No 0059
Mar 28, 2025
Facing Discomfort
A sales call you’re going to make in a few minutes.
A tough conversation with a teammate.
An interview you’ll be making for a podcast.
The launch of a new thing.
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A sales call you’re going to make in a few minutes.
A tough conversation with a teammate.
An interview you’ll be making for a podcast.
The launch of a new thing.
There’s a special category of buyers that you can avoid.
The defender comes under many personas. The manager that’s incentivized to only preserve. The high-status, well-known individual, trying to avoid scandal. The struggling person that’s stuck in limiting beliefs. The leader with a scarcity mindset.
The consequence of a changing market is that people are in motion, and some are ready to buy. People who want progress.
We’re looking to spot their energy, their momentum, away from a situation that can no longer work. To spot their “enough is enough” moment. “I’m ready for something else now”.
You’ve heard the idea of being goal-oriented. It helps to have a goal, because it focuses your intentions, and removes your natural barriers to progress.
So let’s explore that a bit.
They say that people buy things rationally, but that’s only half true.
They say that reason alone can help you make good decisions, but that’s only half true too.
The hustler has been stealing the show.
When times are good, and there’s plenty of work to go around, you’ll be tempted to not ask too many questions of new leads, and certainly not to ask questions about your current clients. When times are good, it’s time to work.
Precision, truth, and honesty might make it hard for you to recommend a product, or a person, to someone else.
Some people hesitate to recommend because there’s a risk that it will tarnish their own reputation, as if a recommendation is a promise you make, personally, for the performance of someone else.
The entrepreneur you follow online is killing it.
The content creator you watch has been killing it too.
One of your former clients has been killing it.
And maybe you want to be killing it too.
Selling is about convincing, and convincing is dishonest.
Selling is about deception.
Selling requires ignoring the truth about the product.
Selling is about adding appeal to something that’s not necessarily a good match.
Randomness has been part of biology since, well, the beginning. Our senses became sharper from the risk of startling predators. Muscles need to be torn to be built. Bones need variations in stressors to remain strong. A tree without wind doesn’t develop its stress fibres. A bit of variability will beat steady repetition during recovery.
“Maybe I can find a dev that’ll be open to reducing their fees just for us.”
“I’ll be able to reassurance the team if I can stabilize the workload and the turnover for a bit.”
“The CEO is asking me about deadlines, and I want to set expectations.”
If you pay careful attention to your personal systems, you’ll notice that your intentions start as wishes, until you make promises, and then until you start keeping them, and then, you look at your personal systems a little differently.
You could make your product be the straight-forward product that it is. A piece of software, a physical product, an online course.
While you’re at it, you can make three other products, one further in the direction of the product, and two more in the direction of the buyer. You’d do that, of course, to help your main product sell.
You know when they say you should take pause, take stock of your accomplishments, and appreciate where life has taken you?
The entrepreneur culture is so driven to be… driven. More exertion, more effort, an obsession with focus and harshness. It’s an option.
Most of us have the wrong relationship with our doubts.
When you see your doubt as a defect to be removed…
When you see someone who is confident and you wallow in comparison…
When you see your intuition as flawed and inadequate…
From this point on, would you do something just for the money?
Say you’re now doing your best work, and someone gave you an opportunity to do something that pays well, but you’re not sure where it’s going to go from there.
As the person marketing your project, you might be comparing your approach to others who talk like this:
“This is the best thing in the world. Trust me, you’ll love it.”
“Are you kidding me? This stuff is made in-house, the best of the best.”
“You won’t believe it when I tell you how good it is.”
We’ve got some work to do with our relationships. A relation, an association with two sides, yours and the other party’s, can be in need of an upgrade.
You can upgrade it, the other person can upgrade it.
You hesitate to announce a discount on your product. You’re debating this when it’s discount season, you’re debating this when sales are low.
You hesitate because a discount cheapens the perception of your brand. It attracts the wrong kind of customer. It might seem desperate.
Too few words, and you sound transactional.
Too many words, and you sound distracted.
If the words are too big, you lose attention.
If the words aren’t big enough, you sound like sound bites.
When you’re giving your guarantee, there are downsides, but many more upsides.
When you’re requiring a guarantee, however, then there are mostly downsides and only few upsides.
