• Avoid failure, study success

    The best way to build a business — a sustainable business, the kind that makes money every month, that pays your bills, that empowers you to live the life you want — a business that grows reasonably over time, and has a stable base… is to not fail.

    That’s it. That’s the secret. To succeed, don’t fail.

    I could waste a lot of words here talking about what failure is and isn’t, why the startupsphere is obsessed with it — but I cut those out of my draft because it doesn’t matter.

    The simple fact is:

    Success comes from avoiding the many potential failure traps along your path.

    Success is, in a very real way, a game of survival… attrition, even. If you can route your way around the traps where ambition-ending failure happens, you’ll make it.

    And, counter-counterintuitively, the best way to avoid those failure traps isn’t to study failure, but to study success. To figure out how people make their projects survive, long term. To learn the outlines of what just about always works.

    Because, when you look at them architecturally, all successful businesses have a lot in common.

    Call it the Amy Karenina Principle: Successful businesses are all alike; every unsuccessful business fails in its own way.

    So let’s take a good hard look at the architecture of successful businesses. I’m not talking the glittery superficial stuff, like the type of product, design, branding or naming, domain name length, target market/niche, the hours or ways they work, kind of founder, or even “company culture,” whatever that means.

    I’m talking the irreducible core.

    The template. The framework. The foundation.

    What do all profitable product businesses have in common?

    I’ve spent a lifetime thinking about this, studying this, teaching this, and experimenting with this.

    Here are 7 major success principles I’ve found, plus 1:

    1. Every business that exists to sell a product started and finished a product.
    2. Every product business that makes sales is able to charge for and deliver a product. They created it, finished it, shipped it, with a price tag, and the infrastructure to exchange money for goods and services.
    3. Every business that consistently makes sales has created a product people, who spend money, are willing to pay for. They don’t waste time trying to sell to people who aren’t interested.
    4. Every product business that makes a profit earns more money than it spends. That means the pricing is right. The product delivers more value to customers than it costs to build, sell, service, and grow.
    5. Every product business that is consistently profitable grows profitably, often, ultimately, through word of mouth from happy customers; they don’t over-leverage themselves by spending ten times the Lifetime Customer Value to acquire new business.
    6. Every product business with happy customers, that spreads via word of mouth, designed a product customers need and want.
    7. Every successful large and complex product started as a smaller, simpler product and evolved, in the market, over time.
    8. Bonus: Nearly every business that is successful and profitable with a large suite of products started with one product.

    This is the simplest possible framework for success: Eight pillars that every sustainably profitable product business has in common, or at least had in common when they became a sustainably profitable product business.

    To succeed, you must build these core pillars for your business, with your process.

    But — and this is key — you don’t have to copy, and you shouldn’t. Nobody is dictating to you what form those pillars must take, or how to build them. These eight pillars offer an almost infinite range of possibilities, style, execution, format, flavor. So much room for activities!

    Naturally, there’s also lots of room for you to make mistakes on the way.

    But so long as you end up with a finished product you can launch and operate, that people want and need, that people are willing to pay for, which is affordable to run, and which can spread by word of mouth…

    You can’t fail.

    You will eventually succeed.

  • What *is* failure, anyway?

    What is failure, anyway?

    This is a question you’ve gotta ask, because while it’s talked about constantly, it’s so rarely defined, even while being praised and excused.

    Failure is more than just a setback. And failure certainly isn’t just “less success than you’d like.” Those are simply the impermanent but inescapable outcomes we all experience from living in an imperfect world, and being imperfect people.

    Failure is so much more final than that.

    I define failure as The nonnegotiable end of an attempt. Emphasis on end. Fin. Game over.

    What could failure — an end you can’t undo — possibly do for you?

    Failure doesn’t increase your chances for future success.

    Failure may teach you valuable lessons, sure, but it also puts an end to your ambitions and it wastes your time, effort, and emotional energy. I guarantee you you could learn those same lessons in a less dramatic way, at much lower cost.

    Failure is non-deterministic.

    You can’t promise yourself, well, 1 out of 10 projects succeed, so if I just fail nine times in a row, the 10th one’ll be guaranteed to work! Failure may be a tollbooth, but it certainly isn’t dues, and it’s not a negotiation.

    The best way to succeed is to avoid failure altogether.

    The best way to build a business — a sustainable business, the kind that makes money every month, that pays your bills, that maybe empowers you to hire help — a business that grows reasonably over time, and has a stable base… is to not fail.

    That’s it. That’s the secret. To succeed, don’t fail.

  • The yips, the twisties, and Lost Skill Syndrome

    “The yips”: You’re an expert at some precise physical movement — swinging a golf club, say — and one day, your muscles rebel. You go to do a thing you’ve done a million times before, and your hand jerks — against your will — and you whiff it.

