Don't Be A Nightmare Client

We all have stories about that client. The client who suddenly became an expert in the thing they’ve hired you deliberately to do. The client who revels in screaming, belittling, bullying, and micromanaging you because they believe cutting a check permits them to be indecent. Let’s not forget about the client who refuses to understand that the minor task they’ve asked you to do doesn’t take five minutes because doesn’t everything take five minutes?

While the majority of clients are delightful, every freelancer will regale you with their Rod Serling-level tales. We try to blot out the nightmare project and the client’s torture tactics, and we tell ourselves to watch for the signs. The five-alarm fires and flares that tell you to run, not walk, away from the project. Because there are limits to what one will endure for a paycheck.

I’ve spent half my twenty-year career on the client side, and the remainder in client service and the simplest and most profound lesson I’ve learned is this:when you treat people with compassion and respect, they will go the distance for you. When you demean people, they will deliver the bare minimum: no bells, no whistles, no glinting red blows at the end of the engagement. Instead, the freelancer will collect their check, scream expletives about you into pillows, and move on to the next.

If you want great work with all the trimmings, set your ego aside and take some advice from someone who’s straddled both sides of the career fence.

You Hired An Expert. Stop Acting Like One

The smartest and most successful people know what they’re good at and what they’re not good at. They’re not insecure about the fact that they don’t know how to amortize equipment on a balance sheet or program a website or segment their customer base. Instead, they hire experts to do the work that will move the business forward. From the visionary, Steve Jobs:

It doesn’t make sense to hire smart people and then tell them what to do; we hire smart people so they can tell us what to do.

If you were satisfied with your vetting process and the freelancer’s portfolio and case studies, why would you second guess their work or doubt their competence? If they’ve done the thing that you’ve tasked them to do, repeatedly and successfully, why don’t you trust them?

This is not to say that you shouldn’t challenge your consultant or ask them tough questions. A consultant’s job is to educate you about the process and the solution they’re implementing for your business, and they should provide adequate and informed answers to your questions. But at one point, you need to shut up and trust them. The more you act like you’re the expert (because reading a Wired article or watching how-to YouTube videos does not an expert make) and the more you question and micromanage every aspect of their work, your consultant will spend more time managing you instead of the work you’ve paid them to do. I’ve heard freelancers joke about adding an “asshole tax” to clients they know will be combative and difficult.

If you’re hiring a web designer, your job isn’t to be a web designer. Your job is to make sure that what they’re developing will satisfy your objectives and resolve your challenges. You ask them questions as it relates to your business, goals, and objectives to ensure that they’re on task and on time — not how they do what they’ve done hundreds of times before you. Successfully. For clients who weren’t as insecure.

You Take Forever to Pay Them

How would you react if I told you that your biweekly paycheck was going to be a few weeks, perhaps a few months, late? Mortgage, food and car payments don’t magically take care of themselves, and if you expect work to be delivered on time, freelancers should expect to be paid on time. Don’t treat them like a character out of Oliver Twist.

Your Freelancer Isn’t Your Full-Time Employee or Personal Manservant, Punching Bag, etc.

On the brand side, I’ve worked for terrible people. People who were manipulative, abusive, and abrasive. People who hurled salad bowls — filled with salad — clear across a room. However, that’s no excuse to use your freelancer as a punching bag or a repository for your pain or frustration. Company bureaucracy and politics are not their problems — they’re your problems. You hired an expert to help you solve a problem for your business, not to bear the weight of your professional baggage.

And from a pure decency perspective — why not treat people they want you would want to be treated? Your consultant isn’t a vendor; they’re a trusted partner. And your abuse doesn’t grant you more power — it’s a glaring spotlight on your insecurity and character.

The simple act of respecting and valuing the experts you’ve hired will ensure you get the best out of them instead of the bare minimum.

Also, it’s important to recognize that freelancers aren’t full-time employees. While freelancers are glorious for your P&L, you have to face reality. Freelancers are not available 24/7, on your schedule. Freelancers do not have to adopt all of your systems. They’ve designed and perfected a workflow, communication and systems processes that ensure a standout work product. If they’re spending time learning how to integrate your systems into their workflow and dealing with your desperate need to hop on a call every five minutes — guess what? You’re taking time away from the work you’ve hired them to do because now they’re dealing with the bureaucracy that is your company and the attitude that is you.

