Don't Sivilize Me, Bro

Your chapter neXt is something of an Centrum Silver walkabout, a fiber-filled bildungsroman, or a sensible walking shoe version of Kerouac’s On The Road (read it again - its still good - though more misogynistic than I remembered, but…). But The Adventures of Huckleberry Finn, I think, said it best:

Many of us when we are cracking open the pages of chapter neXt, we think about being “responsible” and “pragmatic” and other stupid stuff. You've had five or six or seven decades of being “sivilized”. It's time to throw off those shackles and think about doing it some other way.

Lighting out for the territory is scary. Something I've seen, especially in first-time entrepreneurs, is the desire to hide their fear in a crowd. You figure if you hire people or go into partnership with somebody, you are going to minimize your risk.

There is that old African proverb, “If you want to go fast, go by yourself. If you want to go far, go with others.” And I think that is largely true, because for many of us, our ambition outstrips our singular abilities. But in the early days, adding other people, other voices and other stakeholders creates more variables in the equation.

Adding travelers creates complexity & complexity kills progress.

Before you decide to go far, you need to be able to move fast. In the first 100 days of a new enterprise - it doesn’t matter if you are just doing what you’ve done earlier in your career but this time for yourself or if you are trying something brand new, you probably don’t know enough about your new landscape to be able to carry the weight of an employee, or partner with a significant voice.

You need to be able to prove that what you do works before you start adding complexity and extra weight.

You should leverage your personal and professional networks to talk through your thinking. In my business, for instance, I decided to shed employees a few years ago. I belong to a group where a bunch of folks who who do things that are very similar to what I offer chat about what we are succeeding and struggling with…

We are all competitive in some respect, but we connect.

And that means we aren’t alone.

So maybe go fast, then go far.

Investors face a dilemma. Headlines everywhere say tariffs and AI hype are distorting public markets.

Now, the S&P is trading at over 30x earnings—a level historically linked to crashes.

And the Fed is lowering rates, potentially adding fuel to the fire.

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chapter neXt is a newsletter/community/guide for entrepreneurial folks in their 50s and beyond. It is published by Julia Kelahan (check her out on LinkedIn, her amazing strength-based learning center & her ADHD & Executive Function coaching business) and Tim Kilroy (check him out on LinkedIn & his agency growth business & his agency-focused newsletter). They are the proud parents to 5 kids, they live near Boston & their dog’s name is Fred.