The Ultimate Resource Guide for Freelancers

Hold onto your pantalones, my friends, because you’re in for a resource RIDE.

Don’t worry, I haven’t forgotten about my Second Act challenge. I thought I’d give you a breather to sit with your answers because next week we’re going to talk about how we build something new, step-by-step, from your foundation. I’m not talking Vesuvius, friends. This isn’t scorching the earth to start anew. This is about taking what you have and making it into something real and tangible.

This week, I’m talking about resources. Resources I use in my business and day-to-day. Believe me when I say that I’ve tried EVERYTHING. I’ve signed up for every email list imaginable, and have downloaded dozens of tutorials and tried all the software platforms. However, I’ll save you the heartache of the hunt. Today, I’m sharing what works for me and why.

Whether you’re a freelancer or rocking a 9–5, I know you’ll find something useful here because I believe that knowledge should be shared and abundance far outweighs competition and scarcity.

Buckle up. Let’s get this resource party started. For efficiency, I’ve divided up the goods by section for ease of scrolling.

1. Client Management/CRM

Dubsado: When it comes to client management, I believe in the path of least resistance. I don’t want complexity; I crave simplicity and Dubsado is the ONLY client CRM system that I’ve stuck with. I’ve tried Honeybook and Freshbooks and I always return to Dubsado. Here’s why:

They have a super simple contract management and invoice system: If I want to send out contracts or invoices, Dubsado makes the process super simple with sample templates you can customize and a means to track document opens and responses. No more wondering — did they get??? YOU KNOW.

Their lead management tool is the tops: Using simple code, you can embed a contact form into website that will drive and sort leads into Dubsado. This is great because I get to track leads, update status, and convert them to jobs when I’ve closed on deals.

Cool workflows: I can’t tell you how much time I’ve saved by creating workflows. For example, when a prospect emails me, I have auto-responders set up based on query type/desired services. I also have workflows established for new clients. As soon as a contract is signed, they get an automatic email outlining our engagement and next steps.

Unfuckwithable Words: I am on board with whatever Ash Ambirge is selling. I started out with her free email challenge, 25 Days to $100K. I loved the depth and specificity of her recommendations — tangible tactics on how to make more $, price yourself, etc. Then I made the leap and purchased her Unfuckwithable Words, 300 scripts to navigate all areas of client, vendor, and employee management. If you have an issue, she has a script. I can’t tell you how much I’ve used this and it’s saved me the anxiety of drafting emails for those DIFFICULT conversations. She also has a stellar legal kit that has a crapload of contract templates for every imaginable freelancer scenario. I ONLY recommend things on which I’ve spent my hard-earned money and her tools are worth the investment.

2. Cash Money Management: I’ve hired bookkeepers and half the time I don’t even understand the reports they send and I wished that everything could be digital and mobile-first. Enter Bench. They manage your books, expenses, and all that jazz for $115/month. Tell me what bookkeeper competes with those prices! Learn more about their features. More importantly, I use them as a conduit for my tax filings. They organize my life such that when I hand over my docs to my accountant, filing my taxes is a breeze. And there’s nothing that gives me more stress than the IRS. Real life.

I use for accounting and I can’t tell you how smart and methodical Brittany is. She’s been my accountant for the past two years and I’ll never go back. I used to work with an old bro who would make judgments about my financials and I got tired of feeling ashamed. Plus, Countless is run by whip-smart millennials who get digital and the freelance game. They’re also up on all the latest tax laws and rules, by state. Note, I live in California and they’re in NY filing my taxes virtually.

3. Time Tracking/Meeting Scheduling: I use Timely to track my hours on a project so I can get crystal about over-work and profitability. They have an incredible interface that tracks your time automatically based on applications and browsers used when you’re logged into your desktop/mobile. I use Calendly to schedule meetings, as I got tired of the back-and-forth of when are you available?

4. Email: Words cannot express how much I HEART Mailchimp. You can be an idiot and use it. I like it because it’s easy to use and their tutorials are first-rate. A lot of my blogger friends swear by ConvertKit and many of the big dogs use Infusionsoft since it has advanced targeting and segmenting capabilities (i.e. you can get fancy AF when sending emails).

