“I don’t know if I can sell strategy”

One common objection that crops up when someone starts to contemplate ditching the proposal, launching a roadmapping service (, and selling strategy is:

“I don’t know if I can sell strategy. I’m not a strategic thinker. What if the client needs strategic help on something I don’t know how to do?! Ahhh!”

Which, fair objection.

If you, for example, sell SEO services to Shopify stores and someone shows up and asks for your strategic insights on, e.g., solving the environmental impacts of their product packaging, you might struggle.

If you’re looking to sell roadmapping (and strategy) on easy mode, this is where specialization, expensive problems, and the law of raspberry jam come into the picture.

#1: Avoid Problems You Can’t Solve

See, barring some exceptions, you shouldn’t attempt to sell strategy to everyone for everything. That way lies madness and spreading yourself across a million different topics, diffusing any strategic insight you might be able to share.

The law of raspberry jam tells us:

“The wider you spread it, the thinner it gets” — Gerald Weinberg

If you have too wide of a stance with your strategy-focused service offering, you’re going to struggle to make your service and marketing resonant with your target market.

Instead, you need to make your strategic offering _ laser-focused_ on places you can provide strategic insight.

How can you do that? Three ways:

#2: Focus On Problems You Can Solve

A) You need to be specialized

If you aren’t specialized, you’re going to be selling to too many people for your marketing message to cut through the noise.

And when you’re marketing to too many different target markets, the problems people ask you to help with can get very dissonant, which leads to you working on problems you can’t solve.

Instead, you need to focus your strategic roadmapping offering (and all your marketing and services, really) on a specific target market, platform, or vertical (e.g., SEO Growth Strategy for Shopify+ Stores, Digital PR Strategy for THC and CBD Brands).

That specialized focus allows you to target the strategic problems you already have insight into solving.

What contributed to that insight? You picked it up from:

  • The years of work you’ve done in this space
  • The experience you’ve had solving problems for your clients
  • The knowledge you’ve picked up reading and researching in this line of business

All that adds up to strategic insight on a specialized, expensive problem.

But specialization alone isn’t enough.

B) You need to focus on a painful problem

You need to focus your strategic offering on a painful problem your target market is experiencing. The problem, ideally, should be costing your clients/the market time or money or preventing them from making money.

Why? Because if you aren’t focusing on a painful problem, the value math doesn’t work out for your service.

Imagine that you’re focused on sharing strategy for a problem costing your prospective clients, e.g., $50/yr. You’re charging $500 for your strategic offering to help them define a plan to solve this problem.

Why should they purchase? The math doesn’t work out in anyone’s favor.

But if the problem they’re facing is costing them $5000/year, suddenly your $500 (or $1,500) strategy-offering looks good. Invest a bit of money, get strategic insight, and understand how to approach solving this high-cost problem in a way that will make an impact.

3) You need to align your strategic offering with the implementation services you already sell

The easiest way to sell strategy on easy mode? Align it with the implementation services you already sell (if you sell done-for-you implementation services).

Let’s say that you sell rolls dice something like one of the following done-for-you implementation-focused services:

  • SEO services for Shopify Plus stores
  • Digital Public Relations for THC and CBD Brands
  • Brand and Web Design services for early-stage YCombinator Startups

If you want to launch a strategy-focused roadmapping offering, make it the precursor step to what you already sell. That might look like:

  • SEO Growth Strategy for Shopify Plus stores
  • Digital PR Strategy for THC and CBD Brands
  • Brand Strategy for YCombinator Startups

You already know that you’re successful selling these done-for-you services. So, launching a strategy-focused offering that’s a precursor step to your done-for-you implementation services aligns everything so nicely.

Some clients will show up and already have a clear understanding of their strategy.

With those clients, you can jump to the done-for-you implementation services. They don’t need a strategy (or don’t need a lot of strategy), so you can focus on implementation

But other clients will show up with a need for a clear strategy.

Maybe they need someone to define a plan for them. Or perhaps they’re searching for someone who can clearly explain the issue and the best approach to them.

For those clients? You want to direct them to your strategy and discovery-focused roadmapping offering. It’s what they need.

Putting this all together

If you want to get started selling roadmapping and strategy-focused services (, ditch the proposal, and protect yourself from time-wasting tire kickers, you need to focus on:

  • A specific, specialized target market
  • An expensive problem that’s costing your target market money
  • Offering a strategic roadmapping service that aligns with the implementation services you sell

That’s the high-level strategy, but what does the implementation look like? How do you get started selling roadmapping?

