How to Pull High-Paying Jobs Out of Your Butt

August 21, 2019

Over the past five years, I’ve traveled to 37 countries — while working as an independent consultant and “digital nomad” (though I hate that term — I feel more like a “busy tourist”).

I’ve been hired for a variety of jobs from $12 for writing useless clickbait, to $1,000 for a few years of part-time work (I had to pay my dues) … to $500 an hour, and $45,000 for a 6-month, part-time contract.

Naturally, the conversation comes up every time I meet someone new. How the hell do you make money?

I’ve been paid for:

  • editing books
  • ghostwriting books
  • marketing books
  • publishing books
  • outlining books
  • online marketing strategy
  • copywriting
  • writing/productivity coaching

And a few other things I can’t remember.

But I’m not formally “qualified” for any of those jobs. I’ve pretty much made up my career on the fly, and it has changed every few months.

My process is simple, but not easy. I get ignored. I get rejected. But the successes are all that matter.

I find companies and people I admire, find their top priority, figure out a way to achieve it for them, then sell the process in an attractive package.

Every job looks slightly different, but I combine my skills and connections to get people what they want.

As crazy as it sounds, there’s a method to my madness -- and I’m confident anyone can do it (if they’re as crazy as me). The principles apply to all skills and industries, and can be repeated ad infinitum.

So, let me tell you exactly how I pull jobs out of my butt, and you can too.

Step One: Don’t Look for Holes to Fill — Look for Holes to Dig

When people set out to work for themselves, they generally search for jobs they can perform.

That’s Mistake #1.

There are only two ways to find jobs as an independent contractor, and they both suck.

  1. Scour job boards like Upwork
  2. Ask his network if they need help with a specific skill (ex. “do you know anyone in need of copywriting help? I just quit my job and am looking for work”)

Your chances of finding a well-paying, enjoyable job like a $45,000 rewriting/marketing/indie publishing contract like that are virtually nil.

That’s the life of a freelancer, and almost nobody dreams of being a freelancer.

Generally, the pay is low, competition is high and jobs are boring.

Don’t think of yourself as a freelancer. Think of yourself (or at least sell yourself) as a consultant.

The word freelancer has a negative connotation (constantly hustling and underpaid), but in reality, there’s only one difference between a freelancer and consultant.

  • Consultants create jobs
  • Freelancers do jobs (created by consultants, entrepreneurs or employees)

Consultants and freelancers are often equally talented. The difference is: Consultants are proactive and freelancers are reactive.

Step Two: Find People and Companies You Admire or Patronize

If you’re creating a new, strange job, nobody will knock on your door. Which means: the only way to get paid is to knock on doors (literally or digitally).

When starting out, you’ll need to do outbound sales.

Cold outreach sounds impossible, but most people do it wrong. It’s how I’ve gotten every single one of my first jobs in the various skills and results I’ve sold.

In my past life, I was an Associate Editor for a sports blog that received ~3 million monthly unique visitors.

Every day, I’d get about 50 PR pitches that looked like this:

“Subject: Amazing book I wrote, me me me me memememe”

“Dear Mr. Matthew Rudinsky [last named spelled wrong, to person who goes by Matt],”

My client, Name You’ve Neverheardofson, has written one of the year’s best books. It’s about BLAH BLAH BLAH YOU’VE NEVER HEARD OF THIS

[insert 500-word, boring summary]

Mr. You’ve Neverheardofson is available for interview. Please reply and we will set something up.”

This is what most business proposals look like, too.

“Hi, I offer web design services. Here is my portfolio. I hope to hear from you soon.”

This never works.

Cold outreach is about personalization and quality, not quantity.

Don’t send 100 emails in an hour. Send one or two.

With impersonal emails, you’d be lucky to get a 1% response rate. With personalized emails that demonstrate a clear benefit for the recipient, your response rate will easily 10x (probably more).