When it comes to email marketing, I will say that I think Jenna Kutcher’s List Building Lab was pretty formidable. She even has a free webinar if you want to learn more. I’ve purchased two of her classes and was pleased with how much I’ve learned and the ease in which the information is presented. If you want smart emails in your inbox about all things…email, check out Val Geisler’s missives.

5. Social Media: I’ve been in the social media game since 2006/2007 so I know what’s what. I created a free doc on the automation tools I love and use. Also, check out this guide to using social if you’re an entrepreneur, and here are docs I’ve downloaded/compiled that help you navigate InstagramFacebook (including FB ads), and Pinterest.

6. Website: I am a HUGE fan of Wordpress for blogging and more sophisticated content management system. I used because there are fewer limitations when it comes to customization and plug-in integrations.

When it comes to my P&K site, I use Squarespace since it’s super simple and the templates are pretty stellar. I will say that I’m NOT a fan of Squarespace’s TOS where they can use your work in advertising. I wouldn’t recommend this platform if you are an artist. However, if you’re creating a simple site for your business, it’s easy to use and customize. If you can’t shell out the cash for a web designer, I recommend using Empress Themes. I used them for my Wordpress blog and found the designs to be clean and elegant and the integration simple. If you can afford a designer, I recommend my friend, Lorissa of Being Wicked.

7. Podcasts: I LOVE podcasts. Here are some of my essentials: Being BossGoalDiggerAmy Porterfield’s Online Marketing Made Easy, Seth Godin’s AkimboPat Flynn’s Smart Passive IncomeThe Creative Class Podcast. I always get pragmatic, practical information. For the millennials in the house, I think you’ll like The Creative Empire Podcast (though I’ll be honest and say that one of their recent shows gave me a rage blackout because they had a brand strategist who didn’t understand what brand strategy meant and conflated copywriting and brand strategy. However, if you ignore that nonsense, they have some pretty great episodes.

On a side note, I will say that I am ALL ABOUT The Touré Show.

8. Smart People: Whenever Regina sends an email, I open it. Immediately. Her courses and content are free of jargon BS and are actionable. Whether it’s creating group coaching classes or building your email list, her insights are spot-on and her advice is smart, pragmatic, and results-driven. Her free resources are RICHES. If you download anything today, download Regina’s gospel. It’s real. I’m trying to be low-key about this but I’m a total fangirl.

9. Brand Development and Strategy: I’m going to be honest — there are a lot of brand predators posing as house pets out there. People who do not actually know the discipline that is brand development and strategy and they reduce it to copywriting and logos, which is infuriating and couldn’t be further from the truth. I can crank out marketing plans in my sleep, but brand work is HARD, methodical, and intensely data-driven. I found this excellent FREE book on the basics of brand strategy and development. Read this before you ask questions. If a strategist doesn’t start with data (and I’m not talking about scraping blog comments and amazon reviews), RUN.

I ranted about this on Twitter this week because there’s nothing more aggravating than people who don’t know what they’re talking about, peddling their services on the cheap, which it makes it harder for pros like me to convince a client that brand work should START at $8K.

10. SEO: When it comes to SEO, I recommend that you hit up my friend Cariwyl if you need a pro.

11. Free Design Resources/Templates: Half the time, I can’t afford to get fancy so I go to Creative Market for most of my needs. You can find ANYTHING here. I’ve purchased fonts, portfolio and document templates, PPT presentations — you name it. All super affordable.

12. Podcasts: I recommend Pat Flynn’s podcasting course. It’s INCREDIBLE.

13. Everything Else: I’m loath to use the word “hack,” but this Hack Guide is the utter truth. I’ve also written dozens of articles on all things business, career, and writing. Read them. Learn how to quit procrastinating. You have 8,760 hours per year. How to use them. And don’t forget the comprehensive guides, tutorials, and templates I’ve created for you.

Let's talk about brand story + voice

It’s seems as if everyone in a five-mile radius is talking about brand voice and story. What it is, how you get it, and how you apply it to your business. Some get it right while others maybe mainlined too many Gary V. videos and get it terribly, terribly wrong.

If someone doesn’t understand the difference between brand development, brand story, and branding, RUN. Building a brand is not about a logo and color palette and brand development involves data, insights, and market research.

If someone starts talking about how content is king and engagement is queen, RUN. Preferably to the nearest shower so you can cleanse yourself of the nonsense. Nothing’s “king” or “queen.” Stop re-engineering the basics into newspeak. This is about you, your story — what you say and how your say it — and how that story connects with your intended audience in a way that’s honest, real, and meaningful.

