Hillary Weiss is the kind of person you discover on the internet and are so glad you did. She has one of the strongest internet presences and voices I’ve ever encountered, and her badass attitude is nothing short of inspiring. Here she discusses why she loves being a copywriter, how to pitch clients (and win!) and the honest money lessons she’s learnt from being self-employed. Enjoy! It’s one of my favourite interviews yet.
You’re a renowned copywriter and content extraordinaire. Why do you love what you do? Has anything surprised you about your chosen career path?
I love what I do for so many reasons.
Firstly, because writing has always been the only thing I’ve ever been good at.
Seriously: I’m awful at math, I’m not naturally very organized or very neat, growing up I tended to, uh, resist authority, etc. So being a writer – and a self employed one at that – has been the perfect path for me in a lot of ways.
Secondly, I adore my job because it gives me endless opportunities, every day, to transform lives and business, just by giving a voice to ideas.
So many brilliant human beings bite their tongues when it comes time to share what’s in their hearts, or even talk about the stuff they’re experts in. They don’t know if it’s the right moment. They don’t know if they’ll say it the right way. They aren’t sure how people will react, or worse, not react. They wrap themselves up so tightly in a web of fear and doubt, their songs go unsung, and uncelebrated. Being able to step in, and be the one to say “Yes, this idea is worth sharing, and I can help you share it,” is a true privilege.
I don’t always know what I’m doing either.
I don’t always know how people will react, or whether an idea is as good as I hope it is.
The only difference is that I have the experience-tempered audacity to shut my eyes and pull the trigger anyway.
As for surprises? I’m surprised constantly – there’s something different in my job every single day. But the one thing that constantly makes me lean back and say “Wow!” is just how much the right words and tone can change things.
Knowing what to say, and how to say say it is the difference between success and silence; inspiring and being ignored. There’s something magical about it to me, even 5 years in.
I’ve seen people with such incredible ideas go YEARS without the recognition they deserve because they’re not speaking to the right people in the way they need to be spoken to. And when they figure it out? Everything changes. Something unlocks and suddenly, not only are raving fans, readers, and buyers finding them by the score, but the creator themselves starts to feel absolutely electric with their own ideas and creative flow. So they make better stuff, sooner, for people who really want it.
When it comes to pitching new clients, do you have any tried and tested methods you can share?
Two rules of thumb for clients: 1) Never work for anyone you don’t believe in, and 2) Always create a container for your clients.
The reason you should only work for people you believe in is simple: if you aren’t convinced what they’re saying is true, or don’t feel in your bones that they’re in integrity? It’s gonna come through in your work. So start there!
Now, why the “container” rule? Because especially when it comes to pitching yourself for service-based creative work, people need to trust you, and feel supported immediately. They need to know that you’re a pro, and that you have a plan, and a series of steps for every moment, so they never feel like they’re dangling or lost in space.
You’re not just providing a service – you’re creating an experience.
So next time you pitch yourself, write down the step by step process. How will you begin? How will you submit first drafts, or initial versions of whatever it is you’re working on? Will they receive notes? How many revisions will you offer? How do you wrap up when it’s all over, and make the client feel everything’s wrapped up in a virtual velvet bow?
Explaining your process like this clearly will both cement their confidence in you, and help them picture themselves in your world (which means you better your chances of being the winning pitch!)
Oh, and one more thing: always be as friendly and warm if you can! Collaborative creative work needs to begin on a foundation of trust, so building a rapport from that first email, or the first moment you hop on the phone, is essential.
Being self-employed, what money lessons have you learnt along the way?
I have a saying I’ve developed over years of feast and famine in the industry: Money in, money out. Like breathing.
For a long time, I was broke.
Like, ham-sandwiches-every-night broke.
Like, “Sorry I can’t make it for 1 beer I can’t afford it. Yeah, really.” broke.
So when I began to make actual money, instead of going crazy, I became obsessed with protecting it. I tended to the little piles I managed to save the way a gardener tends to her rose garden.
