Want to Write for a Living? The 7 Things I Wish I’d Known

Many people dream of becoming professional writers. Getting paid to share your thoughts with strangers is a pretty good gig. I’ve been a full-time writer for over a decade, and in the spirit of my last post on college advice, here’s what I wish I had known before I started writing.

First, though, some caveats. Writing is tough. Few who write regularly make a living doing it, and many of those who do barely scrape by. As with entrepreneurship, most people would probably be better off with a regular job than trying to earn a living writing.

That said, even if writing isn’t your primary source of income, it can still be worthwhile. Writing, like painting, music or languages, is fun. It can also be a great source of opportunities because it has spillover into other professions. Thus, becoming a decent writer is often a good investment.

Finally, writing is a broad discipline. I make money through courses and non-fiction advice books. Therefore, what I have to say will mean little to someone who wants to be a journalist, novelist or poet. Although the underlying skill is similar, the industry isn’t. Don’t expect my experience to transfer if you’re hoping to be the next J.K. Rowling or Tom Wolfe.

That said, here’s my advice to people who enjoy writing and wouldn’t mind being paid for it, too.

1. Your Audience is Your Most Valuable Asset

Success as a writer depends almost entirely on having a critical mass of people who want to read what you write.

A common mistake new writers make is trying to monetize too quickly. Many new writers have only a handful of subscribers, yet they try to write books or create courses to sell.

I understand this impulse. There’s a desire sometimes to validate your writing early on by proving you can earn a little money from it. But this gets the difficulty of professional writing backwards. The hard part isn’t coming up with something to sell, but having people who plausibly want to buy it.

A good general principle is not to try to sell anything (including writing a book) until you have 5000 regular readers. If that sounds like a lot, it should! Getting 5000 people to read your writing consistently isn’t easy—but it shows that you have something people are interested in. That’s why building your audience should be your priority.

2. Don’t Worry About Quality Until You’ve Written 100 Essays

Many writers obsess over their style when they haven’t produced enough to have one yet.

One hundred essays is probably a good benchmark to hit before worrying about whether what you’re writing is good or not. Again, if that sounds like a lot, it is! Writing one hundred essays is probably a year’s worth of work. But it’s a year that will tell you what kind of writer you are and give you a starting point for trying to improve.

Writing this much will also get you over your inhibitions about putting thought into text. Trying to produce the perfect essay right out of the gate will only lead to crippling writer’s block.

3. Write What You Like to Read

Emulate the writing you enjoy reading. There are two reasons for this:

First, it’s next-to-impossible to write well in a style you don’t enjoy. A good piece to write is something you would choose to read.

Second, imitation can be a starting point for creative success. While I don’t condone plagiarism, there’s nothing wrong with dissecting a piece of writing you like and trying to produce something similar. Often the finished product will look quite different, but learning what makes other writing work will help your own writing improve.

A side-effect of this process is that your writing will often start out looking like a second-rate version of an author you like. This is normal, and it doesn’t last forever. My early writing had a bit too much influence from Steve Pavlina, for instance. But over time, you add more and more influences, and your style will evolve spontaneously from the unique amalgam.

4. You May Never Feel “Smart Enough”

I’ve never felt qualified to write. I used to think the feeling would go away as I learned more, grew older or gained recognition. But I believe now this feeling of insecurity is a stable illusion caused by the very act of improvement.

Two factors influence this insecurity. The first is that your taste inevitably outstrips your ability. You can always appreciate writing that is better, smarter, more thorough and incisive than your own. You get better as a writer—but improve even more as a reader. The confidence gap widens, even as your absolute abilities grow.

The second factor is that there is no end to mastery. You can always learn more about a topic. And each piece of learning tends not to consolidate your views but fractionate them—providing more opportunity for nuance and distinction. Every piece of writing beneath your current understanding seems over-simplified. Every piece that’s above it seems pedantic. Your level of understanding rises, but the two sides forever remain.

I don’t prescribe blind confidence. Instead, acknowledge your perspective will always be imperfect and find the courage to create something anyway. Use the doubts you feel as a motivating force to better yourself, not as a barrier to prevent getting started.

5. Don’t Write Alone

Success as a writer means navigating the ever-changing sea of systems, social media networks and outlets people use to find success. While marketing alone won’t make you successful as a writer, it’s also true that an absence of this knowledge can be fatal.

Unfortunately, this type of information is nearly impossible to learn from a Google search. You need friends who also write. That way, you can share what is working, learn about opportunities, and refer to each other’s work.

Networking and marketing savvy tend to be force multipliers. They won’t help you if your writing is paltry, but it becomes easier to make friends who will help you if you write enough interesting stuff.

6. Look for Extreme Bets

Most writing will never be read by anyone. Of what remains, the vast majority will stay confined to the narrow corner of the internet they were birthed into. But a few pieces will travel widely. It only takes a few such pieces to build a career.

The easiest way you can increase your chances of success is simply to write more. Writing has a large random component; thus the optimal strategy tends to be prolificacy.

However, there are also predictable components to what makes writing interesting. Producing something one-of-a-kind doesn’t guarantee people will like it. But if they do like it, then at least you won’t be competing against the hundreds of near-substitutes.

The MIT Challenge remains my most popular project. Much of that I couldn’t have anticipated. But part of it is that it was such an extreme bet that there was little else like it online.

I still recommend quantity-first as a strategy. But once you’ve written your first hundred essays, start thinking about how you can push into an extreme that will set you apart.

7. Use Writing to Build Indirect Opportunities

Despite all my previous advice, it is rare to achieve success solely from writing. Given that I make money from selling courses, it’s not even clear if I count in this regard.

However, writing can be a good tool for leveraging other opportunities. Sometimes that means landing a more prestigious job, getting on a cool start-up, or just meeting cool people. Being an engineer, accountant, or manager who also writes well is a powerful combo.

While it’s great to make a living writing, it works best when you’d be happy to do it for free.