talking shop | Hillary Weiss

Footwork, headwork, heartwork: How I cracked $10,000+ in sales on my first product launch

I watched with horror, almost in slow motion, as my fist collided with the side of my Sifu’s face.

Fortunately I’m still very new to the martial art of Wing Tsun, so I don’t pack enough power for a Paak Sau — a blocking technique — to hurt.

… Which is probably why my instructor Sifu Ethan immediately started laughing as I frantically began to apologize for my wobbling punch.

Ethan is the extremely patient, extremely awesome teacher at Brooklyn Wing Tsun. He’s skilled at his craft, passionate about his work, terrifyingly fast, and (in that moment) wholly determined to drill into my skull one very important detail:

“OK. Think back. What did we learn last week?”

“Uhhh….” I mumbled, stuffing my hands into the pockets of my uniform, still recovering from my split second of humiliation.

He pointed down to my flat black Wing Tsun shoes.

“Oh! Right!” I cried. “Feet! Arrow step!”

(This is the foundational move of any Wing Tsun practitioner. It allows you to move quickly toward your opponent without losing your fighting stance, or letting your feet too far off the ground — which prevents an aggressor from sweeping your legs out from under you.)

“Yes!” He threw his hands in the air victoriously. “Footwork. Do that and everything else falls into place.”

I practiced the step again, shuffling forward.

“Good.” he confirmed. “You wanna go faster? Footwork. You wanna hit harder? Footwork. OK. Let’s try again…”

That’s one one of the biggest things martial arts has taught me, much in the same way dance did in middle and high school:

It’s easy to get distracted by what’s immediately in front of you — your arms and fists, your opponent and competition, and your visions for what you can do— but in reality?

The most powerful tool you have is your foundation. Your footwork.

I thought about this moment a few weeks later as I watched, in shock, as my sales totals passed $10,000 after the launch of my first course, The Wordshops.

The cart had been open for just under a week.

I’d launched on Friday, and the live version of my course had sold out by Tuesday.

Now it was Thursday, and the D.I.Y. versions were continuing to sell.

While a part of me was completely elated, a noisier, squirmier part of me was completely confused and a little alarmed.

My email list was tiny. I’d spent a whopping $35 on Facebook ads for the blog writing challenge that led up to the launch — which ended up attracting close to 350 awesome participants almost entirely organically! — but none for the course itself.

I’d intended this to be more of a “soft launch” to test concepts, while the big ad push would rain down later this winter. (Not to mention I’d realized all too late that I was launching parallel to one of the biggest copywriting courses in my industry.)

So… how was this happening right now?!

While I work my ass off and have been blessed with a lot of incredible luck in my 6 years of business — I’m also a realist.

First product launches are incredibly challenging. I’ve seen countless gifted people invest thousands, only to have their initial push deliver so-so results, or none at all.

Reason being? There’s a huge difference between people liking you (even loving you!), and wanting to give you their money. Let alone a lot of their money.

Yet there I was, standing in my kitchen in my PJ’s, pouring whipped cream into my coffee because we were out of half and half, staring in shock at my little Shopify Sales graph.

The first thing I said out loud, before I could even consider celebrating, was: “Why?”

Sure, I’d done my homework. I’d talked to my audience first, and tested everything.

Sure, I’d done a decent job drumming up excitement with a blog writing challenge, and talking about the launch before it happened.

But I’d seen a lot of crazy smart people do that and flop. In fact I was almost certain I’d be one of them.

Maybe I just had a lot of beginner’s luck?

I’m sure luck was part of it. But maybe there was something else…

That’s when I remembered the words my Sifu used:

“Footwork! Do that and everything else falls into place.”

During the official launch of The Wordshops, I was constantly distracted by what was in front of me — and boy, was there a lot in front of me.

There were emails to write, creatives to pay out, messaging to nail, and final course components to QA.

But what I was forgetting about in that moment of shock at the money coming in was everything that came before — and all of the work that had gone into my building my reputation and tribe before a single logo was designed, or photo taken.

I was forgetting that the two beta rounds I’d run of the course that had turned a few students into raving fans.

I was forgetting the hours spent on free coaching calls, podcasts, and on stages.

I was forgetting spending far too long in my Facebook and Twitter PM’s helping other writers and entrepreneurs however I could.

We talk a lot in the industry about how to market yourself; or how to come up with your concept, how to attract leads and nurture them into buyers, how to muscle through the challenges…

But what we don’t talk about enough is the foundation we need to lay beforewe offer something to the world .

