What Does it Actually FEEL Like to be a Specialist?

In terms of feelings that we have simple names for, the life of a successful specialist is marked by the feelings of wonderment, trust, dissatisfaction, confidence, and humility. These feelings spring from the specialists’s shifting relationship with opportunity and mastery. Much of how these feelings manifest over time is determined by whether the specialist has focused within an open or closed system.


No one has asked me flat out what it actually feels like to be a successful specialist, or a successful self-made expert, but I suspect that many of you wonder.

Let’s get one thing out of the way right up front.

The hedonic treadmill, also known as hedonic adaptation, is the observed tendency of humans to quickly return to a relatively stable level of happiness despite major positive or negative events or life changes. According to this theory, as a person makes more money, expectations and desires rise in tandem, which results in no permanent gain in happiness.

Source: https://en.wikipedia.org/wiki/Hedonic_treadmill

Part of what spurs human progress, improvement, and striving is a fantasy that we’ll get free of the hedonic treadmill. This is an incredibly useful fantasy but let me be clear: you won’t be freed from the hedonic treadmill, not even when you’re an in-demand, successful, effective specialist. I hope this doesn’t reduce your desire to specialize. I hope instead it simply reminds you that you’re subject to the human condition no matter what, even if lots of things in your business get better because of specializing.

After you’ve validated a specialization hypothesis, one of the first memorable emotions you might experience is wonderment.

Wonderment: a cause of or occasion for wonder, astonishment, surprise.

I should be clear: the process of validating a specialization hypothesis — and possibly iterating through multiple hypotheses — can be frustrating.

But when you find that alignment between your hypothesis and what the market wants, the emotion that often follows is wonderment. A sort of awe that finally, the market is not working overtime to ignore you or devalue you. Instead, the market wants what you have to offer and, by extension, wants you.

I remember Connie specializing in marketing for yoga studios and feeling for the first time that the market wanted her services specifically.

I remember Tom starting to recruit participants in a small-scale research project that reflected a specialized focus and getting enthusiastic expressions of curiosity and interest in his work at a level he had never seen before.

Those are concrete examples of situations that produce a feeling of wonderment. In colloquial terms, you hear yourself saying, “Oh my God, this is actually working!”

“You get used to anything; sooner or later it just becomes your life” — “Straight Time”, Bruce Springsteen

When those wonderment-producing situations repeat themselves regularly enough, hedonic adaptation kicks in and mutes the feeling of wonderment. Wonderment is replaced with the feeling of trust in the effectiveness of your specialized focus.

Trust: dependence on something future or contingent, hope.

“I am thinking of the way the intangible air passed at speed round a shaped wing easily holds our weight. So may we, in this life trust to those elements we have yet to see or imagine” — “Working Together”, David Whyte

David Whyte is talking about the most delicate form of trust — trust in the yet-to-be seen or imagined. The specialist could experience that kind of trust, but it’s most common for them to trust what has already been happening: the market wants what they have and there are invoices and checks to prove it.

This is distinctly different than what I remember of being a generalist, where I kinda sorta trusted my ability to improvise, hustle, and bullshit enough to grab opportunity whenever it floated by.

The specialist starts to trust that opportunity will seek them out. In reality, this must not lead to complete passivity in business development, but this feeling of trust that the demand for the specialist’s expertise is greater than the supply of that expertise does allow you to relax some.

This happy situation persists for a while before the next emotion creeps in.

Dissatisfaction: expressing or showing lack of satisfaction; not pleased or satisfied.

The dissatisfaction you begin to feel springs from thinking that you’ve entered a slump. The usual pattern goes like this: you find a specialization that works (wonderment), you get traction and momentum (trust), and your early client work is mostly successful. You’re solving problems and improving your client’s condition left and right. And then… your perceived or actual success rate with clients starts to drop.

Maybe the projects start getting harder or more complex. Maybe the clients are more demanding. You start to feel like you might be in over your head.

Alternately, you start to feel like you weren’t actually a real expert when you started, and you were solving simplified, “cardboard cutout” versions of the actual problems. This is because you were actually not a real expert, and you were actually solving simplified versions of the actual problems.

This movement into dissatisfaction happens, ironically, because your specialization is actually working. Those early wins got you access to more ambitious client work either because you’re increasing in confidence or bizdev acumen (or both).

The move into dissatisfaction is totally normal. You are awakening to the true scope and complexity of the problem (or market or audience) you’ve focused your business on. The normal response is a craving for mastery.

Closed system: A business system with centralized control and little or no uncontrolled flow into the system. The entire system is relatively knowable. Examples: the legal profession, the Salesforce software platform, the Apple App Store.

Open system: A business system with distributed control or no centralized control and lots of uncontrolled flow into the system. The system is too complex to be entirely knowable. Examples: the topics of sales, marketing, and strategy, the Amazon AWS platform.

In closed systems, it’s possible to achieve nearly-complete subject matter mastery. In open systems, technical mastery remains elusive so instead you master the ability to help your clients thrive in a dynamic environment. You help them deal with the uncertainty and relatively high rate of change that are major features of the system they operate within.

The dissatisfaction you feel about your client work failures and underdeveloped expertise fuels investment into deeper, more robust expertise. Dissatisfaction -> growth.

Confidence: a feeling or consciousness of one’s powers or of reliance on one’s circumstances.

When your investment in deeper expertise starts to pay off, you start to cultivate genuine confidence. It’s not the frothy, eager version of confidence you felt earlier on. This one is more calm and seasoned. It’s tempered by a realization that some of your earlier successes were mere luck, and some were enabled by you getting 30% of the equation solved correctly and others getting the other 70% right.

And yet, you’ve… seen some shit by this point in the journey. You’ve learned a ton, and you’ve embraced how the context surrounding any problem is just as important as the problem itself, and you have a more nuanced approach to your work.

This all combines to create a real confidence within you. You say no to bad-fit opportunities more readily with a defensible explanation, delivered with kindness. You say yes to good-fit opportunities after you’ve explained to the client what’s realistic, even with the help of your expertise.

Humility: not proud or haughty; not arrogant or assertive.

For many, the journey of specialization is a passage from feeling like you are “crushing it” to a feeling like you are being crushed by the nuance, complexity, & context of the real world to a feeling like you are again crushing it, this time using principles, a framework, a model, or a repeatable method for managing the nuance, complexity, & context.

A TEI participant gave me elegant wording to describe what comes out of this journey: humble hubris. This is a combination of humility and an audacious swagger about what’s possible.

You’re in a sort of “emotional hammock”, suspended between humility and hubris. You’re propelled to this destination by those early feelings of wonderment and trust. They gave you just enough overconfidence to help you tackle clients and challenges that were too big for your actual level of expertise. This created necessary painful failures.

Those failures fused with your resilient personality to create a dissatisfaction-fueled desire for mastery. Because you’re smart and hard-working, the mastery happened. You cultivated real expertise that gets real results.

As you did, your feelings of confidence and humility grew up like fraternal twins. Together, these two feelings create a productive tension, and from within that tension you attract opportunity and create impact.

I hope that this article has helped you understand what it feels like to be a successful specialist. If you’re looking for more context and detail on specialization and positioning, then read my free guide to specialization for indie consultants.