Photo by Jeff Weller
2017 in HWeiss Landia was, above all, a year of talking and writing about things I genuinely give a damn about.
(It was also a bizarre, tumultuous, topsy turvy, exhausting year for a number of us — but one of the greatest gifts of being alive and creative at a time like this is the response it inspires, and the quests it sends us on.
I can’t speak for the rest of the world, but in my case, 2017 seems to have flipped on my “transparency switch”.)
Of course, there was other stuff happening beyond my intimate relationship with my keyboard and my blog, too.
I put out a course. I released 50% of my clientele. I spoke on stages in Brooklyn, Austin, and Phoenix. I spent a ton of time talking to newbie writers, and veteran entrepreneurs. I stopped taking sugar in my coffee.
But more than that? Sometime early last year, when I stared at my semi-populated blog, I realized something: I was bored.
Omg. Sooo bored with what I was writing.
Don’t get me wrong — I enjoyed all the pieces I wrote before 2017 began; they felt deep and gratifying and important to pen.
But I was spent. I’d felt I’d hit all the “stuff copywriters/writers should write about” notes I wanted to hit, and felt ready to move on.
But what was next? I wasn’t sure.
So I tilted my platform a little bit, and decided to scrub away the “Serious writers talk about This Serious Thing” must-do’s on my list, and started gabbing more about the stuff that mattered to me — about experiences, about point of view, personal philosophy, and creativity rather than conversions and sales.
That began to leak into everything I did; from my blogs, to the way I taught, to what I shared on podcasts and interviews.
So, after spending the last couple of weeks chewing the cud away from my desk, I decided to take a peek back at the things I wrote and said in 2017 — and the tales behind them.
What was I most proud of?
What surprised me?
What did I wish I’d done differently?
And now in the spirit of the only roundup season NOT involving cowboys — A.K.A. END OF YEAR ROUNDUP SEASON IN THE BLOGOSPHERE — I present these musings to you.
Without further ado, I present the 10 favorite things I made in 2017 — and the stories behind them.
Thing #1: I hopped on The Copywriter Club Podcast for an interview.
To date, this is probably the strongest interview I’ve ever done on the subject of copywriting.
I say that both because on this blessed interview my accursed “ums” and “yknows?” are fewer and farther between, aaaand because my parents listened and immediately called to excitedly tell me that finally, after 6 years, “We have a better idea of what you do now!”
One thing also missing from this story, however, was that I showed up to the interview 15 minutes late and flustered as all hell. I’d gotten the time of the damn interview wrong. Blessedly though, Kira Hug, co-founder of The Copywriter Club and an old friend of mine, pinged me to find out where I was before banishing me from her roster forever. So the Hillary you hear here is a little extra anxious, but extra excited to be there all the same.
This was also the first time I’ve ever talked in-depth about the connections I make between the music I love and the words I write — and no one laughed at me or called me a stupidhead. That felt unexpectedly awesome.
“I think music, in that sense, music can teach us a lot as writers, because when you get to a certain point with your writing and your craft, it doesn’t necessarily become about the individual words or even the sentences. It’s about texture and rhythm, and you see things more in block form.
You’re thinking about it in a sense of how people are going to react to these ideas, not just the ideas themselves, and I think hip hop is a great example of how to do that.”
You can listen to the full interview or read the transcript behind the link.
This post was probably the least-read of the entire year, but it was still near and dear to my heart.
I’d actually written the first draft of this post at my former business partner’s kitchen table on a snowy afternoon in 2014, but it was much darker, and much more shame-faced than the version you see here.
Since then, time has not only made me tougher when being open about failure, but it’s forced me to continue to face it down and acknowledge when it happens so I can learn the most from it.
This post was also a chance for me to talk about my, uh, background in writing fanfiction, and how it helped me get some creative faceplants out of my system early.
(This was much to the delight of Copywriter Club Podcast co-host Rob Marsh, who is determined to find my old fanfiction pen name to this day. I can assure you: He will never succeed.)
“The opposite of creative shame is creative courage. And you can’t have one without the other.”
Thing #3: I wrote “What it Takes”.
This was the first in what would unwittingly become a series of pieces on the reality of entrepreneurship and the more physiologically and psychologically painful effects of pushing oneself to the limit.
It popped into my head at 10 PM on some busy Tuesday. My partner was out with co-workers for the night and so I used those extra few hours to do what I often do when I’m given the wiggle room of additional time:
I was working late.
At the time I was putting the finishing touches on my course and launch plan, and figuring out how to restructure my business.
I was not feeling good. In fact I was so tired I felt almost ill… but I had to keep going.
It’s a piece on willing things into existence that I’d probably rewrite knowing what I know now, and seeing where it led me— but it’s a piece I’m proud of all the same.
“Sweat begets ease eventually, if you know where you’re going.
