Move Into Advisory Services Work

I’d like to help you learn how to generate leads for advisory services

My Indie Experts email list is a place where I do that. If the transition from getting paid for implementation to getting paid for your advice is interesting to you, please join. Two ways to get this insight:

    [Indie Experts] Same market; two sizes

    The exact same market could have two different effective sizes. Why?

    This is false if we think of a market size in terms of demographics: number of companies, etc.

    This is true if we think of a market size in terms of opportunity.

    Two different businesses could be focused on the exact same market but have access to very different amounts of opportunity because they have different levels of expertise, different services offerings, and so on.

    The exact same business at two different points in its growth and maturity could be focused on the exact same market but have access to very different amounts of opportunity because the more mature, sophisticated version of that business is better at identifying, pursuing, and winning opportunities that might have been there all along, but the less mature version of the business simply couldn’t see those opportunities.

    The smaller your focus; the bigger it is.

    Meaning that in most markets, a narrow disciplined focus will lead to increased opportunity over time.


    [Indie Experts] You can’t win. Or can you?

    If you ever want to read a short, enjoyable biography of an actual hobo, I recommend “You Can’t Win” by Jack Black (no, not that Jack Black): You Can’t Win

    It’s a wonderfully interesting read, and I’m close to placing it on my “recommended reading for small business owners” list. Oh, and Wikipedia says it’ll be a movie soon-ish.

    Portrait of Jack Black by Edward Weston

    This “you can’t win” idea keeps popping up on my perceptual dashboard.

    Bill Callahan recorded a wonderful cover of a Kath Bloom song, “The Breeze/My Baby Cries”. There’s this passage from the song:

    “Yesterday I talked with my father
    He said that we could never win
    It’s so hard to tell
    Where I end
    And my father begins
    So if you see me passing by
    Please hold me deep in your heart”

    • • •

    What constitutes winning?

    I think there are multiple valid answers, and a variety of contexts in which winning might look different.

    For me, in the main, winning is maintaining a healthy average velocity. IIRC, I picked up this lovely way of phrasing it from Shane Parrish.

    This defines winning based on inputs that I have more control over rather than outcomes I have less control over. I like that. It’s goal-setting 101, but good to remind ourselves about this anyway.

    What does winning look like for you?


    [Indie Experts] Specialization workshop – sample video #2

    Registration for the specialization workshop closes tomorrow.

    Here’s another one of the workshop’s videos for you to sample:

    The details:

    Workshop purpose: The pivotal moment in the specialization process is not making the decision, it’s getting the first feeling of traction as a result of the decision. That moment is what fuels the determination and resolve that are critical to a good implementation of the decision. That first feeling of traction energizes you for a good implementation of your specialization decision.This workshop is about getting to that feeling of traction.

    Price: $700 per seat, 4 seats available at reduced or no-cost scholarship price.

    Meeting time: Weekly at 10am to 11:30 am Mountain time on Fridays, from May 15 – July 3.

    Approach: Experiential learning. 20% concepts, 80% application of those concepts.

    More details and signup form here:


    [Indie Experts] Cutting

    I have learned a few things about cutting hair in the past few months.

    For example, I have learned that if you cut away everything that doesn’t look like the haircut you want, you might — just might — get the haircut you want.

    (I don’t know what the back looks like, but my wife hasn’t said anything, so I assume we’re all good there.)

    Specialization can work the same way: cut away everything that doesn’t look like the business you want.

    This kind of cutting can be difficult. OK, let’s be honest; it can be terrifying. “Will there be any kind of business left after I cut away the stuff I don’t want?”

    The validation we do in the specialization workshop (80% of the workshop time!) helps with this kind of fear.

    The first workshop meeting happens this Friday, May 15. I’ll take registrations up until Wednesday, then I need to cut those off.

    Sign up here:


    [Indie Experts] Getting it right

    “Real truth about it is, no one gets it right

    Real truth about it is, we’re all supposed to try” — “Farewell Transmission”, Songs: Ohia

    There you go. The core of a pretty good philosophy of business from the brilliant, depressed alcoholic musician Jason Molina, who literally drank himself to death: No one gets it right. Try anyway.

    Jason saw something true about human life; a double bind we’re all in. We won’t get it right — none of us — but we’re invited to try anyway. We’re all supposed to try.

