2019—A Year In Review

JessieUncategorized 6 Comments

For the past few years, I’ve been doing a Year In Review. It’s a behind-the-scenes retrospective on everything that’s been going on for the past 12 months—in my business and beyond.

See past ones here:



These posts are always much more personal in nature. And in all honesty, this was one of the toughest things I’ve written in a while. I’m quick to share what I’ve learned business-wise, but the really personal stuff? It’s a bit uncomfortable! But I think sharing our real selves is so important. So I do it anyway.

But let’s ease in:

Notable events of 2019

2019 was full of new experiences—some good, some bad. I mean, it’s life. These were the most memorable:

Discovering the joys of conferences

Guys, conferences are the best. It’s like a business vacation where you get to hang out with other people who Get It. Here’s where I went:

The Copywriter Club IRL

The Copywriter Club is a community I joined when I first started my business, and their annual conference was in Brooklyn. I traveled cheap-o backpacker style so I could splurge on the hotel. That meant taking a red eye in with a carry-on, navigating the subway system with this giant honkin’ mass attached to my back, feeling like a badass arriving at the swanky hotel around 8am, and settling into a nearby coffee shop to get some work done before my friends arrived.

This was my first time navigating a new city on my own. And it was an incredible experience. I mean, except the redeye (goodness no). But the rest. Walking down the street with everything I needed literally strapped to my body was freeing in a way that I hadn’t experienced before. Plus the conference itself was FANTASTIC.

Copywriters unite!

Jenny Shih’s Make It Work Online LIVE

In June, I continued my conference kick by attending a small conference for students and coaches of Jenny Shih’s Make It Work Online program. I had been a copy coach for her students in the first half of the year, so this was a chance to show up not just as an attendee, but a teacher too. I got to give a talk at the event, and I realized that—holy smokes!—this public speaking thing is my jam? I want to do a whole lot more of it?

Entrepreneur Experience

In October, I drove out to San Diego for Amy Porterfield’s Entrepreneur Experience. I’m not typically one to fangirl, buuuuut I definitely rushed to the front of the line to get a picture with the woman who inspired me to start freelancing all those years ago.


Weddings, weddings everywhere

In the summer, Rick and I flew out to South Dakota for my cousin’s wedding. I so rarely get to see my cousins because we grew up so far apart, so it was a treat to be able to celebrate with them! I also got to reconnect with some other cousins I hadn’t seen since we were kids. I have quite a few cousins. And we all turned into cool adults! Amazing.

And speaking of weddings, funny story—In college, my friends and I went to a Valentine’s Day dance. We were super into swing dancing back then. And there was this one guy who asked me to dance on and off all night. We didn’t exactly hit it off, but I was newly single and feelin’ good and was sure I was going to walk away with his number.

Toward the end of the night, I mentioned my hunch to my childhood-friend-turned-college-roommate-who’s-like-a-sister-to-me. She was confused, then awkwardly told me, um, he’d just given his number to her instead.

Turns out MISTER DANCE BOY was using OUR dances to covertly learn more about my friend. And my oblivious brain didn’t even notice.

But I mean, I can’t blame him. Look how cute they are together:

Yeah, that’s right. Mr. Dance Boy pursued my girl Brigitte for years, and they finally got married this summer. We all cried. I’m so stinkin’ happy for them.

But I’m still gonna tell this story ’til the day I die. ?

Congratulations Brigitte & Jon! <3

Living in medieval times

In August, Rick and I flew to Quebec for… a more unusual vacation. See, there was this event I’d heard about on YouTube, and it sounded cool. Rick agreed. So… we went. The event was called Bicolline. It’s a week-long, family-friendly medieval/fantasy role playing event a few hours outside of Montreal.

Yes, the official language of the game is French.

No, we do not speak French.

(But we survived with the help of new friends and gracious bilingual Quebecois.)

Bicolline is like living in a renaissance faire for a week. You stay in a medieval tent, wear fantasy clothing, and role play a character of your own creation for the whole event. And, um, it’s our new designated summer vacation. I’m working on my costumes for next year.

Solo road trips (are you sensing a theme?)

This year I discovered #vanlife. And not being in a position to buy and rennovate a van into a mini-RV, I decided to take my Kia Soul out into the wild instead.

I spent one night sleeping in my car up in the woods a few hours north and made a video about it. And then, a few months later, I drove out to Moab for a car campout with a bunch of other solo-on-the-road women.

Some folks have been a bit surprised by my desire to travel alone. I get that it’s still a little unusual for a woman to travel solo—especially road trips, and especially when she’s got a husband-o at home.

Here’s the thing. Rick loves to experience new things with me, but he isn’t big on road trips. He also works at a traditional job with traditional hours. I, on the other hand, am realizing that getting out of town helps me feel like I’m living a full, interesting life. And I can work from the road if I need to. It works for us. And that’s all that matters. ?

The not so good stuff

Some things this year were not great.

In February, we lost my husband’s grandfather, Don. He was 92 and sharp as ever.

Don was a fixture in my husband’s life—they went out to lunch together every Saturday since Rick was in high school. He was a constant presence throughout Rick’s and my dating years and early marriage, and I loved getting to know him for the time that I could.

Don often shared stories of growing up in the dust bowl and creating a life for himself as he traveled across the Southwest. He even left behind an extensive collection of poetry and stories he wrote about his experiences. I’m currently working on helping my mother in law compile his writing into a book. I look forward to sharing it with our kid/s one day.

Business retrospective

Onto the business side of things.

On December 7th of 2018, I journaled that my theme for 2019 would be creative freedom. At that point, I’d been doing website copywriting full time for a year and a half. And I was seriously questioning whether or not I wanted to continue.

As a result, 2019 evolved into The Year of Pivots. This whole “creative freedom” thing meant I ended up trying a lot of new business directions—and some non-business ones. Here’s the full list:

  • Started the year with the announcement that I was going to be… an artist!
  • One month in, I realized that as much as I love art, it doesn’t fill my soul the way writing does. Awkwardly backtracked.
  • Started doing copy coaching in Jenny Shih’s program and loved it. So I started offering copy coaching to my own clients.
  • Lost my focus in the summer and wrote up a job application to be a social media manager at a cool startup. Almost submitted it.
  • Actually DID submit a job application to be a content manager at another cool startup. (Never heard back—something I’m grateful for now)
  • Decided that I missed being on a team and the best solution was to change careers and become a project manager. Paid for a membership with the PMI institute to start studying. Soon realized how much I’d miss running my own business. And that I’d just wasted $150. ?
  • Realized that my business model still wasn’t a 100% fit, so I decided I wanted to scale into an copywriting agency.
  • Started seeking a client to try out the agency model with. Got an interested lead… then suddenly felt everything in my gut screaming NO NO NO.

Ah. So it goes.

As you can imagine, my business was not particularly profitable this year. I still worked some amazing clients (I love you guys!), but overall my volume was lower as I spent time exploring some new paths.

This is real life, baby!

But toward the end of the year, I decided that it was okay. We were still paying the bills, and being super profitable wasn’t actually my goal this year. If it was, I could have done things differently.

My real goal was finding a path I could commit to in the long term. And I fully believe this discovery period will pay off in the long run.

There’s this narrative out there that you’re supposed to quit your job, start a business, and fall right into a business that you love that makes you $100K your first year. That’s possible, sure. But for a lot of us, that’s not realistic. It’s going to take some finagling to figure out your focus and business model.

And that’s perfectly okay.

What worked well

Now, the benefit of experimenting is that some things stick.

There were lots of lessons, habits, and commitments I’m carrying into 2020. But here were two experiments that proved to be really good decisions:

Tuesday Talks

I’ve been blogging for a while, but I wanted a way to interact with you on a more personal level. So since August, I’ve been going live on Facebook every week with a fresh training. It’s been so cool seeing your live responses! (And there’s now a nice lil’ library of trainings that you can access on my page whenever you like).

In 2020, I’m going to continue doing some Lives, but they might not be on the same weekly basis. Details to come.

The Facebook group

For years I’ve been telling new subscribers “Welcome to the community!” when they signed up for my emails. But one day I realized that a one-to-one conversation isn’t really a community. Huh! So why don’t I create a real one?

Love Your Online Business is a free Facebook group for online entrepreneurs, freelancers, and coaches. And it’s my new favorite place to hang out. We have over 70 people in there so far, and they’ve been doing a killer job of bringing great questions to the table and supporting one another. This community will continue to be a focus of mine in 2020. (And Id love to have you join us!)

Books & courses

In 2018, one of the things I noted that didn’t go well was the fact that I didn’t read enough books. This year, I read more… But it still doesn’t feel like enough!

