Paul Graham is one of the most famous figures in the startup world. His company Y Combinator helped launch household names like Airbnb, Dropbox, and Reddit. His writings have influenced many more companies and founders.

I love his writing. Every one of his essays is pure signal. It’s the kind of writing I aspire to.

As I’m thinking about this idea of quality over consistency, I wanted to see if he was a follower of it.

Turns out, he is.

He has 196 essays on his site, and the earliest essay on his website is from April 2001. That’s on average about one essay every 36 days or 5 weeks. But it isn’t consistent. Some months he writes more than one, and usually just one a month. He dates his essays by month, not the day because he publishes the essay when it’s ready not because he’s a on a schedule.

In an FAQ asking how long does it take to write an essay he answers:

Usually about two weeks. What You Can’t Say took a month, partly because the topic was so dangerous. How to Start a Startup took a week, because I started it a week before I had to deliver it as a talk. Writing, Briefly was the fastest, at just over an hour.

I think this idea of quality over consistency is more for creators who aren’t trying to make a living directly off of their writing. Writing high quality essays like Paul Graham, who is not a full time writer, gives you many benefits other than revenue.

• You become an authority on the subject.
• You attract a network of like minded people.
• Most of all, your own thinking and ideas become clearer because you are putting it through the sieve of writing and editing.

If you are wanting to build a business with a blog or a newsletter, then yes consistency is definitely something to consider. But there’s much more that comes with building that business than consistent publishing. Unique positioning, branding, and benefits is needed, all of which is becoming much harder to do because of how saturated we are with content.

Ben Thompson, the creator of the excellent newsletter Stratechery is an example of this. This is how he makes a living and he devotes all his hours writing and promoting his work. Graham’s priority isn’t his essays, it’s Y Combinator.

So as I wade more and more into this life as a writer, it’s about deciding whether I want to be Thompson or Graham. You can tell which way I prefer, and it’s a helpful model to use to filter all the advice and content out there about all this.

This tweet from one of my favorite writers has incepted into my mind:

PSA: you don’t have to send your newsletter every week. Send it as often as it’s actually interesting.

I’ve seen no marketing evidence that you have to “stay top of mind” at a high frequency.

In an era of extreme content saturation, consistent high quality stands out.

At first I was offended. It felt as if my weeks of showing up consistently in Upstream was discounted. But putting my pride aside for a second and there is much truth to this idea.

We are in an era of extreme content saturation. There is no top of mind when readers are bombarded with content everyday (there are 4.4 million blog posts that are published per day).

In a world of intense noise, quality is the signal that stands out. And if signal is what we’re after, it’s unlikely epiphanies come at a weekly cadence.

The advice that we have to publish consistently conflates the needs of the creator and the experience of the reader. Creators do need to develop a habit of consistently creating and shipping work, but it doesn’t mean it has to be a content strategy. Readers don’t have to read everything you write.

It’s counter to 99% of the advice out there and the advice I’ve given. But what’s worked for the past 20 years will not neccesarily work work for the next 20.

Quality does matter. If we were to fully prioritize quality over consistency, then the practice would be to focus our energy on doing the best work and share it when it’s ready not because it’s Monday morning.

Definitely something to think about.

After a month and a half of posting everyday, here are some lessons I’m learning of how to make this sustainable and more importantly enjoyable.

Write Down Every Idea

Use whatever you have in front of you (I use the app Drafts on my phone) to write down an interesting idea.

This ensures that you never have to start with a blank page. Having a bank of ideas for you to read is your own personal writing prompt. I have a folder called “Spark” in my text editor with all my ideas.

This helps you get through all the “meh” ideas until you find one you really want to write about.

Write and Edit in Batches

The secret for me in posting everyday is to write in batches throughout the week. At any given point I have 3-4 posts I’m drafting or editing. Then you schedule them for the future.

One Idea Per Post

This was the hardest thing for me with the newsletter and these posts. Before writing consistently I feared I had nothing to write about, and then I realized I had too much to say.

Blogging daily has helped me work through one thought in a clear and compelling way.