  • What questions should you ask?
  • What should you charge for your roadmap?
  • What documents, emails, templates, or resources will you need?

If you’re looking for additional perspective, guidance, or direction on how to get started selling roadmapping services, then I recommend you check out Quick Start Roadmapping.

Quick Start Roadmapping will give you the tools, resources, templates, and guidance you need to get started with roadmapping.

One bonus included with your purchase? A 50-minute video interview with Kurt Elster (of Ethercycle) about how Ethercycle uses roadmapping in their service offerings. You’ll love learning how a successful agency is succeeding with roadmapping. You can watch the recorded video interview or read the human-generated transcript.

Read more about Quick Start Roadmapping, what you’ll receive with your purchase, and the all-new ‘Quick Start Roadmapping plus Strategy Call’ bundle right here:



p.s., here’s that link one more time:

National Hammock Day

Today is a holiday. Roadmaps are excellent, and tomorrow we’ll return to our usually scheduled letters about the benefits of selling strategy — but today?

Today, I want to evangelize to you about something near and dear to my heart.

Hammock Time

Hammock Time has become one of the essential, non-negotiable parts of my life and business.

What I’ve discovered over the years is that many of my most profitable and productive business ideas happen when I’m stretched out in my hammock, watching the clouds, and just enjoying the sun and breeze. The muse rarely shows up when I barricade myself in my office with a persistent thought that, ‘if I just put in a few more hours, I’ll figure it out.’


Humans need to rest.

We are meat-computer-brain thinking machines. And like any high-powered machine, occasionally you need to flip your switch to ‘idle,’ grab a drink, park yourself somewhere lovely with a view in the sun, and just rest.

That’s why I love Hammock Time.

Hammock Time allows me to say, “You know what? There’s a lot going on right now and a bunch I could focus on, but if I don’t take a break and rest, how much good work am I going to be able to do?”

Right now, I have the hammock set up in my backyard. ~2-4+ times a week, I find myself stretched out in the hammock after a call to just idle, rest, think, and contemplate. It’s one of the best parts of my day.

  • Taking a call on my phone? Into the hammock!
  • Need a short nap in the sun? Into the hammock!
  • Need a short lay down after lunch? Into the hammock!
  • Extra time between Zoom meetings? Into the hammock!
  • Need to think about a problem/opportunity and don’t want to be distracted? Into the hammock!

Procuring Your Hammock

I suffered for years as one of the hammock-less masses. And then my buddy Eric Davis (no relation) of Little Stream Software clued me into portable hammocks.

One of the best purchases I ever made (back in 2018, ~10 years ago) was a portable hammock like this one.


If you (like me) have an internet job where your schedule is often a choose your adventure, why not treat yourself to a bit of relaxation along the way?

You could get a hammock and plop it in your yard — or put it indoors/in your office. The location doesn’t matter.

What’s important is that you’ve made space for Hammock Time for when you need it.



Build A Moat; Keep The Tire Kickers Out

Tire kickers — people who ask for proposals without ever intending to buy from you — are wasting your time and dragging down your close rates.

If you could wave a magic wand and undo all the proposals you wrote for tire kickers (who never intended to purchase anyway), your overall close rate would go up, and you’d have saved a bunch of time.

Well, we don’t have a magic wand.

And we can’t go back in time to save you from writing those proposals.

But what we can do is protect Future You from time wasters, tire kickers, and proposal writing by building you a moat.

That’s one of the reasons I love selling paid discovery and project roadmaps. Roadmaps act as a moat, protect your time, and keep bad-fit clients away.

Once you’ve launched a roadmap service offering, it’s easy to position it as the recommended (or required) way to start working with you.

That way, when a lead or prospective client asks you for a proposal, you can politely nudge them onto the track with a short message about how you best work. Here’s an example of what you could say:

Thanks for asking for a proposal. Currently, the only way I start working with new clients is with {my roadmapping service}

Over the years, I’ve discovered that my client projects are much more successful when we start our work together with a small discovery-focused project to identify our target goals and outcomes and define our ongoing strategy before writing a proposal.

Beginning with an initial discovery project is what I’ve discovered works best for my clients, team, and business. As such, this is the only way I work with new clients.

If you’d like to get started working together, you can purchase {my roadmapping service} right here (<link>). Once you purchase, you’ll receive an email with the next steps to schedule our kickoff call.

Here’s the thing

Will some people object to your building a moat, selling roadmaps, and protecting your time? Absolutely.

But what I’ve discovered first-hand is that the people who get the angriest about your moat are the same tire kickers who ask you for proposals and then never end up buying what you’re selling.

So is it a bad thing if those non-buyers end up stuck on the opposite side of your moat from you?

I think it’s a win.

After all, when you start selling roadmapping:

  • You’ll save time
  • You’ll start selling strategy instead of implementation
  • You’ll get paid for what you’ve been doing for free all along (writing proposals)

If you’re wondering how you can get started selling roadmaps (and build a moat for your business), then you should check out Quick Start Roadmapping (

Quick Start Roadmapping has everything you need to start selling, running, and delivering strategy-focused roadmapping projects for your clients.

You’ll receive the book, email templates, questionnaire swipe files, video overviews, and more resources with your purchase.

Read more right here:



Specialization Alone Won’t Get You To Where You Want To Be

Today, a thought exercise. I want you to imagine a small but growing agency (“Tiny Nibble”) and think through their specialization, opportunities, and challenges.

To start, let’s say that Tiny Nibble has specialized and niched down on a specific market and expensive problem. With that, they’ve:

  • Picked a specific target market to focus on
  • Specialized in solving a specific expensive problem for their clients
  • Developed processes for a done-for-you service to solve that expensive problem for their clients (“We specialize in solving X in just three weeks for a flat, one-time fee”)
  • Focused on optimizing their processes and delivery so they can delight their clients

Altogether, is that enough to differentiate them from their competitors? Command higher rates? Succeed in their market? Grow and thrive?

I’m not confident that it is.

After all, what’s to stop one of Tiny Nibble’s competitors from:

  • Picking the same market
  • Specializing on a similar expensive problem
  • Developing a similar done-for-you service offering
  • Optimizing their processes and delivery to delight their clients

Sure, it might take them a year or two to get traction and grow. Still, once it happens, Tiny Nibble faces a challenging situation: their competitor is now offering a pretty identical service offering for the same market.

To a buyer, what are the differences between these two providers? They provide the same outcome, have similar positioning, have identical service offerings, and look mostly the same.

Tiny Nibble has become — alas! — a commodity.

What’s the most likely end-state of this commodity competition? Well, if Tiny Nibble and its competitors have similar positioning, specialization, and service offerings, then what’s left as a differentiator?


If so, good luck, and enjoy that quick race to the bottom 📉.

Remember Tiny Nibble’s marketing message?

We specialize in solving X in just three weeks for a flat, one-time fee

One challenge that Tiny Nibble is experiencing is that their positioning devolves down to:

“We do X for a fee!”

If your messaging is “We do X for a fee!” you have positioned yourself as a commodity in your market.

And if that’s the case, it’s elementary for a competitor to come in, play the Amazon card (“Your margin is my opportunity” — Jeff Bezos), copy what you’re doing well, and steal your profits.

How can you differentiate yourself from your competitors?

To stand out in a crowded/competitive market, attract clients, and differentiate yourself from your competitors, your need to show that your expertise goes far beyond just providing a service you specialize in.

You need to consider how else you provide value to your clients.

  • Because of your deep insight into and experience providing your services over the years, you can help your clients understand why they might need to take a particular approach (or not) for their project.
  • Because you understand the benefits (and costs) of different approaches, you can communicate with your clients about the various benefits they’ll experience or how a particular process will help given the current situation.

Phrased another way, to differentiate yourself, your need to start selling strategic services.

Selling strategic services is an excellent way to decommodify your business.

Instead of being just another pair of hands to handle implementation, you’re positioning yourself as someone who can both contribute strategic insight into how to best approach a project and who can address the done-for-you implementation.

And just like that, you’re no longer an apples-to-apples commodity comparison with your competitors. Because you offer strategy-as-a-service, you’re differentiating yourself from your competitors.

But how can you get started selling strategic services?

One of the best ways to start providing strategy-as-a-service is by selling project roadmaps as a service offering.

Project roadmaps are paid discovery & strategy projects sold at a fixed fee (no proposals required). You meet with the client, discuss their situation/problem/challenge, and define a strategic approach to solve their problem. (You’re most likely already doing most of this discovery and strategy work for free when you write a proposal or meet with a lead and talk through their situation.) 

When you start selling paid project roadmaps, you:

  • Capture the value of your strategy work
  • Differentiate yourself from your competitors
  • Position yourself as a high-value consultant

Want to get started selling strategic services and project roadmaps?

Read more about how to get started selling, running, and delivering project roadmaps right here:



What is Search UX?

When was the last time you’ve put yourself in your visitors’ shoes and checked out your website from their perspective? (i.e., searching for a keyword, looking at all the results, clicking your site, and looking at the landing page with fresh eyes)

Today I want to talk with you about an SEO concept I’m increasingly enamored with.

