Must We All Be “Killing It?”


I’m an upbeat guy. I have kept at it for years, as an entrepreneur. Sometimes I feel like I’m about to hit the big time, sometimes I feel like I’m over the hill and toast.

That’s normal. Mostly, I feel like I’m going to hit it, that this year, I’ll knock ‘em out and inhabit my potential.

Thing is, that’s only most of the time. These days, there is such a bias towards positivity that if you say you had a bad day out loud people give you those pitying looks.

But the thing is: it’s hard. Of course it’s hard. It was always hard and it’s always gonna be hard. Building something from nothing takes verve, moxie, restraint, patience, balls, ignorance, knowledge, skill.

Some days it doesn’t go well.

And since we’re all social now, some days we vent. And the responses are so exhausting, “Wow, Chris, I thought everything was going so well for you.”

Because of one rough day, I get treated with the condescension reserved for frustrated six year olds or suicide attemptees.

Fundamentally, I’ve got a ton going for me.

I’m reasonably young (38). I’m smart, I’m strong. I have done everything a man can to ruin his body and I still have great health. I have great kids. I can close deals.

I can make something out of nothing.


Sometimes customers make things hard. Sometimes people fire me.

Sometimes I goof up and wind up on the wrong side of a deadline.

Sometimes stuff happens.

I don’t want to have to say “I’m killing it,” to avoid the perception of failure.

But it seems that I do because of inflation.

Gestures (A Brief Rant About Client Service)


A lot of client work can be made better by simple gestures.

You have to acknowledge and empathize in advance their issues. It’s not enough to be technically correct in your position – it could be an unfortunate circumstance that means that there is a delay, or something is less than optimal.

But the way you say it is everything, and it’s so much harder than it looks.

The Wrong Way To Handle Things

The way that places like Comcast/Best Buy deal with it is to admit nothing. Stonewall. They say things like “I’m sorry you feel that way,” or “I understand you’re upset,” as a front-line, catch all response to any circumstance.

At best, these phrases are disingenuous. A phrase like “I see you’re upset,” doesn’t really share empathy. It’s become more of a gas-lighting response to issues.

The Right Way To Deal With Customer Service Issues

So there are going to be issues that come up on a regular basis with most companies – even good ones – will have failures of effort, systems or even communication.

If you do 200 + projects, each of which has 100+ touchpoints,, then you’ve got 20,000 instances. You’ll misfire on a few.

First, don’t go on trial. Sometimes customers are truely shitty people. They are sharpshooting everything because they are (a) antsy, or (b) they’ve been burned. Or (c) an expectation that was unspoken was not met.

Trying to get them to vindicate you – in your eyes – isn’t useful. Rarely will you stand your ground and suddenly convince them of your point of view. Even if you succeed 10% of the time, 90% of the time you’ve pissed them off. This is a tough part of the issue, but it’s an economic decision. They will often make narcissistic and obtuse self-centered remarks.

Generally, it’s best to simply ignore that nonsense.

Second: tell them what to expect – and stick to it. And tell them what to expect after that, too. Sweeping it under the rug (i.e. a missed deadline that goes unspoken) isn’t a respectful way to treat customers/vendors/partners. When you’re behind just tell the truth, acknowledging the deadline issues.

Third: restate their mutual expectations. This means that you have to salvage all you can. “Sorry we delivered in red! I know you wanted blue. We can get red Monday at 4 if nothing goes wrong. I’ll call you monday morning to confirm we’re on track.

Then a question: as long as we do that, does that work for you?

An ounce of Prevention
People are generally reasonable and patient.

Even when they don’t call you on it, they know what happened. They aren’t dumb, but they don’t call you on everything.

Meaning: when you aren’t acting exactly correctly, you expose yourself to a customer service debt. That sometimes can get wiped out by overdelivery in the product (i.e. Apple has crappy customer service, but nobody minds because shiny). But only sometimes. What generally happens is an overreaction to the one thing that pushed them over the edge.

A scenario:
-your contract needs to be sent twice. Because the first version didn’t have all the details right.
-a scheduled call is 5 minutes late. Mild annoyance but nobody says anything.
-a delivery has a typo somewhere. Easily corrected. unspoken.
-you’re sick one day – the flu
-an email has a bunch of irrelevant information on it that the customer doesn’t care about. Noted.
-client is sick and can’t get back to you.