It’s not sexy, it requires a ton of effort, and there’s little you can do to quantify it while it’s happening.

But if you lose sight of it, or think you can move forward without it? You might find that none of your punches end up landing.

I’ve come to realize: Building stuff for the world requires a combination of work: headwork + heartwork + (most importantly) footwork.

First, the headwork: You must come up with an idea people want to invest in.

This is the heaviest mental lifting piece. You’ve gotta ask around, find out what people are looking for — and then you’ve gotta build that dang thing.

That means pouring the best of your most desirable expertise into what you create, while finding ways to make it unique-to-you and original. That means finding out how to translate what you instinctively do onto paper, and into simple steps.

So I did hours of customer interviews and created pages upon pages of shorthand notes in Google Docs detailing my own mental processes. It’s also the reason I ran the two beta test rounds so I could get complete 360 feedback from my students.

(I talk a little about how I built The Wordshops here, and don’t worry: I’ll bore you all to tears with even more info on my process soon.)

Then comes heartwork: You’ve gotta learn how to talk about what you’re selling to the people who’ll want to buy it.

Ah, marketing.

If only you were as simple as throwing a sales page at people and watching money roll in.

But nope! Today’s consumers aren’t just smart, they’re incredibly discerning.

If you wanna get results? You’ve gotta throw your heart into the way you share your ideas. You need to make sure your concept is something your audience will understand and jive with — so you have to find a way to pull the curtain back on all the soul you poured into it, the value your customers can get, and exactly what results you can help them create.

It’s the reason I decided to start with the blogging challenge to make sure the tribe I wanted to serve connected with everything I could do for them. No smoke, no mirrors, just tools and help from my end, and a little dedication on theirs to make things happen.

Then, when it came time to write my promo emails? I stripped the gimmicks and formulas and shot for honesty.

While future campaigns promoting The Wordshops may lean a little heavier on the persuasion side of things? For this one I just put my heart on the table and told the story of how and why I built ’em.

And why did all that headwork and heartwork pan out? I’m willing to bet it was because of the final (or perhaps first) piece of the puzzle: my footwork.

My clients and colleagues would tease me mercilessly about the fact I hadn’t put out my course yet after 3 years of talking about it.

But what they maybe didn’t know?

I was perfecting my foundation — my footwork.

I’ve been in this field for long enough now to understand: You can have the flashiest branding, the best concept, the fanciest special guests and bonuses — but if no one knows you from boo? You’re screwed.

So you’ve gotta pound the digital pavement. You’ve gotta put yourself out there, over and over, until people start to take notice and recognize you. You’ve gotta build trust. You have to show, instead of just tell, why people should invest in you long before you offer them anything for purchase.

That’s why I spent the 18 months before launch teaching wherever, whenever, and however I could. I was making friends and cementing relationships with potential future students and dropping hints about the course to build excitement. When someone approached me to ask me a question (in person, on Facebook or Twitter, or in my inbox), I tried to give them every bit of help I could — not because I was secretly hoping they’d buy my future course, but because I love to teach and share what I know, and I love having the kind of expertise that can really make a difference for entrepreneurs across the planet. That’s what I’d really dig being known for, and a huge part of the reason I built The Wordshops.

So, sometimes consciously, sometimes subconsciously, and universally imperfectly: I was doing the slow burn work of establishing myself as a visible writer and writing coach. I was practicing my footwork.

But hey, let’s make no bones about it: You can have all your headwork, heartwork, and footwork in place and it’s still easy to get overwhelmed by a first launch.

Scratch that: It’s easy to get completely crushed by the weight of the conceptual freight train you’re trying to push along, the punches you have to throw and the obstacles flying at you along the way. (Thanks for nothing, tech gremlins.) It almost happened to me, too.

And I won’t pretend that there wasn’t a huge chance the first Wordshops launch could have tanked.

But if it had? I was prepared to dust myself off, drape my dignity around myself, and march on, determined to do better on the next round — because that’s just business.

Fortunately, it didn’t pan out that way. And I thank my footwork for being the biggest force carrying me through to the success I saw.

Is it possible to launch first, and then focus on footwork? Absolutely.

(After all, your course may give you the material and focus you need to build up your foundation in the first place.)

But it’s like perfecting punches before you move across the mat while throwing them: it’s a different way of learning — and you may suddenly realize you have to re-learn how to throw your fists once you start to incorporate the rest of your body.

