Congratulations, You’re a Substack Bestseller — Now What?

Nurturing readers, exploring promotions and navigating what it takes to achieve sustainable growth without losing touch with your creative spark

It is a truth universally acknowledged that a small business doesn’t turn a profit in its first two to three years. And it turns out, the same is often true for a paid newsletter.

Today, after a slew of back-to-back calls, I found myself energized and crystal clear about this essay that’s been quietly taking shape for a little while. So here I am, showing up late in your inbox to say…

The moment you start making money from your newsletter, you’ve also stepped into a world where growth happens in fits and starts, and where resources — your time, energy, focus and actual dollars — are constantly under pressure. From hiring virtual assistants to investing in tools or consultants, the demands can start to feel endless.

So if you’re a bestseller — or dreaming of becoming one — I’m here to tell you that a paid newsletter is thrilling and exhausting in equal measure, just like any entrepreneurial venture. Statistically speaking, you’re unlikely to pay yourself much (if anything) in those first few years, all while working 20+ hours (maybe more?) a week on something you (hopefully) love. And here’s the kicker: the most important relationship in all of this isn’t with your writing or creativity: it’s with how you relate to and respond to failure.

Because the job of an entrepreneur isn’t just to create something great — it’s to get comfortable experimenting (in public) without guarantees of success before you launch. In a lot of ways, publishing a newsletter with your heart-filled, creativity-exploding writing is the ultimate experiment. I haven’t encountered a venture that pulls on more layers of who I am, what I want and where I think I’m called to speak.

Both paths require learning to abide with the churn: the churn of revenue, the churn of ideas, the constant nurturing it takes to keep things growing. The pressure to have multiple sets of eyes on all the moving parts of your newsletter can often make it feel you’re just along for the ride on a runaway bull.

Drawing from a Decade of Entrepreneurial Lessons

How do I know this? Because I’ve been an entrepreneur for over a decade. I’ve run my own businesses, advised solopreneurs and small businesses and worked alongside my partner in his two software companies, both of which were eventually acquired.

I’ve worked inside business systems trying to address the very challenges that your newsletter will likely bring to you. I know the pressure of hundreds of thousands of dollars and livelihoods (mine included) on the line; I know the feeling of a contract disappearing overnight and having to let contractors go; I know the pit in your stomach when there seems like there is no good option available, only several less sucky ones to choose from.

And in newsletters, it seems the balance is all encompassing in a very specific way: it is relational, personal, creative, financial, strategic and so on. There is a constant balance between learning how to nurture your customers, defining and pivoting inside your product, exploring and testing marketing strategies that feel right/authentic — and above all, learning how to scale sustainably without losing touch with why you first started on this crazy adventure to begin with.

The thing I’ve learned is that the key in growth is knowing yourself (easier said than done, I know), what you want (and what you’re willing to give up), learning new skills and knowing how to pivot when new challenges arise. Because once you hit 5,000, 10,000 or even 20,000 readers, the game changes quite iteratively. As complexity grows inside a system, so do the resources it needs. What got you here won’t necessarily get you to the next stage.

And that’s what I want to explore today: what happens after your newsletter starts to grow beyond the creative project it once was? How do you not lose track of that original spark? And what will you likely need to learn next in order to keep growing a newsletter that readers also love? Let’s talk about a few of the things that I think are wise to turn your attention toward when the engine of your newsletter starts to really pick up steam.

Learn How to Nurture Your Readers’ Relationship With You and Your Product

So, whenever I feel stuck around my writing, there’s a classic piece of advice that I’ve turned to time and again: write to one specific person, as if they’re the only person who will ever read what you write. And while this often works for unblocking creatively, it doesn’t always translate into strategies for engaging a growing audience — or moving them to action. As your newsletter grows, there’s a ton of value in learning what moves them to action as a group and using that as a metric inside your creative production.

I think about this a lot and like to ask people when we talk about their newsletters: what kind of connection can you genuinely nurture with your readers? If your newsletter were a brick-and-mortar store, what would be valuable enough for customers to gather around in person — and how can we translate that into a platform like Substack? Do you know why readers keep coming back to what you create? Is it your perspectives, your ability to educate or entertain or the sense of belonging you create?

Because somewhere inside this analysis of our work, we have to remember that our newsletters exist on a digital shelf. We are being compared to other alternatives both inside and outside of Substack, which is why authentic relationship nurturing should start early and reflect what you know can be derived from the work you feel called to do.

