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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 think proposals were a boring administrative task. Now I see them as one of the most important parts of my job. And since I usually collect 50% of a project up front, I think of the proposal as its own project that I’m getting paid for.

If I’m charging $5,000 for a project, I tell myself that the proposal is worth $2,500. Obviously that’s not true, but it reminds me to give every proposal enough care and attention—and salesmanship.

2. Perform deep work

Peter Drucker famously said that only two things make money in business: innovation and marketing.

For freelancers, I might swap innovation for deep work, since that’s the activity that pays our bills. Deep work is when you stay focused on a particular problem or task without distraction. In my work as a copywriter, deep work takes the form of research and writing.

There are many other responsibilities in my business—administrative tasks, customer interviews, bookkeeping—but writing is what ultimately pays the bills. The more time I can spend writing for clients, the more I earn.

And this is similar for many other consultants and freelancers within the knowledge-work sector. Writers, designers, developers—we make our living solving problems that require long stretches of uninterrupted, focused attention on a single challenge.

My best work days are centered around deep work. Things like responding to emails, recording expenses, and engaging on social media are very low priority, so I try to save those activities for the afternoon slump. My best work (and therefore my deep work) always happens in the morning.

3. Systematize generating leads

When it comes to lead gen, systems are more important than one-off tactics.

As a kid, I could have spent days knocking on all the doors in my neighborhood to find lawn care clients. Instead, my dad was clever enough to find a single inflection point that generated dozens of passive leads for just a few minutes of effort.

How do you systematize your lead gen?

Sarabeth and I use several templates to streamline recurring email conversations with prospects. We’ve also invested a lot of time into our website to make sure the copy, branding, and individual pages do most of the selling for us. By the time we get on a call with a new prospect, we want them to already be convinced we’re the right team for their project.


A lot goes into running a business on your own. Many freelancers want to offer industry-leading professional services—while also operating as their own CPA, administrative assistant, and sales expert.

With so much on your shoulders, it’s easy to put in twice as much work and earn half as much money as you would at a normal 9-5 job. But freelancers who learn to organize their calendar around their business inflection points can make a flexible, comfortable living as entrepreneurs.

And that’s when freelancing really lives up to the hype.


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