… And you also might end up accidentally punching your teacher in the face.

So I want to remind you, whether you’re about to launch a new concept, or whether you’re dreaming up one right now:

Don’t get so lost in your visions for the future ahead that you forget to pay attention to what’s beneath your feet, and the platform you’re building for yourself, right now.

If you’re choosing visibility, you can’t lose sight of how you’re standing and moving through the world in your chosen field.

“You wanna go faster? Footwork. You wanna hit harder? Footwork.”

And if you flub it anyway?

Square your shoulders, fix your stance, get back on the mat and… go another round.

The fire & fury of whole-assery: How my course The Wordshops finally got made

DON’T KILL YOUR BLOG: A love story

Something’s waiting for you:

It was 3 AM in late December 2015. I was sitting on my childhood bed in my underwear because the AC was broken again. Of course.

I was at my parent’s house in Florida for the Christmas holiday. And while I was supposed to be taking time off from work, I’d spent the last few hours tossing and turning with a restlessness that could only mean one thing:

I had an idea… and I needed to write about it.

But it wasn’t just any idea, and it definitely wasn’t an idea that fit into my regular blog lexicon, which included such glorious, wholly-expected titles like The Art of Crafting Awesome Client Experiences, and The Unwritten Rules of Making it as a Freelance Digital Creative.

Nope. This didn’t fit in with what I was “supposed” to blog about at all.

(Which isn’t saying much. In the copywriting world you’re “supposed” to write about copy strategy 101, conversions, persuasion, building your business, and something something selling through story…

… Which is probably why I’d spent the previous 4 years avoiding it like the plague.

Besides — I was way too busy writing everyone else’s blogs anyway, right?)

Still: This was different.

It was about my childhood. It was about my own personal philosophies. And it also painted a pretty unromantic picture of the way I see the world.

I’d tried to write it a few times but all I had to show so far were a few half-hearted drafts, and most ended with some variation of:

“F — K IT. NO IDEA WHERE I’M GOING WITH THIS, OR IF PEOPLE WILL EVEN CARE. DELETE.”

But as I laid in bed that night, the idea began to pull me by the hair and poke me in the ribs. And it wouldn’t leave me alone.

It was clear sleep wasn’t coming. So I threw off the sweaty covers, sat up, and dragged my laptop onto my bed.

I made a quick list of bullet points that combined the story I wanted to tell with the “takeaway”, and got to work.

Imagine my surprise when the idea suddenly began flying out from under my fingers.

Instead of feeling draining and tedious, as blogging so often did, this felt energizing, like I was finally getting a chance to throw and shape clay I’d been carrying around inside me for years, unsure of what it was.

By 4 AM, I had a finished rough draft, and went to bed.

The next morning I read it anxiously over my coffee.

And… I didn’t hate it. In fact, I liked it. A lot.

The thought of publishing it made me simultaneously uncomfortable and elated that I’d hit on something so true for me, and managed to get it organized enough to share.

But what if people didn’t like it? Or worse — what if no one cared at all?

As Neitzche once said, to the delight of many a goth 17 year old: “If you gaze long enough into an abyss, the abyss will gaze back into you.”

… Bet ol’ Friedrich didn’t know the same was true for blog posts.

I read it over again. And again. Made a few changes, tightened a few concepts.

Then I gave it a title:

“Notes from an unremarkable child: How painful average-ness equipped me with a life philosophy”.

Closed my eyes…

… And hit “Publish”.

A few minutes later I shared it on my social media channels and turned off my phone, determined not to care if and when no one took notice of it at all.

Then, when I returned a few hours later… I was blown away.

My phone started to buzz with texts, PM’s, emails, and social comments and shares in a way it never had before. While it wasn’t “viral” by any means, the response I received was almost shockingly heartfelt.

“I went through exactly the same thing, I just didn’t know how to put it into words,”

“I can’t believe this is your story! I’d always assumed you were a straight-A student…”

“I love this so much! Thanks so much for the truth talk!!”

At that moment, my love affair with blogging really began.

But before I go any further, let’s talk about the elephant in the room:

As brands, business owners, and writers, we all know we’re “supposed” to blog. So why don’t enough of us do it — or really enjoy it?

Yes, we know we should use it to “build our brands and businesses”, but when you’re boring yourself to tears, or spending hours researching “50 SEO Secrets of Sparkle Unicorns”, only to get 0 response to what you create?

