Getting Paid Like a Boss

While this site is about making money, it is not a "make money online site". Our goal is to help experienced professionals who are "in transition" find rewarding opportunities in the highest levels of the gig economy or build a sustainable side business using their expertise. There's more to the gig economy than driving around for minimum wage. New here? Check out Stacking the Deck - Raising Your Odds of Winning.

"...but what I do have are a very particular set of skills. Skills I have acquired over a very long career..."

My interest in this topic became intensely personal earlier this year, when I was laid off alongside 400 of my co-workers in response to a corporate tragedy. With less than a month of severance.

Given that the job market is dysfunctional mess for a middle aged senior manager, drumming up a few options to generate some cash flow became an immediate priority.

The ideas behind this website emerged from that search, supplemented with the assistance of a team of freelance writers with experience in these gigs and side businesses. We recruited them, fact checked their stories, and asked the writers with the best ideas to tell us how they got started.

More About Why We Built The Site

There are a lot of sharks out there. On one hand, I was gratified by the large number of "business opportunities" and "networking discussions" that popped out of the woodwork once I updated my LinkedIn profile. That faded when I learned that most of these "opportunities" were one-sided deals that couldn't be offered to people with a day job. Or wanted me to clean out my savings and hand it to them. No thanks.

Unlike many of my peers, I've had a succesful side-hustle for years as a digital publisher. My spouse and I build websites and share them on the internet. Once they reach a sufficient size, we put advertising on them and earn money. It wasn't an easy to start - we had to swim by a bunch of sharks to find a place - but it worked out.

We wanted to bring other voices into the conversation, to diversify the perspective. Our writing team was immensely helpful in assembling this material. Read these guides with a grain of salt. These are intended to serve as a starting point rather than an explicit guide. Use them to get ideas and go do your own exploration of the opportunity. You'll find a few twists on the original idea that will make it an even better gig or side-hustle.

Timing Your Income

A sharp witted reader asked me why I just didn't go to work on digital publishing full time.

So the answer is pretty simple. While digital publishing can be a very rewarding long term business, the cash comes very slowly. You're building websites today that will earn next year. This was not a problem when I had my corporate job; we lived off my paycheck and the websites were a bonus. But once the paychecks stopped, we needed another source of short term income.

This is actually why we decided to publish a very wide range of opportunities on this site. For example, I'm not wild about the idea of working for a content mill or selling on fiverr. That is literally the bottom of the market, in terms of rates. However:

  • 100% Remote, On Your Schedule
  • Zero selling
  • Plenty of work
  • Pay quickly
Would I quit my job and go do that? Absolutely not. But if you need a buyer of last resort for unused time who asks no questions, inflicts no drama, and pays quickly, they nail it.

There is a huge range of opportunities in sales and consulting. The biggest challenge is learing how to pursue and retain high paying clients. There are people on Upwork who are regularly biling $100 - $300 per hour. And have billed several hundred thousand dollars of work at that price. Privately arranged consultations can be priced even higher. And there is always a need for a good salesperson in many high paying industries.

And for others, unemployment represents a unique "hall pass" to experiment with more ambitious opportunities. Perhaps you have a creative side that you would like to develop a bit. Or maybe you want to take a shot at building a larger service or e-commerce business. Since the typical job search doesn't usually take more than 20 hours per week, that leaves 20 - 40 hours free to invest in the opportunity of your choice. Heck, it will probably make you more employable than updating your knowledge of the current daytime television series or the latest video games. That being said, approach these as longer term investments - be ready to wait a while for the cash to come it. They are, however, some of the highest earning opportunities on the site.

Ready to Begin?

While there's a lot of great stuff, here are a few of my personal favorites:

The piece on content mill writing is recommended reading for new visitors. We show how to take a $10 per hour piecework gig and leverage it up to over $50 per hour (as a freelance writer) and push it even higher if you learn how to do digital publishing (primarily learning SEO, copywriting, and advertising management). Even if writing isn't your thing (I'm not a writer either), the ideas we share in the process analysis can certainly be applied to many other freelance opportunities.

Tired of haggling with recruiters and HR departments who want to beat you down for a discount? Then take a look at our article on expert networks, a rare but lucrative little niche if you've got the right kind of industry expertise. Then go think about how you can get in front of these same high paying investor clients and help them solve similar problems at high rates.

Remember the movie "Office Space" and "Up in the Air"? It turns out there really are freelance HR consultants - read our story here.

Want to help non-profits raise money? We spoke with a grant consultant. Use your writing, marketing, and communications skills to help raise funds for a good cause (and pay the bills).

Or perhaps you would like to get your hands dirty, clean up the world and do some recycling in the process? Check out the article on setting up a junk removal business.

And finally - if you know how to sell and want to swing for the fences, we've found some interesting ideas related to starting a white label services business. You may have heard of white-labeling and private-labeling products on Amazon. This takes that same concept and applies it to local service business opportunities with potentially less competition. Or if you just want to dip your toe in the water without a major committment, check out Amazon Merch or building a micro-service on Fiverr. (Lower return but also less risk / investment)

In any event - good hunting and good luck!