On work, words, websites, and what happens next: everything I’d tell you if you asked to pick my brain

business n' branding, Creativity, talking shop, Uncategorized


It’s pretty nerdy of me to say this: but I love answering questions about my job.

I love digging into my brain to give people the best I can offer.
I love sharing my story.
I love finding out what’s scaring people about their own entrepreneurial ventures – and (hopefully) talking them through whatever stuff stands in their way.

But unfortunately, it’s impossible to answer everyone all the time.

That’s the bad news.

The good news is, over the stretches of years and conversations, I find certain questions repeat themselves.

So, while I can’t accept every invitation for coffee or drinks or lunches (at least, not until my clones come in) I figured: why not consolidate, and put all of those answers in one place – no espresso necessaro?

Now, without further ado, I present: every single thing I’d tell you if you were picking my brain at Starbucks.

(Don’t see something you’re curious about answered here?
Leave your question in the comments.
I’ll dish the answers – or maybe pen a part 2 post!)

Let’s get into it.

“How did you get your start in the industry?”

WHEW. There’s a long answer to that, along with some tips to get you started. You can read all about it right here.

But, here’s what I don’t mention in the article:

Around my senior year of college I was introduced to a copywriter by the name of Alexandra Franzen. After following her for some months I approached her about a job via Twitter, and by crazy coincidental luck, she was on the hunt for some support.

I worked as her transcriptionist for a spell, and from there, she gave me my first client. 6 months later, I started picking up more and more paying clients, and took things full-time.

“What did you major in in college?”

Public Relations (dislike.)
Anthropology (very like.)
English Literature (easy like.)

“What did you do for your first website?”

Before there was the Youngblood Sourcery landing page and website.
Before there was the badass HillaryWeiss.com
There was… MY ABOUT.ME PAGE.

Real talk: I can’t believe it’s still up after all these years. It wasn’t anything fancy, but it worked.

“I hear most writers are broke. Do you make a lot of money?”

HA! Aw, that’s not very nice. Who told you that?

Wealth is relative, but I did break 6 figures last year. That means I’m doing “OK” by NYC standards, and “pretty well” anywhere else.

Except maybe San Francisco. Sorry ’bout the even crazier taxes, West Coast.

“I hear the first year of business is the hardest. How did you survive?”

I lived in a $500/month apartment in Coral Gables, FL.
I cooked almost all of my meals.
I didn’t socialize a lot.
I didn’t drink much.
I shopped at Goodwill.

I also pulled out all the stops, all the time, for all my clients. Midnight email for edits and I’m awake? You’ll get ’em by 2 AM. Emergency project over a holiday? Sure, I mean what even is Christmas Eve really, anyway?

I was ready to pour my blood, sweat, and tears into my business – and it was either succeed, or move back home. Turns out, I had an inner workaholic ready to be unleashed. So, out she came.

Yes, it sounds like a lot. And I don’t necessarily advocate that absolutely everyone should work their fingers to the bone the way I did — I definitely worked myself sick, quite literally, more than once. But I knew above all that it was crucial for me to lay the foundation as an indispensable asset, and I don’t regret a second of it.

“You were 22 when you started. How did you convince your clients to take you seriously?”

Easy. I didn’t tell them.

Amazing how that works!

I refused to lie about it though, and would always tell people honestly when they asked my age. The few that did were surprised, but usually (mercifully) in too deep and too familiar with my work to write me off.

Plus, I kind of enjoyed the “wunderkind” staple. What can I say?

“Why did you decide to move to NYC?”

Why not? Next question!

“How do you stay motivated to finish projects?”

Wanting to do my job well, and enjoying what I do. Also money.

The second part sounds superficial, but consider how terrible it would feel to drop a ball drop for a client who’d put thousands of dollars into my hand. That’s just rude, y’all.

“Did you have a mentor? Do you think I need one?”

For all intents and purposes, no. I’ve never had a mentor.

And… meh.

To be completely honest, I once wished I had a mentor. I even kicked around the idea with a few of my clients who wound up just being a bit too busy to make it happen.

Looking back, I wanted a mentor because I was afraid of what would happen without one. I assumed I’d fall off the rails, or lose my motivation, or make some seriously stupid business decisions that would cost me my career.

And yet… that mentor never materialized.

So, to supplement, I kept a close eye on the stories and people who had gone ahead of me, and succeeded in creative and interesting ways. I read up on their success and failure stories. I took notes.

Today, my business is the product of a number of well-researched decisions and goals. I guess you could say a fair few internet personalities have been my mentors, unbeknownst to them. But either way, here I am, overall mentor-free.

