious inhibitor of growth. It’s easy to see how they interfere with our goals. But there’s a second, more subtle way I sabotaged myself in my quest for independence. And it’s also an outgrowth of imagination.

Ideas. I love ideas. I love having them. I love chasing them. But I’ve reached a point where new ideas often do more damage than good. I think many of us have.

I was always a dreamer. I built my own Lego creations, I made my own video games and I could fill books with business ideas. And for years, dreaming was all I did. When I finally set out to take action, I thought this excess creativity would subside.

I now realize I was wrong. It got worse. I didn’t just think of solutions to problems that were not there, I would now also go out and build them. That’s how I’ve wasted a lot of time.

Saying “no” to my own, possibly good ideas is the hardest “no” I’ve ever had to practice. And I needn’t even say a word. We like to think we’re clever in our ability to spot opportunity. The excitement tricks us.

How many of your ideas are actual shortcuts to the same goal? How many are really just detours? We can never truly know, but deep down, inexplicably, we still do.

New paths are tempting. Before long, momentum fades all the same. Yet, it’s enough to abandon our efforts in forging the opportunities we need along the path we’ve chosen in favor of the ones we drew out of our own hat.

All it takes is a new idea. A spark of imagination. And off we go. Into the wrong direction, once again.

I may have lost a lot of time running from my imagination’s dark conjectures, but it pales in comparison to the fuel I’ve burned chasing its illusionary treasure.

Ideas are our fear of success’s prettiest cloak. We know what to do. What’d get us there — there being different for each of us. But we change course to follow the sun instead.

“I know every single step I have to take to get to $10,000/month.”

I said that at the kitchen table yesterday. Mostly to myself. As if that’d somehow cement it in reality.

“Now all I have to do is remember to take them.”

Looking back as clearly and honestly as I can, I see no good reason as to why I haven’t so far. Only a real one: I sabotaged myself. I chased ideas and conjured crises for no cause other than stalling my own progress.

We like to think we’re the captain of our own ship. Often, it’s imagination that is actually at the wheel, steering right towards the iceberg of self-sabotage.

But if we take control for just a second, we can at least think of a question:

How is your imagination ruining your course today?

10 Cognitive Biases and How To Fight Them Cover

10 Cognitive Biases and How To Fight Them

Irrationality rules the world. Quite literally, these days.

Global leaders behaving like little boys, threatening each other with their oversized toys. Fake news spreading like wildfire. Needless technology receiving millions in funding.

It’s a great time to be alive, but sometimes I wish Plato were still around to remind us of one of his big ideas: Think more.

Frustrated by the tendency of his fellow Greeks to act mostly on impulse, he always prompted them to examine their own lives. The goal was to think for yourself and be less trapped by doxa — the Greek word for common sense or popular opinion.

This is why we love Elon Musk so much. We see someone, who can objectively look at the world, build their reasoning from the ground up and then make decisions grounded in reality — and we think they’re a genius.

Actually, he’s just doing what we were supposed to all along: think for ourselves. It’s that we do so little of it. As Tim Urban notes on Wait But Why:

“We spent this whole time trying to figure out the mysterious workings of the mind of a madman genius only to realize that Musk’s secret sauce is that he’s the only one being normal. And in isolation, Musk would be a pretty boring subject — it’s the backdrop of us that makes him interesting.”

So how do we get back to rational? How can we think more and more clearly?

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This Is Life's Worst Trap Cover

This Is Life’s Worst Trap

Most of the time, life looks like above.

No matter where we stand, the grass is always greener on the other side. It’s that little patch of green across the horizon, where the sun always seems to shine.

  • A better job.
  • A beautiful woman.
  • A million dollars.
  • A Louis Vuitton handbag.
  • A sixpack.
  • A surfing vacation.
  • A new home.
  • A better habit.
  • A few more fans.
  • A piece of insight.

So we spend our days chasing the light at the end of our tunnel vision. We fight, we struggle, we complain, we throw others under the bus and we forget ourselves completely in the process.

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The Evolution of How I Think About Money Cover

The Evolution of How I Think About Money

I thought a lot about money this week. I think a lot about money every week, to be honest. Often not in a good way. I’m very paranoid about it. I tell myself it’s out of necessity, but that’s not true.

It’s really just a subconscious mechanism I use to motivate myself. To not lose sight of my goals. It’s efficient in that regard, but in no way is how I view money perfect. So I can’t give you “the ultimate way to think about money.” Because I haven’t found it.

What I can do is tell you how I thought about money at different stages of my life. Because there has been progress. Maybe you’ll recognize yourself. Maybe following my evolution of thinking can help speed up your own.

Let’s find out.

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How To Improve Your Writing With 6 Questions Cover

How To Improve Your Writing With 6 Questions

A writer’s job is to bring order to chaos. It’s our duty to descend into the cluttered world of ideas and then structure whatever insight we manage to wring from its hands.

Therefore, writing is by definition a messy process. The goal of this post is not so much to get you to adopt my version of it — although I will give you the tools if you wish to do so — but to get you to examine your own.

When I recently did, I found I constantly ask myself six questions about writing. Before, after and during. All the time. They’re definitely not a checklist. More of a blurry circle my mind spins in.

I want to show you those questions. Show you you’re not alone. Seeing my lose structure should help accept your own. Then, you can set out to find the little that’s there. So you can build on it. That’s the plan.

Let’s go.

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If I Was More Honest Cover

If I Was More Honest

If I was more honest, I would tell you that I’m way behind. I’m behind on my job, behind on writing this, behind on writing something else, behind on school, behind on spending time with my family and behind on caring for my community.

