Everything for the trail, by topic
The full collection — field guides to read and field notes to flip through. Start with the quick notes, or dig into the guides by topic.
Field Notes
How Much to Save Before You Go Freelance
A six-slide field guide to sizing your freelance cash runway: why an empty buffer is the real career-killer, the 3-to-6-month rule, how to size it to your true monthly costs, and the cheat code that lowers the number.
6 slidesIs Freelancing a Good Fit for Me?
A field guide to the five honest checks that decide if you're ready to freelance, and what to shore up before you quit your job. They weigh more than your portfolio.
8 slidesHow to Get Your First 5 Freelance Clients Without a Portfolio
A field guide to the five sources that reliably land your first freelance clients before you have a portfolio, and how to approach each one without a job board in sight.
6 slidesThe Misunderstood Reality of Imposter Syndrome
A field guide that reframes imposter syndrome for freelancers: the fear of being found out isn't proof you don't belong, it's a growth signal. Here's how to read it, and the three-move protocol that turns it into fuel.
7 slidesField Guides
Freelance Business
Field GuideWhy You Need a Business Plan When Freelancing
The simple, four-part freelance business plan that keeps you focused and off the odd-jobs treadmill.
2 min read
Field GuideCalifornia's New Freelance Law Includes 8 Powerful Protections
SB-988 took effect January 1, 2025. What it requires, and the protections that make late-paying clients think twice.
2 min readGig Platforms
Field GuideIs Upwork Dying? The Numbers Behind the Marketplace Contraction
Upwork's own filings show active clients falling while spend per client rises. Here's what the contraction actually looks like, where the work went, and what it means for a freelancer standing in the marketplace.
5 min read
Field GuideFiverr Alternatives That Don't Take 20% of Your Income
An honest guide to Fiverr alternatives from a 25-year freelancer: what Upwork, Contra, and the clones actually change, what Fiverr's own filings say it captures, and the open-market model that keeps you at 100%.
6 min read
Field GuideUpwork vs. Fiverr: The Comparison Neither Platform Will Publish
A neutral Upwork vs. Fiverr comparison from a 25-year freelancer: the real fee structures, what sellers actually earn, both platforms' shrinking client numbers, and when the right answer is neither.
6 min read
Field GuideAre Upwork and Fiverr Worth It? What the Economics Actually Say
I've freelanced for 25 years without a gig platform. Here's what the actual earnings data says about building a career on one - and what the successful freelancers do instead.
9 min readMaking The Transition
Field GuideWhy You Shouldn't Quit Your Job to Pursue Freelancing
The case for building your freelance business on the side first, and how to know when it's finally time to leap.
2 min read
Field Guide4 Reasons Your Freelance Business Should Not Be Built Around a Brand-New Skill
Four reasons real, hands-on experience is the moat that wins better clients, and why faking it backfires.
2 min read
Niche & Positioning
Field GuideHow to Find Your Freelance Niche: A Working Freelancer's Method
A step-by-step method for choosing a freelance niche from a 25-year freelancer: how to narrow a market until you can name it, the four filters a niche has to pass, how to turn its expensive problem into a productized offer, and how to test the whole thesis on ten prospects before you commit.
9 min read Field GuideFreelancing and the Long Tail: Find Your Niche and Thrive
Why taking every job keeps you stuck, and how to find an overlooked long-tail niche and own it.
2 min read