Chances are you’re gonna think: “Nah. I don’t need to do this.”

And yet! That doesn’t make blogging any less essential for branding yourself, developing your messaging, and building a business.

It was on that fateful, muggy Florida morning, I realized: I’d been going about this blogging thing all wrong.

While yes, I had to keep the basic rules o’ blogging in mind (write something your audience will find valuable, have a lesson and a takeaway people can utilize, have a call to action, etc.), the limits I’d been placing on myself in terms of subject matter were totally zapping my creativity and energy.

Tl;dr — I wasn’t blogging because I was bored.

So I decided to take another approach.

Yes, of course it was intimidating to write an article for myself after a long day of writing for clients.

But when you’re a creative who’s genuinely excited about an idea? You tend to get a second wind, don’t you? It’s the reason so many of us get shiny object syndrome when we’re in the middle of a launch. #guilty

So: Instead of writing what I thought I should write, I decided I was only going to write what I wanted to write, and what made me genuinely excited to create — as long as I could make it valuable to other people (and I’d save the rest for my diary).

I also refused to put myself on a strict schedule.

I rolled back on that annoying voice that squeaks:

“If you’re not blogging at least once a week, why bother?!”

And replaced it with:

“I’ll aim to blog once a month about things I’m genuinely excited to say and share. And if I miss a month? I won’t beat myself up.”

2 years later, my blog posts have helped me amass thousands of followers (particularly on Medium), and attract a huge range of phenomenal connections, opportunities, and projects — because, as it turns out?

When you’re crazy excited to write, create, and share ideas, people find them crazy easy to connect with.

Make no mistake: Writing a blog is still not:

A fast and easy way to make money.

The way to become an instant internet celebrity.

Just the ticket for soothing our own need for validation and support in our creative endeavors online. (Quite the opposite, really.)

In fact, if you ask a dear internet-famous blogger friend of mine how to make a living off blogging alone, she’ll probably tell you, “OK so go back in a time machine to 2008, and…”

But blogging is a whole heap of even more valuable things when it comes to building your brand and business.

For example…

Blogging helps you get in the habit of shaping your most important ideas.

Because that’s just what it is. A habit. The more often you share your own concepts, the easier it is to edit and expand on them, and figure out what your unique point of view is. (This also helps to suss out your brand and business’s “why”.)

Your blog is your training camp and your off-season game. The more you practice giving form and life to your own perspective and beliefs, especially if they’re outside the norm for your chosen field? The stronger your unique point of view becomes, and the easier it will be to share it with clients and customers.

Being able to translate your experiences onto the page is almost like learning another language. You’ve felt it, seen it, and done it all — but how can you give your reader a taste of your experiences and ideas so they can really understand?

That alone is a massively valuable practice worth starting and maintaining.

Blog posts can be repurposed for pretty much anything.

Want to write a new freebie? Got a course module you’re working on? Need some sort of subject matter for your video series? In search of a story for a marketing sequence?

Maintaining a blogging habit, even if it’s just once a month, can offer you a whole heap of your own content and original ideas to pull from, as well as cementing which stories “work” for your particular niche and industry.

Blogging gives you space to experiment and mess around.

In the last year alone I’ve shared a number of posts totally unrelated to writing — and they’ve been some of my best. Because I’ve found there are so many things to discuss on this entrepreneurial journey; like willpower, radical self-trust, the shadow side of creativity, and the value of rage.

But without giving myself permission to write Notes of an Unremarkable Child a few years ago? I never would have known that was even an option.

Blogging is less pressure than a book, and more formal than a Facebook post. (Though you can absolutely re-purpose a long Facebook post into a blog post. I’ve done it many times.) That makes it the perfect practice platform.

A few evolutions of my brand ago, I’d call my blog “The space for my words to run free after I’ve spent my days corralling everyone else’s.”, and I think that makes more sense to me now than it did when I first wrote it.

Blogging gives you something to do that’s just for you. It’s for your audience too of course, but on your turf, they have to deal with you talking about ideas the way you want to. That’s ultimate creative freedom.

Blogging helps you meet people, and maintain those relationships.

Truth be told, there’s nothing quite like getting those magical little emails that say “Yours is the only blog I ever read anymore”, and “I loved this so much,” “I needed this today, thank you so much,”.

It’s a great feeling to have people inviting you to guest blog, or appear on podcasts, or contribute to a course or article.