    “The twisties”: You’re a gymnist, flying and twisting through the air, and you have an innate sense of where you are irrespective of the sense of gravity (which you can barely feel) or what your inner ear tells you (bc it’s fucking confused), because you have to have it. Until one day, you don’t. You’re in the middle of a spin and you… lose track of the ground.

    “Lost Skill Syndrome”: You’re an expert, you’ve practiced, you’ve performed, and then one day you wake up and… just can’t do the thing. Like you never learned it in the first place. Only now you’re not just a beginner, you’re an anxious and worried beginner.

    I’ve learned these terms since Simone Biles famously stepped down from the team competition at the Tokyo 2021 Summer Olympics. She had the twisties. She lost her sense of where she was during a vault. She could’ve died if she kept competing.

    And I find it all too relatable.

    I’ve never been good at locating myself in space; I can’t play instruments, I quit wood turning because I yipped and nearly got a bowl gauge to the face. I had no trust in my ability to get the angle of the gauge just so. I couldn’t feel it.

    But the chaos and trauma of the last 18 months gave me the mental version of these physical syndromes. I’ll get better, and I’ll get worse again. It’s really tough and it sucks. But it’s nice to have a word for it.

  • stages of freelancing

    Stages of freelancing:

    1. The tool — you do what the client asks for
    2. The interviewer — you realize that clients don’t actually know what they want, and so you try to figure it out by asking questions and “eliciting requirements”, and then you do what the answers tell you
    3. The detective — you realize that while asking questions is still very important, you can’t trust the answers; clients say they want one thing, but what they actually want (as demonstrated through their actions + your long experience) is something completely different; you model the projects based on this assumption, trust nothing, but investigate everything, ye olde 5 Why’s
    4. The white knight — in this stage you do your interviewing and research and then, with your proposals and nudging, attempt to save the client from themselves… this sometimes comes earlier in the process but it virtually never works
    5. The hard-working cynic — you realize that work for any client is rarely if ever about the actual work product itself, but generally driven by murky personal or political motivations, and thus it doesn’t really matter what you do, but you still give the same effort to all the right steps bc you’re a professional
    6. The consultant — you accept that the client is paying you mostly to… scratch a personal itch or build a personal hobbyhorse, get resources for their department by spending their budget, or look good to their boss, or offload their workplace disagreements onto you (“hey, they’re an outsider, and…”), or cover their ass by being able to point to you and say “Look, I hired a consultant!”

    Now here’s the trick: You are your own client.

    Which stage are you at with yourself?

  • the key to overcoming procrastination? trust

    well, i did it.

    i wrote the email i’ve been putting off for ages.

    the trick to getting shit done isn’t to be a machine, or to never stumble. it’s to get back up. to prepare for your own return and make it as easy as possible.

    and trust yourself.

    the trust is really a crucial ingredient…

    try to beat yourself into submission, or bribe yourself into action, and not only will it make your procrastination *worse*…

    you also communicate, through your actions, that you believe you can’t be trusted.

    working with someone you can’t trust is horrible. it’s worse when it’s an inside job!

    if you don’t trust yourself, you won’t give yourself the things you need to succeed.

    so even if you do manage to trick yourself into doing the work, you won’t be able to do your best.

    a lack of self-trust burns energy: you have to split your psyche into two: the driver, and the horse.

    the driver monitors, goads, and whips. the horse tries to evade (and feels guilty).

    that’s a lot of energy wasted that could be poured into living and doing instead

    trusting myself means that when i avoid some task, i ask myself… why?

    maybe i don’t feel well enough to tackle it bc it’s complex.

    maybe i didn’t prepare enough.

    maybe i have worries i have to resolve.

    maybe i need something i don’t have yet.

    maybe i need advice.

    solving procrastination requires curiosity. you can’t be curious about something you don’t trust.

    even if you’re not too busy monitoring and manipulating to think to ask, you won’t trust the answers.

    sometimes the answer is “i just can’t do it right now”

    and that’s ok bc if you trust yourself, you trust you will try again

    without guilt or recriminations or avoidance, bc sometimes the simple truth is “i can’t today” and you tell it to someone who believes you.

  • Thinking about Pep

    I keep writing and deleting this and making it way more complicated than it has to be. This is my fast-casual blog! I don’t have to explain every goddamn thing to the nth degree!

    Let’s talk about Pep real quick.

    Pep is the future I see for our company: a productivity tool people will live in, do their work in. Contrast to Noko, which is a great product and a great business… but one that suffered a huge cut in the early days of the pandemic because time tracking is a work-adjacent activity, not the work itself.

    Pep is also in a holding pattern.

    Our work on Pep stalled out for lots of reasons, but the big one was feeling that I complicated myself into a design corner that I couldn’t find a way out from. I know what direction the product ought to take for the most impact. I know people want the tool I’ve described and demonstrated to them.

    But it’s an extremely sticky design problem. And I got stuck.

