I wrote my first post on this blog in November 2017. Since then I have (more or less) been writing weekly. I started the blog as part of my job search process trying to find a job in venture capital. It has evolved into something so much more than that. Part professional development. Part mental health therapy. All me.
When I started this blog I wrote solely about the world of venture capital and technology startups. Over time, and especially after I got my job at a venture capital firm, the blog became more personal in nature. I liked this transition. I now write about whatever I want to write about. Turns out that venture capital still continues to be a meaningful part of that. But I also sprinkle in my personal development, views on pop culture, and lyrical waxings for flavor.
In this post, I will share some of the lessons I have learned along this journey so far.
Begin.
I will start with the most important part of writing. Starting it. The most common response I get from people who have read my blog is “I’ve always wanted to write!” Well, what is stopping you? I’m not trying to be insensitive. I know how hard it is. In some ways, it gets easier with practice and in some ways, it doesn’t. A blank page and a deadline are always intimidating. But there is something truly thrilling about it as well. The hardest part of writing something new every week is just writing that first sentence. Once you get going, it generally flows pretty easily. (In fact, if it isn’t flowing once you have started, that is usually a pretty good sign that you picked the wrong topic to write about.) My biggest piece of advice I can give is simply to start. I recently read the book Bird by Bird by Anne Lamott and it is the book I recommend to anyone trying to write more. The anecdote she shares on the back of the book superbly sums up writing.
Thirty years ago my older brother, who was ten years old at the time, was trying to get a report on birds written that he’d had three months to write. [It] was due the next day. We were out at our family cabin in Bolinas, and he was at the kitchen table close to tears, surrounded by binder paper and pencils and unopened books on birds, immobilized by the hugeness of the task ahead. Then my father sat down beside him, put his arm around my brother’s shoulder, and said "‘Bird by bird, buddy. Just take it bird by bird.
If any of you are procrastinators like me I imagine this hit similarly close to home. It’s easy for writing to feel overwhelming. Whether it is a blog post, a novel, or even a tweet, it is always difficult to create something out of nothing. The best way to get over that hump is simply to start putting one foot in front of the other. To take it bird by bird. It doesn’t even have to be about what you ultimately want to write about. If you are struggling to come up with something to write, get out a blank piece of paper and jot down a running stream of your thoughts. You will be amazed by how much easier it is to start writing once your thoughts have started flowing.
The Power of Writing
Writing has gotten me into rooms and conversations that I had no business being a part of. I by no means have a massive following on this blog, but even I have seen huge asymmetric benefits come from it. Writing is the best kind of bet you can take. The downside is capped. For me the downside is time. I sacrifice an hour or two a week to write. It’s not nothing, but it also isn’t that big of a deal. I probably spend more time watching Hearthstone videos on youtube each week so if I need to cut something out that will be the first thing to go. A small sacrifice in the face of the potential upside. You never know who is going to read your work and reach out. You never know if what you’re saying will strike a chord with someone. I have had many personal and professional opportunities crop up solely because of my writing. And the best part is that writing compounds over time. The longer that I consistently write, the more it differentiates me. Things like writing are the best kind of flywheel. The more you do it, the more benefit you see from it, which makes you want to do it even more.
The Pocket Knife of the Mind
Recently I have gotten into pocket knives— ahem I mean multi-tools. My parents got me a fancy new backpack for my birthday and since then I have been into the idea of the “Everyday Carry” (or “EDC” if you are especially hip and yes, this really is a real thing). As part of that newfound interest, I have acquired a couple of new multi-tools. The thing that I have found with multi-tools is that if you don’t regularly use them, you don’t see any use for them. That changes as soon as you have one. Suddenly you see all kinds of uses for it everywhere. Writing is the same way. Once you get into the habit of coming up with stories, you start to see them everywhere. I write a post each week, but I generally come up with 2-3 ideas for new posts each week. When I am in the habit of keeping an eye out for those nuggets of an idea, I see them when they pop up. I am not special. You have these ideas too. You just aren’t used to seeing them that way since you aren’t used to the pocket knife of writing.
Develop a system
So all these little golden ideas I just mentioned. Everyone has them. But almost no one captures them. The world’s best idea won’t do you a lot of good if you don’t remember it when it comes time to start writing the next day.
It doesn’t really matter how you do it. You can use a notebook or an app or you can simply send yourself text messages. I have a page set up in Notion to capture all of my blog post ideas quickly from my phone. Whatever works for you, so long as you are able to quickly and efficiently capture and store those ideas so you can come back to them later and turn them into your magnificent writings.