But more important than any compliment or accolade is a blog posts’s ability to put you in front of people who may never have met you, or read your stuff before.

I’ve developed friendships across the street and across the planet just by writing and sharing posts each month. I’ve had people stop me at conferences to say they’ve read every one of my articles (after which I try not to choke with excitement and surprise). And, whether they’re heavyweights, “influencers”, colleagues, potential clients, or newbie writers just getting their start — each one of those relationships has a whole heap of value and potential.

And finally: My blog helps me take the temperature of my audience — and vice versa.

Make no mistake: Sometimes an audience’s level of response can be relative. Sometimes algorithms don’t work in your favor, and you have to share a post a few times to really gage a reaction.

But usually? The reaction to a given post will help you sniff out what your people most want you to talk about — which has the power to energize you, and make you excited to keep talking and keep sharing about the things that matter to you.

And writing about topics that interest you, and light you up, also gives people who won’t jive with you the ability to self-select out of your corner of the internet.

All of this to say: If you think you’re ready to give up on blogging — DON’T.

You have hundreds, even thousands of ideas knocking around in your skull every single day, whether you realize it now or not.

If you don’t practice putting them out there? They may never see the light.

So focus on keeping it low pressure. Keep it fun. If you’ve quit blogging, start up again by focusing on what excites you — and you might just find those little off-beat ideas create some of the most impactful, thought-provoking, infinitely-shareable articles you’ll ever write.

You know: The kind that attracts the kind of clients, cash, and accolades that makes blogging such a feel-good long-term enterprise in the first place.

And if you need a little help? I’m kicking off a FREE blog writing challenge September 18th — 22nd.

http://thewordshops.co/blog-challenge

It’s called The Blog Party Challenge, it’s $0, and you’ll spend 5 days with me in your inbox and a private Facebook group (where I’ll teach LIVE mini video classes and lead Q&A) brainstorming, outlining, writing, and sharing a post that feels ah-mazing to write and share.

And after we wrap? You’ll be able to follow the same bulletproof process again and again. Because writing brand-building blog posts should never be boring.

In fact — it can be the most gratifying, eye-opening thing you ever do for your own creativity.

So if you’re ready to put your toe back into the blogging waters, or step your current blog game up?

Click here to come join me, and I’ll show you exactly what I mean — and exactly how I write posts like these.

The worst way to price anything ever (from someone who fell into the trap).

Photo by Ian Espinosa on Unsplash

(This post is an excerpt from The Wordshops, my copywriting course for unconventional entrepreneurs launching this September. Wanna know more? Drop me a line right here and you’ll be the first to hear when it rolls out.)

In my second year of business, I hit on an awesome idea for an offering:

1–1 copywriting intensives over 1, 3, and 5 days.

Just one client and one project a time, with total creative focus on my end, so I could get their project in and out the door quickly.

I’ve had a lot of bad ideas in my day. But this, I was certain, was not one of them.

This style of work would help me get more clients, prevent contracted deliverables from dying a slow death from the professional cholera of endless revision rounds, and help me build up my experience levels with a huge range of projects.

(Another side effect? It would also make me a turbo-speed writer, but that’s another story.)

In a day I could write a landing page and some emails, in 3 days a long-form sales page, and in a week a full website.

Veteran writers out there: I can feel you cringing from here. Stay with me.

The moment I launched the offer I excitedly sent the sales page to my colleagues in a small, trusted writer’s group I was part of.

The first response?

“This is an awesome page… but Hillary, as soon as I saw your prices, my heart sank.”

Ah shit.

My prices?

$400 for the day.

$800 for 3 days.

$1,000 for the week.

But hey. I hadn’t been in the industry long. I didn’t know what I was doing.

So naturally, I jumped into the thread to justify my decision.

I was still pretty green.

I didn’t have a ton of experience.

I wanted a lot of people in and out the door.

I didn’t want to price myself out of the market.

But in reality? I’d priced myself so low because I was afraid.

Terrified actually.

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.

But I wasn’t drawing those conclusions because I was stupid or misinformed.

My point of reference was just severely skewed.

At the time my only other professional experience had been waitressing work and $8/hr agency gigs (thanks, U.S. Recession). I’d never made anything close to $400 in a day. I couldn’t afford to pay someone $800 or $1,000 in one fell swoop.

That’s probably why my logic went like this:

“Why would anyone want to give that kind of money to me? I couldn’t afford to pay someone that.”