That’s the fascinating thing about the world of digital business. It’s really still such a fresh platform (relatively speaking) with so many resources out there, you really can make your own way without stumbling into too many glaring errors.

“How do you think I should get started (even if I’m not a writer)”

Start finding examples of people in your line of work (or similar) who you really admire.

While I’ve gotten through most of my career without a proper mentor, that doesn’t mean I don’t constantly ask for and receive advice from my long-term clients and friends in the digital space.

All you really need is one person to hold open the door for you and invite you to walk through it. So start asking.

Yes, it’s up to you how you keep up your momentum, and keep people coming in and finding you, but it all starts with connection.

So you write every day, all day. How do you stay inspired?”

I don’t give myself the choice not to be.

Also I ask a lot of questions, often and with relish.

“Do you still write your own stuff?”

Not as much as I like, but it’s as much as I make time for. So if a book or blog post of mine is gathering dust, I’ve got no one to blame but myself.

It’s a perpetual disciplinary work in progress. I’m doing aight.

“How do you convince your clients to keep coming back?”

I’m nice to them, and I genuinely care about them and their businesses.

No, really. That’s about all it takes.

Be friendly, do your work, and get your shit in on time. Put your ego away and focus on service. Then, watch folks come back like magic.

“What’s the best way to get great feedback/testimonial gems out of my clients?”

I send all my clients a testimonial questionnaire. (If you shoot me an email at h@hillaryweiss.com, I’ll send it to you, too.)

Many of my clients just aren’t crazy confident writers – after all, they wouldn’t need me if they were. So, giving them prompts, like “What did you enjoy most about working together?” and “If you could change anything about your experience, what would it be?” offers them an easy way to dish honest answers, and seriously useful feedback that you can turn into paragraph testimonials.

Pro tip: One thing I do recommend including in your feedback form is asking your clients how the process of working with you feels.

What jumped out at them? How did they feel at the beginning/middle/end of the experience with you? What freaked them out? What impressed them?

“You talk a lot about your interview process with your clients during the creation phase. How can I make the most about my client interviews?”

Hands down, the best way to get the gems and sound bites during the interview process is to ask “why” a lot, and take. obsessive. notes.

This is where my transcriptionist history came in handy, as I can type extremely quickly while also listening. It’s a skill I fully recommend building.

Don’t mind the typos or shorthand sentences, just write down everything you’re hearing, then go back and read through it, highlighting the most important bits. Pay attention to what repeats, and where you remember your client getting excited. It will AMAZE you what you’re able to find when you review.

“How much do you use analytics to inform your decisions? From what I see in your personal content, it feels very organic and properly targeted. What’s the balance?”

If I’m being really real: I probably don’t use SEO or analytics as often as I should.

I know copywriters who’ll sit down and comb through every little piece of their content to optimize it, paragraph by paragraph. That’s fantastic for technical writing; for the health or tech or legal industries, etc.

However (and this is where I get a little hippie as a content creator on ya) I like to do things the natural way.

For starters, I’m completely clear on my audience: I write for creative professionals and creative-minded humans interested or invested in the world of digital business, who are sick of jargon-y bullshit and enjoy reading different perspectives. They’re intellectually up to speed on the basics, but worn out by the same ol’ snoozefest of the online world, and prefer to join a conversation… instead of being marketed to/sold to constantly.

As of now, building my list up to thousands of people isn’t my priority. Delivering value is.

So I write in the way I’d like to be written to, about stuff I think will be really valuable for the people I’m talking to. Then, it’s up to the people to deciiiide maaaan.

Of course I pay attention to who’s reading/sharing what, and which posts get the most attention. If what I share ain’t landing, what’s the point? But it’s more of a check-in tool than the end-all-be-all of my creative process.

“Do you ever turn away clients because you’ve already worked with too many other clients in the same niche? Or do you just love the challenge?”

That’s actually a little from column A and a little from column B.

Yes, there are certain topics I feel like I’ve written myself into an early grave over. However, it’s not usually the subject matter that keeps me from moving forward. It’s more the state of the client.

I can write 50 sales pages on, say, the power of green smoothies for 50 different people if they’re all prepared and know their angle. Otherwise, if the client needs a little extra clarity, or isn’t sure what makes them different after all – I’m open & honest about the fact I may not be the right fit for the project.

Signs and symptoms include:

– Not being able to answer a direct question like “What are your specific needs for this project?

– Repeated asking of “What do YOU think?”

– A desire to imitate in order to stay safe.