Freelance projects are short-term in nature. Respect their boundaries and systems, and you will get the solution you invested in, and they’ve promised. Your work will be delivered on time, on budget.

I learned this while I was heading up online marketing at HarperCollins and a consultant taught me how to be a good client. The result? I got the work I wanted, delivered ahead of schedule with a few extras thrown in for good measure. In a serendipitous twist, years later they would become my client.

The World is Small, and People Love to Talk

Years ago, I fought with an executive at a major cosmetics brand. Even though they were in the wrong, I was a smug, overbearing, annoying asshole. When I became an equity partner in a digital/social agency in New York, our CEO pitched this exact person our services. I had to deal with the ramifications of my bad behavior, and I ended up swallowing my pride and apologizing to this executive. We won the business, but not without telenovela-level dramatics. I learned that the world is smaller than we think, and the people we abuse in our come-up are the ones we report or defer to on our way down.

People talk. Word-of-mouth can crush careers. You may be the smug client calling the shots and cutting the checks until circumstance reminds you that karma always has your direct dial. You never know who will be your boss or who you’ll need for that professional recommendation or job. And you never know who’ll be the person who surfaces in your life in ways you least expect and the way you’ve treated them in a former life haunts you in your present one.

Be kind. Be decent. Be respectful. Because you never know under what circumstances you’ll face your freelancer again.

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How to Write Winning Freelance Proposals

When it comes to new business, I’ve learned that you have to be clear, concise, and comfortable with asking for the sale. In a former life, I was a partner in a digital agency, and I grew our portfolio from $1MM to $20MM in four years. In the process, I gained thirty pounds, got grey hair and frequent anxiety attacks, but that’s a conversation for another day. When I quit working for a narcissistic sociopath six years ago and started consulting, I used the tools I’d acquired to convert prospects into clients.

My win rate exceeds 95%.

How do I do it? I’ve designed a simple three-step process that starts with a conversation and ends with a bulletproof proposal. Here are the keys to your win rate.

It’s Not About You

You’ve had the initial call with your prospective client and you let them do the talking. In thirty minutes, you learned about their business and pain points. Closing a client comes down to demonstrating that you know the client’s challenges and you’re the one to solve them. Many consultants make the big mistake of using the proposal to talk all about them — their experience, their portfolio, their capabilities, and their fluffy cat. If your prospect doesn’t know your background and experience before the intake call, you’ve lost the business. As soon as I get a lead, I send a brief note outlining my background and experience, attaching my portfolio and case studies. Making the case for “why you” is about their assuaging doubts and cultivating comfort. Clients want to know they’re talking to a seasoned, results-driven pro. You want zero doubt before that first call.

After the call, it’s all about the client.

Open the proposal with a recap of your discussion, restating their challenges, goals, and objectives. The rest of the proposal is proving you’re in the solutions business.

Remind Clients of Your Results

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 and vertical expertise. You can highlight previous case studies where you’ve solved for similar challenges using the CAR format:

  • Challenge: Define your mandate.

  • Action: Outline the action you took.

  • Result: Show the results.

Essentially, you’re reminding them that you’ve done what they’ve tasked you to do before and successfully. Also, proposals are often circulated internally for feedback and review, and you want to show the team that you’ve heard their concerns and why you are the best person to address them.

Speak to the Solution

This is the most essential part of the proposal! I’ve seen vague outlines that are an open invitation for scope creep and agita. In concrete and succinct terms, articulate your services and the components of those services that will ultimately satisfy the assignment. For example, let’s say a client’s social media content strategy is serving as the primary cure for insomnia. They’re making too many rookie moves and they’re not connecting with their customer. They have zero engagement rate and the CEO is frantically waving their phone with your competitors’ social channels bookmarked. Your proposal would outline:

  • Outline your discovery process: how you’ll immerse yourself in the brand, business, and target customer. Although you’re a direly needed fresh pair of eyes, you also want to make sure you can craft a strategy and content that compels and converts.

  • Define your social media content strategy approach: Be clear and specific on the steps you’ll take to design a winning content strategy. From competitor and adjacent industry research and mood boarding and brainstorms to mapping out their 3-H content strategy, share what your client should expect to receive.

  • Explain how you’ll optimize and measure for success: Marketing is all about measurement, so you want to be precise on the qualitative and quantitative measures you’ll employ to establish benchmarks and define success. Also, be clear on your optimization approach. Do you plan on evaluating content performance on a monthly basis? Do you A/B test, etc.?

  • Quantify and specify how often you’ll create content calendars, how many posts you’ll create per channel, per week (original and 3rd party reposting), and whether you’d be responsible for creating original visual and video content. If so, what kinds of content? Images, video, gifs, Lives, etc. How many pieces of visual content will you be editing and formatting? This is important because this is where scope creep can take a project from profitable to blood-sucking leech-level unprofitable.

When it comes to your solutions, BE SPECIFIC.

Explain Your Process

Believe it or not, this is the second crucial 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 and workflow — the tactical nuts and 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 and feedback process?

  • The software, tools, and technology you use to get the job done: For example, I use Dropbox, Asana, Google Suite, and Slack for file, communication, 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 and purpose, benefits, RTB, and key messaging statements.

You’ll gain tremendous insight into your client relationship based on their response to your proposal. I joke that this is the phase when all the nightmare clients 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 2:30 am when I have insomnia and I’m firing out emails?

Be Clear About The Deliverable, i.e., what they get.

While clients appreciate the strategy, advice, and best practices, they also want to get clarity on the deliverables. I often create a chart where I outline my services in one column and in the next column I’ll specify the deliverable’s format and timeline. Let’s say a client wants you to manage all of their influencer marketing efforts monthly. 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. You don’t want to send a Keynote file when everyone in the organization uses PowerPoint.)

  • List of targets, asks, and assets, budget, timeline

  • Campaign copy, influencer pitch and 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 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, 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 how 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 bar the use of subcontractors. Also, your client will want to get to know their partners and all the members of their dream team!

Show Me the Money

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 only charge project rates), 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 collect if they’re negligent in paying you.

Set 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 the invoice. That’s where I start, and I’ll go up to N30. I also require 50% of payment up front. If it’s a mix of project deliverables and a monthly retainer, I’ll do a 50% of the project fees at signing 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 (i.e., 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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How to Score That First Freelance Client

The most agonizing part of being a freelancer is managing deal flow. Most of the time, you’ll have your head down doing your work until you complete a particular project. When the dust settles and you’ve collected the cash from your final invoice, you look up with abject terror to realize there’s nothing on the horizon.Or maybe you’ve taken a hacksaw to the chain that’s been binding you to your 9 to 5, only to realize you’re a newbie, fresh product — no one knows that you’ve quit your job and are now in the freelance game

How do you score those first few important clients when you’re new to the hustle or you’ve found yourself in a financial Sahara?

First, let’s talk about gig sites. Repeat after me: Just say no to Upwork.

Competing on price is a zero-sum game. You will always be the loser.


There’s nothing more demeaning than a financial race to the bottom. Sites like Upwork and Fiverr benefit those who are hiring because they force freelancers to compete on price. And let me be crystal clear about this: Competing on price is a zero-sum game. You will always be the loser. There will always be someone who will offer to do the work for half your rate in half the time, regardless of whether the product is garbage.

Upwork is the biggest con going. Trust me, you can build a legitimate freelance career without having to devalue your work or deal with a middleman taking a princely cut.

Okay, whew. Digression over. Let’s get back to business.

1. Decide What You Want to Do

Don’t freak out. This isn’t a lifelong commitment. For my first two years of freelancing, I only did social media projects until I woke up one day wanting to tear my hair out. I was good at social media strategy, but I hated social media strategy. That’s when I realized that just because I’m good at something doesn’t mean I need to do it for a living.

But don’t feel bad if you have to take gigs you don’t want at the beginning or during droughts. Sometimes you don’t have the luxury of being picky. I’ve taken on projects because, at the end of the day, I had bills to pay.

Now, get clear and specific about your goals by asking yourself the following questions.

What do you want to do?

Decide on the products/services you want to offer. Let me share three magical words with you: multiple revenue streams. Generating income from various sources not only minimizes the risk of not getting work, it also diversifies your work. Your ideas are fresh and you rarely get sick of what you do. I have five streams going right now: strategy work, 1:1 coaching, writing, performing audits (i.e. I tell you what’s wrong with your business), and products/courses (coming in 2019). All of my work comes from my experience in storytelling and marketing, but I’ve chosen different ways to use my skills to make money.