I didn’t realize it then, but I was making one of the worst errors you can possibly make in sales and pricing:

I was mistaking myself for my ideal client.

Because I couldn’t afford it, because it felt like a huge amount to me, I scared myself stiff.

Because I knew intellectually that higher price points = higher level of clientele, but from where I was standing I couldn’t make myself believe it fully.

And because I was putting my own fears around money-making and pricing in the front seat — instead of my goals for my business.

As a result, I started attracting clients who were… a lot like me in my first year. I found myself working with a lot of low-budget, not-totally-clear-yet, can-you-make-me-sound-like-the-biggest-name-in-my-industry type folks.

And you know what?

None of that changed until I learned to stomach asking for several thousand dollars for a sales page because the types of clients I wanted to work with could afford that.

Not because I could afford it or felt OK with it right off the bat. But because they could.

It took a lot longer than it should have — about 2 years to be exact — but eventually I realized I wanted to be working with elite-level businesses in the 6 and 7 figure range.

So slowly, cautiously, I started to raise my prices.

They didn’t blink when my price for a sales page went up to $1,000.

Or $2,000.

Or $3,000+.

… Then I started to feel dumb I’d ever waited that long.

Switching my focus away from what I thought I was worth and towards how much I was worth to my client was a muscle that took time to build — but it was a worthy one.

When I took myself out of the equation, it became a lot easier…

To ask for more money. (I was working like a dog and charging like a mouse, and that benefited everyone but me.)

To hip check clients when they went out of scope.

To fearlessly send those estimates knowing if they couldn’t afford it? They weren’t the right client for me. (Also, when you’re charging $2,000+ per page instead of $400? You just don’t need as many clients.)

So if you’re relatively new to the industry, and asking people for their money gives you the heebie jeebies, I’ll remind you of this:

It doesn’t matter how you’d feel being charged the same amount you’d charge a client.

What matters is being able to pinpoint your price point from the perspective of the results you get, how much experience you have, and what kind of clients you want to be working with.

Put that front and center when you’re pricing your offerings and services and getting ready to ask for the sale, and watch the way you charge change.

You are not your ideal client.

(Nor should you be.)

So stop pricing for YOU. And start pricing for THEM.

** And oh hey before I go! This was an excerpt from The Wordshops, my copywriting course for unconventional entrepreneurs launching this September.

Wanna know when it rolls out? Click here to drop a note in my contact form and tell me: “I can’t wait for the Wordshops!” I’ll make sure you’re on the list to hear when I go live.

No, you are not too young (to start a business)

Photo via Unsplash

If I could send a letter to my 22 year old self, it would start like this:

“Hey Me. It’s You.

First: I love your flower skirt. Please don’t donate that one to Goodwill, you’ll regret it.

Second: Listen, I know what everyone’s trying to tell you.

They’re trying to gently explain that this writer thing isn’t going to pan out.

They’re trying to imply — with love — that you’re nuts for going freelance, or trying to start your own company when you’d be classified as “entry level” in pretty much any agency you apply to (Though, let’s be real, all those free hours you spent interning should really count for more. #millenialproblems).

I know you’re doubting yourself, every minute of every day.

I know that despite the clients you’re attracting, the work you’re creating, and the money you could make, you’re terrified it’s all temporary, and soon your inexperience will to catch up with you — and you’ll make one major blunder that sinks the whole ship.

I know everyone else you meet in your field has 5, 10, even 20 years on you, and whenever anyone asks you your age you break out into a cold sweat.

I know almost no one believes you can do this, except maybe a couple of your best friend and family members.

But I believe you. And you believe you. At the end of the day, that’s all you need.

Keep your head down, and keep pushing. You’re going to be better than alright.

See you in a few years.

Love,

You.”

Can I be honest about something?

I turned 28 a few days ago. And even as I start flirting with 30, my age is still my biggest frustration.

Spilling that number — which feels like it should be totally arbitrary after 25, when my frontal lobe stopped developing — has never felt comfortable for me.

Since the beginning of my business, my age has always inspired a reaction: of surprise, of doubt (even distrust), or of total bewilderment.

(And I’m not even that young or rich! Seriously, here are at least 40 people who were millionaires before they were 20. I’m not that extraordinary.)

Don’t get me wrong: It’s felt cool to be called a wunderkind once or twice. But historically, by no real fault than society’s expectations, my age has largely only served to make me feel reduced.