That said, here were a few favorites:

You Are a Badass by Jen Sincero

Took me long enough, I know. This is a classic for the modern entrepreneur. And I get the sense I’ll be returning to it again and again.

The War of Art by Steven Pressfield

Do you know how many misunderstandings I had trying to order this from a bookstore over the phone? The War of Art, NOT the ancient Chinese military treatise. Anyway, it was a must for anyone who struggles with motivation or procrastination around creative work.

Soulcraft by Bill Plotkin

I saw this on someone’s shelf in the background of a YouTube video, and ordered it at my library based on the title alone. It was a great decision. The book is a handbook of sorts for the soul’s journey through nature that dives into the crossover between spirituality and the psyche. An interesting read for those interested in the work of Carl Jung and Joseph Campbell, or who are interested in their own spiritual journey overall.

Hey Whipple, Squeeze This by Luke Sullivan

Weird book name. But it’s basically a lot of copywriting techniques from the ad industry. Important to keep my skills sharp!

The Ultimate Sales Letter by Dan Kennedy

Another copywriting book, focused on sales letters (obviously). More techniques filed away in my back pocket.

Stu McLaren’s Tribe course

I don’t invest in a lot of courses, but this one I was ALL over. Tribe is an online course that teaches you how to start a membership or subscription-model program, taught by Stu McLaren—a guy who’s been embedded in membership businesses for years. I learned a ton, and it’s definitely been informing my thinking as I move toward the next stage of my business. (More on that in a few!)

Key life lessons from the year

At last, the part of the show where I try to quantify the experiences of 12 months into a few lessons to carry forward into the New Year!

We shall now take a hard right turn from the business stuff and delve back into the personal side of things. Buckle up.

Lesson 1: Your body knows what it needs

Content warning: This section lightly discusses dieting and eating patterns. If those are topics you’re trying to avoid right now, feel free to skip this part!

Lessons come in funny ways.

Toward the end of last year, I got really interested in intermittent fasting and all of its supposed health benefits. I gave it a try. For a week or two, I skipped breakfast. I found that on some days, I was ravenous. On others, I was perfectly fine without it. So instead of sticking to some dogmatic eating pattern, I just started trusting what my body told me. It started with breakfast, but quickly expanded to other meals. Did my body want to finish that sandwich? If yes, enjoy! If no, just put it away.

This is called intuitive eating. And for some of you, eating is already… well, intuitive. But for others who have been influenced by the diet culture of “good foods” and “bad foods” and hard rules of what’s okay and what’s not, you know that this mindset isn’t straightforward for everyone. It hasn’t been for me.

(I’ll have to write a more in-depth post about this one day.)

What amazes me, though, is how this body intuition has stretched into other areas of my life. In the same way I’m paying attention to how my body reacts to a food decision, I’m noticing my reaction to bigger decisions as well. Like that feeling of constriction when I agree to an activity I don’t really want to do. And how different that feels from fear or plain ol’ lazy-pants resistance—which just come with the territory of doing new things.

Which is all to say, your body knows stuff that your brain doesn’t. Getting in touch with that can be extremely powerful.

Lesson 2: Birth control is complicated

How much is TMI to share on here? Eh, my blog, my rules. I don’t think we talk about these things enough.

I started on the pill a few years ago, after years of extremely painful periods. It was instantly amazing. Instead of crying myself to sleep in the middle of the day every four weeks, I could go about my days like a relatively normal person. I enjoyed clearer skin and fewer mood swings, and I felt better in my body. I thought I was a success story. 

Somehow, though, I didn’t notice a quiet anxiety rising in the background.

A year after starting the pill, I started to find myself wide awake at night, ruminating on all the awkward/embarrassing/stressful things I’ve done in my life—something I’d never experienced before. I’d wake up with my heart pounding from those same thoughts.

And then it started happening earlier. In the hours before bed, I’d be glued to my phone in a frenzied scroll through social media, desperately trying to distract myself from a growing sense of despair that I couldn’t quite place.

Some days I couldn’t bring myself to work for more than an hour or two.

I chalked it all up to just getting older. The natural side effect of working to grow a business.

But halfway through this year, on a whim, I stopped taking the pill. Just out of curiosity. I’d been on it for a few years. Who was I without it?

Turns out I was me. The old me.