Why did you get into this business? What did you set out to achieve? Why do you think you matter? What are your values? How do you show up for your customers? How do you convince them that you’re not just another mouthpiece spreading the disease that is noise and viral videos?

This is what you need to focus on, not listening to the “guru” of the moment.

In this short guide, I’m going to tell you what a brand voice and story are, why you need it for your business, and how you can map it out over the course of a few days. If you’re not shilling or shady, life is simpler than you think. I’m also sharing a 33-slide slide deck on creating your brand positioning and purpose. Enjoy and share the riches.

Who am I? I’m a marketer who’s been doing this for 20 years (brand side, agency side, and out on my own) and I have all the grey hair to prove it.

What’s a Brand Story?

The Brand Story tackles both the big questions and the minor ones. Why did you create this business? What motivated you? Who do you want to serve and why? Is there a glaring gap in the market, which you feel confident you can fill?

But let’s make it plain and simple.

You meet someone at a party. You hate parties because people and obvious feelings of awkwardness and psychological despair (OH, THAT’S JUST ME? OK.) You make small talk about how you know the host and then you exchange the perfunctory, so, what do you do?

You wouldn’t blurt out a manual or copy from a sales funnel page, right? At least I hope you wouldn’t. No, you’d tell them about the business you created and why you did it. Maybe you’d talk about your vision and mission. Not everyone’s in for the money and maybe you want to leave your mark in this world in a particular way. What bolts you out of bed and keeps you up at night? What struggles are you discovering along the way.

You tell this story in your own words and voice — it’s unique because it’s from you. You might speak super fast and act animated when you get excited or maybe you’re thoughtful, measured, and wistful. But there’s a story that you want to tell and it comes from inside of you.

And how you tell it? Well, let’s keep reading.

“One of the best things about stories is they’re totally unique to you. So nobody has your story and nobody can copy your story. So this is a very intelligent and strategic way to leverage your uniqueness in the marketplace.”
— Marie Forleo

Who’s your customer?

This is where I see everyone fuck up royally. They build their brand, their voice, their content strategy, logo, website — the whole shebang and they kind of forget one important, seriously crucial, how the fuck can you forget this…


Everyone gets into the ME ME ME game that they forget that customers are all about ME ME ME and they’re the ones with the money to get you on the tropical island vacation you want so much.

I got my story all gussied up, ready to PARTY but where do I take the story? Who do I tell it to? A lot of marketers develop brands and then they take that package and shove it down the customer’s throat. I like to do things in a common sense way. Understand my customer from the jump and then tailor my voice and messaging accordingly.


Getting to know your customer

This is also hard because we make projections who we think our customer is and what they need and want and often we are wrong. Do the research. Dig into Amazon reviews, comments on blog posts, forums where your customer is hanging out, social media, and how your customers are connecting (or not) with your competitors. Talk to your intended customer, look at data online (resources like Pew, comScore, Nielsen, reputable statistically significant studies can now be found online, for FREE), conduct surveys and informal interviews. You want to know:

•Behaviors: Who are they? What do they love?. Go deep. Everything from the magazines and TV shows they consume to how often they use their smartphone. This is not about demographics. This is about sketching out a real person. I like to do this by imaging a “week in the life of” and jot down all the things my customer did when they woke up to when they collapsed into bed. In detail.

•Pain-points: What keeps them up at night? What do they need to make their life easier or better? When they complain, what do they complain about?

•Motivations: Why would they come to you? What experiences have had they had with products/services in your sphere? How have your competitors served them? This leads me to…

•Their Journey: Get a notebook and write down their complete experience (from the trigger that’s the problem to post-purchase and in between points of purchase) as a diary entry. Research and talking to your customer will help with this.

•Influences: Who shapes their opinion?

Here’s some math for you

Your Story + Knowing Your Customer’s Story =

(drum roll)

Your Brand Voice Guide

What’s a brand voice guide?

Consider the Brand Voice Guide a blueprint for how you communicate. How you bring your story to life and create the tone + tenor for your brand.

