➡️ Before we dive in —If you want to see the exact message that landed me a $20K memoir client, you can download it free: The 5-Minute Memoir Ghostwriting Pitch

A few days ago, I hosted a Substack Live with someone I have been following and learning from for a while. Maya Say, a monetization strategist who has worked one-on-one with two thousand solopreneurs.

She has:

* 10+ years of solopreneurship under her belt

* Hundreds of 5-star reviews on Fiverr

* A business that now includes copywriting, digital products, Substack, and even real-estate flipping

And she does it all while working around 2–4 hours a day, picking up her kids, going to Pilates, and working from coffee shops.

Meanwhile, I am over here refreshing Stripe, chasing invoices, and wondering why my 25 years of experience are not translating into the peaceful, abundant solopreneur life I imagined.

This conversation was a bit of a pattern interrupt for me. Here are the ideas that hit hardest.

1. A solopreneur is not “someone who works alone”

If you Google “solopreneur,” you get a sad definition about “an entrepreneur with no employees.”

Maya laughed at that.

You don’t define a singer as “the person in the band who doesn’t play an instrument.”

Her definition is much more useful:

A solopreneur is someone who delivers the core value of their business themselves.

So:

* If I write the memoir and hire help for admin, design, social media, or bookkeeping, I am still a solopreneur.

* If a copywriter hires other copywriters to do the writing while they manage clients, that is no longer solopreneurship. That is an agency.

The key question is: What is the core value of your business, and are you still the one delivering it?

That one definition already made me feel less “small” and more like a deliberate choice, not a failed agency owner.

2. Maya tried the agency dream. She hated it.

There was a moment in her journey when she landed her first 5-figure client (12K for a copywriting project).

Her first thought:

“I must not be good enough to do this alone. I need a team, an office, and an agency if I am going to work with clients at this level.”

So she did it.

* Rented a trendy office downtown

* Hired a couple of people

* Filled her calendar with meetings, research, user testing, management

And she realized she had accidentally built a business where she no longer wrote.

So she shut it down. Let the team go. Closed the office. Went back to being “just” a solopreneur.

But now she knew something important:

She did not need to become an agency in order to work with high-paying clients. She needed better offers, better pacing, and better boundaries.

3. Multiple income streams do not mean “scattered”

Today, Maya’s income looks roughly like this:

* Around half from client work (copywriting)

* Around 10–15% from digital products, Substack, and Medium

* A new stream from flipping real estate, where she uses contractors for the physical work

On paper, that looks like a lot. In practice, she built it slowly:

* First she was “just” a copywriter.

* Years later, she added Medium.

* Later still, she launched Substack and digital products.

* Only now, with a stable business and history, is she experimenting with real estate.

It did not happen all at once.

Her rule:

You can be multi-passionate, but you cannot build four things from scratch at the same time.

Start with one, get it stable, then layer on the next.

4. My bottleneck: Do I need more clients or more money?

When I described my situation to her –

* Ghostwriting memoirs (most of my income)

* Book coaching that grew organically

* Corporate newsletter ghostwriting

* Constant feeling of being on a financial hamster wheel

– she stopped me and asked a deceptively simple question:

“Is your problem that you need more clients or that you need more money?”

Because those are not the same.

If I double my prices and halve my clients, that is a very different life from packing my calendar with more and more work at my current rates.

Ouch.

5. “With your background, 20K for a memoir is not enough.”

I told her my current memoir pricing. I braced myself.

She did not flinch.

“With your experience, 20K for a memoir is not enough.”

Her point was not “charge wildly random numbers.” Her point was:

* Raise your confidence first. Believe there are clients who will happily pay more.

* Make your process so good that even you think, “this is underpriced.”

* Add things clients really care about: structure, interviews, research, maybe user testing of titles or positioning, support around launch, etc.

* Then go after bigger clients on platforms where they are actively looking to buy.

I immediately felt my own resistance rise:“But where do I find these magical premium clients?”

Which led us to the part that surprised me most.

6. Fiverr is not “for cheap clients.” It is a buyer-intent platform.

We love to dismiss platforms like Fiverr and Upwork as “race to the bottom” marketplaces.

Maya built her entire business on Fiverr. She has:

* Thousands of reviews

* Long-term client relationships

* A recent client who turned into a 40K project and works with the US government

Her distinction:

“There are not cheap platforms. There are cheap sellers on good platforms.”

