What Few People Understand About Earning Online

Monday rolled around—7 a.m. I was still in bed, stuck in the neverland of partial, morning lucidity. And my phone chirped. 

I lethargically pulled it from under the pillow… 

The chirp was a notification from freelancing website Fiverr, welcoming me back from my time away, and automatically setting my profile to “Available.”  

I shoved the phone back under the pillow, rolled onto my side, and closed my eyes…until construction on a new, children’s playground in the courtyard below my apartment sent the sounds of augers and electrical saws into my open, bedroom window four minutes later. 

If there’s one lesson I’ve learned over the last year of freelancing, it’s that it doesn’t have to be the grind so many people assume it to be. 

In this particular instance, I’d been in Malta for 10 or 11 days on assignment, as you likely know from my recent writings. I knew before I left on my trip that I’d be swamped with meetings, and flitting about the island, and walking around for my research.  

I really didn’t want to alight back at the hotel every night only to have to spend a couple hours doctoring screenplays. (That’s the part-time online freelance gig I’ve picked up over the past year and which currently earns me five figures in additional income annually.)  

That would have been too much. 

So, I turned off my freelance gig—or, technically, I set it to “Out of Office,” for the duration of my trip to Malta. 

And for those days I was away, not a peep. 

I didn’t concern myself with deadlines. I didn’t walk to lunch thinking about how to reframe Act 2 in some writer’s psycho-drama.  

While I was on assignment for my real job, I was on vacation from my side-hustle. I don’t think I even gave it a moment’s thought. 

But the minute I was “Available” again, the gigs started landing immediately. In the first five days of my reappearance on Fiverr, three orders worth $565 popped up in my inbox. 

That’s one of the facets of my side-hustle I’ve come to appreciate in the last year: the freedom to earn when I want, and the freedom to turn it off when I want, pretty confident in the knowledge that when I flip the switch back on again, I’ll have clients waiting to hit me up. And the money starts flowing. 

To be sure, this is 100% a function of legwork early on. 

When I first started my script-doctoring gig, I never turned on the “Out of Office” function. When I was in Istanbul with my girlfriend/now-wife, I was doctoring a script late at night after she fell asleep. Same when we were in Montenegro getting married last December (she’s saintly in her accommodation of my life as a writer). 

I did that because I wanted to build a track record. I wanted to build a broad base of reviews (93 5-star; 1 lousy 4-star) so that potential clients were certain they’d be paying for a high-quality experience and a top-notch product. 

I knew from a conversation I had with a woman who has earned more than $1 million as a writer on Fiverr that a strong profile would serve me well when it came time to scram for a few days or a couple of weeks. 

“People will see that and, unless it’s an emergency, many will hold out until you’re back,” she told. 

She was right. 

Now, I don’t even think about it.  

Whenever I go anywhere on assignment or holiday—“Out of Office” all the way.  

If I get backed up writing Field Notes, our monthly Global Intelligence Letter, or the various assignments I have with International Living magazine, same thing…flip on the “Out of Office” sign and get down to business in my day-job. 

Honestly, that’s the way it is across a lot of life. You pay your dues, you grunt through the hard work, giving up weekends, losing a few vacation hours, staying up late into night to give the client a product that surpasses that client’s expectations…and then you magically reach a point where you’ve earned the perks of your position. 

You are in control of your side-hustle instead of your side-hustle controlling you. 

It really does morph into an income opportunity that you can turn on and off at will.