The idea is that if someone was gagged and blindfolded, they could distinguish — based on what you say and how you say it — your brand from the pack. The BV guide outlines:

• Brand essentials: These are the basics: positioning + purpose, benefits, and reason to believe. You need a foundation to refer back to. Think of this as your starting point.

• Brand voice, tone, and personality: Are you chatty and conversational or formal? Are you witty? Do you use slang? Are you more focused on being a trusted authority or a trusted friend/colleague? Think of how Blue Shield talks to its customers vs. Glossier, Peloton, or BMW.

• Language: What kind of words do you use and how do we use them? Are you about the 50 cent vocabulary or down-home and simple?

• Details ON who your brand would be if it were a person. Their habits, behaviors, tastes, and preferences. This is you bringing your brand to life.

• Brand voice do’s and don’ts.

• Examples to give context and see the voice in action.

Why do I need this?

There is SO MUCH NOISE out there and the specificity of your story will help you stand out. No one wants the sea of same or a shameless rip-off of an original. What I’m getting at is that your brand voice and story forces you to be focused and consistent. It shows how you’re different than every other kid on the block. And you’re forced to make deliberate choices about your business.

Consistency. Focus. Uniqueness. ARE KEY.

Imagine your voice is all over the place. One day you’re dropping slang like “glow up” in a newsletter (I did this) and the next you’re formal and using every multisyllabic word in the thesaurus. One day you’re saving the manatees and the next you’re talking about cash money millions. You can be more than one thing, but you have to be consistent, focused, and unique about your story, values, and voice.

Otherwise, it’s kind of like meeting someone with multiple personalities. It’s inconsistent and exhausting. More importantly, you don’t establish familiarity. That means no trust. That means no business. If people have to work to understand you they’re not going to work with you.

Don’t be the flavor of the moment. Be what your brand demands you to be. Lean into customer expectations and wants. Be consistent, true, and honest to your story, voice, and your business.

How do I create a brand voice and story?


Think about a simple story. Why did you get into the game? How you think you can change it. Maybe you lost everything and decided to rebuild your life? We like to call that a transformative moment. Maybe you got fed up with your crazy incompetent boss screaming in your face?

Maybe you took a trip that changed your life. Now, the goal here is to find stories that can either teach your customer something or create a more meaningful connection.

Grab a sheet of paper. Write this story down.

THINK ABOUT YOUR CUSTOMER. What are they expecting from you? What do they want and need? What are their behaviors, pain-points, motivations, journeys, and influences?


Why? Because if you don’t know how to speak the language of your customer, they won’t listen. These inputs will shape your brand voice guide.


Ask yourself the following questions:

• How would you describe your brand? Use adjectives.

• What adjectives do your customers use when they talk about your brand? Are you in sync?

• How would you NOT describe your brand? What adjectives would make you WEEP if you heard your customer use them about your brand?

• What personality do you want for your brand? What kind of tone do you want to use? How do you want to communicate?

• If your brand were an individual, who would it be? Map out their person’s traits, habits, behaviors. I create a complete profile of a person and map out their day. The more specific you are, the better.

• What are words you use a lot? What are words (language) you don’t use?

• Do you have copy or tone quirks that make you special or stand out?

• Are your sentences long or short? How do you use punctuation? Are you about visuals/emojis?

How do I use this in real life?

1. Perception is EVERYTHING. Write a few documents in your brand voice. A letter, an Instagram post, the About page on your website. Show it to people. Ask them what they think.

Are you making the impression you want to make?

You can also use a site like to test your messaging in front of real people and see what works.

It’ll take a few tries to get it right and that’s OKAY. We’re looking for PROGRESS not PERFECTION.

2. Use the guide as the foundation for all the copy you create. Remember, consistency is key. But also remember this: even though your brand voice should be the same across all platforms, you might have to tweak it and tailor your content so that it works for the platform. And by platform, I mean social media, email, television, paid advertising, influencer campaigns, press releases, etc. Every platform is a little different so you have to exercise nuance in your copy to account for typical behavior on the platform and what customers can expect from you.

Know that if you’re talking to everyone, you’re talking to no one. Be specific, don’t be afraid of having a point-of-view. When you try to attract everyone, your voice and story become generic and vague because you’re trying to appease the masses. Ironically, when you’re specific on your difference and the customer you’re serving, you’ll attract the right people to you and this is what the game is all about.

Social media management should be EASY. Here are my top ten automation tools!