Of course, this requires that you actually understand the incentives and goals of the person you’re pitching.

And the easiest way to do that is to only email people or companies you’re familiar with.

That way, you don’t need to do hours of research.

Here are my two favorite ways to find potential clients:

  • Comb through your credit card statement
  • Comb through your email inbox and search “unsubscribe” (to find companies marketing to you)

Then ask: Do any of these companies need something that I can provide?

Don’t limit yourself to hard “skills” you have. Think in terms of results. Even if you have a friend that could help these people, serve as the middleman.

Step Three: Get In Their Heads — What’s Their Next Step?

Every person has a next step or goal they want to reach in their lives.

Businesses and CEOs are no different.

Generally, they want:

  • More leads/reach/customers
  • More money
  • More time/freedom/fulfillment
  • More safety (less risk)

Ideally, you know this by following them. What is currently their top priority?

When in doubt, pitch something with a clear financial ROI.

There’s no better pitch than: Pay me $1,000, and I’ll make you $10,000.

(Or, conversely, pay me $1,000, and I'll save you $10,000.)

For example, I pitched and sold a 7-figure online course creator by citing Amazon search-engine stats for his niche. “This topic gets 27,000 searches per month, and your book could easily beat the mediocre competition. Convert just 1% of those at a $9.99 price point, and you’ll make $2,700 in royalties per month. If 1% of those conversions buy your $1,000 course, that’s another $27,000 in monthly revenue.

At that point, my $20,000 fee is triviial.”

Of course, this is much easier said than done. Lucrative opportunities like that exist, but you’ve gotta dig deep to find them.

For the publishing contract, I knew the guy was already very financially successful (he was a real estate mogul). His online presence suggested he was writing a book for impact and to spread a message to tons of people versus making lots of money.

So, I told him a story about why my pitch would spread his message to the most people possible. He thought that would be through marketing, but I explained why it was through a rewrite and republishing of the book.

It took some convincing, but I was speaking directly to his top priority.

Step Four: Figure Out How to Get Them There

I didn’t go into the conversation saying: “Let me rewrite your book.”

I went in saying: “I’m confident I can get your book to as many people as possible.” Then slowly explained how I would do that.

Don’t pitch a job, pitch a result.

Then reverse-engineer the best way to get there.

That’s why my “jobs” have ranged from coaching, to editing, rewriting or full-on ghostwriting. Every client needed something slightly different for their unique circumstances.

Your priority is to adopt their priority. This isn’t about selling them on your ideas; it’s about getting them what they want, by any means possible.

Step Five: Put a Fancy Package Around It

Sometimes, you’ll find the job you’re gonna do doesn’t have much precedent. You won’t know what to charge, or even what to call it.

One time, I realized what a corporate executive needed was to take his vague idea and turn it into a clear plan to finish his book.

Basically, he needed me to interview him on all of his ideas, streamline them and create a ~15 page outline.

So I called it “outline consulting” and charged $2,500.

When it worked well and the client was happy, I added it to my standard offerings and have sold it a couple of times since. Last time, I raised the price to $8,000 as I realized how much it was truly worth (and I was more confident in the results I could provide).

But it’s less about the package, and more about the taste.

“Outline consulting” is kind of a stupid name. But when selling it, I paint a clear vision of what it will get them (instead of staring at a blank page wrought with anxiety, they’ll have a clear plan to write the book, step by step, and hold it in their hands within a year).

Paint a vision of their ideal future. Rid them of fears and pains.

For the course creator, it was: Imagine having a bestselling book with your name and your brand on it. Any time someone searches your name, it comes up. They learn exactly what you’re about and who you’ve helped. It’s a resume on steroids, out there selling for you.

Go to a conference, bring books. Give them away, sell them, it doesn’t matter. Anyone who reads will be hooked and funneled right into your course — where you can help them maximally, and profit accordingly.

Then call the vessel whatever the hell you want.