    There’s a mindset that helps immensely as we navigate this double bind: self-forgiveness. The third ideal of The Expertise Incubator is based on self-forgiveness:

    Ideal #1: Anything you create in this program should be good enough to spread by word of mouth alone.

    Ideal #2: Anything you create in this program — if you give it away for free — should be good enough that some would gladly pay real money for it.

    Ideal #3: You should be willing to work daily for 2 to 3 years to make ideals 1 and 2 become true in your work. In other words, you should be OK with not living up to ideals #1 and #2 at first so that you can build up the skills you need to ultimately achieve those ideals.

    Self-forgiveness helps, as far as mindsets go. And there’s a method that helps too: iterative experimentation in the wild.

    Experimenting in a lab is good, but it brings with it the requirements for scale and control. Lots of data, with extreme levels of rigor and control applied to the sampling; control of the environment through literal control by working in a literal lab, or statistical control for bias and other sampling errors. This level of rigor routinely delivers scientific breakthroughs, but small business breakthroughs tend to come from other approaches, namely: listening to the market, small high-value experiments, and iteration.

    The upcoming workshop will help you run a small high-value experiment around specialization. Not in a lab, but out there in the world.

    I’ve started to get the videos for this workshop back from my editor, and I want to share a few of them with you.

    The workshop is really about taking action, but the lecture videos (there is generally one lecture video per week) help you get a sense of what the workshop is about.

    Here’s the first one I’ll share with you:


    BTW, if you are curious about the content of the upcoming third edition of The Positioning Manual, the video above is a pretty good 1-hour summary of that book’s argument.

    Back to the workshop…

    The first workshop meeting is a week from today (Friday, May 15), so if you want to participate in this workshop, sign up here:

    If you might want to participate but have questions, hit reply and we’ll figure it out.


    [Indie Experts] No-BS Amazon launch info?

    Hey, does anyone in the hallowed halls of this email list have a recommendation for me?

    I’m looking for ideas, guidance, or expertise on doing a good job of launching a book on Amazon. I’m not interested in “game the NY Times Bestseller list” approaches (Tim Ferriss), or information that’s theoretical, or information that’s overly slanted towards non-fiction titles. This will be a DIY thing for me, so I’m not looking for expert consulting help, but expertise packaged and made usable by non-experts.

    Thanks for replying with any pointers you might have!


    [Indie Experts] Embrace them constraints, y’all

    There might be something good over the horizon if you do.

    The unflinchingly commercial message you are HERE FOR: Lest you forget that I sell services, let me remind you that there’s an online workshop on specialization coming up. It’s 20% concepts, 80% market validation test. Starts May 15. Details:

    Pitchfork — the notoriously demanding music review site — recently gave out a perfect 10 for an album, for Fiona Apple’s latest album. That’s rare (if you need a summer stay-at-home project, you could do a lot worse than listening to every one of “Pitchfork Perfect 10’s”: I get goosebumps just reading over the list.).

    A Pitchfork reviewer gave out a 9.0 for Andrew Bird’s Bowl of Fire’s, The Swimming Hour back in 2001. It’s not a 10.0, but it’s pretty much a glowing review. You’d think that would be some kind of golden ticket to success.

    Well… Wikipedia picks things up from there:


    In 2001, the Bowl of Fire released their third album, The Swimming Hour, a dramatic departure from their previous recordings. It featured a mixture of styles, from the zydeco-influenced “Core and Rind” to more straightforward rock songs such as “11:11”. Due to this eclectic nature, Bird has often referred to it as his “jukebox album”. Although gaining critical praise (The Swimming Hour received a 9.0 from indie music website Pitchfork), the band failed to attain commercial success or recognition, playing to audiences as small as 40 people. In 2002, Bird was asked to open for a band in his hometown of Chicago, but fellow Bowl of Fire members were unavailable for the date. The reluctant Bird performed the gig alone, and the surprising success of this solo show suggested potential new directions for his music.

    Early solo career (2003–2005)

    The Bowl of Fire unofficially disbanded in 2003, and Bird went on to radically re-invent himself as a solo artist.



    Did you catch that? “Critical praise” blah blah “9.0 from Pitchfork” blah blah “audiences as small as 40 people”?!?!?!

