Pillar Three

Work for YOU

Client pipelines, revenue math, and the honest truth about working for yourself. These dispatches cover everything from finding your first client to building a sustainable business — without an office, a commute, or a performance review.

All Dispatches

The first real money I made on my own was forty-seven dollars. A consulting template I built on a Sunday afternoon, sold through a payment link I shared in two forums and forgot about. Three days later, someone in Minneapolis bought it. I have never been more proud of forty-seven dollars in my life.

This page is the honest guide to building income that doesn't require a commute, a boss, or the specific kind of death that comes from sitting in a conference room while someone reads bullet points off a slide you can already see.

Why "Work for Yourself" Is Not "Passive Income"

Let me be direct: "passive income" is a phrase invented by people selling courses about passive income. Working for yourself is work. It's often more work than a regular job, at least at first. The difference isn't the effort — it's the ownership.

When I invoiced my first client two hundred dollars for a forty-five-minute strategy call, the amount didn't matter. What mattered is that nobody scheduled it for me, nobody took a percentage, and nobody sent a follow-up Slack message asking me to "document the takeaways in Confluence." I saw a need, offered a solution, got paid, and moved on.

That's a fundamentally different relationship with work. It's not easier. It's yours.

The Three Revenue Models That Actually Work

After two years of building income on my own, from a rooftop in San Miguel de Allende, I've found three models that produce real, recurring money without requiring venture capital, a large team, or pants:

1. Consulting and Freelance Services

If you spent years building expertise in a corporate role, congratulations — you have a skill set that companies will pay hourly rates for. The same strategic planning I used to do for a salary, I now do for clients at rates that would've made my HR department uncomfortable.

The key insight: companies don't hire consultants because they lack smart people. They hire consultants because they need an outsider who can say the uncomfortable thing without worrying about the next performance review.

Getting started:

  • Pick a niche so specific it feels too small. "Marketing consultant" is invisible. "Revenue attribution consultant for B2B SaaS companies" gets calls.
  • Set your rate at the number that makes you slightly uncomfortable. If it feels reasonable, it's too low. Corporate budgets are calibrated for expensive. Cheap makes them nervous.
  • Start with your network. Your first three clients are people you already know. Not because of nepotism — because they've seen your work and trust it.

2. Digital Products

Templates, frameworks, guides, tools — anything you can build once and sell repeatedly. My forty-seven-dollar template was the first. It's not a fortune, but it scales without requiring more of my time.

The math is simple: if 200 people buy a $47 product, that's $9,400. Build four products, and you have a small business that runs while you're at the market buying avocados.

What works:

  • Templates that solve a specific, annoying problem. Not "productivity system" — more like "quarterly board reporting template for Series B startups."
  • Calculators and tools. I built a FIRE calculator that does what a hundred free ones do, except it includes the specific scenarios that matter (geographic arbitrage, variable withdrawal rates, healthcare costs abroad).
  • Guides with real numbers. People will pay for specificity. "How to move to Mexico" is a blog post. "The exact cost breakdown of relocating a family of three to San Miguel de Allende, with visa timelines, neighborhood comparisons, and school enrollment steps" is a product.

3. Content and Audience Building

This site is itself a revenue experiment. Not through ads — there are no ads and never will be. Not through affiliate links — same policy. The revenue comes from building an audience that trusts you enough to buy your products and services when you offer them.

The newsletter, The Dispatch, is the core of this. Every week, it reaches people who opted in because they wanted honest information about the topics I write about. Some percentage of those readers will eventually want a deeper engagement — a consulting call, a template, a guide. The content is the top of the funnel, but it's also the product. Both things are true.

Working from Mexico: The Logistics

Practically speaking, running a business from San Miguel de Allende requires three things:

  1. Reliable internet. We pay about $30/month for fiber that delivers 100 Mbps. It's fast enough for video calls, screen sharing, and uploading large files. It goes down occasionally — maybe twice a month for an hour. I keep a Telcel hotspot as backup.
  2. U.S. banking. I kept my American bank accounts and credit cards. Clients pay in USD to an American account. I transfer to Mexico as needed via Wise (formerly TransferWise), which gives rates within 0.5% of the mid-market rate.
  3. A workspace that isn't your bedroom. The rooftop is romantic in theory, but the sun makes the screen unreadable by 11 AM. Most days I work from the dining table. San Miguel has a few coworking spaces if you need the structure — Selina and a handful of smaller spots. A monthly pass runs about $100-150.

Tax-wise: if you're a U.S. citizen, you owe U.S. taxes regardless of where you live. The Foreign Earned Income Exclusion (FEIE) can shelter the first ~$120,000 of earned income from U.S. federal tax. Mexico taxes residents on worldwide income, but the temporary resident visa has nuances — consult a cross-border tax professional. I use one. It costs $800/year. It's the best money I spend.

What Nobody Tells You About Working for Yourself

The first month feels like freedom. The second month feels like unemployment. By the third month, if you haven't built some structure, you'll be watching Netflix at 2 PM and calling it "ideation."

The loneliness is real. Not the social kind — you can solve that with a coffee shop and a few expat friends. The professional kind. Nobody is going to review your work and tell you it's good. Nobody is going to set quarterly goals that give your week structure. Nobody is going to promote you. The feedback loop that corporate provides — even when it's annoying — disappears completely.

You'll need to build your own. Mine looks like this: ship something every week, review revenue monthly, and keep a list of what I said no to. That last one matters. When you work for yourself, the biggest risk isn't saying yes to the wrong thing — it's saying yes to everything and ending up with a worse version of the job you left.

Who This Is For

If you can't walk away from income entirely — or don't want to — this pillar is for you. You don't need to be a tech person. You need a skill that other people will pay for, a tolerance for uncertainty, and the willingness to invoice someone without apologizing for the amount.

The dispatches below are the real version. First clients, first failures, revenue math, and the specific kind of satisfaction that comes from making money that nobody approved, scheduled, or measured against a KPI.

Dispatches

The Work for YOU Files