Why Proposal Automation Isn’t a Hack—it’s Your Growth Lever (2025 Edition)

When most freelancers or agency founders hear the word “automation,” their first thought is: Oh great, another tool that saves me 10 minutes here and there. But in 2025, proposal automation isn’t just about saving time—it’s about compounding growth. It’s the difference between running in circles and actually moving forward. In our earlier piece, “Why … Read more

Cold vs. Warm Proposals: How to Win Clients on and off Upwork

When it comes to landing freelance jobs, especially on competitive platforms like Upwork, your proposal is everything. And not all Upwork proposals are created equal. Some feel like spam. Others feel like a personal pitch crafted just for the client. That’s the difference between a cold proposal and a warm proposal. Knowing when and how … Read more

How Pendown is Changing the Way Freelancers Win Clients

Freelancing is an art, a hustle, and a full-time business rolled into one. You’re not just a designer, writer, developer, or consultant—you’re also the marketing team, the customer service rep, the accountant, and yes, the proposal writer. And let’s be real: proposal writing is one of the trickiest parts of freelancing. You might have the … Read more

Top 5 Proposal Mistakes Freelancers Make (And How to Fix Them Instantly)

Freelancers often lose projects not because they lack skill, but because they miscommunicate their value in proposals. If you’re sending dozens of pitches and getting crickets in return, you might be making one (or all) of these five common mistakes.This post breaks down the biggest freelance proposal blunders and shows you how to fix them … Read more

How to Write Winning Upwork Proposals (Even If You’re Not a Writer)

Upwork is a goldmine for skilled freelancers and agencies—if you can crack the code of writing winning proposals. Unfortunately, most people are great at what they do but struggle to sell it convincingly. That’s where this guide comes in. Whether you’re a seasoned developer, designer, or agency owner, you’ll learn how to write proposals that … Read more