Stop Optimizing Dumb Shit Cover

Stop Optimizing Dumb Shit

I have a friend. She’s brilliant at arts and crafts. Every time I enter her place, she’s tinkering. Decorating. Customizing a birthday gift. Preparing a surprise package. And it all looks amazing. Bar none.

But when she tells me the story of how her current project came together, I always die a little bit inside.

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14 Life Lessons From and for a 28-Year-Old

The most memorable birthday wish I ever received was my dad’s in 2017:

“Stay as you are by changing every day.”

I’ve tried to heed this advice ever since, but it never seemed more relevant than today. 28 does feel different. At 27, I still thought of myself more as “a kid in his 20s” than “an almost-30-year-old.” But I don’t think it’s the numbers. They’ve never mattered to me all that much. I think it’s the experience.

In the past twelve months, cumulative growth has really kicked in. Personally, professionally, financially. I don’t feel like a greenhorn anymore, struggling to build a foundation. More like a survivor, sitting on a base plate made of concrete. Battered, but here to stay. Here to make a serious dent.

There’s much foolishness left in me, but it’s a lot less than it used to be. I now am, as Oscar Wilde said, “not young enough to know everything.” I am, however, old enough to realize I know very little, that it’ll always be very little, and that that’s okay. As I keep finding more dark spots on the map, I question which ones I need to shine a light on. If I really need to close all the gaps.

The following lessons have been 28 years in the making. They’re both from and for a 28-year-old. Reminders about which gaps to close and which ones to leave alone. Hang in there, kid. Stay tough. Keep surviving. Here’s to 28!

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The Best Things in Life Are Self-Paced

The 7th most popular TED talk of all time covers an issue that affects us all:


In a funny, all too relatable analysis of the human brain, Tim Urban breaks down the interplay of three driving forces in your mind.

  • First, there’s the rational decision-maker, who’s long-term oriented and gets things done, but can rarely grab the steering wheel, because of…
  • The instant-gratification monkey, who’s entirely engrossed in doing fun and easy things, especially when it’s no time to do them, except when…
  • The panic-monster wakes up, who sends the monkey packing for brief periods of time so we can barely get our work done to meet the deadline.

Recapping this ménage à trois, Tim says:

“And this entire situation, with the three characters — this is the procrastinator’s system. It’s not pretty, but in the end, it works.”

To his surprise, readers of his blog, where he shared this theory, did agree, but weren’t nearly as comfortable nor even remotely satisfied with this system.

“These people were writing with intense frustration about what procrastination had done to their lives, about what this Monkey had done to them.”

Reflecting on the discrepancy between his and readers’ perceptions, he found:

“Well, it turns out that there’s two kinds of procrastination. Everything I’ve talked about today, the examples I’ve given, they all have deadlines. And when there’s deadlines, the effects of procrastination are contained to the short term because the Panic Monster gets involved. But there’s a second kind of procrastination that happens in situations when there is no deadline.”

As examples of this second variant of the “let me do this later” game, Tim mentions launching a creative career, founding a startup, seeing your family, working out, managing your health, and getting in or out of a relationship.

“Now if the procrastinator’s only mechanism of doing these hard things is the Panic Monster, that’s a problem, because in all of these non-deadline situations, the Panic Monster doesn’t show up. He has nothing to wake up for, so the effects of procrastination, they’re not contained; they just extend outward forever.”

It is this second, long-term kind of procrastination that’s the source of true unhappiness and regret, and thus, by extension, also our more superficial frustration with the first. Tim made people realize they were wasting years.

“It’s not that they’re cramming for some project. It’s that long-term procrastination has made them feel like a spectator, at times, in their own lives. The frustration is not that they couldn’t achieve their dreams; it’s that they weren’t even able to start chasing them.”

Now if this second kind of more expensive procrastination affected only a small number of extreme, extraordinary goals, all of this wouldn’t be too much of a problem. But that’s not the case. The set of desirable things that aren’t naturally deadline-based is much, much larger than its counterpart.

All of the best things in life are self-paced.