Who do you want to do it for?

Visualize your dream client. And no, your dream client isn’t just someone who pays you on time, although that is certainly dreamy. What kind of business are they in? How large is the company? What are the company’s values, and do they align with yours? How does your client value you? For example, I’ve shifted my model this year to use my 20+ years of experience to help women-owned businesses and POC/marginalized business owners. The majority of my clients are small to mid-sized companies, and they view me more as an integral partner than as a vendor. These businesses aim to create products and services that truly meet the needs of their customers. They operate from a place of honesty and integrity, which aligns with how I want to live my life.

Why do you want to do it?

Yes, we all want to make money, but that goal isn’t self-sustaining. After a while, you’ll realize money is a thing, but not the only thing, and then you’ll risk being resentful of the work you do. Do you have big dreams of leaving the world in better shape? Do you have a skill that would truly help and transform other people or make their lives easier? A sense of purpose can be a constant motivator.

Where do you want to work?

Does your work have a geographic component? Where are most of your ideal clients located? Do you want to work virtually or one-on-one with people, in person?

2. Validate Your Idea

Do the research. Is there a demand for your work? What are people paying for it? Make sure you price yourself wisely — there are scores of online calculators that can help you figure out your rate. Determine if you want to be paid by the hour or by the project. I could write a whole piece on

hourly vs. project, but for now, I’ll just say that at this point in my career I only do project rates.

3. Shout It From the Rafters

Tell everyone you know that you’re freelancing: your mom, your best friend, your dog, the barista at Starbucks… you get what I mean. Work can come from anywhere, but no one will offer you work unless you announce that you’re looking for it. I routinely send brief emails to my network outlining the kinds of projects I’m taking on and asking if they or someone they know is looking for a bomb-ass consultant. Email everyone in the free world: Do you need help? Do you know anyone who needs help?

4. Work Your Network

I’m a shy introvert. The idea of networking gives me palpitations. I used to go to networking events and just stand in a corner — the only thing that was getting worked was my cheese plate. But don’t worry: You can expand your network without being smarmy about it.

Join private Facebook and LinkedIn groups related to your industry

Connect online with people who run in similar industry circles. Why? Because who doesn’t want support — a place where you can field questions, punt ideas,and help others. Here are two more magic words: overflow referrals.

The more people you have in your corner, especially if they’re good at what they do, the better; you’ll find that work gets shared. I’ve seen countless freelance gigs posted in the Dreamers // Doers Facebook group, as well as a ton of other groups. I’ve also made a few friends online and those relationships have scored me projects.

Work your contacts

I have a philosophy that if I don’t like you, I can’t get on the phone or spend time with you. I want the time I spend with people to be gratifying. Have coffee with your peers. Schedule Skype/FaceTime dates to talk shop or buddy up with a peer for ongoing mutual support as accountability partners.

Ask your friends for specific introductions to people in their network, but don’t be vague. Don’t just say, “Can you hook me up with someone in your network?” Rather, say, “Do you know someone in nonprofits who works in social media marketing? I’d love to hook up with them for [X reason]. Could you make an intro?”

A key point: Never ask for or make blind introductions. Always ask each party if they want to be connected. It’s good professional etiquette and it ensures both parties are interested and not put in an awkward or compromising position.

Connect with past employers/former clients

You’re probably thinking, Oh, if they need work they’ll just know to contact me. Please stop thinking this. People don’t have elephantine memories and they’re not psychic. People can only see a few feet in front of them, so you have to be in front of them.

Reconnect with old clients or past employers and ask if they need help with something. Assess their business, sites, emails, and social channels and suggest ways you can help take their business to the next level. It shows you did some legwork and you have specific ideas on how to make their business better.

5. Be Open

Sometimes you need to get crafty because you have bills to pay. Work your revenue streams, but also think about smaller projects you can take on that will provide some quick cash. Recently, I created portfolios for fellow freelancers by pairing my wordsmithing and positioning abilities with designed templates on Creative Market. When you need cash, nothing is beneath you.

At the end of the day, you just need to find that person to hire you to do one thing. That’s enough to get the ball rolling.

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.