    I hope whatever heights of success you’ve reached in your career, hearing stuff like that keeps you humble. And likewise, whatever challenges you’re currently facing, I hope it keeps you inspired and moving forward.

    Andrew Bird is not Justin Beiber, who has more songs in Spotify’s Top 100 most-streamed list than any other artist. But Andrew Bird has a solid, productive career, and he creates music that is unique and enjoyable.

    Some of that success surely comes from reluctantly performing a gig alone in 2002, without his backing band (crutch?), and then following where that constraint led him.


    If you’re interested in the upcoming specialization workshop but have questions, please let me know. Just hit reply.

    [Indie Experts] The question stops here

    Jim Thornton is on fire right now.

    (You can listen to me read this email out loud here:

    You don’t need to call 911. I just mean some of his recent posts are on fire.

    And they’re personally for me, I don’t know if they’ll hit you the same way. But if you publish a lot and see yourself as cultivating self-made expertise by doing so, you’ll probably find his recent posts as useful as I have.

     • • • 

    Vickie Thompson ignored me so hard it hurt in the 7th grade. I’ve done the same with Google and SEO in general, except I don’t think I’ve caused Google any pain at all by doing this.

    At the same time, I’m committed to understanding how self-made experts can best earn visibility and trust. So if there’s something out there that can be of use to a self-made expert business, then I have to understand it.

    My effort to have this kind of objective understanding of search engine optimization has been clouded by a stereotype.

    This stereotype is well-described by almost any article online that talks about the so-called “skyscraper technique”. One such example (the top-ranking one in the search I just did!):

    An excerpt:

    Here’s how it works: You start by researching popular trends, topics, and already well-received pieces of existing content across the topic areas your business typically covers. Then, you look for new and unique ways to create content that communicates a similar message — with a twist. This might mean that you leverage a new, more engaging medium, update the statistics, or employ a better design.

    Once you’ve created a new and improved piece of content, reach out to the folks that have already linked out to similar content to put your piece on their radar … and hopefully earn a link.

    There’s a lot of ways expertise works, and all of them ain’t that.

    There’s not just one way self-made expertise operates, but in general, one or more of the following are true:

    • The expert seeks the overlap between risk and business impact
    • The expert shapes a market rather than chasing the market
    • The expert explores a focused topic more deeply or rigorously than others have
    • The expert knits together an assortment of ideas more interestingly or usefully than others have

    None of those approaches to expertise remind me of the skyscraper technique, which I tend to think of as the tail wagging the dog. That’s fine, but the problem is that I have let the skyscraper technique — and my negative feelings about it — start to serve as a proxy for SEO in general. That’s a stereotype.

    One of the ways Jim’s thinking has been so helpful for me is by breaking this stereotype.

    Here’s an example, from a recent email Jim sent his list:

    You want to help your audience transform. You seek to elevate a client’s status to the peak of their desired outcome.

    But today, they are focused on reworking their twitter bio. And so they run a Google search, “how to write a twitter bio.” You see that you are getting traffic for related terms on a “best twitter bios” post.

    For you, the easy thing to do is to turn your nose up at that. Go back to focusing on deep insights.

    If you instead you asked: what is true about these people right now? Where is their mind? you could better bridge that divide.

    The user needs help with their… twitter bio?

    That agitation is like the neck pain from your hip flexors being too tight.

    The underlying intent of those users is wanting to portray themselves effectively and appropriately in public.

    The underlying issue? Maybe its a communication problem, a positioning problem, a confidence problem, or maybe they just want to be done with it.

    Go deeper and it’s because they don’t know themselves. At least not in that context.

    But you can’t write a post on how to know yourself to solve for people looking for twitter bio help.

    Google won’t get it. Even if Google connects those 5 dots, the user certainly won’t get it so they aren’t clicking that result. They aren’t ready.

    They just want their to do list to show new twitter bio done for the day.

    Jim is very helpfuly and effectively reframing things here.

    I’ll paraphrase what he’s saying here, and has said in other recent emails: Google can do two things for experts. 1) Provide hints about the questions their audience is seeking answers to and 2) Route audience members from to your answers to those questions, if you will get off your damn high horse and make it possible for Google to do so.

    I still see the skyscraper technique as the tail wagging the dog. I see it as ineffectively crowdsourcing the leadership that experts should be handling on their own.

