Creators are ideas people. We have a concept for a business and we go for it, often without building a concrete model for monetization first. I, for one, have made countless mistakes since I started my freelance writing gig roundup newsletter, Opportunities of the Week, back in 2018. And nearly all of them would have been avoidable had I given my project an ounce of respect— rather than viewing it as a silly way to win the affections of my peers in the media industry. 

So whether you’re starting a newsletter, hosting a MasterClass series, or launching a serialized comic, here’s my advice for you. 

1. Understand the value of your labor

I originally started the newsletter as a free service for freelance writers who, like me, were on the lookout for writing opportunities at big-name publications. I thought it would last for one year at most, enough time for me to make industry connections that would ultimately lead to more work and a sustainable income. 

But after a few months of marketing my newsletter as a free service, I found myself looking for part-time jobs to support myself while creating this resource—and realized that with the amount of work I was expending on producing Opportunities of the Week, I was creating something worth charging for. So instead of calling my newsletter “free” and asking for donations (which I rarely received), I reframed it as donation-based with a suggested amount of $1/month. I offered the option of getting it for free—what I refer to as “sponsored”—as long as a reader reached out to me directly. I’ve since bumped it up to $4/month, but maintain the same pay-what-you-can model. 

If you’re making a quality product, don’t just give it away. Find a monetization model that corresponds to your overall mission and financial goals. 

2. Find platforms and software that can accommodate your growth. 

If I’d had any kind of foresight that one day I might turn my 20-hour per week unpaid venture into my primary source of income, I would have started the newsletter on a platform that had the capability to handle payments. Instead, I sent the newsletter through Mailchimp. 

Big mistake. 

What I should have done was dump Mailchimp along with my free labor, and rebuild the newsletter on a new platform that could both send emails and process payments. Opportunities of the Week was still small enough that I would only be trying to convince a few hundred people to make the leap—and I could have set myself up for hassle-free pricing adjustments in the future. 

3. Don’t try to please everyone

Instead of dumping Mailchimp fast, I established a Patreon to process monthly payments AND allowed people to pay me through PayPal or Venmo (or even check, Cashapp, Zelle, or Wise!) if they preferred. My thinking was that this would let people pay me whenever they could, from wherever they lived, and for however much they could without modifying their subscription status—even if they were unable to pay me for a few months, they would still get the newsletter. 

While I stand by my donation-based model and have yet to find a platform that would allow complete flexibility for subscribers without making my content public, it is arguably a horrible way to do things. 

Believing you can accommodate everyone is pure fantasy, so it’s best to swallow any guilt you might feel about being difficult or alienating potential clients. This means maintaining hard rules about the amount people pay you, when they pay you, and how they pay you. If someone doesn’t want to learn how to use a new payment platform (a problem I run into frequently given the number of older subscribers I have who are uncomfortable putting their credit card information online), then provide them with one alternative, two if you’re really desperate for them to like you. You can only do so much. 

Think about it this way: if you went to a restaurant and they didn’t accept credit cards, would you try to negotiate with the manager to make an exception so you could have dinner in exchange for a tap dance—or would you go to the ATM on the corner and get cash? Probably the latter, unless you’re a famous tap dancer, in which case maybe you have some leverage. Point is, you’re the business owner and you’re allowed to set these kinds of boundaries. 

4. Choose a payment platform wisely

It is incredibly difficult to get people to switch to a new platform en masse. That’s why despite switching to Ghost (a platform I endorse wholeheartedly), I still allow people to process their payments through Patreon (a platform I tolerate at best). Granted, when I started the newsletter, there were fewer options than there are now; Substack had yet to become the newsletter platform on everyone’s lips, Ghost was merely a twinkle on the horizon. But if there are multiple options out there, do your due diligence and compare them all. 

Check: 

• What are the upfront fees? 

• Do they take a percentage of your earnings? 

• How do they process payments? 

• How often do they pay out? 

• Do they charge you for processing errors?

• Is there a minimum and/or maximum monthly pledge amount? 

• Is there an earnings threshold that you must reach before they start sending you money? 

• Can they accommodate multiple currencies? 

• Are they as customizable as you need them to be? 

• Are they easy to use for both you and the customer? 

• How’s their customer service for creators and for subscribers? 

• How comprehensive is the platform’s FAQ and resources section? 

• Do they send payment reminders and receipts to subscribers? 

• Do they make it easy for a subscriber to update their credit card information? 

• Do they notify subscribers if their payments don’t go through and do they troubleshoot directly with the subscriber or put the onus on you to figure out what’s wrong?

Transparency is key, so if you don’t understand how the platform works and their customer service reps aren’t helping, run away fast. 

Five years and nearly 10,000 subscribers in, I’m still experimenting with Opportunities of the Week to find improvements for everyone involved. It’s been a lot of trial and many errors, but slowly, it’s becoming a well-oiled machine.