That’s why, for every nauseous moment on your living room floor, for every sobbing dancer collapsing just offstage, there are 100 moments of pride, accomplishment, and certainty in one’s own abilities.
For every question of “Why do I do this?” the answer comes back the same, but stronger: “You can quit. But if you love yourself, and the future you’re creating enough, you won’t.”
Thing #4: I wrote “The Persistent, Precious Habit of Self-Belief”.
Some posts take time and effort to chip away at, while others flow out of me like clear, cold water. This post — and also the only piece I wrote in June of this year — was the latter.
I wrote this one after comments from a friend forced me to examine why the hell I always keep going.
It’s not as though Imposter Syndrome or self-doubt pass over me. In fact, I’m beginning to suspect I’m one of their favorite targets. But the struggle against such demons isn’t ended by a sudden magical eradication of the hate and disappointment and shame that threaten to eat you up.
It never ends. We can never win — only hold the line.
So the question becomes: How do we do that?
And the answer is… what I wrote about in this post.
“There’s the old adage you’ve seen on countless inspiring statues and high school senior quotes:
“Courage is not the absence of fear, but the triumph over it.”
Similarly, self-belief is not the absence of self-doubt.
My self doubt is my grey ghost, the monkey on my back. It is excruciatingly painful, and it comes complete with limitless energy and an unstoppable will to slow me down so it can eventually tear me apart, piece by piece.
I had no choice but to find a way to stand against it — or I’d surely perish.
But it didn’t feel heroic to me. It didn’t feel strong. Some days it feels like hanging from a penthouse balcony by my fingertips.”
Despite the fact I recorded this interview with Allie & Adam of The Wonder Jam on the first day of The Wordshops launch…
Despite the fact I’d gotten barely any sleep the night before…
Despite the fact I’d slept so little because I wound up sleep walking that night for the first time in my life…
… This interview was still one of the best things I recorded this year. Not only because I adore The Wonder Jam (they designed the sales page for The Wordshops), but our interview turned into open season on connecting pop culture to branding mastery.
That’s right: They let me riff on two of my favorite icons the world loves to hate — Kanye West and Kim Kardashian.
“ Hillary tells us about how Kim Kardashian has informed her as a business owner — “She’s a branding master, she just is.”
Thing #6: I wrote “The Worst Way to Price Anything Ever, from Someone Who Fell into the Trap”.
Possibly the only “traditional” business-y piece I wrote this year was sparked from a conversation I was having in one of my writer’s groups.
A discussion on rates and pricing was illiciting responses of:
“I just don’t think I’m worth that much…”
“Who would pay me that?!”
And (most importantly):
“I could never afford that. I can’t even think about it.”
Off went my writerly spidey-senses, and out came the words — all about the sneaky reason WHY so many creatives undercharge, and what to do about it.
“But in reality? I’d priced myself so low because I was afraid.
I was afraid of people rejecting me, laughing in my face, and pointing out that I didn’t have anywhere near the experience levels to charge anything even remotely resembling a higher-end price point.
I was afraid of being seen as a fraud, overcharging and under delivering, and generally getting too big for my britches.
All of that was bullshit of course.”
Revelation of the year: BEING ON VIDEO IS FUCKING DIFFICULT.
Especially when you’re selling a thing that’s yours.
Fortunately, I had my dear friend and brilliant creative Juliet Warren by my side who carried me through about 3 hours of totally unusable scripted footage that I singlehandedly ruined by looking down at my makeshift telepromter, and into a version borne of some handy Q&A.
I think this version works way better anyway.
“I wish someone had told me when I was getting started that my strangeness, the way I choose to speak about things, the slang I tend to use, the language I discuss things with when I talk to my clients — that all of that mattered. That all of that was supposed to be coming through in my copy. Because if it doesn’t? Then you’re getting lost, and the last thing you wanna do is get lost.
Because you have people who need you, who’ve been waiting for you. And if you don’t introduce yourself properly? They’re not going to be able to find you.”
You can watch the full vid on its own behind the link.
Thing #8: I wrote “No, You are Not Too Young to Start a Business”.
While this is another piece that falls into the “under-seen” category from earlier this year, it’s a topic near and dear to my heart.
I spend a lot of time chit chatting with young business owners, and every single one of them worry their lack of experience outweighs their youthful exuberance and eager desire to serve and succeed.
Short story: I started my business when I as 22 and green as a string bean.
Long story: In the long term — that actually ended up helping my business more than harming it.
Entrepreneurship, at its core, is an extended exercise in both self-trust and self-reliance (and, in some awkward hotel lobby moments, self-depreciation).
That means the only person who will ever know if you can really do this is… you.
(Not your parents, or your best friend, or your current boss. You.)
The only person who can be certain you’ll put in the work to create the success you want is you.
The only person who fully understands your instincts, skill set, and determination level is you.
So, what do you think? Are you ready, according to you?
Thing #9: I wrote “On my Deep Misinterpretation of Mental Toughness”.