Finding a partner, starting a family, creating your dream career, excelling at a sport, specialized skill, or art, even just learning to be more mindful or open-minded or content with what you have, there are no deadlines and no urgency around any of those things. And so most people never begin to work on them.

I think the first step is realizing that we’re everything. We’re the rational decision-maker, the instant-gratification monkey, and the panic-monster.

No one does anything to us. We’re doing everything to ourselves. The teasing with pleasure. The surrender to the impulse. The dreaded last-minute course corrections. It’s all us, all in our heads. If we let that go, we could just start.

But what I find most fascinating is that it’s the exact same force that brings down the heroes that defy the odds — the Tim Urbans and Sara Blakelys and Usain Bolts of the world: a lack of compassion for ourselves.

There are millions of blogs out there, floating around the web like a bale of hay in a ghost town; lifeless, outdated, dead. All of these people had done the hard part. They got started. They built some momentum. They overcame their lack of deadlines. And then they stopped. Not good enough. Not fast enough.

Think about it for a second. Think about how many people have stopped chasing their dreams, the things they most want in life, for the sole reason that they weren’t getting them fast enough. That’s crazy to me. Because if that’s the alternative, why not keep going and learn to be okay with being slow?

Learn to like your pace and you’ll learn to love your place.

If you’re okay with having started, if you can settle for slow, you’ll always feel like you have enough time. If you can take solace in the fact that you’re working towards getting what you want, you’ll enjoy where you are on the journey. You won’t need to have it all tomorrow. Most importantly, you’ll find something no procrastinator ever can because of the hectic, bouncing triangle in their brain: true peace of mind.

You’ll still lose much of your precious time. Rome wasn’t built in a day. But at least you’ll fully exercise the power that separates us from monkeys: a sense of self-awareness for where we are in life and the choice that that’s always worth being kind to ourselves.

3 Lessons From 4 Years of Writing Cover

3 Lessons From 4 Years of Writing

I published my first article in November 2014. I had no idea what I was doing, but I had fun. Ironically, the only way to keep this fun around long-term was to consider writing the most serious job I’ve ever had. So I committed.

Now, over four years later, nothing is the same. Except that part. The fun’s still here. I even have a slightly better idea of what I’m doing. But writing online is different from anything I’d ever imagined or associated with that word.

Here are 3 lessons I rarely see others mention, but that helped me get to now.

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Struggling Is Not The Only Way You Can Grow

Hawthorne is as American as it gets. Smack dab in the middle of California, the little town of 90,000 takes its name from world-famous writer and novelist Nathaniel Hawthorne — who was born on July 4th, Independence Day.

Today, it hosts what may be the country’s greatest entrepreneur and his most magnificent endeavor: Take a right on Crenshaw Boulevard, turn into Rocket Road, and you’ll hit SpaceX headquarters, one of Elon Musk’s companies.

In June 2012, that’s exactly what VC rock star Tim Draper and his 40 students did. The pilot class of his now highly acclaimed startup accelerator took an in-depth look at Elon’s moonshot, including a Q&A with Musk himself.

Standing way in the back is a scrawny French kid, hoping, like the other 18-year-olds, for the most inspiring speech they would ever witness. “But instead,” Thomas Brag explains, “we got a brutally honest Elon-answer.”

And it wasn’t one any aspiring entrepreneur would want to hear.

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How To Communicate Better: 7 Simple Lines to Express Your True Thoughts, Beliefs & Feelings

Good communication is always simple.

What’s hard is having the courage to let it be. To say “I don’t love you,” rather than concoct some elaborate web of intricate, lesser truths — or even outright lies — hoping the other will stumble into it, trip, and fall over all on their own.

In the movie Hitch, titular character and communication expert Alex says:

“60% of all human communication is nonverbal; body language. 30% is your tone. So that means 90% of what you’re saying ain’t coming out of your mouth.”

It sounds intriguing, but I think it grossly underestimates the importance of truth. Even our subjective one. If you’ve ever sheepishly confessed something, shaking like a wet poodle, you know what I mean: A powerful sentence uttered poorly may be weaker than it could be, but it doesn’t turn the truth into a lie. People can tell what we tell. And they’ll react accordingly.

