#195 · The Future of AI Chatbots After 2025
Don’t tell Upwork clients you’re a beginner; it raises risk perception. Instead, create a sample system for yourself so you can truthfully say you’ve built it before. Then back your service with a 100% results guarantee—if you don’t deliver, refund the client. This reduces perceived risk and positions you as competent.
Don’t worry about whether you can deliver until you actually have the project in front of you. Many people disqualify themselves early by over‑thinking the unknown. Focus on getting the job first, then figure out the details as you go. As Grant Cardone says, saying “yes” builds confidence; even if you don’t fully understand the task now, committing to it forces you to learn and find a solution. This psychological commitment raises your skill level over time. By repeatedly committing to deliver, you’ll become better at delivering, even if you start with limited knowledge.
Yes, it's harder, but you can stand out with a short, tailored pitch showing you've done similar work; focus on quality over quantity; remember others face challenges too.
Success is mostly a volume problem. Sending only 23 Upwork applications in three or four months is extraordinarily underperforming—I recommend 165 in the first month, which you could finish in two days, not four months. It’s not just about volume; it’s about your expectations being misaligned with the effort required. If this is new to you, don’t expect results in a few hours. Keep grinding: send lots of Upwork apps, cold emails, cold DMs, and community posts. When you don’t see results, don’t quit or get frustrated—just keep iterating and increasing your output until you start winning.
Most clients on Upwork don’t want to work with agencies. I recommend not using Upwork as a primary agency growth channel; treat it as a way to get an initial foothold while you’re still freelancing. When you’re selling yourself, you want the client to feel they’re hiring you, not an agency. Avoid agency language on your profile—use “founder” if you like, and bring up any consultants only during calls after you’ve secured the project. Start as a freelancer, deliver a high‑quality first project, get a great review, then gradually introduce others or a consultant on later projects. Don’t say you’ll hand the work off to an agency; keep the work yourself initially. In short, don’t label yourself as an agency on Upwork—position yourself as an automation specialist or similar, because Upwork users dislike the word “agency.”