The Generalist–Specialist–Opportunist Framework That Made My Business Less Fragile

One piece of advice I give to freelancers, consultants, and agency founders is be a generalist, specialist, and opportunist.

I’ll tease out some of the nuances here because this advice sounds self-contradictory.

Every creative and service provider is a generalist, given that we can all do more than one thing. The assortment of things we know about and are good at have broad application. This versatility is a blessing—all the options!—and a curse—all the options!

Therein lies the problem with freelancers who talk about “being a generalist” as though it’s a differentiator. It’s not. You might as well as “I’m creative.” A client thinks, “Okay, thanks for that information, but what does it mean for me and my problems?”

Being a generalist means that you can solve a variety of problems, and though that is useful in business and useful to clients, people don’t know which square in the bento box you occupy.

They find it difficult to remember what you do specifically and thus to recommend or refer you.

And worse, even after they’ve hired you to do an assortment of projects and after you have performed admirably, they may still default to hiring a specialist because they didn’t know you could do that too.

I understood this conundrum better after I graduated to being a fractional CMO, which meant I was the one either doing the hiring or recommending someone to my client.

They rarely needed a talented generalist, and if a client had asked me to suggest one, I would have said, “Uhhh… I’ll have to get back to you on that.”

They did ask me for specialists:

• Webflow designer willing to work on an as-needed basis
• Identity and packaging designer for consumer products
• Marketing packages for home services companies
• Landing page copywriter for a medical practice
• Email marketing campaigns for outdoor brands

Being a generalist works okay, at least for a while, if you have a broad and deep network and are good at keeping in touch and getting in the way of opportunity.

I stayed a generalist for the first seven or so years of freelancing.

I didn’t starve.

But then, my financial needs changed, my wife and I started having kids, and I wanted to work less. I hit a few dry spells and learned that it’s difficult to market yourself when your value proposition is creative handyman.

Positioning yourself as a creative handyman, one-stop shop, or Swiss Army knife is the same as having no positioning at all.

If you don’t pick your box, you don’t become associated with anything in particular.

Circa 2016, when I finally did specialize for the first time—content marketing retainers for tech founders—I discovered what more astute freelancers, consultants, and agencies already knew. The best positioning happens when you point yourself at a specific, painful, and expensive problem that your dream clients have.

Until you specialize in solving a specific problem for specific people in a specific way, you are hard to remember.

And once you do become associated with a specific problem and desired outcome, other people, including other freelancers and consultants, can recommend you.

Mind you, you will never really stop being a generalist. You can’t help being a generalist anymore than you can help being creative.

But specialization simplifies marketing, outreach, and lead generation and makes being remembered easier.

Then, a funny thing happens as time passes. Your knowledge and experience deepen, and you become an expert generalist.

You may specialize in ad creative and paid campaigns for DTC food & bev brands doing less than $1 million in revenue. Yet, you’ll know more about brand strategy than less experienced folks who specialize in that.

What happens when you have a specialization and then opportunities outside your specialization come along?

You can be an opportunist and take your pick of interesting projects, even if they fall outside of your specialization.

Wait, wouldn’t that hurt your positioning or cause you to miss out on the benefits of specialization? No and yes.

No because your positioning, messaging, and marketing will still be building strong associations between you and the work you want to be known for.

Yes because there’s always the danger of being unfocused, saying yes to too many different types of projects, and spreading yourself too thin.

In my case, writing a Wikipedia article, delivering a sponsorship package to a tech company, serving multiple one-on-one coaching clients, and doing a 1-Day Growth Sprint all in December 2025 made operations more complex.

Being a generalist, specialist, and opportunist has made my business less fragile, and I’ve found there are two things required to do it well:

1. Being conscious of tradeoffs like added complexity. Knowing what I’m doing and why and for how long, and what else I’d prefer to do instead given the opportunity.
2. Having well-defined offers. At this point, I have a couple dozen offers that I can deliver efficiently at a moment’s notice while reasonably expecting a high effective hourly rate.

As an unreformed opportunist, I keep “unpublished” offers on ice for those occasions when I want to deviate from my specialization, for whatever reason:

• This new client is a strategic relationship, and they can open other doors for me.
• I don’t have enough of the main work you do right then.
• I would enjoy some variety.
• A friend asked for help.
• I want the money.
• I just wanna.

When in doubt, pick the option that leaves you with the most options.

This generalist-specialist-opportunist way of thinking has opened more doors than it has closed for me. I hope it helps to make your business less fragile and open doors for you, too.

If you need help with your offers, reply to this email. I’m doing my first in-person Mastermind next month. Maybe you should come and work on your offers with me.

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