Nothing bad happens for a week or two. Then there’s a more substantial situation happens, say, a milestone slips, a detail is missed.

Then there is a disproportional client response. To the one detail.

Because they aren’t reacting to that detail at all. , they are reacting to everything – all at once- but they may only be talking about one issue at a time.

Things don’t happen in isolation.  People don’t just wake up mad-  when they hired you they had high hopes.

The solution is to make impeccable the new baseline. And it’s not complicated to do that. You just have to be realistic about your commitments, both internally and externally.

Just because they didn’t say anything


Just because they didn’t say anything doesn’t mean they didn’t notice.

They noticed you forgot to update them, you didn’t get them the email. They are aware that you missed the deadline. They are just polite. Making the best of a tough situation. Lectures don’t do any good.

We all do the same thing. They didn’t say a word about the fact that it was wrong/shabby/late or misshapen.

Nobody wants drama, but it happened.  So they pay their bill, they go on, and they quietly get you out of their lives.

The consequences to having a mediocre meal are indirect: we don’t complain to the staff. We just shake our heads, “what the hell has this world come to? Why bother if you don’t care…” and we walk out.

But they noticed, and you lost.  And that’s the hardest thing to understand. People expect lousy.  So it’s easy to exceed those expectations.  Everyone – just about – is an incompetent flake.

But they dream of competence. They yearn for it.  So instead of exceeding expectations – which have been pummeled by places like Chase and Comcast and Delta, let’s try and exceed their dreams.


Planning A Year (It Really Is This Simple)


So you’re doing business, selling something, whatever.

You want to plan a year.


Let’s show you how easy that is to plan:

Revenue (how much money you’ll earn).
Units sold (how many widgets you’ll sell)
Average Price (how you’ll get there).
Closing percentage:  (What percentage of leads you’ll close).
# of leads you need: (units/closing percentage i.e. 100 units /.50 if you are a 50% closer)
# of subscribers you need (someone on your mailing list – usually 1/10th of those become leads for agency businesses).
# of blog posts /whatever to create subscribers.

That’s it.  That’s the soup-to-nuts version of how you do this stuff.  It’s easy enough to plan.

When you sell different things, like “cheap things” and “expensive things,” you  may need to then recalibrate a little bit and probably have a list for each line in cases where averages won’t make sense (i.e. I sell both Maybachs and Hyundais.)

But that’s a year. Most people get addicted to the shiny and do nothing.

A different system for freelancers

One of the things that freelancers do poorly is planning.

They feel like all work is good work (it’s not) and that the client is always right (they aren’t).

What I do instead is to create inventory.  My company Simplifilm will have 108 deliveries next year, at three different prices.

Each is schedule on a date, and each is sold as a unit.
That way you have something to sell.

That way you have real scarcity. “You’ve got 40 projects to sell this year, if you want this delivery, act now.”

The Clients You Deserve



It is so scary to say no to clients.

The hardest thing I have to do is turn away people who are willing and able to spend money.

It’s always the best thing when you do.

Both short and long term.

Every time you get that spidey sense, don’t ignore it.

Work hard enough to generate enough that you can say no, so that you can earn the right to be (respectfully) choosy.

Sometimes people are in a bad frame of mind. Sometimes they are crazy. Sometimes they aren’t yet a good fit.

Say no. Do it respectfully. But say no.

Sometimes I get it. You can’t. Bills, problems.

Yes, it’s really easier to find a good client than it is to say yes to a bad one. But it never feels that way.

When have to say yes to the type money that comes with a side of crazy, you have to bear it with grace.

When you have to say yes to a client that is going to wear you out, annoy you, it’s your own doing.

Why? Because your business is in a state where you had to tolerate mediocre clients.

You didn’t EARN the right to say no to the nonsense.

You didn’t generate good things so you have to tolerate it.

Embrace it. Let the nonsense wash over you. Laugh at it.

“This is the client I currently deserve. This guys lunacy is my fault. What am I gonna do to deserve better.”

Write it down. Mitigate the damage that the current client does, and move on to the next one.