I remember when there was one social media channel. One. Companies were still buying billboards and full-page newspaper ads. Yes, that’s me in the corner chilling in my sarcophagus, passing time with my abacus, and sending emails from my Hotmail account.

But I digress.

Then the last decade happened and then the deluge. Then the big cultural shift. And then every kid on the block had a Facebook, Instagram, Pinterest, YouTube, LinkedIn, Twitter, and insert 50 other social media channels.

Here’s the thing. Social media is work. You have to create content, post it, monitor it, optimize it, and then you hope and wait for the magic—a connection with your customer. But then…there’s, you know, the rest of your business to run. Emails to respond to. Problems to solve. A life to live with your friends and loved ones.

Imagine if your load was a little lighter. Imagine if some parts of your day were a little easier. Enjoy this resource list—my top ten must-use social media automation tools. What’s automation? Technology that takes care of some of the work—leaving you time for what matters most: your business.

I'm about to drop a FREEBIE. Yes, you don't need to subscribe to my email list. This is TOTALLY FREE. Here are my top ten social media automation tools!

How to write new business proposals that actually win business!

When it comes to new business, I’ve learned three things: be clear, concise, and ask for the sale. In a former life, I was a partner in a social media agency, and I grew our portfolio from $1MM to $20MM in four years. I got grey hair in the process, but that’s a conversation for another day. When I went out on my own five years ago and started consulting, I used the tools I’d acquired to convert prospects into clients. In 5 years my win rate has been 95%.

How? I’ve cultivated a simple three-step proposal process that starts with a conversation and ends with a solid proposal. I’ll outline the process in an upcoming medium post, but for now I’ll share the nuts and bolts of writing a winning proposal.

Restate the goals and objectives

You’ve had the initial call with your prospective client. You’ve learned about their company, stakeholders, and more importantly, their pain points. To close a sale, you have to know the client’s challenges and explain how you can solve for those challenges. Many consultants make the big mistake of using the proposal to talk about THEM — their experience, portfolio, and capabilities. This is what the intake call is for. The proposal is all about the client. Start the proposal with a recap of your discussion and what you believe to be their goals + objectives. The goals and objectives set the stage for the story you’re about to tell.

Define what you bring to the table

Although I just went on a mini-rant about how to not make the proposal all about you, you do want to reiterate specific aspects of your experience that make you their ideal partner. For example, you can call out industry/vertical acumen and expertise. You can highlight previous case studies using the CAR format:

  • Challenge
  • Action
  • Result

Proposals are often circulated internally for feedback and review, and you want to show the team that you’ve heard their concerns + why you are the best person to address them.

Tell them the solution + the services you offer

This is the most important part of the proposal! I’ve seen so many proposals that are vague, which is an open invitation for scope creep. In concrete and succinct terms, articulate your services and the components of those services that will ultimately satisfy the client’s goals and objectives. For example, if you’re offering to write content for a client’s social media channels, you should define:

  • How many posts you’re creating per channel, per week (original + 3rd party reposting)
  • Are you responsible for creating original visual content? If so, what kinds of content? Images, video, gifs, etc. How many pieces of visual content Will you be editing and formatting the visual content?

When it comes to your services, BE SPECIFIC.

Get specific about your process + approach

Believe it or not, this is the second most important part of the proposal because in this section you’re communicating how you work. Not setting clear expectations from the onset is often the reason projects become a psychological nightmare. This is the place to define:

  • Your process: Your communication + workflow — the tactical nuts + bolts of your day
  • Communication: Get specific on when and how often you communicate. Do you have weekly check-in calls? Do you guarantee a response within 24 hours? Do you not work on the weekend or do have specific office hours? Do you send call recaps to ensure you and your clients are on the same page? How a do you structure the review + feedback process?
  • The software, tools, and technology you use to get the job done. For example, I use Dropbox, Asana, Google Drive, Skype, and Slack for file and workflow management. Do you use Hootsuite to manage social media? Show what’s in your toolkit. Know that some of this will be a negotiation with your client because you don’t want to impose a process that impedes progress. Each client is different, and you’ll have to negotiate the tools you’ll be using.
  • Your approach: This is your secret sauce. Your big-picture strategic workflow. This is how you get to the solutions that will solve your client’s problems. For example, on my brand strategy projects, I outline the first two week’s of activity to get to positioning statement, key messaging, benefits, and narrative. I’ll also show where the clients are involved in the process:
  • Week 1: Asset Request + Review (FS)
  • Week 2: 2-day discovery work session (FS + Client), recap report, which details key learnings and opportunity
  • Week 3: Delivery of brand provocations, positioning + purpose, benefits