Be a Broken Record

Not even my mom or my wife has read everything I wrote and they are the ones who are legally obligated to do so.

Only person that will be annoyed in hearing the same thing again and again is myself, and that’s ok. Plus, there’s no guarantee that the one time I expressed an idea was the best expression of that idea.

Using this space as a practice as much as a place to publish is the way this becomes exciting and enjoyable.

It was a phrase I heard in passing during the certification of the election. A clerk said it in regards to the House voting to “reject the objection” to Pennsylvania’s electoral votes.

What a time we live in to have to hear such stark language. I haven’t fully understood the importance of this history we are living through, but it’s exhausting to be a witness of it.

I thought about this past weekend, where I had one of the most important conversations with my parents in my adult life. It wasn’t since 2009, when I told them I’m going into full time photography, did we sit down to talk like this.

My dad and I hadn’t talked since April because of a falling out we had. Words were spoken by him that he regrets, and I had no emotional energy to work through. But eight months later we were able to work through it all and come to a resolution, as it were. A certification of our faith in our family and our relationship.

What does it take for us to reject the objection? What kind of courage and strength do we need to face it for ourselves and for each other?

I can’t help but tie this back to the work we are doing. Our work flows out of who we are and what we fundamentally believe.

The contribution we make has to be for or against something, and the bigger that something is, the more courageous we have to be.

For me it’s about putting a stake in the ground and standing up for what is true, generous, kind, and hopeful.

These are the ways I can celebrate, when the world feels like it is rearranging itself for me. Where I embrace the parts that are out of control and say it is working for me, not to me.

• Me, July 11th 2020

This was something my friend Shawn and I started to say to each other during our calls. We met in a mastermind group, and we both started new businesses around the same time.

There was a clarity in what we were doing at that moment. There was a sense of all of our experiences and ideas converging at that moment to produce something new, compelling, and inevitable.

It also means we had to be patient. What we were hoping to do, wasn’t going to happen tomorrow, or really anytime soon. Our vision was bigger than what we could do in a year.

But it’s only going to be a matter of time. Whatever it is we are trying to do, it starts with showing up everyday, while keeping our eyes far ahead to our north star.

It’s a tension we have to be able to hold until we get to where we want to be. It’s not convincing ourselves we’re right, it’s about putting a stake in the ground and believing what we are doing is what we’re meant to do.

Privilege is a veil that blurs empathy.

Privilege is what allows someone to storm into a government building, break into someone’s office, pose in her chair, and walk out of the building unharmed.

Privilege is what allows you to fabricated lies in order to exploit others for your own gain.

Privilege is a luxury many people do not have. There are those who live in real fear, desperation, and anxiety. Their voices are never heard. They are drowned out by those who have privilege.

My life is full of privilege.

Privilege allowed me to be home safe from a pandemic.

Privilege is what allowed me to pivot, thrive, and make sense of this past year.

And the only way I know how to reconcile this is to move forward with gratitude and generosity.

Gratitude because I’ve done nothing to deserve what I’ve been given. I am not entitled to what I have because of my privilege.

Generosity because all I can do is steward what I have been given and use it in service of others.

The only way to change culture is to create more of it. - Andy Crouch

This one idea completely changed the way I look at art, creativity, and my work. Growing up in a conservative Christian home, we always wondered how we can save a broken and sinful world. We had to be change makers, we had to make things right.

The way we’ve been shown to change the culture was by condemning, criticizing, or copying it.

The first two, condemning and criticizing culture, makes me livid. It makes me embarrassed and ashamed to be a Christian. We’ve seen too much of that from ignorant, self righteous people. Their bigotry and ignorance has made my faith a caricature.

Copying culture makes me cringe. Those that try to offer a “Christian” version of popular culture have been worse versions of what they are imitating.

It takes no real effort to condemn, criticize, or copy. You get to stand in the sidelines and point fingers so you can feel better about yourself, and feel as if you’re doing something important.

But creating more culture? That’s hard work. That’s putting skin in the game, taking responsibility. Culture is the way human beings make something of the world. It affects every aspect of our lives. The only way to change it is by creating more of the kind of culture we want to see.