When I fail to communicate clearly, to say what I want to say, it’s almost never because of some complex combination of circumstances. It’s that I’m too afraid to say what I really — like really — think and believe. I have wiggled my way around questions, nodded my head when I should have shaken it, said “yes” when I meant to say “no,” shied away from asking for help, neglected giving compliments, and hated saying “sorry.” All in hopes of the truth magically finding its way to the light, which, of course, it never does.

Because it’s my job to take it there. The job, really. A job for all of us. The only one that matters. I’m not sure how much of what we’re saying comes out of our mouths, but I know that 90% of what does is a weak version of the truth. We may soften it to be polite, censor ourselves to maintain our image, or ask for less than we want because it’s more than we think we deserve, but, at the root of it all, there’ll always be fear.

There’s no way for me to bestow the power to act in spite of this fear upon you or even myself. It’s a war fought in countless battles over one’s lifetime, and you’ll need to summon the courage to be honest time and again. But it helps to keep some truths at hand. A little vial filled with beacons, all but ready to release. You’ll still have to uncork it each time, but at least it’s close by.

I’m only 27, but I’ve had — or would’ve had — to use all of these hundreds of times already. Here’s hoping that, in the future, you and I both will.

1. When you don’t know something, say:

“I don’t know.”

People will respect you for it. It’s a chance for them to say “I don’t know” too. And then you can figure it out together. We think of this line as an admission of defeat, but it’s actually the beginning of taking your power back.

2. When you don’t understand something, say:

“I don’t understand.”

People will explain again. Actually, most of the time, they’ll be happy to. It means they can double-check that they understood what they told you themselves. If you think about how comfortable you are with explaining things multiple times yourself, you’ll see why others will likely be too.

3. When you don’t agree with something, say:

“I don’t agree.”

People will respect your opinion. At least tolerate it. At least most of the time. Don’t launch into an immediate defense. Just plant your flag. Stand your ground. Stay still and watch what happens. Will they stand theirs? Start an attack? Or even join your side? Very few things in life can neatly be separated into right and wrong, which means very few ideas really need justification.

4. When you don’t want to do something, say:

“No, thank you, I don’t want to do this.”

People will find a way without you. They always have in the past and they always will in the future. No one is indispensable forever. Just like time heals all wounds, it makes everyone replaceable eventually. Spouses. Neighbors. Parents. Bosses. Leaders. Friends. You’re never too important to say no.

5. When you have a hard time going it alone, say:

“Excuse me, can you help me with this?”

People will be happy to give you a hand. Like “I don’t know,” asking for help makes people more likely to trust you, not less. After Benjamin Franklin borrowed a book from a rival legislator, they became lifelong friends. In fact, showing vulnerability is probably the only way to truly overthrow animosity.

6. When you like someone, say:

“I like you.”

People will like you back. Maybe not as much. Maybe more. But, when in doubt, most people opt to be friendly. They might not like you enough to kiss you, or to give you a job, or to go on holiday together, but they won’t stand in your way. And even if they thought about it before, now, they won’t cross you.

7. When you know you made a mistake, say:

“I’m sorry. That was my fault.”

People will forgive you. The word ‘default’ is made from ‘de,’ which means ‘out of,’ and ‘fault,’ which means ‘guilt.’ When we ‘default’ to doing something, that’s a safety mechanism meant to cover us in advance. We hate admitting mistakes more than making them and so our default reaction is to shamefully sweep them under the rug. True guilt, however, is too painful to just shake off. So we fess up and fix our mistakes. Therefore, it’s a feeling worth embracing.

In a world full of information, sending signals through the noise is more important than ever. In a world full of devices, it’s enough that the medium twists the message. And in a world where technology dominates everything, communication is a uniquely human differentiator. But only if we keep it real.

May the above sentences help you do just that. Oh, and whenever you find the courage to speak them, leave some room for one more thing: listening.

