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3 Inflection Points to Skyrocket Your Freelance Income

Updated: Nov 28, 2021



I was 11 years old the first time I mowed my family’s lawn. As soon as I finished, I ran inside and asked my dad if I could turn my new-found skill into a full-blown lawn mowing business. He insisted I needed a little more practice. So the next time I mowed the lawn, I asked again. And then again...


My dad eventually gave in.


Instead of letting me navigate finding customers on my own, he drove me to the community office at the front of our neighborhood. We trotted inside and he introduced me to the woman behind the desk. “My son is starting a lawn care business. If anyone in the neighborhood needs their yard mowed, would you mind recommending him?”


I was booked all summer and never had to knock on a single door. New leads came almost weekly and I had a booming lawn business. (At least, booming for an 11 year old.)


One simple action unleashed a cascade of passive leads.


Are there similar points of leverage in freelancing? I believe so. Here are three powerful inflection points I think offer the biggest financial impact for your time.


1. Create powerful proposals

Does this situation sound familiar?


You just finished your first video call with a new prospect. Everything felt perfect. You built rapport on the call, showcased your expertise, and the client even said they’re impressed with your background and that you’re the right person to solve their problem.


It feels like a shoe in. Spoiler alert: This is where many freelancers lose business, including me. The temptation is to send a mediocre proposal because at this point, sending the proposal only seems like a formality.


The problem is, you don’t know who else is part of this decision-making process. There may be a board, CEO, or even spouse that you also need to impress.


A proposal is your most critical sales document as a solopreneur. It should sing your praises, emphasize your expertise, and most importantly: convey how you’re going to solve your prospect’s problem.


If your proposal doesn’t build the same rapport or make the same powerful first impression that you established on the call, you can easily lose the project you felt so confident about. This has happened to me many times. So, I recently started tracking proposals to take them more seriously.


As James Clear says, “The things we measure are the things we improve.”


Here’s what that process looks like in my business:



I track six factors: Client name, the type of work I bid on, whether the proposal was accepted, the day I sent the proposal, the day I received a response, and how I originally connected with the lead.


I used to