Don’t get me wrong. These particular clients are GOOD people, who are GREAT at what they do, and there are copywriters out there who will be able to walk them through those clarity processes.

However, due to the nature and speed of my work, I just can’t offer them that same support — though I always try to recommend them to someone who can.

“What is your favorite writing/creativity resource that you always have at arms length?”

*cracks knuckles*

Alex Franzen
Seth Godin
Amy HarrisonTalking Shrimp
The War of Art
Andre 3000
Kanye West
The Mountain Goats

Annnnnd this quote:

“If you want to build a ship, don’t drum up people to collect wood and don’t assign them tasks and work, but rather teach them to long for the endless immensity of the sea.”
(Antoine de Saint Exupéry)

All Marketers are Liars and Great Leads are also sitting on my shelf – but I still haven’t completely finished either. Please don’t tell on me.

Pro tip: Overall I find books like this are great ways to lay your knowledge foundations, but don’t hesitate to break rules in the pursuit of your own style!

There are certainly wrong ways to do things, but no official “right” way to do things in this field.

Entrepreneurship is a rollercoaster. How do you get through the ups and downs?”

I have a seriously fantastic support system, who I’m grateful for every day. My family, friends, and partner who love me deeply, and are always there to lend a listening ear — even if they aren’t quite sure what’s going on.

A huge part of that support also includes a tight-knit, private writers group I’ve been a part of for the last 3 years. They’re incredible – and I wouldn’t be where I am without them.

That’s another part of this digital entrepreneurship puzzle. You’ve gotta find your people. It’s too big of an ocean to cross all on your own.

“Your writing voice is so “you”. How did you manage to to carve out such a unique tone?”

I come from a long line of people who love to hear themselves talk. So I just… listened in a little closer.

To give you a more technical answer though: I feel like my voice has only really come into its own in the past year or so, and only because I became very clear about what I didn’t want to be or sound like. That wide preferential net spans just about anything I wouldn’t say IRL.

So, for example, you’re never going to see me repost the quote “FEARLESSLY PURSUE THE THINGS THAT SET YOUR SOUL ON FIRE”.
You will not hear me talking about “living my best life”.
You will not see me talk about “manifestation” or “mindset” over practical tweaks and tips.

I also like to fiddle with words. Synonyms and metaphors are my loaf and spread.

“How did you come up with the aesthetic concept for your website?”

I hired my crazy talented photographer friend Jeff.
Then, I found a BALLER designer named Vanessa, told her I wanted a Nastygal-goes-to-Brooklyn vibe.
Then, I hired a kickass developer named Lindsay who brought the whole thang to life, seamlessly.

Again, just like with my voice, as I prepared for the rebrand I began to think about the things that genuinely interested me, and caught my eye. I thought a lot about what I loved about other websites. I also thought a lot about what I hated.

I didn’t want “girly” – no pinks, glitters, or loopy fonts. I’m proud to be a woman, and I’m extremely feminine, but I wanted my site to represent who I was without blaring from the rooftops “DID YOU NOTICE I’M A LADY?”

I’m not targeting a specific gender or age group. I’m just here to be a lighthouse for the people who want to know more, do more, and write more. Because those are my goals, too.

“How do you continue to hone your craft?”

I pay attention to the things that catch my attention.

Music, especially hip hop is a big influencer for word play.
Comedy is also something I play close attention to, especially the way it leans on pacing.
New York City subway ads are endless inspiration for ways to engage, amuse, and inspire thought while stuck in a space for long stretches.
I read quite a bit.
And I do my best to write it all down.

I also ask myself WHY things inspire me, when they do.

WHY did I sit up and listen to that lyric again?
WHY did I giggle at that NYC apartment rental quip?
WHY does this storyline engage me, and what makes it different?

Over time, I start to see patterns. And when I can see patterns, I can play, and find new and interesting ways to express my ideas.

All of that matters, and is part of the process of learning to trust my instincts and taste, even if it seems a little too weird at the outset.

“Why do you share all this? Aren’t you afraid of someone stealing your ideas?”


There’s not much included here that isn’t general business smarts (a.k.a. work hard, stay alert, and be nice to people.)

Plus, if someone managed to read this post, catch up to me in record time, and steal all my clients? Frankly, I’d just be impressed. Not because what I do is so mysterious, but because I just can’t do all the things you do. I’m not actually good at all the things you’re good at. And vice versa.

So these notes form me are more like building blocks than cheat sheet guidelines. Take the advice you like, and ignore the advice you don’t.

Then, go on ahead and make stuff.

Take your time, think it through.

And make it yours.

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