I don’t think the following communication expert had as much research as Hitch to back up his statistics, but then again, the numbers of nature never lie:

“We have two ears and one mouth so that we can listen twice as much as we speak.” 
— Epictetus

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The True Purpose of Productivity

There’s a reason why most productivity advice fails to make any meaningful difference in your life over the long run. It’s not that the hacks and tricks and techniques don’t work. They do.

It’s that we see this kind of advice as the best possible way — the pinnacle, really — of improving our productivity. But it’s not. It’s based on a set of false assumptions. It misses the true purpose of being productive because it neglects how humans function at a biological and psychological level.

Imagine the perfect week. A seven-day stretch where you manage to do not just everything you aspire to do, but all the little things you conceive of along the way. The “I need to call mom”s and “I should pick up milk on the way home”s too. Where your plans fit into your calendar like a key into a lock, and your work assembles itself like a neat puzzle, perfectly abiding by the ever-looming deadlines of the ticking clock.

If you’re like me — a human being subject to their own, chemical reward system and a host of cognitive biases — this week has never happened in your life. And it never will. Because it’s a myth.

But that’s exactly what endless time optimization strategies are chasing. They pretend this week exists. If only we could chase it down once, we’d know how to catch it again and again. That’s nonsense, and its underlying assumption is deeply flawed: If you can hack yourself to do ever more, you’ll eventually reach a point where you can do everything you need to in any given week.

If you’ve ever had even a great week, you know that’s not how humans work.

First, our brains are wired to seek problems. Calm isn’t exactly our default state. So whenever we’re done fixing one thing, we naturally look for the next. Second, we love the dopamine hit of hitting even the tiniest goal way too much to just pass up on the opportunity to complete another one. Finally, we tend to think that all our time is ours, that life won’t interrupt, and that we know not just how much we’ll be able to do in advance, but also how long any given task will take. None of these are true, all victims of the planning fallacy.

Clearly, the do-more-until-you-can-do-everything approach can’t work. And that’s why gimmicks and tactics can’t possibly be the best productivity advice.

But what happens if we reject it? If we flip the basic assumption on its head? Maybe, we’d find an entirely new purpose of productivity. I think we would.

If you assume you can never get everything done, that you have no way of knowing how much time you’ll have available, and that you’ll often misjudge your own abilities and the hours required along the way, going for the maximum number of tasks instantly becomes a wholly futile effort.

By imagining the opposite, you’re forcing yourself to come up with a new definition of what being productive even means. To me, it means making good-enough progress on what I care about the most amidst the chaos of life.

The way you do that is by managing your expectations of time, much more so than managing your time itself.

Once you accept that life is riddled with chance, coincidence, luck, you’ll see productivity in a new light, with a new purpose. You’ll feel incentivized to build a different system. One with lots of buffers and room to fail. A system that’s optimized for minimum stress instead of maximum effort.

You’ll still have your goals, your to-dos, your milestones, but you won’t throw a tantrum every time you fail to check every one of them off your many lists. You’ll have compassion for yourself. More for others, too. You’ll learn to flow with life, around life, through life, rather than compartmentalizing it. You’ll be happier, less prone to burnout, and taste more of that elusive state of calm chasing checkmarks can never bring.

True productivity happens in your mind, not the outside world.

It happens when we learn to sit with our pattern-seeking machines without acting on them. When we say “thanks for the dopamine” and choose not to chase another hit. When we begin to find true comfort in the fact that we are imperfect beings acting in an imperfect world, rather than fighting the truth and the time we have so little of.

Only if we build our idea of this important concept on the fundamentals of what it means to be human can we erect a construct that lasts. An understanding that’s not sprawled with flawed assumptions.

Maybe, at the end of the day, we’d even get more done. Not that that matters.

Because that’s not what productivity is about, is it?

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Fall In Love With Someone, But Don’t Fall Out Of Love With Yourself

We all have them. The friend that rode into the sunset and never came back.

That, one day, introduced you to their new partner, telling you you’ll see a lot more of them, only to disappear from the face of the earth the next day. It’s not like we mind. At least not initially. Their new blob-like, unanimous, hydra-esque coupleness was insta-annoying anyway.