    To paraphrase the sign that sat on President Truman’s desk: “The question stops here.” That’s the mindset self-made experts should bring to their area of focus. This mindset combined with disciplined execution over the course of years leads to real authority in the marketplace.

    I still see Google as a business with a lot of power. Just like I probably accidentally kill a few insects every time I go on a hike or drive in the car, Google accidentally kills businesses all the time, just from making small adjustments to how they handle search. So I still see heavy reliance on Google — or any other Super Aggregator — as a liability to be avoided.

    But thanks to Jim, I no longer see the skyscraper technique as a good representation of what SEO is.

    Instead, I now think of SEO as, first, noticing the hints Google provides — hints about the questions my audience is asking — and then combining those hints with my own insight into my audience. Google’s firsthand knowledge of search behavior combined with my firsthand knowledge of actual people.

    • I think of those questions as ones that some audience members would like a quick transactional answer to.
    • Other audience members intend to take self-directed action on the answer to the question, and for them I’d like that action to be effective.
    • Yet other audience members are happy to work with a guide; perhaps by joining an email list, or perhaps by paying for that guide’s services.

    After I’ve noticed those hints, there’s the task of making my answers to my audience’s questions accessible. The more I make them accessible to audience members in a simple, easy-to-discover way, the more likely Google is to route potential audience members from to my answers to those questions.

    This idea of accessibility is the other big reframe that Jim has effected in my thinking.

    I’m grateful for it.

    Read more of Jim’s writing at

     • • • 

    REMINDER: I’m running an 8-week online workshop on specialization, starting May 15. The price is $700 per seat, and attendance is capped at 20 (4 seats are available on a reduced price scholarship basis). My workshops teach you what you need to know, and then push you to take action. Most of the learning comes from the action you take in those 8 weeks and beyond:

    [Indie Experts] What’s the pH level of this decision?

    The pH level of any business decision is probably lower than you think.

    (Listen to an audio version of this email:

    By the way, I’m making a hilarious dad/science joke here, even though I’m neither a dad nor a scientist.

    The “pH level” of a business decision is the potential for harm inherent in the decision. The potential for loss or harm is one component of risk; the other is the uncertainty involved in the decision.

    With most of the folks I work with, the potential for loss/harm inherent in the decisions they make is pretty low, at least if you step back and look at it from a global, your-entire-life perspective.

    If a business doesn’t make it, you can probably get a good job instead, or work for someone else for a stint before you get back into the self-employment game.

    If a client works out badly, you can fire and replace them.

    If the market rejects an attempt at specialization (which they do by ignoring you harder than that high school crush who helped you understand how deep the unrequited love rabbit hole can go), you can experiment with other specialization options.

    The act of specializing begins with a decision about focus. Where do you want to focus? You could focus on a target market, focus on type of problem you want to solve, focus on a type of change you want to effect, or focus on a specific and possibly unique way of delivering your services. There really are only 5 fundamental ways you can specialize.

    After you’ve made the decision about where to focus, you apply time and discipline to grow this seed of a decision into a desirable market position.

    The decision about how exactly to specialize is the seed, time and discipline are the nourishment that seed needs, and the plant we see growing out of the ground after some time passes is the market position.

    Seeds are small and inexpensive compared to what they can become.

    When a seed takes root and turns into a sapling, you become willing to invest more resources — water, fertilizers, weeding, pruning, that kind of thing — into its care and future potential.

    Because seeds are small and inexpensive, they give you freedom to experiment.

    The upcoming workshop on specialization, starting May 15, is this kind of experiment. You’ll spend 2 weeks figuring out what kind of specialization seed you want to experiment with planting, and then you’ll spend the rest of the workshop getting and interpreting feedback from the market.

    Depending no how you look at it, this workshop is both high and low risk.

    It’s possible the market will ignore your specialization experiment harder than Vickie Thompson ignored my awkward attempts at love in the 7th grade. This is the high-risk part, kind of. It’s uncertain that the workshop will lead you directly to a specialization that the market wants. At the same time, the potential for harm (the “pH level” of the workshop) is quite low. After all, we’re dealing with inexpensive seeds here.

    Even if the market ignores your specialization experiment, you’ll get hands-on experience with an validation method that you can use repeatedly on your own. This is the low-risk part. Low uncertainty and low potential for harm.

