How to Gracefully Start Sending Your Newsletter Again

When you run your own business, sending content regularly to your prospective customers can be a great way to build that relationship. But what happens when you stop mailing regularly and want to get back in the habit again? Read on to find out.

1.     Let yourself off the hook

Many of the coaches, healers, and self-employed professionals I work with tell me they feel terrible about falling out of touch with their mailing list. That’s normal, but it actually doesn’t help the situation.

The truth is, most progress is “two steps forward, one step back.” Being consistent in sending content to your prospective customers is hard – that’s why most people don’t do it. Be kind to yourself. Raking yourself over the coals doesn’t do your prospective customers any good. It just slows you down and makes you feel bad.

2.     Notice why you fell off the wagon

One of the things I teach my students is the concept of “iterative learning.” That’s a fancy term that simply means: don’t expect to be a master at something on your first go (or the seventeenth). We have a motto in our community to remind us of this: Learn One Thing. Every time you put a piece of marketing into the world, learn one thing. Every time you screw up, learn one thing. Every time you sit down to write marketing for your business, learn one thing.

Too many healers and coaches paralyze themselves with expectations of 100% Perfection All The Time. Because they can’t quite do that, they don’t do anything. This is a problem. ‘Learning one thing’ reminds us that progress is incremental, and happens for people who show up, come hell or high water, again and again and again and again.

3.     Change something so this time you’ll be set up for success

What did you notice about why you fell out of touch with your mailing list? Maybe there was a family member who needed care. Maybe you lost touch with your message. Maybe you moved house. Whatever the reason, run a quick diagnostic about why you stopped being in touch… and then come up with a way of tweaking your process so you decrease the likelihood it will happen again.

The magic question here is: what can I do differently in the future so that doesn’t happen again?

Maybe you need to schedule a weekly shut up and write time for yourself. Maybe you need to get an accountabilibuddy that you text every week when your newsletter goes out. Maybe you need to write a bunch of articles in one sitting. Everyone’s needs are different, but this step is worth its weight in potatoes. (You’ll never go hungry if you have potatoes.)

4.     Acknowledge what happened

Just like any other relationship, your relationship with your mailing list isn’t about being perfect. Imagine you had a friend you liked but stopped hearing from for awhile. You like them. You aren’t sure why they went away. But when they finally get back in touch to say, “hey, I just had the craziest 6 months and that’s why I fell out of touch”… you’d probably be pretty forgiving and understanding. You wouldn’t need them to make a big deal out of it. You’d just say, “I know what that’s like!” and move on.

You can do the same with your mailing list. Briefly tell them what happened (if you feel so inclined), then give them some great tips or tools. Because that’s what they signed up for! It really can be that simple.

5.     Get back on the horse and keep going

Once you get back in touch with your list, then the real work begins. Consistently sending content to your prospective customers is a habit. And like any other habit – exercise or eating your greens or brushing your dog’s teeth – it takes a while to establish. It’s also hard to do on your own. So grab a buddy or join Write Club and join forces with others who are working on getting better at this, too.

When it comes to your relationship with the prospective customers on your mailing list, it pays to be forgiving – especially with yourself. The motto here is “rupture and repair.” Like any relationship, there will be times when, despite your best intentions, you screw up. The healthiest thing to do – both personally and for the business – is to simply and gracefully move forward (imperfections and all).  No one expects you to be perfect. But they will notice when you keep showing up to make their lives better, consistently and meaningfully, over time.

Want help getting started with a shut up and write practice – or getting back in the habit? Check out our Write Club community. There are multiple Shut Up And Write sessions throughout the week, in a range of time zones (including the Middle East and Europe!)

Stella Orange teaches her clients how to effectively market their business by telling a better story in their marketing— the story of the hero answering the call to more. A professional copywriter whose writing has generated millions of dollars in sales, Stella knows that the story we tell in our marketing matters a whole lot, because on a fundamental level, it shapes how people think about themselves and what’s even possible for them. Three times a month, Stella hosts a 90-minute Shut Up And Write session via videoconference for members of her Write Club community. She is based in Buffalo, New York, where she lives with her husband, the Philosopher, and their dog, Chachi. Get a copy of Stella’s position paper The New Marketing: How to Create Clients Without Feeling Gross, Icky or Manipulative at

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