Jenna Rainey


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I’m Jenna Rainey. 

I'm an artist, self-taught designer, and multi-faceted creative entrepreneur who is hell-bent on teaching everyone how to find their inner creative voice.



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A highly creative nerd with a unique breed of humor and the proud earner of a self-bestowed award for being the world’s most curious and driven human.

Hey I'm Jenna!

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It’s like Netflix-binging Bob Ross videos, but with a dose of dry + quirky humor and fewer happy little tree references. 

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5 Steps to Create Your Annual Promo Calendar

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Stuck on the content hamster wheel? Today I want to share 5 steps to create your own promo calendar for the entire year’s worth of content. 

If you've been following me on Instagram for any number of months, then you've probably seen that I have literally planned out every single launch, every single broadcast email to my newsletter, every single podcast episode, every YouTube video tutorial…for the entire year. 

So if you've been wondering how to make up for lost time or if you're like, How do these people have all of this time to post on Instagram, to have a YouTube channel, to also have an email list that they're nurturing and blogging and showing up for their clients

This, my friends, is the bread and butter of getting your time back. 

Content planning and content producing are two very different things. And the people that are producing content willy nilly are losing time. I used to be that person. I used to just fly by the seat of my pants. But we're no longer doing that in my business, and it has absolutely saved me time. I want to help you do that. 

Planning out an entire year’s worth of content, worth of launches…anything that has to do with your business, whether you’re a products-based business or a service-based business, can sound very daunting and overwhelming. 

But listen up. This took me one day—one day! 

That was it. A focused amount of time for anywhere from four to six hours to plan out my entire year's worth weekly Instagram posts, weekly YouTube tutorials, weekly email newsletters, 2 podcast episodes per week, my quarterly course launches, and finally small promotions like when my licensing products are released. 

With everything planned out, I have a very, very clear direction and purpose for what I'm talking about that day and what I have upcoming. I know what to prep my audience for and how I lead my potential students into purchasing a course from me through podcasts episodes or newsletters—not in a conniving or overly strategic way. It's more so that I can help my students glean more from my content. The more I talk about what is covered in my courses, the more my students can get out of my course. And I know that 100% because I've seen that result. 

It also helps you get some time back. 

If you can only plan out four months, that's fine! But planning really helps shave off that time every single week that you're spending scratching your head and wondering what to post about or forgetting to send out an email to your newsletter again this week. 

I highly recommend you follow these five steps to create your own annual promo calendar. 


Step #1: Identify the 4 main categories in your business

Sit down, grab a planner, a blank sheet of paper, your favorite pen and boil down your business into the four biggest categories or products or promotional periods that you have within your brand or business. 

So let's say you’re a service-based business for example—a wedding stationery designer—you have a few different seasons of potential customers. You have engagement season in January in December since the holiday is the peak season for engagements. You can talk about the best ways to save money. Or you can be talking about how to plan ahead for your wedding and where to start saving money in certain areas and budgeting, etc. Then, the majority of people are getting married in the summer and in the early fall. So you can be talking about and planning out your entire annual calendar around the topics and the conversations that are already floating around in the minds of your potential customers/clients. 

If you're a product-based business, maybe you have an online shop with some prints, maybe you have categories of different types of prints that you can promote for different times of the year or you have four different times a year that you're offering discounts or some sort of incentive to your potential customers…whatever it may be.

Sit down with that paper and pen. And really, really get down to those four things. And if it's five or three, that's fine, but try and aim for about four because there are four quarters and that just makes it straightforward. If you’re stuck, think: What are your main moneymakers? What are you really passionate about? Because THAT is what’s going to be easy to sell when it comes time to promote and sell.

All of your social media, all of your newsletter, emails, all of your blogs, etc, will fall into place once you have those four written down. 


Step #2: Set aside a dedicated time to plug the main promos in your calendar

So once you have those four written down, I want you to see where they fit well into your calendar. 

For example, newly engaged couples are looking to send out save the dates. So maybe in the first quarter of the year, right after people are getting engaged over the holiday season, you do a promotion for your save the date services. Maybe you've discounted your flat rate or your packages, or you're lumping in a free save the date with anybody who hires you for X, Y, and Z package for your wedding stationery design services. 

You want to lead your potential clients and customers to the sale. You don't want to spring the sale on them. You don't just want to, Hey, we're doing this discount. It starts today and it ends in a few days. You want to lead them, warm them up to the idea and have it in their minds. When it does come time to sell to them, they're already aware of what you do and why they should hire you or why they should purchase your products when they're on sale. 


Step #3: Put on the tunes, grab your favorite beverage and schedule out all your content!

Set aside a full one to two days to do this. Schedule the time so that you'll show up and you'll do it and you'll want to get it done within the timeframe that you give yourself. Put on the good music, grab some wine and food that gets you in the zone and have fun with it! 

I bought one of those full-year wall calendars, we nailed it to the wall behind John's desk and we got out the dry erase markers. It's the ugliest wall calendar you've ever seen. John and I stared at that thing for about four hours while listening to Kanye and we nailed down the entire year together. If your employees, assistant, significant other, or friend wants to be a part of the planning phase with you and they enjoy that, then by all means… It's really fun to have somebody to collaborate with and to bounce ideas off of. John and I did it while the baby was sleeping!