    The workshop price is $700 per seat, and attendance is capped at 20 (4 seats are available on a reduced price scholarship basis). Sign up here:


    [Indie Experts] “Zoom and Skype” followup

    Regarding the recent “Zoom and Skype” email…

    Retail is a good example of a vertical that’s polarized by the coronavirus. Right now it’s all disruption and chaos, I imagine.

    But the response within retail to the extreme systemic distress of physical store closure is where the polarization will happen. The responses will happen along a spectrum from doubling down on what used to work to innovating.

    Innovation won’t automatically work. Doubling down won’t automatically not work. There’s risk (uncertainty and the potential for loss/harm) in both approaches.

    Both approaches benefit from expertise.

    I’m certain that the world’s MBA programs have supplied us with lots of knowledge that’s been refined into expertise to help with cost-cutting and increasing efficiency and squeezing ever more blood from the turnips of existing retail business models.

    I’m naturally attracted to a different sort of expertise; the sort that can, for example, innovate around new uses for retail space that are more socially valuable than depressing laser tag arenas or haunted houses.

    Kevin Hillstrom’s recent email, “Kara… The Future of Retail” is a delightful example.

    I don’t know Kevin personally, but he’s an interesting self-made expert.

    If we remind ourselves of the POVSpace map I use with self-made experts, we’d map Kevin as a pedigreed insider arguing from data, using a somewhat disruptive style, but focused on optimization.

    Recently, though, he’s been talking a lot about transformation because, well, what other option is there for his clients in retail?

    What does it mean for an expert like Kevin to be “right”? Before the coronavirus pandemic drew its grim reaper scythe from the folds of its moldering, black cloak and started to lay waste to the retail vertical, being “right” could look like arguing for easy optimizations based on good data, or extensive experience.

    But now…! We’re reminded of this line from Chef in Apocalypse Now:

    “I used to think if I died in an evil place, then my soul wouldn’t be able to make it to heaven. But now, fuuuuck. I don’t care where it goes as long it ain’t here.”

    Being “right” as an expert serving the retail vertical now looks a lot more like inspiring directionally-correct action to help your clients get anywhere that ain’t here, and guessing a lot as you do.

    It’s been really great to see Kevin respond in that way, as we do in his “Kara… The Future of Retail” email. An excerpt:


    Do you know who causes us to visit a store in the future? Kara!!

    Kara is the person who provides a safe work environment. Been in Target recently? Kara is everywhere with a squirt bottle of disinfectant. Kara makes sure there are wipes for the shopping cart. Kara is stocking shelves at 2:30am.

    Kara is also making $12/hour today, and that’s going to change, because Kara is about to be appreciated for how invaluable she is.

    In three months will you trust Conrad, the lone employee left at Macy’s, or will you trust Kara, the personal shopper you call because you need a bluetooth speaker solution for your bike and she recommends this item (click here) … not only does she recommend it to you via text, but she tells you to be at Best Buy at 11:15am … just drive up and she’ll run it through checkout for you and will put it in your trunk. Easy!

    Yeah, Kara will do all that for you. And you’ll pay Kara a modest $5 concierge fee that Best Buy will allow Kara to keep all to herself, because Best Buy is going to need to make a ton of gross margin dollars going forward. All of a sudden Kara is making $40 an hour. Think other people will want a job like Kara has? Think you’ll have a competitive advantage that will allow you access to the best labor on the planet?? Everybody wins.



    Again, I’m using Kevin as a stand-in for self-made experts in general here.

    Is Kevin “right” about the future of retail?


    Is he serving a vital function in improving the condition of the vertical he’s focused on?


    If you follow Kevin online, he’ll regularly remind you that he has services that you can buy. This is marketing.

    You’ll also notice that he uses his presence with and connection to the market to help shape the market. This is a characteristic of brand marketing.

    Direct response marketing uses the lagging indicator of data to chase markets. Brand marketing uses presence with and connection to the market to generate insight that helps lead the market someplace better. Like Kevin is trying to.


     • • • 

    REMINDER: I’m running an 8-week online workshop on specialization, starting May 15. The price is $700 per seat, and attendance is capped at 20 (4 seats are available on a reduced price scholarship basis). My workshops teach you what you need to know, and then push you to take action. Most of the learning comes from the action you take in those 8 weeks and beyond: