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Chapter 15: Decide How to Specialize

I'm an unabashed advocate for specialization, because over and over again, I see it making the best parts of self-employment better and the worst parts less bad.

A specialization is a beachhead. You eventually move beyond it either into a deeper specialization—or alternately, a broader one—when it has served its purpose of helping you get traction and then ultimately achieve escape velocity from a situation you'd like to improve.

None of this happens if you decide but then fail to act. The decision to specialize is both easy and difficult.

Understand and Defeat The Fear

The difficult part of specializing is The Fear—a basket of related fears that surface at the worst possible moment during the specialization process. I've already touched on some of the components of The Fear.

In Chapter 8, I explained how the main risks with specialization are overevaluating the potential for harm in the specialization transition and flinching, which is exceeding your risk profile, and then hastily responding to a feeling of fear that arises during implementation.

In Chapter 9, I explained how specialization decisions are not permanent nor are they a life of renunciation and monotony. Specialization is not Mike Tyson joining a monastery.

The Fear, very unhelpfully, does not surface the moment you consider specializing. Instead, it surfaces when you are about to take action. This means you've done the decision-making work in a relatively optimistic context, and just as you're about to implement, the context suddenly changes to a pessimistic, stressful one.

This is problematic because implementation is where specialization decisions succeed or fail . The quality of your initial specialization decision matters, but not nearly as much as the quality of the implementation. And so, it's so incredibly unhelpful  for The Fear to surface right before you begin the most important phase of the specialization process.

It's disorienting that The Fear surfaces at this point because you'll hear yourself saying something like: "Things were going fine  with the specialization decision, but because of how this feels  now that I'm about to make real changes to my business, I wonder if I actually made a bad decision."

If you've ever had a boss, you're used to having to implement someone else's bad decision from time to time. You get through it. But feeling like you're about to implement your own  bad decision is something else entirely. It kills momentum. It makes for half-baked rather than full-throated action. And very often, it causes you to stop moving forward entirely and reevaluate the decision.

If you do that, you're screwed. The problem becomes circular and paralyzing at this point. The decision probably wasn't flawed to begin with; reevaluating it won't really help because all you'll do is come up with a different-but-not-actually-better decision that evokes the exact same fear  when you attempt to move from the planning to the implementation phase. In other words, if you give in to The Fear, you'll get stuck in a circular fear loop. You'll think that the problem is the quality of your decision, and so you'll keep revisiting the decision, making slightly different but not-significantly-better versions of the decision and you'll feel the exact same cold, prickly fear about each one and respond by revisiting the decision. Eventually, you'll give up on specializing.

The problem is not the decision. Instead, you need to understand The Fear.

You already understand that specialization is not Mike Tyson entering a monastery. You won't find it monotonous or boring because:

  • After you decide and commit to the decision, you'll feel this burst of energy and creativity because you finally know who  you are speaking to in your marketing.


42: It may, but if you also move up the value chain as you gain subject matter mastery, you'll continue to have a fresh, interesting learning curve ahead of you.

  • If your technical area of focus ever becomes routine and easy, [42]  you'll enjoy the higher profitability, greater pricing power, and business scalability that leads to.

  • As a small business owner, you'll always have a diverse range of stuff to deal with. Invoicing, interviewing CPAs, and evaluating new software tools are not in themselves highly fascinating activities, but they contribute to the variety of a small business owner's life.

Specialization is not a life of renunciation; it is a life of engagement and growth with a narrow area of expertise within the broader, challenging, somewhat chaotic world of being a small business owner.

Imposter Syndrome’s Contribution to the Fear

As you specialize, yet one more reason for you to avoid charging more for your services evaporates, leaving you alone in a room with the real  reasons you're not charging more. For many, myself included, those reasons spring from imposter syndrome. We simply don't feel worthy  of charging fees or rates that are actually representative of the value we create.

Imposter syndrome also surfaces before we specialize as we're mentally "trying on" the idea of calling ourselves a specialist, expert, or similar superlative. We can imagine cultivating some  expertise, but we worry that it will be lacking in some critical way. Or we worry that if we're not extremely careful in the application of this future expertise, we'll accidentally cause harm to our clients in some way. Or we worry that our expertise is not legitimate because there's no licensing body to endorse it the way there is with physicians and other accredited professions.

Both of these facets of imposter syndrome are part of The Fear.

Loss Attention’s Contribution to The Fear


43: This is not exactly loss attention the way it's defined by those who have studied loss attention and the related phenomena of loss aversion, but it's close enough that it's reasonable to use the same name to describe it.

The final component of The Fear is loss attention. As we're mentally trying on the idea of specialization, it's easier for us to visualize the kind of opportunities we would say no to or lose out on than it is to visualize the kind of opportunities we'll gain access to simply because we have more lived experience with the former than we do the latter. The loss is easier to visualize than the gain. [43]

Even if the potential gain of specialization outweighs the likely loss, we can get cowed into inaction by the distorted picture of the future that loss attention produces. We can easily size up the lost revenue from the clients we will eventually say no to, but it's harder to measure the gained revenue from specialized work.

The reality of specializing is that it's a transition over time. You choose a beachhead, a specialized focus for your business. And like the smart business owner that you are, you transition your revenue base as quickly or as slowly as necessary to maintain stability during the transition. If you picked a beachhead that aligns with a strong "head start" for you, then your transition may be quite rapid. But maybe your transition is more gradual. This gives you the a chance to learn through experience what the opportunities that are available to a specialist look like. And this experience gives you the courage to let go of even more old clients and opportunities.

For me, it took about ten seconds to complete the mental aspects of this transition and about three years to execute the physical part. Ten seconds is how long it took to scan the first email I got asking me for business strategy advice after I published the first version of this book. I was immediately hooked on a new vision for how my business could create positive impact. It took three years to reposition my business in the market as a purely advisory services business and to iterate some of the core service offerings that are both unique in the market and compatible with my odd set of personal preferences.

Loss attention eventually goes away. You just need evidence that the gain is worth it, and that comes with time. The problem is that the evidence doesn't arrive until after you start implementing your specialization decision . The solution is to implement your decision very quickly, and prioritize marketing and sales work that will give you the quickest possible win. Chapter 17 guides you through an implementation process that prioritizes quick wins.

The Fear Is Complex and Insidious

The Fear is complex. It is made up of flawed risk analysis, overreacting to fear (flinching), overestimating the permanence of your decision, overestimating the level of monotony entailed in specializing, an unhelpful delay between deciding and feeling The Fear, imposter syndrome, and loss attention.

The Fear is also insidious; it strikes at the worst possible time—when you're moving from the important-but-easy part (the decision) to the important-and-critical part (the implementation). That's why I've spent an extravagant amount of time describing The Fear. The benefits of specialization are so compelling that I'd hate for The Fear to interfere with you obtaining them.

How to Make the Specialization Decision

There is a structured, broadly usable process for deciding how to specialize an indie consulting business. I've developed it over years of client work with hundreds of coaching clients and workshop participants. It's relevant to small services businesses where expertise plays an outsized role in value creation.

It's here:

It's on my website because it's easier to update there; print books are kind of hard to update as things change. Unlike many other business books with companion website resources, I don't ask you to provide an email address to access book resources.

In extremely brief form, the process looks like this:

  • Inventory your areas of relative advantage

  • Assess your risk profile

  • Use #1 and #2 to develop a shortlist of reasonable specialization options

  • Apply guardrails to eliminate long-shot specialization options

  • (Optional) Conduct a live market test to get feedback on your specialization decision


Again, a thorough process for making this decision lives here: