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The Plight of the Expert Generalist

The Plight of the Expert Generalist

“In the beginner’s mind there are many possibilities, but in the expert’s there are few.” ― Shunryu Suzuki

Simplicity is hard af. 

Life tends to flow from simple to chaotic, from hot to cold, clean to messy. 

Maintaining simplicity takes effort, lots of it, and problems arise when trying to maintain simplicity in a wide range of areas.

Especially with above average proficiency in all of the areas.

Let’s take for example the solo founder building a digital e-commerce company… hypothetically.

Launching, scaling and maintaining an online business requires a serious arsenal of skills.

  • Website building and maintenance

  • Branding and design

  • Product ideation and development 

  • Distribution logistics

  • Content creation

  • Customer communication 

  • Marketing 

… to name a few.

And as the founder progresses, she develops a deeper understanding and wider skill set for each modality. 

What was once simple, isn’t. The top layer yields to deeper understanding and further complexities and non-simplicities.

What starts a simple task with a singular focus blossom into a number of sub-tasks. 

Here’s an example: 

  • “I need email marketing…”

  • “That means I need to collect emails on my website…”

  • “Which means I need a pop up to collect emails…”

  • “Which means I need to design a pop-up email collection…”

  • “Should the pop up offer a discount? Or incentivize another way?”

  • “I should test different pop-ups to see which one works best…” 

  • “Once I get the email, I need a welcome sequence...”

  • “Now I need to send them emails weekly to keep them engaged.”

What seemingly starts as a simple process grows until a full set of tasks. 

And for the expert generalist who’s honed his tool kit with varied skills and knowledge, this same problem happens in all the areas…. and in those area’s areas.

Instagram, releasing new products, designing a landing page, hosting an event, organizing a collaboration, producing content… the list is forever, and so are the sub-lists.

Each singular focus becomes deeper and deeper with a full task list attached. 

And because the founder is well-versed in each, she knows each task sequence is essential for complete execution… and she’s able to do it, until a point.

But even at that max point, stretched thin, each of focuses yields more necessary focuses, ad infinitum.

So how does she stick to the basics when she knows the basics won’t cut it, that simplicity is costing sales, undermining the effort and leaving tasks half-finished?

When everything needs to be done, and she can’t do it all, but she can do it better than most people, what’s the move? 

Say no to opportunity? Choose one route, neglect the other probably-just-as-important options? 

Even slimming down the innumerable options still results in a spiraling list of sub-essentials.

  • “I’m sticking to Instagram because I can’t focus on all social media channels so ” 

  • “I’m going to post 5 days a week.”

  • “I need a hashtag strategy.”

  • “I also need to engage with other accounts.”

  • “What about stories?”

  • “Instagram is used for eventual sales leads so I need to optimize my bio.” 

  • “Video is important, how do I include that?”

  • “What about IGTV?”

...etc. etc. etc, spirals of necessary opportunities. 

Sure, stick to one. But how to pick the best one?

And when eventually that one becomes many, how to stick to just one, again?

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Going Back to How It Used To Be

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