I've been building automations for a few months and want to start selling them, but I have no experience and haven't worked with anyone. What's your advice to start selling? Also, I don't feel confident applying to work for free on Upwork in case I can't build the automation correctly or something glitches — what should I do about that?
You just have to start selling — I wish I had a more satisfying answer, but you have to put yourself in the arena and figure it out; it's uncomfortable but the only way through. On the confidence issue: offer a guarantee. A guarantee lowers the client's perceived risk and simultaneously aligns your incentives, because now you feel obligated to deliver — your own money is on the line, which paradoxically increases the odds you actually pull it off. The higher the risk you put on yourself, the more likely you are to rise to the occasion. Once you've done that, your personal confidence level matters a lot less.
Learn to pitch your work as a deliverable rather than as time, and back it with a guarantee. If the deliverable doesn’t meet expectations, the client pays nothing, and you’re both happy. It may sound odd to offer free work, but you can say, ‘I’ll deliver X as we agreed, and if you don’t love it you owe me nothing.’ This removes risk for the client and eliminates the mental block of ‘what if it doesn’t work?’ If the project fails, the client gets their money back and you haven’t lost more than the time you invested, which is still valuable experience. You can then charge more on future projects because you’ve proven the system works. Even if you have rent and other expenses, you can treat the guarantee as a side‑hustle risk that pays off long term. I learned the hard way in a door‑to‑door marketing agency that never offering guarantees cost me millions; once I started guaranteeing offers, my top line tripled with only a small refund rate, making the guarantee a logical decision.
You don't have to guarantee dollar-sign outcomes — I've worked with these kinds of businesses for about a decade so I have a reasonable sense of what value I can drive, but if you're new to this it's completely understandable that you're not comfortable promising a dollar figure. Offer something else instead. A few variants: tell them you won't charge a cent unless they absolutely love it and ask you to keep going. Or say you'll deliver X, Y and Z, or you'll keep working for free until you do (weaker, but I've used it myself — we did this at Pacific Creative Group with my old business partner). You could also put real risk on the table, like offering to buy them an Amazon gift card or refund them if you don't deliver. Instead of ROI, you could frame it around hours saved per week (hard to track in practice, but usable). Or just offer a 100% satisfaction guarantee — tell them your sole goal is their satisfaction, and if they don't see the value, you won't charge them. A guarantee does two things: it makes people much more likely to want to work with you, and it makes you much more likely to actually follow through on what you promised.
You said you almost guarantee results; I guarantee results—I tell you you'll get X, Y, Z or risk mitigation. There's a difference between an emotional sales decision, where people feel they need to buy now, and an intellectual sales decision, which focuses on positive ROI. A guarantee addresses both: intellectually, it removes doubt about returns; emotionally, it feels like a no‑brainer. If you’re willing to guarantee your service—and refund if you don’t—there’s no reason not to move forward unless there’s another unresolved issue, you’re untrustworthy, or you haven’t built enough value. So, just offer a guarantee. Don’t pitch it as a demo; that makes you perform like a dancing monkey. Instead, frame it as one business owner to another: show them something cool you’ve built, like a lead extraction and enrichment system that worked for a seven‑figure business, and let them see it. That puts you on equal footing and feels like sharing something valuable rather than performing for approval.
For your first sale as a beginner in the automation/services space, the most straightforward approach is to go on Upwork and similar job platforms and try to land a paying customer as soon as possible, even if the pay is low or the scope is larger than you'd usually handle. The lifetime value to cost‑per‑acquisition ratio on Upwork is very favorable — roughly a gross‑profit‑to‑CAC of about 10 : 1, making the economics strong. Think of it like online dating: the platform has already filtered people who are looking for what you offer, so you just need to show you can deliver. Focus on proving you can 'juice' the work and stand out among the many freelancers. Even small, low‑paid jobs build reputation and lead to better opportunities.