    It’s not something that would’ve tripped me up years ago, before my chronic illness decided to become more neurological. But now it is, and has been.

    So naturally I avoided dealing with this design problem over the past couple years bc Pep was still technically in beta, had few customers to disappoint, and I had limited energy, and more pressing issues. And because I didn’t deal with the design problem, doing anything with Pep became harder and harder.

    This is the place where most people would give up, I think.

    But I don’t do that. I either quit actively, and decisively, or I hold the door open to returning at some later date. I never just quietly give up on a project.

    I’m not quitting Pep. It’s too good.

    And now… with so many of my health problems figured out… my brain is working better than it has in a while.

    I haven’t been forcing the Pep issue with my still-pretty-tired brain, but it’s been in the back of my mind.

    Just a couple days ago, I had a breakthrough realization:

    I don’t have to solve the complicated design problem. I can simply uncomplicate it.

    Yes I can take away the major, powerful yet complicated function that’s causing problems and re-grow it more slowly and organically.

    The original core feature of Pep — the powerful recurring, auditable task engine — is enough of a selling point for early adopters.

    I can pull the process stuff, chew it over, work on it out of the public eye, uncomplicate that feature itself — take it in itself back to basics — and then work from there.

    That’s what I should’ve done from the beginning… hell, it’s what I coach other people to do. But I’m as prone to mistakes as anyone. The key is in recognizing them, and fixing them.

    So that’s what we’re going to do: Streamline Pep, and re-launch.

  • What does "audience" mean?

    I haven’t written on STB for about a year, and while that’s objectively not good, it’s also given me a lot of perspective… in the literal sense, I have a newer, different, distant viewpoint on what’s good, bad, and most crucially, missing.

    And what I’ve realized is that a lot of the essays only make sense if you already know the system I work and think in: the way business works, the way it ought to work, why people buy things, and so on. It’s usually an undercurrent and never explicitly defined. I don’t have a glossary or 101 content. And I should.

    Take audiences, for example

    Just the plain English term “audience” confuses people. Much like the word “unicorn,” I used it before it was “cool” — or, at least, adopted by a wide group of folks in the hustle culture. (I used to use it as a joke bc unicorns are a myth. Then it came to mean billion-dollar valuations. Which are, alas, very real.)

    Today everyone else uses “audience” to mean something completely different from what I do, and have done.

    Today most people use “audience” to mean “your readers/listeners/subscribers.” Emphasis on YOUR, less so on audience. The key is possession. (I call that “platform.”)

    I only ever used “audience” in the sense of group identity: “Ruby developers is an audience” — a group of folks who hang together under a specific umbrella, who share tools, ways of working, and worldviews (even if what they share is a long-standing fight about those things), who can be both studied and (for the large part) reached together efficiently.

    I didn’t use the word “market” because just because people are in a group, or collected under a group identity, doesn’t mean they’re a market. Markets by definition buy things.

    While working on this definition problem, I came up with a little nested circle chart. It’s not unlike the ones you’ll find for “total addressable market,” but I have changes…

    My view of the wide world of groups, markets, and audiences

    1. First off, there’s a much broader group of people than the so-called addressable market. However many people know they need a thing will always be much much smaller than the total number of people who could actually benefit from the thing. A tool for project management could be used by basically everyone who does anything – in every industry, and every hobby, and every personal life – but most of them aren’t interested, aren’t tool users, or aren’t willing or able to pay.

    2. The people who know they need the thing are also never going to be a coherent group identity. They probably just use the tool and get on with their lives, generally speaking. Nobody walks around calling themselves “a project management tool user” and they don’t get together to talk about project management tools as a matter of sheer interest.

    3. People who gather to talk about it online are an even smaller subset yet. They’re not necessarily power users, but they have a powerful interest (or a painful problem). They’re active and engaged. And, again, a much smaller group. Or rather… groups. Because “active Photoshop user” is also not an identity that brings people together except in a very few loose circumstances. (E.g. tutorial sites may bring in multiple groups, but they rarely form an engaged community.)

    4. Audiences are a coherent group (even if the coherency is mainly an argument). A group hangs together and has things in common. If you pre-commit to doing stuff with, say, Photoshop, you’ll have to go to identity-specific — audience — watering holes, such as digital artists, photographers, web designers, etc. That’s where you’ll learn about how people use the tools to get work done, what they value, what they hate, what they share. That’s where you can reach a bunch of these folks effectively, at low-cost, with a targeted message tailored to their specific group.

    5. Finally, your platform are people who know & listen to you. That’s your list, your subscribers, etc. You can’t create an audience… but you can grow your personal platform out of an audience. Rarely is this an identity (an exception is popular streamers, influencers, and youtube personalities, but even then, the folks who will call themselves “an X fan” as an identity is a tiny subset of the overall viewership). If your platform is scattered across a bunch of different audiences, you’re going to have a hard time persuading them with the specific messages that work so powerfully for a single group.

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