You’ll gain tremendous insight into your client relationship based on their response to your proposal. I joke that the proposal phase is when all the crazies come out of the woodwork. The, wait, you’re not going to respond to emails within 3.2 seconds of receiving them? I can’t expect that you’ll make edits at 2:30am when I have insomnia and I’m firing out emails?

Give clarity on the deliverable, i.e. what they get.

While clients appreciate the strategy, advice, and best practices, they also want to understand the tactile part of the relationship I often create a chart where I outline my services in one column and in the next column I’ll specify the resulting deliverable. Let’s say a client wants you to manage all of their influencer marketing efforts on a monthly basis. You would detail all the components of the service and the deliverables:

  • Influencer strategy in PPT format (<- Yes, I inform the client of the format because you would be surprised the level of confusion and frustration that ensues in the sending and opening of documents. And no, I’m not joking)
  • List of targets, asks and assets, budget, timeline
  • Campaign copy, influencer pitch + all communication in MS Word format
  • Monthly recap and performance report in XLS format

BE CLEAR on what they get and when they get it.

Define success and how you’ll measure it.

Clients LOVE this because it allows them to rationalize their investment and determine whether your proposed solution actually worked. You’ll sometimes hear marketers use the term “KPIs” or Key Performance Indicators. That’s just a fancy way of saying what kinds of data they use in evaluating the success of a particular strategy or tactic.

Metrics can also be tricky because not all measures of success are quantitative in nature, and they shouldn’t be. With brand work, or anything that involves driving awareness or consideration (preference) for a brand, the results aren’t something that can be immediately measured. Your proposal should be clear on the ways in which you’ll work with your client to establish a benchmark (i.e. a starting point from which to measure) and how you’ll evaluate the efficacy of your work.

Include a project timeline and resources

Every project, even retainer work has a contracted start and end date. Set parameters for the project as well as any additional resources involved and what their roles will be on the project. This is important because some companies actually bar the use of subcontractors. Also, your client will want to get to know their partners and all the members of their success team!

Deal with the money part

Ah, the moment we’ve all been waiting for with bated breath. This guide isn’t about how to set your pricing or whether you should charge a project rate or hourly (I do project and sometimes a project with an hourly cap), however, what is important about this section is to set a fair rate for your work, when they should pay you, and any fees you can collect if they are negligent in payments.

I will say this — draft your ideal terms. Don’t draft what you think a client would want. Remember, this is about YOU making money by providing THEM with a solution. In the past year, I’ve had two clients who have paid upon receipt of invoice. That’s where I start and I’ll go up to N30 from there. I also require 50% of payment up front. If it’s a mix of project deliverables and monthly, I’d do a 50% of project at sign and 50% at term, and then I’ll bill at the first of the month for the retainer.

If your client is legit, they will never have a problem paying for your work. Don’t be afraid to ask for what you want and deserve.

Close with next steps

In marketing, we have a phrase that there should be no dead ends. Every action should lead to another action. I employ this in proposals by setting up a time for review and discussion. For some clients, I’ll outline what the next two weeks will look like (proposal finalization, SOW/MSA, onboarding, etc.)

End the story the way you started it. You heard them and now you’re excited to get started on the solution.


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Sometimes the money isn't worth it. When to fire a horrible client.

Years ago, I landed a whale. This was a client you could casually name-drop in a conversation and put someone’s heart on pause — if you were the name-dropping kind. My team was jubilant. Gifs circulated, music blared, and pizza was ordered. We practically made a template for the inevitable agency case study with the brand’s logo in lights. If only we had seen the arrows pointing to the client with the word RUN propped above their heads. If only we had noticed the chalk outlines of the dozen or so fired agencies, discarded PowerPoint presentations and Odyssean conference calls trailing in their wake. Maybe I knew, but chose to ignore the warning signs that this boldface client would end up becoming a complete and utter nightmare.