First, you could only get them in twos, even when you asked just one person to hang. Next, they played the permission game, collecting approval stamps from their partner for everything from Friday night poker to scratching their ass. Finally, once they realized the toxic nature of this dynamic, they both settled into the friendless couple’s perpetual compromise: they stay at home.

And so it’s not just one, but two people that disappear. Until all you’re left to do is ask: what the hell happened? What happened is that two perfectly fine people fell out of life — and into co-dependency.

Can’t Blur What’s Not There

The reason the stereotype of the inseparable couple is so pervasive, so easy to recognize, is that most of us have been this stereotype ourselves. I know I have.

Your friends are too nice to point it out, you’re too in love to notice, and before you know, you’re cruising on autopilot on the relationship freeway, dreading not just your lack of friends, but the very thing you gave them up for, dying to take the next exit.

In Eat, Pray, Love, Liz Gilbert says it’s an issue of boundaries — specifically the fact that we tend to have none. And, often, it leads to the same result.

“I disappear into the person I love. I am the permeable membrane. If I love you, you can have everything. You can have my time, my devotion, my ass, my money, my family, my dog, my dog’s money, my dog’s time — everything. If I love you, I will carry for you all your pain, I will assume for you all your debts (in every definition of the word), I will protect you from your own insecurity, I will project upon you all sorts of good qualities that you have never actually cultivated in yourself and I will buy Christmas presents for your entire family. I will give you the sun and the rain, and if they are not available, I will give you a sun check and a rain check. I will give you all this and more, until I get so exhausted and depleted that the only way I can recover my energy is by becoming infatuated with someone else.”

All relationships need compromise. But if you never take a break from it, if you never put yourself first, you’ll live in a constant, self-induced state of being undermined. And, since suppression only ever ends one way, we eventually take the most extreme break we can think of: we break up. Or, worse, cheat on our partner.

In the meantime, we’ve managed not just to lose touch with a lot of folks we care about, but we’ve also completely forgotten who we are. Who we were. And what path we were on. Because we only stayed in the carpool lane.

There are a lot of problems with this, some too subtle to notice, others too obvious to point out. But there’s one we almost always miss when we’re completely self-, nay, partner-absorbed.

It’s not just you who loses. It’s literally everyone.

Finding a False Positive

Art isn’t a competition. With more good art, everyone benefits. There might be a lot of art that few people find interesting and much art people wish was better, but none of those hurt anyone by merely existing. At worst, they’ll leave us indifferent. So generally, the more art the better. Especially if you define art the way Seth Godin does:

Art isn’t only a painting. Art is anything that’s creative, passionate, and personal. You can be an artist who works with oil paints or marble, sure. But there are artists who work with numbers, business models, and customer conversations. Art is about intent and communication, not substances. An artist is someone who uses bravery, insight, creativity, and boldness to challenge the status quo. And an artist takes it personally. Art is a human act, a generous contribution, something that might not work, and it is intended to change the recipient for the better, often causing a connection to happen.

When you disappear into a relationship, it’s not just a matter of you losing your sense of self, it’s also a matter of us losing your art. That’s because self-discovery can’t happen in a vacuum. Art is a side effect of finding yourself.

When we’re single, we’re obsessed with creating our own path. With learning, sharing, improving, making. When we begin a relationship, we often stop.

We stop discovering ourselves because we’ve discovered someone. But that someone’s not us. It’s another person, and it’s no reason to quit our own little journey. But we forget and get lazy.

I see it all the time. People are writing or volunteering or really enjoying their dancing class and poof, they stop. It’s Resistance in its worst form: love. Now, all this energy that used to go towards discovering themselves and their larger place in the world is spent on affection for just one.

Until it all fades away.

All Your Wonderful Gifts

Transitioning from singlehood into a committed relationship isn’t easy. But it’s easy to gloss this over when your stomach is full of butterflies. To forget a transition is needed at all. But it is.

You don’t need to nail it or do it all at once or even get it right the first time. But don’t lose yourself in someone’s eyes, someone’s heart, someone’s life. Your time here is yours and yours alone.

If you give up too much of it, you won’t get what you want out of anything. Especially a relationship. Don’t make your partner the center of your life. Make your life the center of your life. Include not just your romance, but everything that’s in it.

Work. Purpose. Family. Friends. Loneliness. Confusion. Discovery. Art. Us.

If you stop changing yourself, finding yourself, reinventing yourself…you stop being yourself. You’ll stop being who your partner fell in love with. And you’ll rob us of all your wonderful gifts.

So go ahead.

Fall in love with someone. But don’t fall out of love with yourself.

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Why You *Really* Should Say “No” More Often

We all know we should say “no” more often. But we’re nice people and so it’s hard to turn down requests. Ultimately, that’s what most of our yeses go to. Requests. Life is full of them.

Your to-do list is a set of requests. So is your inbox. Your Facebook messages, Instagram DMs, Twitter notifications. Requests, requests, requests. And we haven’t even gotten to friends asking favors. Let alone business opportunities.

When you’re starting out in your career, contacts and customers expect your free assistance while every phone call is a welcome distraction from your underdog status. As soon as you’re seeing some level of productivity and success, you’ll be inundated with opportunities. Let’s partner up, be on my podcast, here’s a paid gig. I call it ‘opportunity suffocation.’

But, at the end of the day, they’re all just requests. No matter how well they’re disguised. And don’t we really know what we have to do? Write more. Pitch more. Practice more. Most of the time, it’s more of the same. Answering requests won’t help with that.

Of course, there are other good reasons to say “no” besides focus at work.

Like time. The big one. The first one they throw at our head. “If you agree to every little thing, you’ll have no time left for the big and important ones.” True. But isn’t that more of a long-term problem? Sure, regret sucks, but I rarely feel like small detours here and there really hurt. Of course, you can’t allow them to pile up, but the time argument feels rather weak to me.

Now, energy, that’s a different thing. A much better reason, I think. Every time I say “yes” when I actually want to say “no,” a little piece of me dies. “Yes” is what drags you out the house on a Friday night when you want to stay in. “Yes” is what sneaks you into a room full of the wrong people. “Yes” is what makes your gut twist in the morning when you drive to a toxic job.

Often, it’s not so much time I’m looking for with my nos, it’s relief. Get that burden off of me! I don’t want to sell my soul, to fake another smile, to pretend I don’t know you’re benefitting more from my “yes” than me. Give me peace of mind. Give me the “ahhh, dodged that bullet” moment. That’s what I want. I care a lot more about that than losing an hour, a day, a week.

Saying “no” isn’t as much about happiness as it’s about not being miserable.

Then again, of course, it’s important for contentment too. But not the way we think. Yes, it’s true that we need space to build our own little forts of happiness. But — and I never hear anyone talk about this — we also need room for randomness. Because, actually, happiness is a very random thing.

The best things in life are side effects. The ice cream parlor you found when you were lost. The old friend you bumped into on the train. The new kind of tea they offered at the cafeteria. But without margin, both in time and energy, there’s no room for any of this. If your schedule, your friends list, your life is too packed with obligations, there’s no space for serendipity to even occur.

Because you’re never breathing. Wandering. Allowing yourself an open mind.

I think that’s the real reason saying “no” is so important. Getting ahead at work, choosing your life’s projects, not being drained by toxic suckers, all of that matters. But if after all of that, there’s still nowhere to go for the moments in your life that truly make it worth living, why do it anyway?

That’s counterintuitive. We all know we should say “no” more often. But we think we should do it because we already have so many good things to fill life with. And while that’s true, the best moments of all are the tiny dots that will cover the gaps along the way. And they’re impossible to visualize beforehand.

“No” feels harder to say. More empowering when we do. But it’s really just a singular defense. A lone disaster averted. It needs time to compound. Our yeses, however, are where the real danger lies. “Yes” doesn’t feel special, but it is. Because it’s a thousand nos combined. A thousand times more powerful.

Every “yes” is a “no” to a million other things, some of which you can’t even imagine. But they might still be the best things that’ll ever happen to you.

Make sure you allow them to exist.