Jenna Rainey


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hey friend!

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!

(with me)


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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i wrote some books



international book tour

International Book Tour: A Peek Inside What It’s Really Like



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International book tour?! That sounds flashy, amiright?!

When someone asks me what I do, just saying the words, “I'm an author” as a part of my elevator pitch took me at least a YEAR to feel comfortable saying.

It felt totally awkward for some reason…I really don't know why. Like I couldn't believe it, or I was feeling like the person asking might judge me… “What?! Her?!” “I bet it's barely made any sales”…

But when my book Everyday Watercolor came out in October 2017, I decided to absorb the title of author and lean really hard into the role. I mean, I deserved it…writing a book is a TON of work!

(Related: How to Work with and Find a Literary Agent with Kimberly Brower)

By leaning into the role, I mean I WENT FOR IT. I’d taught hundreds of in-person workshops before, so I thought I’d plan this glamorous international book tour, complete with multiple classes per stop. Book signings after each workshop, and a little cocktail hour with all of my students and “fans” to cap it off in each city…I mean, can you hear where I’m going with this?! 

I spent the summer leading up to the book release, researching, putting deposits down, booking flights, ordering all of the alcohol and catering for the book signings and creating hype around said “International Book Tour.” And I was SO excited.

Untiiiiiiiiil I looked at my bank account.

Yes, that’s right. I’m a published author, and I had to fully fund my entire book tour. Everything from supplies, to hotels and food was on me. I mean, maybe that’s common sense…I know I’m not Oprah, I’m not even CLOSE, but I think a lot of people have this assumption that if you’re a published author, your publisher helps with some of the bill. And my books weren’t put out by some small-town publishing house either…we’re talking about Penguin Random House!!

But before the excitement started to wear off, I kept throwin’ down the plastic and placing all the deposits! *non-refundable* I might add! 

I was SO excited to travel and see places I've always wanted to see and take my workshops on the road, that I hadn’t thought about the impact it would have on my business…I'd traveled within the U.S. with my workshops before, so really how hard could it be?? Traveling to Canada, Singapore, Australia, Europe and all over the U.S., in a 10-week period shouldn’t be a big deal…right?!! 

Let's go back to the booking phase for a bit. When it came to doing the research on where to host workshops in cities I'd never been to, I learned a TON about what locations and types of venues work, and which ones DON’T. And I learned that because I BOOKED some of the locations that DIDN’T work for my tour!

So, if you’re an educator out there and thinking about teaching workshops or taking yours on the road…just because a venue can take really nice photos of their space, doesn’t mean it’s going to be a good experience.

It's SO important to actually do your research on the neighborhood and ask the important questions like:

Will students be able to park (for free!) for more than 2 hours?

What's the square footage of the space?

Will there be enough elbow room for each person at the tables, or will they feel cramped?

Is there air conditioning?! (Singapore is REAAALLY hot, y’all!)

EARTH TO JENNA! It's not just about *going on a book tour*…as incredible, flashy and amazing as that sounds, it’s SO much more than that and it requires a LOT of planning. 

Behind the scenes, while I was in the midst of planning this thing, I was strapped for cash for a few months. I was having to put deposits down on venues for full-day rental fees, flights, hotels, and caterers…with no guarantee that anyone would even SHOW UP!

I was stressed to the MAX because I was still working with wedding stationery clients at the time and had a fully booked calendar while planning and going on this book tour. I had to order all the supplies for these classes, ship my books to each location, and the logistics of making sure everything arrived on time and in at least *good* condition was incredibly stressful.

Thankfully most of the supplies arrived in perfect condition and we packed extra to replace what wasn’t workable…thankfully! The classes mostly sold out which helped recoup my expenses for travel, food, lodging and a dose of fun in between teaching and signing books…but with all of that, I ended up coming back home in DEBT from this *glamorous book tour*.

Granted, it wasn’t much debt at all, and I paid it all off within a week, but between the cute squares on Instagram, I was STRESSIN'.

Now, before I keep going…I'm not saying this to complain AT ALL. I’m incredibly grateful for the experience, it taught me a TON and it totally helped build buzz and create hype around my first book. Along with that, I realize a lot of people never have the opportunity to even travel and I feel so fortunate that I was able to have this experience.

But, here’s my point:

Social media is a curated view of our lives.

As much as we try to be “real” and show the “behind the scenes,” there’s SO much under the surface that is just impossible to show. There’s anxiety, sleepless nights, outbursts of attitude and getting in stupid fights with our partner…and we forget this because there are captions that read: “I’m going on an international book tour,” and we think…”damn. She’s got it ALL.”

When, really, the caption should say “I’m going on an international book tour…I really hope people come to this because I just put down $12K on this thing so far and I’m TERRIFIED about supplies not showing up. So, will you guys come???”

Instead, between those pretty, curated squares, you're assuming that the person you're envying is taking private cars from the airport to their hotel, spending every free day at the trendiest restaurants and coffee shops and, well… That's just not the case.

While there is some of that, there's also a healthy dose of:

– MAJOR anxiety because your boxes of supplies are being held up at customs in Canada and you have a workshop the NEXT DAY.

– Spending HOURS on the phone trying to sort it out and get customs to release your boxes of supplies and books

– Pure exhaustion because you had the CRAZY idea to book a workshop in Sydney (which is a 15 hour flight) ONE DAY after you land, yea, jet lag never hurt anyone!…oh and all my workshop days were 12 hour days.

– Major flare-ups on your health because you're having to eat out all of the time and are eating things your body isn't familiar with, so feeling sick a good chunk of the time.

– I mean, I could go on, but I don’t want to sound whiny, which I fear I maybe already do…

I know this sounds like I'm complaining, but I'm telling you all of this for a couple of reasons:

  1. It's really smart to budget things and to have more than 2-3 months to plan an international book tour and not lose money.
  2. Don't push yourself too hard just because it sounds cool.
  3. Spacing out my travel would've helped me enjoy each and every moment much more, instead of doing back to back workshops and travel days!
  4. DO YOUR RESEARCH. Research venues like I mentioned, research your audience in the cities you want to travel to BEFORE booking, so you can make sure the people will come! 🙂

Anyway. This may not seem relevant to you right now, but think about it…

Are you an artist, designer, photographer, or some type of creative? Do you teach in-person classes or want to? 

Think about this story before you get sucked in by the flashy packaging. Whether that's for teaching classes or not…this applies to job opportunities, accepting free work for exposure, etc. Then, read THIS POST to find out if you're ready to teach or not.

Make sure you follow and trust your gut before getting wrapped up in it all and in the end, ALWAYS make sure you're learning and extracting as much as you can from the lesson as possible!

by Jenna Rainey 

add a comment

  1. Jenni says:

    Thank you so much for that deep insight. I really appreciate your openness on this topic. And you did not sound whiny at all…for me this is a raw and authentic behind the scenes blog post, which really helps to demistify the glamourous life of a creative entrepreneur. I miss this sight sometimes in the online world. So thank you ❤️

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