Last weekend, in my final days of 27, I was sitting in a hotel lobby with a client friend.

We’d both been speakers at a conference, and had spent the last few weeks working closely on her launch. Margaritas in hand, we were laughing about the niche we’re both a part of; toasting its past, present, and future.

Then she asked how old I was turning, and I felt that familiar twinge in my chest.

But I’m older now. I told myself. We’re getting into “take me seriously” age territory. Just spill it, Weiss.

“28!”

Her eyes widened. My heart sank.

What followed over the next 90 seconds is the same conversation that’s played out for me, over and over again, for almost 6 years now.

Her: Oh my god, you’re a baby! I didn’t realize you were so young — you have so much experience and —

Me: Yeah, I got started at 22! But I’ve looked 30+ for a few years, haha, so…

Her: Oh god, no no! I’m not saying you look older, I’m saying —

Me: Oh totally, I wasn’t offended, I’ve just always looked older, so people assume I’m older, and um…

Ugh.

Maybe I should add a “P.S.” to that letter-to-self: We never age out of awkwardness, or making terrible jokes to diffuse situations. Sorry.

But I choose to be open about these stories, and these challenges, because for every 5 conversations I have where someone older is surprised by my age?

I have 1 conversation with someone younger, more hesitant, and as determined as I was 6 years ago to be their own boss.

Those are the conversations that mater most to me.

And these young bucks, full of energy and excitement and fire, all come to me with similar challenges:

I work really hard, but no one else my age is taken seriously. Why should I be?
I’m done being an intern, but everyone’s telling me to “earn my stripes”. I’ve worked for FREE for years for multiple companies. Where my stripes at?
I feel like I’m ready to do this, but everyone’s telling me to wait ’til I’m older. Are they right?
None of my friends are freelancers/entrepreneurs. Some have tried, but they failed. Should I take that as a sign I won’t do well?

Here’s what I say to them, and what I’d say to you (whether you’re 19, 39, or 80):

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?

Let me be clear here: “Ready” doesn’t feel like unshakeable confidence and bravado.

(That’s not “ready”, that’s a light show.)

Ready means you can feel, in your bones, that you can really do something — and make money doing it — if you’d just muscle yourself forward.

Ready feels like the willingness to dip your toe, then your whole foot, and then your entire body into the water and swim for your life — even if you know the current’s rough.

Ready is that steady, calm feeling buried under all those layers of doubt the outside world has seeded into you — the feeling that assures you that whatever they might say, you know yourself. And you can do this.

Ready is focused. Ready is brave. Ready has no illusions about the journey ahead, but is excited about the challenge.

And trust me, my fellow young bloods: you’ll need to be ready, because you’re going to be treated differently for a while.

(Remember: No one needs to know your age. Don’t lie, but you don’t have to lay it right out on the table.)

People are going to tell you you can’t, shouldn’t, or mustn’t just based on the number of times you’ve personally orbited the sun.

They’ll tilt their heads, and click their tongues, and talk to each other privately about whether or not they feel you can do this, and why.

They might place bets. They might try to talk you out of it and feel they’re doing you a service.

But here’s the thing:

They don’t matter. Only you do.

Only you get this one precious, wild life, with all your talent, grit, and beautiful ideas to do whatever you like with.

Could you still fail? Hell yeah! And you should plan to, because you will.

But everybody fails, and everybody stumbles.

Being young may require you to topple over an extra time or two, but besides that? You’ll be learning and growing just like anybody 5, 10, or 20 years your senior.

If failure doesn’t frighten you enough to hold you back — and won’t bankrupt you?

Go for it.

Trust the “ready” you feel — it will guide you well for the rest of your life.

Listen to the voice within you. It’s the only one who’ll be accompanying you on this journey.

And if it feels right, despite everything?

You have my permission to launch.

… Not that you ever needed it to begin with.

This is it. There’s no better time.

Go.

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No, you are not too young (to start a business)

I’ve come to realize: Building stuff for the world requires a combination of work: headwork + heartwork + (most importantly) footwork.

And as a result of all this? I’ve got students saying stuff like:

P.S.:

** And oh hey before I go! This was an excerpt from The Wordshops, my copywriting course for unconventional entrepreneurs launching this September.

Wanna know when it rolls out? Click here to drop a note in my contact form and tell me: “I can’t wait for the Wordshops!” I’ll make sure you’re on the list to hear when I go live.

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