Author, CEO & Founder

Learn More >>

Ass-Scratching Business Conundrum: Is It Worth It to Go Out of Your Way…Or Not?

In: Client Nightmares

You know what's really messed up?

Internet connections.

Here we are building these creepy little awesome robots that get injected INSIDE YOUR BODY to cure cancer….making camouflage suits inspired by the octopus that automatically read their environment and adapt to mimic their surroundings, and coming out with wireless electricity, for the love of Edison…but you think I can get Gmail to load? Forget it.

I'm pretty sure I have an internet curse. No matter where I go in the world, either it's down, the password doesn't work, or some asshole is taking up all the bandwidth. Seriously, you don't want to Skype with me. It might rub off.

This is why it was no surprise that, despite paying over $200/month for the crème de la crème of internet in Costa Rica, a new problem would soon arise: Jackhammers. Because of course there would be a team of eight men working feverishly to dig a massive pool into the cement on the properties of both of my neighbors at the very same time. Of course they would start at 6 o'clock in the morning and end at 6 o'clock at night. And of course it would happen right when I was scheduled to begin my 4-week Sentences & Money business course for aspiring writers.

So of course I do what any other business owner in my shoes would do: Get out of those shoes, put on a god damn pair of heels, and march my way right on up to the United States.

Because the internet gods and their jackhammer cousins will not be ruining my plans, thank you very much.

Fast forward one month later, and we just successfully wrapped the Sentences & Money mentorship course on Friday—but not before having stayed in eleven different hotels across the great state of Pennsylvania over the course of the past thirty days, seeking out the best of the best of internet connections to give this course twice each week, because I will not be undermined. Not by internet connections, not by foreign countries, and not by large men with large power tools. (There are exceptions.)

Fortunately, I'm proud to say the course was a hit and the internet connection cooperated beautifully, in all eleven occasions except for two. (In which case I immediately said: Check, please!) But what if I hadn't proactively made that decision to fly to the United States and spend a month working from hotels? What if I had just “made do?” with the circumstances? What if I had just winged it? What if I had just reacted to what was happening instead of acted?

Would we have had such a successful class experience? Would I have given paying students recordings with jackhammers as background music? Would I have just laughed it off and looked incredibly unprofessional?

I wasn't taking that risk. Because as a leader in a space, and as a professional, you better damn well do everything in your power to ensure a good experience. It's your responsibility to do so. And it's your obligation, too.

Interestingly enough, this theme carried over into the course itself. One of the major takeaways that a lot of folks have cited is learning the importance of taking control over your business outcomes, rather than letting your business outcomes run you.

Some of the student responses, when asked what their biggest takeaway was?

We literally almost cried when you started showing those emails. If we would have known about that process sooner, it would have saved us so much stress. That class, out of all of them, gave us the most confidence.


Taking charge of the process from the beginning.


I need to stop pretending to be in business and start acting professionally… I can't expect clients to take me seriously if I don't take myself seriously.


That I need to run my business MY way using MY personality and MY edge – not someone else's.


Always end with an action step. Act as an advisor. Meatball Dome! Leaders speak first and what would a winner do. 


The biggest thing for me, I think, was just hearing over and over again to trust my gut to do things the way I really want to/not do things I don't want to, and if I marry that to treating people really well (without taking shit), I'll do fine.


These classes helped me see all the pieces involved in creating a first-class experience for clients an potential clients. Particularly, the proposals class filled in a lot of blanks and probably my biggest aha/teachable moment was a piece of research Ash shared in class class 6 about how to become a leader: The leaders spoke first.


My favourite part was the new found confidence I've discovered in my ability to run my own dang business! I feel like I'm ready to blow the socks off of my future clients, and now I actually have a process in place to help them see exactly how I can do that.

And I'm glad that it was a major takeaway here. Because if you aren't running the show, you know who is?

Nope! You don't know. Because it's not you. And that's dangerous, because it means you're running your business blind.

Remember that guy who said that ninety percent of success is just showing up? Well, he didn't mean “showing up” by sitting down to your computer in your PJs and yelling, “OKAY, BITCHES, I'M HERE!” (As fun as that sounds.) He didn't mean physically showing up—he meant mentally. (Because obviously I was there when Woody Allen uttered the phrase and I KNOW THINGS, OKAY?)

And mentally, showing up means:

Doing things you don't want to do.
Doing things no one asked you to do.
Doing things you don't “have” to do.
Doing things other people aren't doing.
Doing things on faith.
Doing things that make no promises.
Doing things simply because it's the right thing to do.
And going out of your way if it means being better.

I think one of the hardest things for business owners is knowing when it's worth it to go out of your way, and when it isn't.

But you can stop scratching your ass about that philosophical conundrum, because guess what?

It's always worth it.

Because when you're a winner, you STEP UP and act like one.

And when you're not?

It's not because you didn't have good luck.