The anxiety has since calmed way down. My intimate life is better than ever before. And miraculously, the period pain I used to feel isn’t nearly as debilitating as it was before.

This is a wonderful discovery, of course. But it does make me wonder about these past 4 years. I’ve spent a lot of time feeling unfocused and unsure. How much of my business experimenting was actually necessary? Or all of my indecision in years past?

Where would I be in my business today if I hadn’t been on the pill?

I’ll never know.

To be really clear, I don’t regret taking birth control. It stopped my pain. And it gave us a lot of peace of mind that our first years of marriage would be child-free. It’s something all people should have access to so they can make their own decisions about their health.

But we also need better alternatives.

Lesson 3: Being cheap is often more expensive

Okay, story time.

Remember the medieval thing? Incredible event. But also one of the toughest weeks of my life.

See, it was a relatively pricey trip. And I’ve always been uncomfortable with spending large amounts of money in one place. So I tried to save us as much money as possible on all the things I figured were unnecessary.

For example, instead of checking an extra bag, I decided we could fit a most of our stuff in carry-ons if we rolled up our clothes in vacuum compression bags. Clever me!

However, because we didn’t have any extra room, I didn’t have space for a backup pair of boots. No matter, I thought. The 10-year-old Payless boots that were quite literally falling apart at the seams would do just fine. The sole was crumbling away, but I had a hot glue gun that got it reattached just fine. I even packed some Gorilla glue just in case.


Well! Turns out shoes that are falling apart a bit while walking on carpet really start to fall apart when you subject them to mud, dust, and rocks for a few days. And there’s no such thing as Wal Mart in the Middle Ages. Instead, the only shoes available on site in my size were $200 handmade, medieval ballet-style leather flats.

Fun fact—the guy who made them was the shoemaker for all the shoes in the movie 300! So cool to meet him.

Not cool to pay $200 for shoes I’ll use once a year, max.

All because I didn’t want to pay $80 to bring the boots I already had. ?

We also spent each night freezing our butts off in the ultra-light sleeping bags that had fit so nicely in our carry-ons. That meant another $25 for a crappy blanket. And instead of investing in waterproof cloaks, I made ours by hand from regular fabric—costing us some very cold, damp nights when it rained.

We came home a bedraggled mess. Amazing trip! But dear goodness, that’s one of the clearest lessons I’ve ever learned.

So anyway, money mindset has a real impact, folks. Heal your relationship with money and learn how to spend it in a healthy way. Because anxiously hoarding every cent you make does not actually equal good money management! ?

What’s coming in 2020

WHEW. With that all out of the way, here’s what’s ahead.

To be honest, 2020 feels like a year that’s been several years in the making.

Back in 2015, the year I first started freelancing, I knew that I wanted to one day create a digital course or product of some kind. But although I had been soaking up a lot from working with some really cool clients in the advertising agency I worked for, I didn’t have the audience or experience to make it happen. So I put my head down and kept working.

Since then, I’ve written more websites than I can easily count. I’ve run marketing for a tech company. I’ve written hundreds of blog articles. And I’ve built a small-but-mighty audience of amazing people. (You guys are my inspiration, and I’m honored to write for you!)

This is all to say: I have finally, to put it delicately, Learned Some Shit.

And in 2020, I’m finally releasing my first product that puts all those learnings to good use. It’s a series of trainings and templates to help you write your own website copy easily, using the same copywriting process I’ve been using for my own clients.

It’s coming out sometime in February. And I’m so excited to share it with you!

That’s it.

Thank you so much for reading this ridiculously long post. I’m so grateful to have you along for the ride.

And as always, let me know if there’s any way I can support you. My inbox is always open.

Comments 6

  1. Wonderful year in review. You make it seem so easy to look back and summarize all you have learned. Well, writing is your super power so that’s what you do best!

    Thanks for sharing the personal stuff too, it’s nice to get to know the personal side of you better.

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  2. Awesome content as always Jessie, sprinkled with humour and some lessons for flavour. Thank you for what you do for the community and for inspiring us with your writing about your journey and lessons. Here’s to an awesome 2020 and the first of many, many successful product launches!

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  3. Loved your honest and brave report of experimentation and moving forward…It’s not easy shaping our offers and creative pursuits out of thin air! It’s like our heart is pulling us towards a reality that already exists, we just need to discover it. Wishing you a wonderful 2020! <3

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