founder & digital wellness coach

Freelancer FAQs: Three Years of Learnings

You wanted to pick my brain? Now you can.
Freelancer FAQs: Three Years of Learnings

Once or twice every week, like clockwork, a familiar email lands in my inbox.

Sometimes it comes in the form of a cold Twitter or LinkedIn DM, but the premise is all the same.

that’s what you call a high-quality cold dm baby!

As a believer in good karma and the power of relationships, I almost always hop on the call.

(I’m busy, but not that busy.)

In some cases, these interactions have led to amazing friendships. But after fifty or so of these calls, I’ll admit…

No matter how enjoyable it is, it can get repetitive af.

They ask the same questions, I give the same answers. The worst part is that 85%+ of these people never go on to begin freelancing anyway. All that free game for nothing.

I love meeting new people, but there’s only so much brain to pick.

That’s not to say that I won’t continue to offer free advice in the future, but in the spirit of efficiency (and selfishly a reason to create some content out of it), I’ve decided to answer these questions once and for all.

The beauty of freelancing is that 95% of the questions, best practices, and challenges you’ll face on a day-to-day basis are the same regardless of your field of expertise.

Just as customer support centers equip their agents with reference sheets to efficiently address frequently asked questions, I hope this piece will serve a similar purpose…

To give you everything you need to know to start your life as a freelancer

Let’s dive in.

After some basic pleasantries, each call starts with the same exact open-ended question you’d imagine.

How did you start?

To answer this question, I’ll an anecdote from a 2016 panel featuring George RR Martin and Stephen King (two legendary writers).

“How the fuck do you write so many books so fast?” George RR Martin asked Stephen King, who responded:

“The way that I work [is] I try to get out there and I try to get six pages a day,” said King. “When I'm working, I work every day [for] three, four hours and I try to get those six pages and I try to get them fairly clean. So if the manuscript is, let’s say, three hundred and sixty pages long, that’s basically two months' work.”

“And you do hit six pages a day?” asked Martin.

“I usually do,” responded King.

To date, the author has published over 60 novels and 200 short stories, on top of essays, screenplays, and poems. He stands as one of the most prolific writers of our time.

In his memoir “On Writing: A Memoir of the Craft” King advises… “If you want to be a writer, you must do two things above all others: read a lot and write a lot. There's no way around these two things that I'm aware of, no shortcut.”

I’m far from a general award-winning novelist, but the same logic applies.

Just fucking write.

I wrote a 220-page book and over 120 blog / newsletter posts before even thinking of venturing into the freelance world.

Did I wait way too long to try to earn off my talent? Yes.

Did having a massive portfolio of 120 blog posts and a published book make it much easier to land my first client? Also yes.

This leads us to the question that nearly always follows…

How did you find your first clients?

My first clients came through relationships that I had formed years prior. Ask most freelancers, and they will likely tell you the same.

From there, my business grew through two channels:

1. Word of Mouth
2. Cold Email / DM

Let’s start with the first one (more on #2 later)…

It’s taken me 26 years to realize that cliches are cliches for a reason: Because they’re true.

The 'Your Network is Your Net Worth’ trope is cringy as hell, but it’s no joke.

Like any service business, the quality of your relationships will make or break your success as a freelancer.

Still, at this time of writing, referrals account for 90% of new leads at Third Wall and I spend hours per week meeting new people, making intros, and attending dinners — all to build a quality network and expand my surface area of luck.

But here’s the silver bullet agency hack that all these ‘I'll help you run it up to 10k/month gurus’ won’t tell you:

There are no shortcuts or growth hacks to building a quality business. Even the largest network in the world won’t save you. You need to do damn good work.

Growing up, I was inherently a people pleaser. Pretty shitty quality to have in general, but great for being in the service business. Especially when just starting, I was maniacal about client satisfaction (and still am).

All my time is invested in delivering as much ROI and as enjoyable of a client experience as I possibly can -- driving revenue, saving time, making the right intro -- you get it.

All of this plays a huge role in retention --- the lifeblood of any business.