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When you’re self-employed, you offer guarantees, and you stake your reputation on honouring them. There are overall few guarantees in your line of work, except the ones you offer and honour. But, honour them often and without fail, and pretty soon, you’ll get to new heights.
Maybe you launched an online course, and it hasn’t sold that much.
Maybe you tried freelancing for a bit, and it hasn’t been easy getting clients.
Maybe the SaaS you’re building isn’t going to grow organically either.
Anybody can draw. That was the claim of the book Drawing with the Right Side of the Brain by Betty Edwards. The part about the brain’s left side being more categorical, and the right more artistic, that part’s probably a myth. But the book still had a point: learning how to draw is less about learning how to draw specific shapes, and it’s more about drawing the shapes (and the shades, and the colors) that you see. Drawing is about seeing.
Imagine trying a marketing tactic that you haven’t seen people use.
Imagine offering a new client something different than what they asked for, risking getting rejected, because you think you’ve read their deeper motivation.
You’ve been brewing a change. Something, soon, will have to be different, because this time, it’s too much.
If you take a snapshot of your emotional state at this moment, it’s likely you’re feeling annoyed, some anxiety, or maybe you’re energized to take a leap. You might do nothing now, but if the problem persists, you’ll be thinking: “I need to take a bigger leap”.
There are a bunch of approaches to avoid when launching a new project. You don’t want to be silent, you don’t want to be insecure, you certainly don’t want to beg.
When you’re really good at your craft, you “have an edge”.
When you’ve achieved mastery and all your tools are at the edge of your fingers.
When you’re well-steeped in a problem, you understand all of the edge cases.
If you talk to a buyer when they’re ending a run, you’re too late, they’re just about done.
If you talk to a buyer when they’re in the middle of a run, you’re too late, they’re in the thick of their work.
Previously, you have been tolerant of your own difficulties with sales, but intolerant of your chops with coding.
Tolerant of being on the side of employment, but intolerant of not having interesting challenges in what you’re building.
Here’s a story of someone wanting progress.
A freelance designer feels like their craft is changing too fast. All of a sudden, the crowd is moving to use new tools, and new practices.
Somebody might give you a compliment, which is free, but if your self-image isn’t great, you won’t receive the compliment. But working on your self-image is not free, it bears a huge cost. A compliment, for some, is far from free.
Every new year, I can expect a slow period in my freelancing work. January and February end up being a great time for personal projects. Usually, the slowdown is short. Nothing to be feared.
“If it doesn’t make money, it’s not a product, it’s a project.”
“You have to be ready for some gruelling months with a slow climb.”
“Build it and they will come, that doesn’t work. You have to dedicate half your time, maybe more, to marketing.”
There’s a way to prepare for a scary sales conversation that resembles the world of user interface (UI) design.
Before UI designers can know whether a screen will work for their preferred users, they’ll navigate their choices, they’ll create prototypes, and then they’ll iterate.
It seems that without conviction, nothing would ever get done.
With conviction, though, you might overdo, underdo, or do the wrong thing entirely.
“I’m convinced that with more efforts, I’ll get more sales.” Maybe. Maybe you should not depend on those sales and put your effort somewhere else. The sales will be a side-effect.
When a person starts following you online, it might not be a good time to try to sell your product.
When a person asks you a question on your online forum, it might not be a good time to try to sell your product.
There are plenty of generalist software devs on the market. And we’re told, that’s not such a great idea.
“You should specialize. You should clarify your positioning.”
And so these software devs start to specialize. “I specialize in domain modelling.”
The culture of business comes with some strong, polarizing beliefs.
“You must maximize your revenue, any way you can.”
“It’s a game, there are winners and there are losers.”
“Attention spans are at the lowest they’ve ever been.”
“It’s a cut-throat market.”
“You should specialize.”
“No. You should generalize.”
You can sell a $59 product, but if you depend on it for your livelihood, you’ll need to sell a lot of them each month.
You can sell a $5,999 product or service package, and maybe you can sell one or two per month and you meet your minimums.
There’s a common belief that many people have about learning. It might be common, but still, it’s invisible.
It goes like this: “To learn is to pile on more learning on top of the old learning.” Put differently: “Learning is an additive process.”
To visualize what happens when someone buys a product for the first time, it helps to think of someone making a hop.
