If you don’t separate what’s working from what you wish was working, you’ll never commit to the right projects. This is a story about learning to tell the difference.
On January 11th, I started a freemium newsletter. I called it “You — A daily email full of inspiration, smart ideas, and emotional support for the most important person in your life.”
Three times a week, it was free. For two extra editions, plus audio recordings, plus community interaction, you had to pay. I launched with a discounted rate of $5/month or $50/year, which later went up to $7/$70. I started with 27,000 email subscribers, painstakingly acquired over the last seven years.
After six weeks, I had about 70 paying customers, for a projected annual revenue of about $3,700. I took a week off for my 30th birthday — and then I quit. I refunded everyone and shut the project down.
Here’s why in 5 lessons.
1. A paid distraction is still a distraction
Two years ago, I had just become a full-time, self-employed writer. Back then, I wrote the following words:
I already struggle to keep doing what I love. Shiny-object syndrome often pulls me into only semi-writing related projects, which I then nuke a few months later when I come back to my senses. Going forward, I want to make a big commitment to writing: I want to self-publish books and maybe even get a book deal.
Now here we are in 2021, and there’s still no book. That’s disappointing, and that needs to change. At some point in your career, you’ll be able to spin any project into making a buck — but that still won’t mean it’s the right project to pursue.
2. The more you (l)earn, the faster you’ll move
Originally, I planned to run You for at least a year. Year-long experiments are great for beginners, and I’d recommend them to any starting writer — because a starting writer’s biggest problem is quitting too early.
I, however, am no longer a beginner, so if I throw more good time after bad ideas, I’ll just waste it confirming what I already know. I have been writing for 7 years. I don’t need another one for each project to determine if it works.
My audience is big enough to show early signs of a big hit, and this just wasn’t one of them, neither in earnings nor in attention.
It doesn’t make you a bad person to not want to spend 50% of your time on something that adds up to 1% of your income, even if the absolute number would sound great to someone who’s earlier in their career. Eventually, money becomes more of a compass than a reward. Do people really want what you make? If not, it’s okay to try and make something better.
My newsletter wasn’t essential. It wasn’t a daily market update for investors. People have reservations about adding another subscription to their already pounded wallet, particularly if it’s mostly to support a creator they like.
All of this is fine by me. It simply means I must move on — especially since I’ve had something bigger waiting for me for a while.
3. Follow the fear — the fear is where the growth is
After writing 2,000 articles, I could easily crank out 20,000 more. I have nothing left to prove. What makes daily posts enticing is that the deadlines are short, ideas are abundant, and you’re always close to shipping the next thing.
Writing a book is a different beast, and it scares the living crap out of me. I spend hours editing paragraphs. Each word must sit perfectly. You can’t change any of them after the fact. You can’t chuck the whole thing into the trash and publish another the next day. A book has real stakes. For months, you toil away in your cave, and only when it’s all said and done will you find out if you get paid.
Sooner or later, just like money, fear becomes a compass. You must follow it. The fear is where the growth is. As a writer, books are my true end game — and it’s about time I start to play.
4. The grind won’t stop until you do
Last year, I quit my job as the editor of Better Marketing because, after six years of always doing it in one form or another, I no longer wanted the daily grind of “writing-as-a-service” — especially considering how much energy it would take to write books. Doing as humans do, I turned right around and started a daily newsletter.
Working on a set, daily schedule has worked well for me. It helped me build a big audience on various platforms. It allowed me to secure my basic expenses early on. The problem with everything that works well is that, in the long run, it becomes hard to let it go, even when it no longer serves you.
As they mature, platforms often dial back the attention and earnings they initially offer, be it by accident or by design. Even if they don’t, ultimately, no amount of money or fame can make up for a job that feels draining. My set schedule always had an expiry date, and now that I don’t need to rely on it, it’s time to lean into a new chapter instead of away from it.
I’m 30. If I don’t choose to stop grinding, the science of habits says I never will. I don’t want to work just to work. Work isn’t everything. I want to embrace my oddly abundant, unscheduled life — and polish the words until they’re ready.
It’s easy to go back to the familiar, even if the familiar no longer works. Don’t be afraid to leave behind what’s tried and true because at some point, every habit becomes a prison, and every rule finds its exception.
5. There comes a time for impact to replace scarcity
Originally, my newsletter was an attempt at fighting my declining income in other places. For a second, I wondered: “Do I need to replace this income at all?” In hindsight, the answer was always “no” — I just didn’t see it back then.
The truth is I’ll be fine, even if it takes me a year to get out a book that sells. I perceived financial scarcity that wasn’t there, and when I realized it, I spent some time trying to make sense of it. The result was — surprise — an article about what I called “the Wheaton Scale of Productivity.” In essence, you’ll go through different philosophies of what it means to be productive as you mature in your career.
I’m at the stage where it no longer makes sense to work myself to the bone to eke out a few extra dollars. Instead, I should think long and hard about what I do and only then do it all the way. What projects really matter? How can I impact the most people in the most meaningful way?
Books are much more powerful than articles. They require investment through time and money — but not too much to scare people away. We buy books on impulse. We gift them to others. If we really “get” the message of a book, we can remember it much better. Books have stood the test of time.
In the long run, I can reach far more people with books than I can with a gated newsletter subscription — so I’ll stop one and work on the other.
The Self-Starter’s Duty
As a creative, entrepreneur, or any kind of self-starter, separating what’s actually working from what you only wish that would is a constant, never-ending task. It requires one thing above all else: Brutal honesty with yourself.
Is this project your destiny or just a distraction? Are you doing it from a position of scarcity or one of abundance? When you look at its metrics objectively, what does your seasoned gut tell you? What are you afraid of? What patterns are you tempted to fall back into?
These are the questions you must ask, and when their answers point you in a new direction, don’t be afraid to quit. You’re here to do your best work, not any work, and there is no shame in walking away from “good” to take another swing at “great.”