Being broke teaches you that while money isn’t everything, having money is freedom. Having money means you can predict what’s coming tomorrow, and care for yourself when you’re sick, or tired, or work takes a nosedive. So I saved as much as I possibly could. I lived in as cheap of an apartment as I could find, shopped exclusively secondhand, and cooked almost all of my meals.
While it’s not a bad thing to be frugal, my mentality wasn’t entirely healthy. The thought of spending more than $100 anywhere in one go made me anxious and sweaty. I counted dollars and cents and checked my online banking 5 times a day.
And yet… no matter what I did, I always found that I was alright. Slowly, as work and income stayed consistent, my overabundance of caution began to ease. I began to worrying over that $20 I spent on lunch that I could’ve put into my already-decent savings. I stopped constantly calculating how much I could, should, or needed to make that particular month.
When I did that? Things began to flow.
When one client dropped, I began to acknowledge another would be waiting eventually. I was not irresponsible. I would not miss the money when it was gone. If I spent it on quality, experiences, and things that lit me up.
Money in, money out. I would be, and still am, more than OK.
What actionable tips do you have for consistently coming up with inventive blog post ideas (note: Hillary sends out writing prompts on the regular and they’re AMAZING. Sign up here).
I wrote a blog post about his recently, as a matter of fact! You can read the full post here. But a good place to start is by asking yourself:
What are you thinking about all day these days?
What is something you think people really, really need to know about right now?
Or what’s something you want to make sure you say to people?
Tapping into what’s lighting you up, pissing you off, or getting you thinking is the absolute best way to keep your content fresh, engaging, and fun to write.
Lastly, what brands and individuals do you think do an excellent job with their tone of voice?
- Jennifer Kem: She’s a long-time client – so I’m biased! – but she’s just so in integrity in everything she does. She delivers so much value to her audience in such a no-bullshit, stylish, hip-hop-inspired, down-to-earth way. She teaches marketing and branding, but what she really wants is to help people change the world with their businesses, and it comes through in everything she does, and every word she writes. The Jen you meet in the real world is the same Jen you see on your website, in her emails, and inside her programs and trainings.
- Spirit Air: I’m a crazy anxious flyer, and last time I hopped on a Spirit plane, I looked out the window and saw on the end of the wing was written the word “Howdy!” And I loved that. It made me smile a bit, and even put me at ease, just because of the level of thought that went into that, and the approachable tone of voice. If you take a look at Spirit’s latest brand evolution, you’ll see they’re now rocking a cheerful yellow color, and a quirky, cartoony voice and style. It works for them – because Spirit has long been a little notorious for exchanging lower rates for slightly lower quality of service (no free food or drink, etc. — which they now call “Bare Fare”) But if you watch their “This Is Spirit 101” video, they find ways to turn that into an asset. It’s a great lesson in finding the right angle!
- Oscar: I use Oscar as an example a lot, largely because they found a way to make health insurance (a notoriously stiff, jargon-y, hard-to-understand industry) approachable and even charming. They meet their customers where they are — which is a space of “Health insurance is hard to understand, expensive, and confusing. Help!” Catering to that gave them a huge cut of the market right at the outset. It’s powerful!
- Kate Spade: I think this brand is genius, because while they’re rooted in plush luxury and quality, every campaign, every handbag, every email and banner ad, has a little wink to it. There’s no snobbery. They’re about fun, as much as they are about creating exquisite experiences. If you haven’t stopped by to check out their products lately, I recommend it.
- Nasty Gal: I love following Nasty Gal because they’re the perfect embodiment of the “cool girl” millennial voice. Their social media, newsletters, and more are worth watching because of the way they play with style and mix old with new. Overall, their vibe is fascinating, and it all sounds like it’s all written by that rad chick you met somewhere who’s a creative director at some elite agency, and wears huge faux fur coats and huge shades over her a bikini in the summertime.