Inconsistently Consistent
As with much of life, when it comes to putting out content, consistency is key. When I started writing I would do a post every 2-3 weeks. I didn’t have a real schedule and it was only ever when I could carve out some significant time for it. Over time, I focused on writing shorter posts more consistently. The one thing every audience appreciates, no matter how big or how small, is consistency. Set expectations with yourself and your audience and then stick to them. You don’t have to be militant about it. It’s your content, if you want to take a week off, you can. But know that the more consistent you can be the more it will positively impact your readership and the quality of your writing. When you stick to a consistent schedule, you get in a groove. You have an easier time getting started and you come up with more ideas of what to write about. My best advice is to pick whatever schedule that you can stick to consistently. It’s better to write something once a month than to write inconsistently every 1-3 weeks. Your readers will thank you for it and it WILL make your writing stronger.
Chop Wood and Carry Water
Writing is about the process. The quicker you can learn to fall in love with the process of writing, the quicker you will become a better writer. I am a big believer in being process-oriented in as much as you can in life. Writing is no exception. If you focus too much on the outcome you will either a) fall short of your goal or b) attain it at unnecessary costs. Focus on the process. Do I write for professional development and opportunities? Sure, but that isn’t my focus. I write for me. I practice writing so I can improve and hone that skill. I find writing therapeutic. Putting my thoughts into cogent sentences really helps me think through them. Sometimes I find myself surprised by the results. That is my focus. This blog would be worth writing even if no one ever read it. That’s how I am able to stick with it. I love that people read my blog. It means so much when someone reaches out to tell me that they enjoyed something I created.
But that’s only ever going to be the cherry on top. Because I have learned to fall in love with the inherent benefits of the writing process, not just the outcomes of that process. I have learned to chop wood and carry water when it comes to writing. And you can too.
Perfect is the enemy of good
At Carlyle, one of our founders had a saying: “By the time you have completed the most perfect due diligence you possibly can, you will have lost the deal.” Perfection is an impossible standard to strive towards and it is one of the biggest pitfalls that nascent writers have. There is this pressure thinking that if you are going to put a blog post or tweet out into the world it needs to be perfect. You should craft it with care, but perfection should never be the aim. If you won’t settle for anything less than perfect, you will never click that ‘Publish’ button. Do your best, read everything over for typos and then send that sucker on its merry way.
Let me let you in on a little secret I have learned about creating content on the internet. Say something uninteresting and no one cares. The algorithms won’t pick it up. It will be like it never even happened. Hate to break it to you, but no one is combing through your old posts to see how you messed up. If you, at some point, do reach the level of quasi-celebrity where someone is doing that, I imagine you have bigger fish to fry. No one will read your subpar writing, but write something good and it becomes a whole different story. Suddenly people are liking and sharing. The algorithms that buried your mediocrity are now pouring fuel on the fire of your achievement. Writing publicly is a totally asymmetric bet. Write poorly and no one knows. Write well and it will blow up. No, I am not saying to just throw spaghetti at the wall and see what sticks. But whatever you do, don’t try to be perfect.
Find What Works for You
As I mentioned, I originally started this blog as a way to land a job in venture capital. As such, my initial writing focused on researching and analyzing specific companies and markets. I wanted to show that I could do the work of being a VC before I actually was one. Once I actually got a job in the industry, my blog started to change. It became more personal. I started writing about the things I was interested in. My posts became shorter and more consistent. I was doing less research and more thinking. That’s what the blog is now. I write about the things I care about. Yes, venture capital and entrepreneurship. But also boardgames. And Arsenal. And whatever TV show I may be watching or book I may be reading. That’s the beauty of having a personal blog. You can be just that, personal. The internet is so big that writing about what I care about is interesting enough for others to tune in every week. And it is WAY more enjoyable for me to just write about whatever I want to write about. Remember, learn to fall in love with the process.
If you are thinking about writing, go for it. It’s a small sacrifice of time for big potential upsides down the road. Come up with a process and then fall in love with it. Don’t try to be perfect, just try to be genuinely you. The internet is big enough that you will find your tribe. If something you write flops, don’t sweat it because no one will read it. But the second you write something good it will seem like everyone will. Consistency over volume.
If even a small part of you feels like you may want to write, then just start and see where it takes you.
And if you get stuck, just remember to take things bird by bird.