From Matthew:

“I work as a technology director at a large school system here in the East, but will be leaving soon to pursue a more travel-oriented career. It has all been in the works for months.

Initially, I wanted to focus on technology in school building projects, which is something that I have experience in doing, am good at and an area which often gets overlooked in school construction.

However, after reading your section about specializing in a niche, now I am wondering if that may be a mistake.

I also have a part-time online business which focuses on marketing outdoor technology. It’s a work in progress?

Is is smarter to go a two-pronged approach, or go with one thing?”


The rule of thumb is, the more prongs the better. Especially when you’re starting out.

Because it’s hard to know what will fly and what won’t. It’s smart to try a few different things. I’ve been freelancing since the late 1900’s and I’m still trying stuff. Multiple prongs of income is a fine thing.

(Wait. No. I’m not advocating ‘jack-of-all trades’ freelancing. “I’ll clean your gutters, design a logo, audit your books, help you quit getting so angry over little things.” That never works. I’m talking about exploring different specialties, different lines of business, different types of clients — each as its own thing.)

The trick of course, is not to run off and start four new freelance businesses every morning. I gave myself a case of the scatters doing that. A few prongs is good. With twelve prongs you have a manure fork.

In your situation, I see no problem with doing school technology consulting during the day. And tending to your e-commerce website the rest of the time. Especially if you’re fascinated by one or the other.

Your prospects for each one?

From what I hear from consultants — who are just freelancers who use bigger words — being a genius in your subject area is not the major factor. The business seems to hinge on being naturally plugged into the people who need your type of advice. If you consult with Marketing Officers, or Department Heads, or fragrance manufacturers, or yoga studio owners, you need to have a direct line to these people. Or know exactly how to find them, and approach them.

In the school technology thing: who’s the buyer? The center of influence? Architects? Electrical subcontractors? School board committees: State bureaucrats? How will you know when a school is being built, or renovated? Where is your opportunity in the cycle? Early, in funding? Later, in the design stage? Are they building schools anymore?  Knowing how to deploy Wi-Fi or ethernet, or configure multi-function wiring isn’t the hard part. It’s getting to the table. Will you have to range out of state to find enough opportunities?

I’m only guessing, maybe you know this already. I’m pontificating from afar.

Your marketing of travel gear seems viable. The key, probably, is not to be just another storefront. Amazon has that sewed up. Maybe the key is to build a tribe, as they say. Maybe your mode is to provide real-world video field tests of each item. Take it in to the bush and show exactly what it’s like to use this thing, for real. Maybe you know this already, too.

Anyway. Try some things. Keep what works.