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I concur with a lot of what Nader has laid out here. Specialization + Content are keys to unlocking much higher pricing power.

Getting started is tricky, but my most profitable side work has been workshops and lunch-and-learns, which is beneficial as I can re-use a lot of the same content between engagements.

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I agree as well. You can be a "cloud consultant" or you can go all in on AWS costs, have a newsletter, keep your face in front of people, etc. Guess which one probably does better.

Of course it has to be a specialization that enough people need to be willing to pay for.

You also have to keep a clear lookup for a new area or areas if your specialty is in decline. You don't want to be the Y2K mitigation expert in 2001. Or the top performance expert for some legacy or discontinued computer architecture.

We started with lunch-and-learns, but eventually moved to beer-and-briefings.

Can you elaborate critical difference between -learn and -briefing or does it just rhyme better :) ?

It just rhymes better!

One contains beer.

If you're not already familiar, I think you'll be interested in the concept of alliteration.

https://en.wikipedia.org/wiki/Alliteration

Both the above are better than dining and whining which folks disillusioned from modern software like me do.

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