Don’t Wait Until You’re Comfortable to Start Taking Risks

Don’t Wait Until You’re Comfortable to Start Taking Risks

Yesterday morning, I sent out my very first newsletter to all seventeen of my subscribers (hi y’all, if you’re out there!).

I had a lot of feelings about this. First of all, I was a little embarrassed to send out my thoughts and feelings in something as intimate as an email. It felt massively pretentious. Who really cares what I have to say? So much that they’d be interested in me sending out my Sunday thoughts? It felt like I was overvaluing myself.

Plus, it was silly that I was sending this broadcast out to only seventeen people. I understand the value of a thousands-strong email list, but in the teens? What’s the point? Why bother? What impact would it possibly have?

I felt indecision. What should I put in the newsletter? What could interest people? What should the name be? When should I send it?

But mostly, I felt regret. I never got around to starting my email list when I began writing on Medium, even though the very first voices, like Shaunta and Tom, that I heard on this platform told me to from day one.

Why? I was afraid.

I’d only just started writing, I didn’t know the first thing about starting a mailing list, and even if I did, who would care what I had to say?

I’ll do it when I’m more established, I thought to myself.

So I waited. And waited. And I waited some more. Somehow I just never had enough time, or it wasn’t quite the right moment, or I’d be in a better position later. I just wanted to focus on writing, on building it into a sustainable career. There’d be time for newsletters later.

I’m way more “established” than I ever thought I’d be, in terms of writing success. I know my way around a keyboard and I’ve written more than I ever thought was possible.

And I finally bit the bullet. I created a mailing list. And the lesson I learned was that the best time to have done this was eight months ago. I should have believed in myself from the start, believed that people would want to stay in touch with me and hear more from me. I shouldn’t have been afraid to run before I could walk, to commit to investing in myself.

Eight months later, I am comfortable with writing, comfortable with my schedule, comfortable in my role here — and I finally started creating my mailing list.

If I took things one step at a time, I would save up enough money at my day job, then take a class in writing, then think of a brilliant book idea, and so on. I wouldn’t do what I’ve done now: jump headfirst into the world of writing while holding down a day job and a separate side-gig. I was passionate about starting writing as soon as I could, so I made it work.

I wish I’d taken the same approach to my mailing list. I wish I hadn’t hesitated, paralyzed by the need to get everything else perfect before I took that next step.

Life passes us by while we’re busy putting one foot in front of the other. Sometimes, that’s the right approach. When you need to build a foundation of knowledge, or if you’re genuinely overworked, it makes sense to have a measured approach.

But I should have realized that was not the right approach for me then.

Luckily for me, even though the best day to start was eight months ago, the second best time to start? It was as soon as I could. Which was, finally, a few days ago.

Now I’m started, and while I’m battling other feelings, like the feeling that nobody cares what I have to say, or that it’s silly to have a newsletter when only seventeen people are signed up to it, I am no longer feeling like there’s something I should be doing now.

Don’t get me wrong — all that stuff appeals to me, and the idea that a newsletter might help me along the way of becoming a writer by trade is a very alluring one. But that’s not my primary reason for creating a newsletter.

What I should have realized was that I have a lot to share when it comes to writing. As soon as I started writing stories about how I’d found success on this platform, or about the tools I use to make writing easier or more fun, or the things I wish I’d known when I started out, I realized I wanted to be able to share that information with as many people as possible.

What I believe is that anyone who wants to write for a living absolutely can and should pursue that dream. It’s more possible now, in my opinion, than ever before. That’s what’s driving me to ask people to stay in touch. That’s the factor that motivates me to write the newsletter. And I wish I’d started sooner.

Everyone reading this, if you have any aspiration of using communication in your side-gig, start building a newsletter. Don’t wait until you have an audience, don’t wait until you’ve thought of the perfect thing to say, don’t wait until you’re completely comfortable in your position — do it now.

You might feel silly.

You might feel like there’s no point.

You might feel like nobody cares what you have to say.

On every count, I have to tell you that you’re wrong. It’s not silly to want to share your voice with a targeted audience. It’s not pointless to start small, today, in the hopes that tomorrow it’ll be bigger. And despite my worst fears, I’ve always found that what I say is important to some people. It’s just a matter of finding those.

Give yourself a chance, and start planning for the audience you’ll have one day.

Want my four-day email course to start making money on Medium? Sign up to my mailing list here.

Don’t Wait Until You’re Comfortable to Start Taking Risks

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