Good work makes clients stay longer. Good work also drives referrals. Referrals lead to more referrals. When you consistently onboard new clients faster than it takes for existing clients to churn, you have a pretty strong business.

It’s not rocket science.

How did you set your rates?

It depends on your situation.

Do you have an existing portfolio? Are you starting completely from scratch?

Are you starting this off as a side hustle or are you relying on freelance income to pay your rent and monthly living expenses?

Are you a single bachelor or do you have a family to feed?

Depending on these answers, I’d suggest putting earning on the back burner for the first three months and focusing on building quality case studies:
(1) Find brands that carry serious social proof and offer to work for free/heavy discounts.

(2) Do great work.

(3) Use those case studies to land more clients and hopefully snag a few referrals along the way.

From there, gradually raise your rates until someone says no. If you never get any pushback on your rates, that means you’re charging too little.

The sad truth about freelancing is that most people don’t know their worth. They charge way too little and brands love it.

When’s the last time you heard a company looking to hire a freelancer say…

“Sorry, that rate is too low, please let us pay you more money?”

Lol keep dreaming.

When the time is right (and if you truly think you’re work is A+) you need to have the guts to command A+ rates. People will say no, and that’s okay. If you never get any pushback on your rates, that means you’re charging too little. On the flip side, if your work sucks, you won’t be able to get the rates you think you deserve.

Ultimately, the market will decide if your pricing is fair.

How do you cold pitch yourself?

If you suck at pitching yourself, you’re gonna have a tough time making ends meet. That’s 75% of the job.

Here’s a few tips:

1. Be yourself (and be human). Everyone’s bullshit detectors are fine-tuned, and most people can sniff out a fraud from a mile away. Authenticity wins, especially when we have ‘growth hackers’-turned-NPCs spamming DMs and comment sections with AI-generated outputs.

2. Build a personal website and buy a personal/professional domain. Then, create an email address with this domain (mine is

This will help you stand out from other freelancers using their ‘’ email addresses.

The bar is pretty damn low.

3. Stay away from freelancing sites. Fiverr and Upwork are complete time sucks. The projects already pay shitty and then they take a 10-20% fee. Plus thanks to the first-come-first-serve nature of these sites, hirers tend to only consider the first few people who apply. Applying to a role that’s been live for more than 24 hours is nearly useless, and is certainly a waste of your time.

4. Don’t be afraid to fail. The majority of cold emails you send will be left unanswered. Don’t get discouraged and don’t be scared to follow up.

To quote the late great Steve Jobs…

“Most people never pick up the phone and call. Most people never ask. And that's what separates sometimes people who do things from people who just dream about them.”

5. Spend time on social platforms where your target buyers frequently interact. For me, this is Twitter and LinkedIn. Maybe if you’re a freelancer targeting high-ticket coaches and info-product gurus, this will be Instagram. As with most things, it depends.

What do you use for invoicing?

I use Wave — it has everything I need from an invoicing and bookkeeping perspective. Quickbooks is also solid.

If you’re looking for an all-in-one freelancer hub, Harlow is a great option — it offers everything from invoicing to contract templates, project management tools, and more.

What do you use for contracts?

I use PandaDoc for all my e-signature documents. They have great modifiable templates and all docs are legally binding.

As mentioned above, Harlow is also great for this.

Ultimately, the defining trait between those who succeed in freelance work and those who treat their efforts as an expression of entrepreneurship. Because it is.

Whatever anyone else says, you are an entrepreneur. You run a business (please actually incorporate yourself and reap the tax benefits of self-employment), even if that business only has you as its standalone employee.

You must think like a business person. You must act like a business person. You must sell like a business person. You must file taxes like a business person (hire an accountant please). If you don’t take yourself seriously, nobody else will.

Only in writing this post did I realize that this is ~5% of what I’ve learned over the last few years, but for the sake of your attention and time, I’ll cut it here.

If you made it this far and you still have unanswered questions, I’m happy to chat.

Reply to this email or shoot me a DM on Twitter / LinkedIn.