Within this nurturing, I also think there’s a point where readers need a clear and obvious distinction between your free and paid offerings. They need to be able to measure and evaluate, month over month, what they’re getting in exchange for $5 or $8 or $20 a month. If they can’t hold that or point to “I paid this and received this thing I love,” you’re going to run into a lot of retention headaches.

Start Exploring How You’ll Diversify and Differentiate What Your Newsletter Is About

As your newsletter grows, you’ll also likely feel the urge to diversify. This is natural and can often be a wise strategic move. Taking what you know is already working inside your newsletter, you might expand your formats (e.g., adding podcasts or video), offer new access points (like higher-tier subscriptions) or create supplemental products (such as guides or workshops).

However, I’ve watched time and again what happens when diversification happens prematurely — before someone has a clear value proposition in the basic essays (or original format) they post. Adding voice overs, for example, to essays that aren’t already moving readers to action is a risky pivot, not to mention exhausting. I like to caution against diversification until you know you can sustain the costs (mental, emotional and financial). (Note: I do think it’s important to have data in the mix for diversification decisions — it can help toddle our dreams back into the reality of what it takes to execute on them.)

One final note about diversification: I’ve seen entrepreneurs build businesses fueled by smart strategies but without innate passion for the work — and burnout inevitably follows. I’ve also seen people with purple check marks on Substack start to grow weary of the topic that got them to this level of success that a lot of us aim for. The reality is that sometimes you will diversify your offerings and you will regret it and you will have to pivot again. How you do so is what counts in the end. That’s why before diversifying, it can be really helpful to be able to identify the difference between a creative block and an engine block.

Get Comfortable With Your Dashboard and What the Data Can Tell You

Your dashboard isn’t just a place to track your subscriber count — it’s one of the most valuable tools you have for understanding what’s working and what isn’t. Learning to interpret the data it provides will help you make more informed decisions about your posts, audience and growth strategies.

Pay attention to what moves readers to action inside your newsletter, and be sure to look for subscriber trends over a significant period of time — not just a one-time blip. Is there a particular type of post that performs well? Do certain subjects or formats encourage upgrades? While data won’t tell you everything, it can give you a clearer picture of what resonates with your audience — and where there’s room for improvement.

What have you found?

The journey of growing a paid newsletter is both exhilarating and challenging — a delicate balance of creativity, strategy and perseverance. Becoming a bestseller is a milestone, but it’s only the beginning of a much larger conversation: what does it truly mean to grow something you love?

As you navigate the path forward, I’d like to invite us all to take a moment to reflect on the skills and mindset we might need to nurture next. For me, I’m deep in learning how to adapt PR best practices in a way that feels authentic to me as a business owner. In my offline work, I’m teaching newsletter creators some of the tried-and-true ways to nurture their audiences without taking out a second mortgage to hire a marketing director. (We’re also often exploring the inner dynamic of creative iteration versus the systems that are somewhat unavoidable inside a newsletter model.)

→ So tell me: What’s been your biggest challenge or surprise as you grow? What skills have you found yourself leaning on — or needing to develop? Let’s start a conversation about what it means to turn a creative passion into a thriving, sustainable venture.

New to Amanda and The Editing Spectrum?

• I meet once a month with my paid members for The Pivot Hour, a live Zoom meeting that’s a freeform space where they can ask about strategy, data, dashboards, editorial pivots and more. Subscribe today and get a free coupon link to register for December’s Pivot Hour in your welcome email.

• Data Audits for Creative Entrepreneurs: When your newsletter feels stuck or needs a new direction, let’s take a look at your data. Together, we’ll create an actionable plan that looks at your pricing (and makes sure you’re in your sweet spot), renews your enthusiasm and aligns with what you’re trying to build — whether it’s fine-tuning your paywall, boosting reader engagement or revitalizing your publishing rhythm. Learn more here.

• Newsletter Nurturing & Strategy Sessions: Feeling stuck on upgrades?Wondering if being a bestseller is even worth it? Let’s connect to talk about the practical sides of business and easy ways you can start nurturing the readers in your newsletter and helping move them to action. Book a session here. 

• Workshops & Speaking Engagements: Invite me to speak or host a workshop for your university, writing community or in-house team. Send me an email at TheEditingSpectrum@gmail.com.