…It's because you didn't go get any.

May 22


10 Phrases You Need to Eighty-Six From Client Emails…FOREVER.

May 22, 2014

Everybody worries about being nice these days. We tiptoe around our own words, soften everything we say, and generally ask permission to have our own opinion. But unfortunately, nice isn’t a selling point. People do business with competent people, with smart people, with successfully branded people, with interesting people, with creative people, and with people […]

In: Client Nightmares


Jul 18


The Secret to Avoiding Pain In The Ass Clients

Jul 18, 2012

If you’ve never had a Brazilian wax, I’m pretty sure you should try it. Not only will you feel supremely sexy, but you’ll also never complain again about stubbing your toe, jamming a finger, getting a paper cut, or getting violently smashed in the face with a crowbar. Compared to the pain of a Brazilian, […]

In: Client Nightmares


Jul 12


The Other 50%: What Your Clients Really Want

Jul 12, 2017

She looked at me with worried eyes. “Do you really think my business is going to be great?” she asked, clenching her hands together. That’s when I knew what she needed. Not more advice. Not more brand strategy. Not more discussion on what she’s selling, and how she should position it. “J,” I said, turning […]

In: Client Nightmares


Jan 16


Your Genius Isn’t Always Obvious

Jan 16, 2014

You know when someone questions one of your decisions, and you smile and nod politely, but in your head you’re all, “I DON’T NEED TO JUSTIFY MY DECISIONS TO YOU! WHO ARE YOU? OF COURSE YOU WOULDN’T SUPPORT MY DECISION, PERSON WHO HAS NEVER DONE ANYTHING, EVER. WHAT WOULD YOU KNOW? YOU DON’T EVEN HAVE […]

In: Client Nightmares


May 7


Sometimes “It Is What It Is” = Best Business Policy of All

May 7, 2017

Yesterday I stumbled across a website called—are you ready for this? Yoga For Bad People. Now, when you just read that, you either had one of two reactions: 1) Fucking love it. 2) Not for me. And that is what the branding is meant to do—attract the people who will love them, while actively repelling the people […]

In: Client Nightmares


Aug 31


The Three-Deadline Rule for Requesting Client Feedback

Aug 31, 2017

I’ve worked with a loooootttttttttt of kick ass writing clients over the years, and you know what’s always the hardest part? Never the writing. Always the logistics. If you do any kind of creative work, at some point you will need to request client feedback before you can move onto the next stage. Maybe you […]

In: Client Nightmares


Dec 3


How to Say No To Your Clients Without Being a Bitch

Dec 3, 2014

I want to talk about managing clients today, because everybody seems to have a love/hate relationship with theirs, and my theory is that the hate part comes from one of two sources: Tightwads. (Don’t work with them.) Not knowing how to tell them to BACK OFF, HOMIE. Begin a slow clap if you’ve experienced this popular scenario: Client pays […]

In: Client Nightmares


Nov 7


How to Raise Your Rates (Without Pissing Anyone Off)

Nov 7, 2013

Money: Love making it. Hate asking for it. (Unless the Tooth Fairy’s involved, in which case it’s all PAY UP, ASSHOLE.) Money talk makes us sweaty and uncomfortable and fidgety—mostly because we’re all trying to pretend money “ain’t a thing” when, in reality, it is a thing, and it’s called shoes. But just because you’d rather talk […]

In: Client Nightmares


May 5


Ass-Scratching Business Conundrum: Is It Worth It to Go Out of Your Way…Or Not?

May 5, 2015

You know what’s really messed up? Internet connections. Here we are building these creepy little awesome robots that get injected INSIDE YOUR BODY to cure cancer….making camouflage suits inspired by the octopus that automatically read their environment and adapt to mimic their surroundings, and coming out with wireless electricity, for the love of Edison…but you […]

In: Client Nightmares


I'm a Bad Influence on Women

Hey, I’m Ash! Twenty years ago I was a small town girl growing up in a trailer park in rural Pennsylvania. Fifteen years ago, I lost my family and everything I knew right as I became the first to graduate college. Fourteen years ago, I found myself leaving everything behind for a new life in the city where I could be “normal.” Ten years ago I realized normal was the most disappointing thing that ever happened to me. Nine years ago I quit my job in advertising and pursued my dreams as a creative writer. Eight years ago, I built a 6-figure business doing what I love using nothing more than the Internet and my voice. And now, today, I’m the founder of The Middle Finger Project, an irreverent media co. that helps other women find their voice and teaches them to use it to build whatever the f*ck they want to. With a book coming out with Penguin Random House in February 2020 (YASSS, WE’RE A PRODUCT IN TARGET!) I’m proud to be a bad influence on women and guide them into doing something disobediently brave with their life and their career.

Enter your email address and I’ll send you my advice column every week sharing everything I’ve learned—and so much more.

But no serial killers. I promise I won’t send those.

Privacy Policy Info Here