It started with the creative director who OD’d on Gary V videos and read one too many Mashable articles. The creative director proclaimed himself a social media expert and proceeded to doubt and micromanage our every recommendation. Every minor tactic (e.g. a Tweet promoting our new launch) had to be backed with research and rationale on the level of a PhD dissertation. However, that paled in comparison to the review process where we went through at least 26 rounds of feedback. I remember inserting a clause into the SOW that stipulated we’d provide three rounds of changes, and then each subsequent round would bear an incremental charge. My boss, the agency’s CEO, deleted that clause from the contract because nothing should get in the way of revenue including his staff’s emotional stability. Pfft. Who cared about sanity or hours burned (thus making the project unprofitable considering the boldface brand’s meager retainer), the days at a time when our client was unavailable or when he constantly pivoted when you’ve got a mortgage on a west village townhouse? #amirite?

After an abusive tirade that brought my account director to tears and the staff to day-drinking, I walked into my our president’s office with the numbers to prove that we were pulling staff away from other clients who managed to be decent human beings (who knew?) and several team members had threatened to quit. By then, I learned that you couldn’t fire lucrative-looking clients in an agency unless they were hurting the bottom line. The account in the red and the team screaming red were grounds for us to fire the boldface client. Simply put, the client took more time and grief than they were worth.

Sometimes, the revenue and the bragging rights aren’t worth it.

For the past five years I’ve been out on my own and I can finally set standards for the clients with whom I want to work. I only work with people who consider me a partner instead of a vendor and I pay attention to the signs during the proposal process to determine whether a client is a fit or if they’d be a PITA.

A solid client-partner relationship comes down to respect and communication. Naturally, you want to do everything to salvage the relationship including stepping up the communication, creating more efficient processes, and compromising because every battle doesn’t need to turn into a war. However, certain situations necessitate firing a client — especially if you’ve tried and the partnership continues to suffer. Sometimes you have to cope with the crazies because you have bills to pay (been there, done that), and everyone has their red line, the limit for how much they’ll take. Also, remember, you’re running a business not a non-profit. If a client is straining and draining, this could have an adverse effect on your other clients. Remember when I had to make the revenue/expense case? That comes into play even more than ever when you’re a consultant.

Here are my top five reasons to fire:

  1. The “Why Are You So Expensive?” client: It’s perfectly normal for a client to ask how you came to an hourly fee or project rate, however, repeated questions are signs of red flags. Repeated requests to reduce your rate, work on spec (no way, no day), or promises of business referrals (if you do great work, you should be comfortable asking for referrals without having to work for less) for a reduced rate should be regarded with suspicion. There have been times when I’ve lowered my fee for a dream or cause client, but I do not compete on price. It’s a losing proposition. Someone will always underbid me and I have enough experience and confidence to know that my work is not a race to the bottom. Be wary of someone who nickel and dimes you every step of the way.
  2. The “This Can Be Done in 5 Minutes” client: Remember when I mentioned respect a paragraph or so ago? The client who believes that everything is so easy, or is baffled as to why something would take longer than ten minutes is a prospect that should send you running for the exits. A good client hires an expert who fills gaps in their business. They should trust that you know how long a task should take and that you would give honest implications of schedule changes and unreasonable timelines. If they don’t, they lack a basic respect for what you do and they will gaslight you every step of the way. I live by the Triple Constraint Concept in project management. You want something fast + high quality: it’ll cost you. You want something fast + cheap: it’ll be low quality. You want high quality + low cost: it’ll take time.
  3. The “I Flunked Communication 101” client: This is probably one of the most important aspects of a client-partner relationship. A lack of established lines of communication could put a project in jeopardy, and communication extremes are just as precarious. If you’re dealing with a ghosting client (do you really like sending 500 “just checking in” emails to then hear from a client that they need X deliverable by tomorrow, 2pm EST or ELSE) or an overly needy client (see #5) — both will get you no satisfaction, as the song goes. I had a client who could never properly articulate what they wanted, even when they were presented with examples, questioned, and coached. Hours and dollars were wasted even when they liked the finished product. Why? They were never quite satisfied with it. Their constant nitpicking on the small stuff took time away from the things that really mattered. They didn’t understand that done is often better than perfect, which leads me to their micromanager…
  4. The “Don’t Mind Me Stalking and Screaming Over Your Shoulder” client: Who feels empowered when they’re micromanaged? While your client may know their brand and business inside out, they hired you as an expert to help them with an aspect of their business. When they get too involved in the strategies and tactics for which they hired you, or if they constantly second-guess or question your judgment, fire them. Micromanaging represents a lack of respect, and it also demonstrates an unhealthy level of control. Micromanagers never grow into leaders because they don’t know how to trust and let go. As a result, your work will be inefficient and you’ll probably be blamed for every misstep and failure — even though the client did the equivalent of wearing earmuffs while you offered your expertise and recommendations.
  5. The “Why Haven’t You Responded to my 35 Emails in 10 Minutes” client: Boundaries, boundaries, boundaries. I used to tell my staff that they should take their work seriously but we’re not curing cancer. Not even close to it. While it’s important to be responsive to your client, you don’t need to be on a gurney answering emails. Set communication expectations from the onset. Now, I even bake into my contracts and remind them in my onboarding email series. I note the hours of my availability in time zone, when they should expect to hear from me, and communication protocol for emergencies. And by emergency I don’t mean, that pixel is off-center. You had better be on a gurney. You don’t have to act like a first-responder when it comes to emails in order to be an effective consultant. Sometimes a response requires time and thought, and it doesn’t always pay to be instantly available and immediately reactive. If a client fails to understand that and has a rage blackout that I’m not holding my phone at 3am, we have to part ways.