Remember that no idea or a piece of content is a bad idea. It's fine. You can write it down, it's dry erase and you can erase it. I do recommend getting a wall-mounted calendar. You need to have it all in front of you so you can see how each bit of content works with the next and leads into your promotional period. 


Step #4: Build in time for you!

Make sure that you reserve time for family days and vacations when you're planning out your annual promotional calendar. 

I decided for the year of 2020 that I'm taking an entire month off in April. And so that was the first thing we did. In April, we completely blacked out all of those days. We still have podcast episodes being released twice a week in April and we still have YouTube videos coming out every single week in April. And we still have broadcast emails going out to my newsletter subscribers. Because I know that I'm taking the month of April off, I am writing an extra broadcast email, recording an extra podcast episode, recording an extra YouTube tutorial every single week leading up to April. So we can stay ahead of schedule, have those episodes and those tutorials nailed down and scheduled to publish while we're away and resting. 

So block out those vacations first. Be realistic with your time off. Be realistic with what you need so that you can pour back into your business with a full cup instead of an empty cup. 


Step #5: Space out the launches to warm up your audience

Give yourself some breathing room!

Let's use my business as an example. Every quarter we are launching or relaunching a course. So I have four courses—Pen to Press, Brand Plus Brand (my licensing course), a marketing course, and a course releasing in March 2020 on creating and teaching in-person workshops and online courses. 

Each of those courses have their own designated quarter. The first week of March is dedicated to launching my workshops and online course course (very meta). I design my online course launches to happen over a one-week period. And so leading up to that first week of March, I have January and February to prep or warm my audience up to the idea of my online course. My potential students are those interested in teaching workshops or creating their own online course or they already are doing both and they just need more insight and input on how to make it profitable. During this time, I am coming out with podcast episodes, blog posts and YouTube videos that are focused on teaching, on the ins and outs of workshops, or on how to find the right venues. Basically, I talk about the WHY behind teaching workshops or online courses.

Then when it comes time to promote the course, my audience is already aware that I know what I'm talking about. They're already aware of the importance behind teaching workshops and online courses within your business and the impact that it can make in your business as a creative entrepreneur. They are more prepped and ready to make a purchase if they are the right student for my course. 

This is something you can do with any type of business if you have an online shop with your artwork in it, if you do licensing, if you are a wedding stationer, whatever you do, think about your year in terms of your different promotional periods and warm your audience up to those promotional periods. That way, you're not just randomly throwing in a sales bit here and there or randomly talking about your products and where they can find them or where they can book you. But you have a clear and scheduled time of the year just for going hard and selling because you know what you offer is valuable.  

Then the rest of the year, all I'm doing is providing free, valuable, insightful content through my podcast, Instagram, email, and YouTube that leads my audience up to what I'm about to promote. 

One-off promos here and there are okay but you don't want to be overselling to your audience. It feels awkward and slimy and sleazy and you want to make sure that you're planning out your content in a way that feels natural, genuine, and authentic. 

I'm not trying to come off in any way that's not authentic. I want you to know that my true end goal for everything when it comes to promoting and selling is always with the idea in mind I know 100% that whatever I promote on Instagram or podcasts is valuable and impactful. And I know that because I wouldn't promote anything that isn't impactful. And so my main focus for planning out an entire year's worth of content is to make the best and biggest impact that I possibly can.

Because with algorithms, busy schedules, kids, soccer practices, business and clients, we are already strapped for time. If you truly believe in what you're talking about—what you're offering your audience—then selling is going to be a lot easier. It will still be strategic, but it's because you have that end goal of impacting people's lives.


Remember the impact you make and the value you bring.

And if you're like, Well I'm not impacting people's lives, all I do is have watercolor prints on my Etsy shop... We have to simplify it. Impact and value are on a wide, wide, wide, wide spectrum. Think about the emotion or the joy or the happiness or the value that you bring to your potential customers when they purchase your print for their new home or purchase your print for that baby shower they're going to and they just couldn't find the perfect gift. 

Boil down the end value or impact that you can have with your products or services and keep that front-of-mind when you're planning out your entire year's worth of content in your annual calendar.


So there you have it! Five steps to create your annual promo calendar.

And one more thing…after you plan it out, here's my free Master Marketing Calendar where you can store an electronic version of your year's content! Now head on over to Instagram and let me know how your planning process is going!

by Jenna Rainey 

add a comment

  1. Elle McKay says:

    Hey Jenna!

    Just thought I’d mention first, after listening to almost all of your podcasts so far, I thought your course was called Panda Press and I thought that was really cute! ..until I read Pen to Press and I guess that probably makes a lot more sense!

    Anyway, I’m a budding artist and I’m still trying to figure out what and how to sell my work (prints, licensing, workshops, tutorials, etc?) and so I haven’t got a product to sell yet, but I’m unsure of the ‘warm-up your audience’ phase. I totally get it with your pending workshop coming up, keeping workshops front of mind, however, I’m unsure of how to apply that with other launches?

    Massive fan our your podcast though, I’ve never listened to one that resonates with me like this. I’ve learnt more in one day listening to every episode than I have in probably the last 6 months!

    Kindest regards,
    Elle 🙂

    • Jenna Rainey says:

      Lol! Panda Press. I talk more about the warming up in this episode so check it out for more ideas from my course launch strategy! You can show people sneak peaks, process videos, behind the scenes, stories, testimonials, and explain the why behind whatever you’re launching. So many possibilities!

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