I feel like I’m behind on life. I should be so much further ahead. I do and do and care and run and do and care way too much and in the end it doesn’t even add up. Am I just faking this? Am I even doing the right things? The important things? Or do I just sabotage myself? So I can then feel behind?

Maybe I’m exactly where I should be. Maybe I’m just standing in my own way.


If I was more honest, I would say I’m sometimes lonely. I’d rather be alone than with someone who’s not good for me, but finding a person to hold on to really sucks.

But I would probably admit that I haven’t tried all that hard. I haven’t put in the time to find someone great and so I don’t deserve someone great just yet. Mostly because I’m busy being behind.

Sparks don’t always fly when you meet someone and even when they do they don’t always catch fire. And sometimes they catch fire but you soon realize you’re the only one sitting by it and so you say “okay” and you put it out and you leave and you try to find sparks elsewhere.

I got tired of chasing sparks. It makes me feel even more behind. So I just sit by my own fire and work and do, so I feel a little less behind. But I’m still behind.


If I was more honest, I would take a break and admit that I’m scared of the future. Yes, I have a plan and yes, I mostly stick to it, but that doesn’t mean all this uncertainty isn’t driving me nuts.

The world is a giant race full of machines trying to beat yesterday’s machines, machines trying to beat humans and, worst of all, humans trying to beat humans. Always. All the time. And fast. Does my plan even make sense? Will it tomorrow?

Anxious parents send anxious kids to anxious teachers who follow anxious leaders and later become anxious parents themselves. No one has a clue what’s coming. I don’t either.


If I was more honest, I wouldn’t use so many stock photos. I’d just take a picture with the shitty front camera of my iPhone, me sitting in my chair in my pajamas, unshaved, with messy hair and glasses and stick it right on top of the post. But I’m never sure if it “works.” I’m never sure if it’s professional enough. And I’m never sure that if I do, does that make me fake because I did it to be “authentic?”

What’s this now? Authentic? Professional? Insecure? Or all of them?

So way too often, I stick the real pictures inside the post or don’t post them at all and the title images continue to look beautiful but none of that answers my question: What does it even mean to be honest when I write? Where is the line? Is there a line?


If I was more honest, I would tell you that I’m even afraid to write this because I really don’t have a reason to complain. I have a happy family, a handful of great friends and I can achieve anything I want if only I work hard enough long enough. That’s more than 99% of people have. Family, friends, opportunity.

The family thing alone feels like it should be a birth right. But it’s not. A strong family is the most basic element of a functioning society, a functioning nation, a functioning world — and more people lack it than ever before. Why is that? I don’t know.

But because I have it everyone always thinks I’m the sane one. For the most part, I am. But it doesn’t mean I never have days where I’m down, days where nothing’s working, days where I just want to give it all up and start over. I’m very lucky and very aware of it but it feels like now I have to smile all the time and be strong and be there for everyone and hold their hand. That gets heavy.

I never ask for it but sometimes it’d be nice if someone just came along and said “Hey, let me hold your hand this time.” I might not even let them but it’d make me feel better.


If I was more honest, I’d never have to use the phrase “if I was more honest.” I wouldn’t have to write it out in bursts like this or muster up the courage to preface announcements with “honestly, if I’m really honest or to be honest with you.” I’d just blubber out the truth, all the time. Because I wouldn’t care what you think. Or he thinks. Or she thinks.

I wouldn’t listen to songs about honesty 177 times in a row and then think: “You know what? It’d probably be good to write something very honest.” I’d just do it all the time and it’d make me feel a lot better every time I did.


If I was more honest, I’d be better with people. I’d tell them they’re lazy when I think they’re lazy and that they’re great and I envy them when they’re great and I envy them. I would share more of my mistakes and the problems that trouble me and maybe it’d help them avoid making and having the same ones. I would feel compelled to apologize a lot less. I would call people out more. Challenge them. In fact, I would probably dare to ask you:

If you were more honest, what would you say?


If I was more honest, I wouldn’t put a fancy pitch for my email newsletter at the end of each post. I would just tell you that you giving me your email address is one of the very few chances I have of making a living at the thing I love. Writing. Because I can contact you now. Directly. There’s no middle man. And I can just talk to you and send you things and ask you questions and the occasional favor.

I would tell you that it’s no pressure and that all I’m trying to do is write stuff that’s worth your time and if all you want to do is read more of it for free for the rest of your life then that’s fine by me. But if one day I ask you to buy something from me and you think it’ll help you and you buy it then maybe, just maybe, one day I can make a living from writing and that would make me really happy.

The Most Important Rules to Break Are Your Own Cover

The Most Important Rules to Break Are Your Own

When I first began learning how to live a better life, I decided to watch a video every day. After 67 days, I branched into more specific habits. With every individual habit, I took the same approach: do it every day.

  • When I stopped drinking, I didn’t drink for two years.
  • When I started writing down my priorities, I did it every day for a year.
  • When I quit coffee, I didn’t have any for 100 days.

Once I started coaching people and helping them with their habits, I found a tool called The Habit Tendency Quiz. I’m an Upholder. The creator of the quiz, Gretchen Rubin, says Upholders are great at picking up and letting go of habits for one reason: they play really well by the rules.

Whether I set them for myself or am handed a guidebook, once I know what the expectations are, I’ll work my ass off to live up to them. But this is also the dark side, Gretchen says:

“Upholders are too driven by getting the Goldstar. They look for the rules beyond the rules. It’s too important for them to know what the rules are. They’re almost boxed in by the rules. They don’t know what to do when there aren’t any.”

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