Should I practice building automations on Upwork before taking real jobs, or just jump straight into applying?

#49 · Selling An AI Automation Company ($0 to $72K/mo)

Should I practice building automations on Upwork before taking real jobs, or just jump straight into applying?

Just jump straight into applying to Upwork jobs. If you build the automation ahead of time and present it to the client, your marginal cost is only a dollar or two per application, and you control whether they see the proposal by bidding high. This gives you a higher reply rate, and Upwork no longer refunds connects, but you also aren’t charged if they don’t accept.

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Related answers

youtube ↗Agency Operations

What types of automations should I build to go full‑time, and does Upwork have an advantage over other freelance platforms?

Focus on revenue‑proximate automations—sales, marketing, and lead generation—because they directly increase income. Upwork is the simplest and most accessible platform, though it costs more than alternatives; its ease of use makes it a good starting point.

automation typesUpworkfreelance platforms

youtube ↗Client Acquisition

What types of businesses or clients should a beginner target on Upwork (or similar platforms) when starting with AI automation?

Accept any and all work on Upwork—think of it as an elevator that instantly connects you to large businesses you’d never meet otherwise. Even as a total newbie, you can land a client doing $10–$20 million a year within a week, giving you a powerful case study like 'I helped a $10 million/year business achieve X, Y, Z.' At this stage, don’t worry about qualifying or tightening the funnel; go broad to bootstrap experience, collect case studies, and start making money. The creator shares a personal example: a friend who jumped on Upwork while he was door‑to‑door went from zero to a legitimate $30 000/month income in three‑to‑four months by maximizing opportunity and landing a big‑ticket client whose needs matched his skill set—something the creator missed while grinding door‑to‑door for $5 000/month.

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youtube ↗Client Acquisition

I’m spending a lot of time learning automation and building systems while also trying to build an Upwork profile and create content. What should I focus on to get my first paying clients?

Focus on the need‑to‑know, not the nice‑to‑know. Get customers first, then let their feedback tell you where to invest your time. Apply for jobs on platforms like Upwork to start earning, and learn the tools you need by actually doing the work for a client. Prioritize outreach—cold email with personalized Loom videos works well initially—rather than spending endless hours learning theory. Once you land your first client, double down on delivering value and then scale from there.

upworkcold emailfocusfirst client

youtube ↗Lead Generation

I have a question on Upwork: many clients request not to work with agencies. What is your experience with this?

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.”

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