How do I get clients when I feel lost after months of trying?

#203 · Automation-as-a-Service (AaaS) in 2026

How do I get clients when I feel lost after months of trying?

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.

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Related answers

youtube ↗Client Acquisition

Does your roadmap to getting your first client involve Upwork, or is it more personalized per trade?

Yes—Upwork is the straightest line to your first customer when you’ve never sold anything before. It lets you get into conversations, learn basic sales, and earn an initial return on investment while paying down client‑management and skill debt you didn’t know you had. However, relying on Upwork long‑term is a crutch because most projects are custom, forcing you to rebuild the wheel each time and making templated delivery impossible. After you’ve cleared that debt, transition to more scalable outbound methods like cold email. Only after a couple of months do you begin exploring scalable inbound or social‑media approaches. The early phase is strictly Upwork‑focused to bootstrap the business.

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youtube ↗Agency Operations

As a beginner on Upwork, should I be open about my lack of experience, and how can I position myself to win clients?

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.

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youtube ↗Mindset

How can I be sure I’ll be able to deliver on Upwork jobs when the client’s requirements aren’t clear, and how can I avoid overshooting?

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.

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youtube ↗Lead Generation

Nick, cold emails versus Upwork. Which one helps move the needle faster to get your first win? Say you got 1K. extremely good skills, unlimited time, 18, a little social proof, and you're starting from scratch. Which of the two would be your go-to method to make a little bit more capital and get the ball rolling?

With $1,000 to bootstrap, go with Upwork. You can submit roughly 200‑300 applications (maybe more thanks to the connects refund policy). In the Maker School community, the average number of proposals needed to land a client is about 40‑60, so you could realistically secure around six clients. If the average revenue per client is around $200, that puts you at $1,200, and you can rinse and repeat. In practice, the average revenue per client is often higher—many close $1,500‑$3,000 deals—so within the first 50 proposals you could reach roughly $6,800 (or about $1,600 after the correction). Consistently scaling up from there will grow your business.

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