The last thing you want to do is cut the cord on a relationship, especially when your livelihood depends on it. In five years, I’ve only let two clients go and trust me, I took a lot before I decided I couldn’t take anymore. However, I’m now attuned to the warning signs in the proposal phase — how a client communicates, what kinds of questions they ask, etc. — so I can avoid the painful process of saying, it’s not me, it’s you.

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Progress is better than perfection

When I was small I wanted to be a lawyer, writer, actress, neurologist, and a baker of many fluffy vanilla cakes. It had never occurred to me that I couldn’t be all of these things at any given time — the word impossible was foreign to me. Children build beautiful kingdoms that adults find ways of ruining with their reason, cynicism, and age. And the once stalwart kingdoms become impenetrable walls we build for ourselves. We cloak ourselves in the familiar and the known, and all that childhood beauty falls way to doubt and fear.

We start out believing we could do everything until we say, well, maybe we can do these three things. We mock that wide-eyed openness and arms outstretched. We say things like, stop acting like a child, as if wonder is something we have to abandon as we age. We’re desperate to get older, to posture and collect years like trading cards until we realize we’ve compartmentalized beauty. All that’s left are pragmatism and reason.

I believe in a life in three acts — the middle is where we make a mess of things and the third is our passage to return to that from which we’ve come. There’s a different kind of wisdom and wonder that comes from the tacit acceptance that we have fewer years ahead. I think about this a lot as I’m still stuck in the betweens, that messy second act. I’ve been in three-decades of the I Can’t Do That, There’s No Time For That, and Why Would I Start Over training programs, and it’s only recently that I’ve stepped back and said, quietly, why not that? Why not return to that kingdom, the mess of children in the wet streets of summer running every which way, but really they’re moving toward what moves them. What makes them happy and whole. There’s something tactile and immediate in that, and it’s something that puts my heart on pause.

For most of my life, I was a wearer of masks. There was the overachieving student, the ambitious writer, and the career executive. All of the masks carried the weight of perfection. The stakes became higher. You didn’t send out manuscripts to editors unless they were polished. You didn’t go on an all-night bender before an exam. You kept your grief out of the workplace and replaced it with a smiling mannequin of yourself, a waxed facsimile of the pained original.

You made calculated, informed risks. You debated. You considered by committee. You reviewed the data and the story it told you.

It only just occurred to me that the masks I wore were walls. The overthinking and obsession with perfection pulling me away from the things that move me.

I’m 42, which I’m told in certain circles, is the new 32. While I’m not entering my third act, I am feeling the weight of mortality. I am thinking about how I’m writing my story and the legacy I leave behind. I’m also conscious of how tightly wound I was for most of my life and now I’ve embraced a different kind of mess. One where I start and stop many projects, and, at times, I’ll have multiple projects going on at once. I’m reaching out without fear of losing face. I’m trying not to obsess over my laundry list of failures. I’m slowly unbinding myself from shame.

I don’t want perfection anymore. I want progress. I want play.