There was a before, the “before” side of the hop. And there was an after, the “after” side of the hop.
The thing about a brain paralyzed by thoughts is that it is stuck in beliefs. And one belief surely stands out among others:
“I am my thoughts.”
The thing about a belief like that, is that it is completely invisible to you. It lies below the surface. It’s like a lens that colours your vision, like a pink-coloured lens or a green-coloured lens, and you don’t know that your perception is changed by that belief. That is, until you shed light on the lens, and you take it out or swap it for a better one.
The white sticky tape doesn’t look like the drill bit.
The massage oil doesn’t look like the bottle of wine.
The expensive pen doesn’t look like the metal watch band.
Starting something new, for me, has always meant being comfortable with the number zero.
Zero new subscribers to the mailing list.
Zero new followers.
Zero retweets.
Zero sales.
The first zero you get is expected. The second zero feels wrong. And the tenth you get is bad news. You will get a zero that you categorize as “the worst”.
When putting together a freelancing service, or a consulting offering, you can offer different options, and each option can be a package of value. Let’s define a few of the ways your clients might define value.
Say you’re launching a new piece of software. You’re thinking of all the quality variables you can optimize for.
You optimize for the quality of the visuals, the edge cases, the robustness to a variety of uses. It should be like this, it should do that. It has to accommodate users like these. It has to have more features.
The other day on Twitter, a guy mentioned that he had trouble with overthink, that his mind was often on overdrive.
I replied. I said that often you think you should think less, but instead I think we should focus on thinking better.
Today’s attention spans are short.
Shortest they’ve ever been.
So you better make your point.
Better keep it short.
A little like these paragraphs.
These short paragraphs don’t feel too good, don’t they? Something feels off. Is it that they’re too short? Curious, because when we read poetry, we’re used to shorter lines. But those lines don’t rhyme, that must be it. Maybe. How about this: those lines feel manufactured, trying to make a point, and your mind is distracted by that effort. Whatever the reason, your mind noticed the flaw. You should keep things short, but not like this.
You can be uncertain about a project. You can be uncertain on the details of the future of a product’s success. You can be uncertain about the side-effects of your business decisions.
If you want to build a software product like everyone else, make a landing page, show features, show the benefits, maybe highlight the outcome.
But if you want to go beyond, you can go in these two directions:
Being a beginner at anything feels about the same: you feel like you don’t master any of the important aspects, you feel like you’re out of your depth, you feel like somebody has the truth, surely not you.
A home owner bought something completely unexpected, something they weren’t thinking about buying even a week ago. While they had been spending weeks looking at the market for bigger houses, they bought two pairs of high-quality headphones to watch TV late at night.
This article contains spoilers.
BBC’s modern re-telling of Sherlock Holmes had me hooked. Here we had Holmes (Benedict Cumberbatch) and Watson (Martin Freeman) meeting in the smartphone era. Instead of sending telegrams from Baker Street, Sherlock flung texts from London Black Cabs. He used social media to sway cases to his advantage, the Internet to do his research.
The car salesman. The type of salesman I told myself I’d never turn into. The type that uses pressure and misdirection to make every sale. Aggressive. Determined. Sleazy. The hustler.
A friend of mine, a software engineer, took a bit of a detour from his career path. After making a good buck from a stint at a large tech company, he decided he’d take up acting for a bit. Completely different mind exercise, and that was the point. He needed to explore new parts of himself.
We’re spoiled that we can learn from some top-notch productivity principles.
Here’s a list.
Getting Things Done by David Allen taught me about always identifying, in a project, the immediate next step.
“$99 a month! Whoa that’s expensive.”
“You find? But you’re going to make a few hundred more per month just by using this tool.”
“Yeah, maybe, but still, I’m going to have to pay this amount every month.”
To beat doubt, there’s little point in trying to create confidence.
That’s because you could say that doubt and confidence are two sides of the same coin. The coin of “results”. They both grow from prior conditions—you can manufacture neither.
If you’re creating something for others, there’s going to be a strong pull to publish only the best you can make.
That’s a bit of a mistake.
That’s because the best products are awful at many things. They’re awful at all the things they’re not meant to do. And they might only be good enough for the thing they’re built to do. And yet, they’re bought, and they’re used, and they’re raved about by the buyers who tell others.