Search UX: the User Experience of searching, finding your website in the search results, taking a risk, clicking your link, and visiting your site.

It’s essential to think through the holistic experience for your visitor:

  • What keyword are you searching for?
  • What does your page title look like in the search results? Is it resonant and aligned? Or dissonant and confusing?
  • What rich results (like this) are showing for your page?
  • When they click, how fast does your page load for them?
  • When they first land on your page, are they presented with helpful information and a clear introduction? Or are they smacked in the face with countless pop-ups?
  • Are you sharing enough of the right information (along with a clear indication of what to do next) so that the visitor can feel they’ve found the information they’re looking for and conclude their search?

That’s what’s Search UX is.

Search UX is about both having a good-looking, fast site and having the right content so your visitor can think, “I’ve found what I’m looking for.”

Altogether, this means you need to think about Search Engine Optimization from the perspective of a visitor and in terms of design, layout, content, and technical SEO.

When I look at the landscape of Search Engine Optimization in The Year of our Lady Two Thousand and Twenty One, it’s increasingly apparent to me that Search UX matters.

After all, if your site is ugly, slow, and has the wrong information, why would Google want to show it to anyone?

One great way to get a professional opinion on your Search UX is with a Website Review ( Altogether, you’ll get:

  • A professional ‘second opinion’ about your website
  • Advice on what to fix along with any low-hanging fruit to improve your site
  • Feedback on your Search UX (and what to do to help Google love your site more)

Wondering what the experience has been like for others? Here’s what Jonathan Stark had to share about his Website Review:

What I discovered was that it turned out that every suggestion or constructive criticism that you gave was about something that I knew I had skimped on or was something that I was unsure of (or forgot to go back and fix!). Having a professional “second opinion” that reinforced my suspicions was super helpful. The actionable advice about how to fix certain deficiencies was icing on the cake! — Jonathan Stark

Why wait? Kick off the second half of 2021 with a professional review of your website AND your Search UX:



What marketing can you stick to on your worst day?

Everyone has a plan until they’re punched in the face. But do you have a plan for your marketing if you find yourself (metaphorically) punched in the face?

Put another way, what’s a tiny bit of marketing you can do (and keep doing) even on your worst day of the year?

What brought this question to mind was a great tweet from James Clear:

When choosing a new habit many people seem to ask themselves, “What can I do on my best days?”

The trick is to ask, “What can I stick to even on my worst days?”

Start small. Master the art of showing up. Scale up when you have the time, energy, and interest.

You want to think about a small, ongoing piece of marketing — a habit — you can have in place even on your worst days. Something you can get in place and then keep in place for the long haul.

That way, you’ll know that you’re keeping up with your marketing and keeping your streak unbroken, even on the bad days.

So, your turn. I’m curious about what comes to your mind as a small marketing habit.

It could be something you’re already practicing or something you’re thinking about starting. Some tiny, atomic bit of marketing you can keep going even when you (metaphorically) get punched in the face.

Tap reply and let me know. I’ll share mine later this week, along with a few (shared with permission) reader responses.



Grit and Stick-with-it-ness

Let’s recap:

  1. You need leads. To get leads, you need marketing. To market consistently, you need habits around your marketing.
  2. The best way to build a habit is to have a documented repeatable process you can follow.
  3. An SOP is a great container for your process. It’s a living document you can read, execute, and update over time.

To succeed with your habit, you gotta have all the parts in place. Let’s set an example goal and talk about how to make a habit:

  • Your Goal: have a hot content summer
  • Your Process: publish and promote one Twitter thread and one email each week for July and August
  • Your SOP: how you’ll research, plan, write, and promote your content each week this summer

How do you make a habit and achieve your goal? You put in the time and do the work. Follow your SOP. Make the content. Publish and promote it. Repeat.

Don’t break the chain. Put in the time, don’t worry about the results. Focus on what’s under your control (doing the thing). Don’t worry about what’s out of your control (results depending on someone else).

  • Publish one thread/week, don’t worry about getting followers
  • Write 250 words/day, don’t worry about getting subscribers
  • Pitch 1 podcast/day, don’t worry about getting onto podcasts

And as with any habit, remember to be kind to yourself. Somedays, all you can do is show up and do the bare minimum (e.g., putting on your running shoes and then taking them off, walking into the gym and then turning around and driving home).

Those days still count. The streak is unbroken. On to the next day.

In other news, Juneteenth is now a federal holiday. About damn time.

Let me wish you an early ‘Happy Juneteenth Day.’



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