When you do the courageous work of creating culture, it’s doesn’t become about us and them, or right or wrong. It’s not about saving the world, or converting the world to what you believe. It’s about connection, generosity, vulnerability, empathy, a contribution that makes things better.

You go from amateur to a professional when you start making something for other people.

Professional isn’t merely getting paid. In 2021, getting paid to do something is easier than ever. If earning money is the only metric you are judging your work by, you’re starting off on the wrong, scarce foot.

I want to offer a different definition: you become a professional when you start making something for other people. Amateurs do work for themselves, for the joy of the work itself. They are hobbyists or enthusiasts. There’s nothing wrong with it. Amateurs are not those hoping to become a professional.

Becky and I did some watercolor painting last week, and I enjoyed it much more than I thought I would. I’m itching to do it again, for the joy of doing it. We all need to be amateurs at something.

You become a professional when the work is done for someone else. When you take that risk to give your work to someone else and have it mean something to them. You’re a professional when you do the work even though you don’t feel like it because others are counting on you. A professional takes responsibility.

For the past few years, I’ve been an amateur writer. My newsletter, although graciously read by people (mostly friends) was a way for me to cement my own identity as a writer.

But this year, I want to write it professionally. I want to write it more for others than for my own enjoyment. I haven’t made a dollar directly off of my writing, but I’m a professional writer because my writing has become a practice for others, not a hobby for myself.

I need to write everyday, whether I feel like it or not, because I want to help others do their most courageous work. It’s not for everyone, some may find it unhelpful, but I have to do it. People are counting on me.

Whatever you are an amateur at, nurture it and protect it. We all need something to do to relax or nerd out on. Whatever you decide you want to be a professional at, create a routine, a discipline and begin today.

Ryan Holiday tells this story about a finance blogger with more than 100,000 email subscribers and a seven figure business. He wanted Ryan’s help to write a book:

As I sat down and read the emails and articles that this site created, looking for the bones we’d build a book around, I quickly ran into a problem: this person was not actually saying anything at all.

The emails were very compelling, don’t misunderstand. They sucked me from sentence to sentence, paragraph break to paragraph break, and then from one article to the next. They were in fact brilliantly written. I just could not figure out what this person was actually selling. The best I could come up with, after really digging into it, for hours and hours, was that the entire premise of this person’s pitch was: Buy options on stocks that go up in value.

This guy was a brilliant copywriter with nothing of value to sell. He knew how to open loops, keep the suspense, and release the tension it at the right time. He made money selling snake oil with flair.

But if you want to do meaningful and important work you have to push yourself toward substance, stretch your capacities until they are no longer such a stretch. If you want to be a person who people respect, you have to stand for something. Not everyone will like it, but if it’s sincere, they will respect it.

This essay haunted me when I first read it a few years ago. I wondered if it was true of me. I had enough skills to start and sustain a business but was I stretching myself? Was I standing for something? There may have been a bit of imposter’s syndrome seeping into the worry but there was a truth to it.

But rereading this essay now, I’m not as concerned about skill and mastery as I am about standing for something. A reason why we are creating, building, and sharing. The answer to that why has to flow out of somewhere deep within us: the place where our deep gladness meets the world’s deep hunger.

We need skill but more than that, a north star.

The internet has made it easier than ever to learn whatever we are interested in. What the world needs more than mastery is people who care enough to risk being on the hook for someone else.

Putting ourselves out there for someone specific, in a specific way, for a specific cause is scary. But that’s the way we can change things for the better.

The only way we know for sure if we are doing things the “right” way is to start walking and then look back. We can’t know anything until we know what we’ve done. Being right is only known in hindsight. Foresight tells us to begin.

This video by Michael Ashcroft about finding a niche is a good example of using hindsight as evidence. His advice is simple: Don’t look for a niche, be prolific instead.

It’s only after a volume of work do you know who it’s for. It’s the way I’ve figured any of this out. It took two years of writing for a newsletter, six months of coaching calls, and a month of consistent writing here for me to look back and find a niche.