On Fiverr right now there are millions of active buyers. That means people who have bought at least one service in the last 12 months, often more.

These people do not go there to “browse content.”They go there to buy.

So if you are offering:

* Ghostwriting

* Newsletter writing

* Website copy

* About pages

* Articles

You can either:

* Try to convince a random LinkedIn follower to hire you, or

* Show up where someone is literally typing “memoir ghostwriter” into a search bar with their credit card ready.

Her question for me (and by extension, for you):

Why are you trying to sell in places where people are not there to buy?

7. Stop chasing trends. Fix your offer instead.

Because she has worked with so many solopreneurs, Maya has seen the same pattern over and over.

People come to her saying:

“Nothing is selling. I need you to write magic sales copy for my offer.”

And almost every time, the problem is not the copy. It is a confusing, weak, or misaligned offer.

No clear “who.”No clear “what.”No connection to what people are already looking for.

On Fiverr, her breakthrough came when she stopped offering “website copy” and started offering About pages.

Everyone was stuck on writing their About page. They felt awkward writing about themselves. Her About page gig exploded. From there, she could upsell homepages, sales pages, full sites, emails, and more.

Sales copy cannot fix a broken offer. But a clear offer often “sells itself” once you describe it plainly.

So before we run to new platforms or trends, her advice is to ask:

* Where are people already trying to give you money?

* What do your existing clients keep asking for?

* Which offer feels like a “door opening” project that leads to more work?

8. Substack: what actually converts free readers to paid

Maya currently has around 50 paid subscribers, and has been higher in the past.

What moved the needle for her was not posting more, but:

* Auditing 200+ past posts

* She tagged them by topic and tracked which ones led to paid upgrades.

* Two of her five main topics reliably convert. The other three? Not so much.

* Sending occasional, honest sales emails

* A pure sales email like “Next week I am running a paid webinar for subscribers on X, here is what you get…” works surprisingly well.

* People do not mind being sold to if:

* The offer is genuinely useful

* You do not do it every day

* Your free content is already valuable

* Giving paid subscribers the “how”

* Free readers often get the “what” and the story.

* Paid readers get the “how”: tools, planners, assessments, prompts, and deeper breakdowns.

* Some tools live on Gumroad (where paid subs get them free or discounted), others live in Google Docs or inside the paywalled section of the post.

Her reminder to me:

If you never actually ask people to upgrade, you cannot be surprised if they do not.

Guilty.

9. Doing less, better

My favorite part came near the end, when I confessed how tired I was.

Her advice was not “work harder” or “add three more offers.”

It was:

“Do less. Choose the thing that brings you the most joy and a decent amount of money. Focus on making that offer better, more expensive, and more exclusive, so you can work less and earn more.”

Because as solopreneurs, our energy is the business.If we burn out, there is no team to keep things running.

Her own days are built around that reality:

* School drop-off, coffee shop writing sessions

* Pilates twice a week

* A few focused hours of work

* Family, house stuff, and occasional real-estate visits

Two to four hours of deep work instead of twelve hours of scattered panic.

10. What this means for me (and maybe for you)

Here are the immediate shifts I am taking from this conversation:

* Revisit my memoir offer and pricing and make the process so valuable that 20K feels like a starting point, not a ceiling.

* Treat platforms like Fiverr, Upwork, and Gumroad as serious options, not “desperate” ones, because that is where buyers already are.

* Send intentional sales emails on Substack instead of assuming people will magically upgrade.

* Audit my own posts and see which topics actually convert or attract the right clients.

* Ruthlessly simplify: fewer offers, fewer platforms, deeper focus.

Solopreneurship is not a cute hashtag for “I do everything alone forever.”It is a deliberate decision to keep the core value in your hands and design a business that works for your life.

If you are a solopreneur (or want to be one), I would love to hear:

👉 What is the core value of your business, and are you still the one delivering it?

Tell me in the comments; I am genuinely curious how you are navigating this path.

Want to connect with Maya Say? Find her at Smarter Solopreneurs on Substack, where she teaches solopreneurs how to make more money by working smarter, not harder.

Thank you Andi Bitay, Gregory Bourne, and many others for tuning into my live video with Maya Say! Join me for my next live video in the app.

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