This post was a big, fat, squirmy, 9-minute-read uncomfortable practice in vulnerability for me.
Because guess what happens when you spend an entire year working as hard as you possibly can, physically and mentally?
Surprise. You burn out, and you burn out hard.
This post took me weeks to write. I kept coming back to it, and hiding from it. Peeking at it through the hands over my eyes, and leaning closer to listen in despite the fact my fingers were firmly in my ears.
And while this was the only post this year that made me wince before hitting “Publish”, the conversations it started to spark were incredible. My inbox and Facebook comments filled with stories, particularly from women, about working themselves into hospital beds (then proudly working from those hospital beds), about bodies crumbling while deadlines were still being hit, and about hitting walls with such an impact it took them 6 months to recover.
So while it wasn’t the most natural thing to share when I pride myself so publicly on my own mental strength — it made me realize that sometimes hard work just can’t be the only route.
But when I’m at my desk, doing my work? I’m titanium. A steamroller. The god damn Punisher, baby.
All I have to do is keep my eyes forward, put my blinders on, and march. I don’t bitch and moan, I (rarely) melt down, and I don’t take overwork personally. If I agree to something, I get it done.
How do you eat an elephant, they say? One bite at a time.
And boy, was I proud of it.
That’s the nuttiest thing about deteriorating mental health as an entrepreneur:
Burnout is hard to spot from afar because you feel you’re required to be blind to it.
We also don’t realize there’s a fine line between working hard and working ourselves into a delusional, exhausted mess.
And finally, Thing #10: I wrote “8 Observations from a Crumbling Niche — And How to Avoid Getting Crushed”.
If there’s a collection of “posts that took on a life of their own” somewhere on the internet, I’d like to submit this to them for review.
This piece on the present and future of marketing in my chosen industry, borne of one comment I left in a FB group, and about 90 minutes of expansion on the points, quickly soaked up close to 20,000 views in the space of a couple of weeks.
It was unexpected. And kinda scary. And awesome.
Unexpected because it was such a quick, fiery piece to write, and because the topics discussed in this piece are not news to anyone who’s been in my industry a while. In fact some of them have been issues for years, they’re just getting hard to hide behind closed doors.
Kinda scary because I knew the people I was talking about in the post would read it… and I didn’t want to make anyone feel badly about themselves. I just wanted to tell the truth. But I also spent a few anxious nights worried I’d written myself out of a career.
Awesome because hey, who doesn’t like feeling like an “online influencer” for a whopping 5 days or so — like the things we’ve seen and said matter, confirming suspicious, putting hearts to rest, and are changing the way people look at things.
(Oh — and pissing people off. That was part of it too. But how good that feels varies moment to moment, and can sometimes stay stuck in the “fucking awful” position for prolonged periods. #Iamnotabadass)
But suffice it to say, of everything I’ve written, this was my most popular piece, as well as my most satisfying.
Sometimes when you say what’s on your mind, when you say what you’re seeing and what’s worrying you — people listen. And that just might be one of the best feelings around.
It certainly makes years spent in front of your laptop as a cog in so many digital machines feel less lonely and drone-like.
“It’s a running joke (among copywriters especially) that the biggest industry names are often the hottest messes on the back end… but I’m not sure it’s very funny anymore.
Even more worrying: These gigantic, nebulous “build your business online and brand and market yourself like a pro because that totally doesn’t take years to learn” programs are still being sold at high-ticket prices while their information hasn’t changed much from 2, 3, even 5 years ago.
And in a space that moves this quickly from one impactful strategy to the next?
That’s. Not. Good. Enough.
The people continuing to sell programs know this. Everyone who passed 9th grade Economics and learned about the law of diminishing returns knows this. Some just willfully ignore it.
We have to do better. We have to set an example. Especially if we claim to honestly give a damn about our “tribes”.
That’s why I’m writing this. As professionals in the space, it’s our duty to speak up, call stuff out, and discuss what’s not working anymore.
I’m also sharing this because my particular industry puts sales strategies and funnel tactic lifespans into fast motion — so if it’s not happening in your niche currently?
It may be soon… though hopefully at a slower, steadier pace than the current tidal wave of challenges facing marketers/brands/businesses where I hang out.”
You can read the full piece right here.
Now: I’m not usually one to self-deprecatingly wax on about WHAT A NAAAAARCISSISTIC PIECE I JUST WROTE I’M SUCH A MILLENIAL — but writing my own roundup kinda felt that way.
So now I’m curious: What made YOUR top 10 list?
Stuff you wrote or made, or stuff you read, watched, or listened to?
Drop 1, or all 10, in the comments below. I’d love to check ’em out.
(And oh right — as promised, a pop culture 2017 roundup is also en route. But strangely, that may take a little more time.)
But in the meantime: Happy New Year, friends. May this year teach us all the lessons we wish to learn.