Step Six: Eliminate As Much Risk as Possible

Obviously, when pitching strangers, they’ll be skeptical. You need to offer as many assurances that you won’t screw them over, and you’ll actually deliver on your promises.

There are tons of ways to do this, and yours will evolve as you get more successes under your belt.

Here are my favorite practices:

  1. Referring to similar projects you’ve done (with clear, measurable, public results)
  2. Offer a money-back guarantee
  3. Offer to do a relatively cheap trial run, then have a check-in to determine if you’ll sign a full contract
  4. Offer to give a free sample of the work (or send it with your pitch)
  5. Offer to work on a commision basis if you don’t have proven results
  6. Testimonials (ideally from public figures)
  7. Basic social proof (mention places you’ve been featured, or noteworthy clients/coworkers)

I recommend using as many of these as possible. When just starting out, you’ll likely have to choose between free samples, commission-based work or trial runs.

In general, just be confident you can deliver. Don’t bullshit; but know what you’re capable of and don’t be afraid to promise it.

Then work your ass off to deliver.

If you can’t deliver, you won’t last long on your own anyway.

Step Seven: The Pitch

Now, everything above should be your eventual pitch, but you don’t want to spring this all on a stranger.

You simply want to tell a quick story that piques their interest.

Your initial outreach should have one goal: Get them to ask for more.

My first ever “consulting” job came when I read an amazing article and the author, Trevor Kraus, mentioned he was “shopping the idea around to publishers.” I realized I could help him publish independently, and thought it would be much easier for him — as well as more lucrative financially and creatively.

So I sent an email with one goal: Convince him that self-publishing was interesting, and that he might want to hear more about how I could help.

All I did was start with a personalized compliment, briefly explain the benefits of self-publishing, and mention my one success (I had recently self-published a book that made pretty good money).

Then asked:

“Are you interested in hopping on a 10-15 minute call to see if I can help you out?”

It’s extremely low-risk and interesting for them. Why not spend 10-15 minutes to see if this guy is full of crap or can help me get what I want?

Step Eight: Iterate

First, catch their attention.

Next, dig deeper into their motivations.

If they want something different than your initial idea, pitch something different. Don’t get stuck on one idea.

On a recent call with a Fortune 500 executive, I was pitching helping him with independent publishing. But he wasn’t sold, and kept mentioning a book proposal. So I pivoted to pitching help with the proposal, and all of a sudden his interest was piqued.

Pitching what you want is selfish. Pitching what they need is generous, and effective.

All you care about is getting them a result. Because that’s all they care about.

That can come in any way, shape or form, and you can create endless new, fancy packages to describe the vessels.

Step Nine: Scale

The above process is how you get started when you don’t have any momentum.

It’s based on startup guru Paul Graham’s philosophy of starting by “doing things that don’t scale.”

One of the most common types of advice we give at Y Combinator is to do things that don't scale. A lot of would-be founders believe that startups either take off or don't. You build something, make it available, and if you've made a better mousetrap, people beat a path to your door as promised. Or they don't, in which case the market must not exist.

Actually startups take off because the founders make them take off. There may be a handful that just grew by themselves, but usually it takes some sort of push to get them going. A good metaphor would be the cranks that car engines had before they got electric starters. Once the engine was going, it would keep going, but there was a separate and laborious process to get it going.

At first, you need to knock on doors and politely ask to help people. Listen to their needs and adjust your pitch accordingly.

You will be rejected, and you’ll have to keep knocking.

Until people say yes, you deliver, and clients start talking.

Eventually, people will knock on your door (if you’re good enough).

Take advantage of every success. Get testimonials. Ask for referrals. Build systems around the ideas that work.

That’s all beyond the scope of this post (and something I’m still working on), but it’s the way to make this sustainable.

But if you haven’t yet signed a few clients, scaling is irrelevant.

You need to knock on doors. You need to scrap your way to relevance.

But if I can do it, so can you.

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