The Worst Advice I’ve Ever Heard About Hustle

Image of Hustler

Money talks.

That’s what they say, and that’s what he said to me.

Dangle $14 an hour in the face of a 14-year old kid, and I’m in. It helps that my buddy was going to do it too: go door to door and hustle porch renovations.

“In six months you could have enough money to buy a car,” he said. Just in time to get my permit. Independence beckoned.

The only problem was I hated selling door to door. I didn’t show up my first day.

You’d think I would have learned.

But no.

Who was I?

When you need a job and you don’t know what you are good at — when you don’t know what you want to do with your life — you take any job. That one selling newspaper subs over the phone lasted fewer than five hours. (At least I showed up for my first day.)

Then there was the time I was a waiter. Somehow I lasted three miserable months. It seems people don’t tip waiters who view customers as leeches.

From there I became a busboy, then a prep cook, and finally a line cook (a stint that lasted one week), before I got out of the restaurant business altogether.

What the hell was I supposed to do?

I’m a man. I’m supposed to make a living. But everything that I did — every job that was abundantly available — I hated. And manual labor was out of the question.

The only thing that I wanted to do was write. But it seemed all the advice I ever got about writing was that it was a great hobby … but no way to make a living. “Be practical, son.”

I was trying to be. But it seems like it was killing me.

A hustler, in context

Fortunately, through a series of circumstances, I finally got the green light I needed to follow my calling. I finished college with a degree in English Literature, took a job in advertising, and fell in love with the discipline.

This was also the first time I worked on the Internet (early 2001). It impressed me since I could find the email address of just about anybody I cared about, mostly writers, and harass them. And they wrote back!

I heard from T.C. Boyle, John Carlton, Billy Collins. A dozen names I forget. It was an inner circle I got to be a part of, because of the Internet. And over time I slowly learned that I wasn’t allergic to hustling — if by that word you meant hard work.

But if you meant “working a room, meeting strangers and prospects at coffee shops, knocking on doors, calling strangers, or chumming it with colleagues on a golf course,” well …

Then yeah, I’d rather starve. Just like my boss Brian Clark.

For people like us, the Internet is a godsend. It’s a perfect medium where communication, connection, and commerce merge. And you don’t have to even pick up the phone. Ever.

Let me explain.

This eight-letter word kept me out of financial ruin

Ever stay in a job too long?

I did that for about 18 months. While the pay was average, the benefits were excellent. The work, on the other hand, was mind numbing. And for a misfit who really wanted to do nothing more than throw his weight behind a meaningful cause, I got into trouble.

Don’t pity me (I deserved it), because I’m grateful for the discipline that followed; it was a wake up call to get out of Dodge. And I did. Without another job lined up.

It was easily the craziest thing I ever did.

Fortunately I had a soft landing due to some contacts in the business who were able to feed me work right off the bat. But it amounted to a third of my previous salary. I needed more work. So I had to find it. Fast.


That eight-letter word saved my financial life. Because I never would have made it if I had to knock on doors and pick up phones to drum up business. (For one thing, my body would’ve buckled under the stress of regular doses of Wild Turkey and Tums.)

Don’t get me wrong. There is still some courage involved in online marketing.

For instance, you still need the confidence to email people, publish content to a critical world, and send invoices to clients. But the grim prospect of grinding it out on the pavement or phone is gone. In this world you can slowly grow that audience one piece of content at a time.

This is life in the year of the rainmaker.

A six-piece lesson in hustle

It took me about five months to recoup all of my previous salary — and then some. I’d attracted attention through my copywriting blog, fleshed out leads through guest writing opportunities, and reached a point where I carefully selected what jobs I worked on.

But something was queer.

I wasn’t enjoying myself. In fact, about eight months in as a freelancer I decided I did not want to do it for the rest of my life. What I wanted was to put my weight behind a meaningful culture and cause. I wanted to be part of a team.

So for the next 10 months I looked for the right position with the right company.

And that brings me to where I am now: Chief Copywriter at Copyblogger Media. Where I still use my skills as a rainmaker to drive traffic to the site, work the social web, and convert non-believers into believers.

So, what is the lesson in this for you? Hustle is good … but only when it is focused on the right thing.

And how do you find that? Try this:

  1. Figure out who you are. What do you love? Can you get really good at it? And can you make money doing it? (These three questions amount to the Hedgehog Principle.) Depending on how creative you are, the answer will probably be “yes.” What I didn’t know at a young age about writing was that you could making a decent living. You just had to learn to be that rainmaker.
  2. Find your voice. Trouble finding your voice? Try this: when are you the most comfortable? How do you behave during that time? Are you funny? Caring? Studious? Cynical? That is more than likely your voice. Get comfortable in it. And use it in public (small doses if it scares you).
  3. Find your tribe. Don’t do this alone (I made that mistake early on). Seek out a community (like Authority) that will embrace, encourage, correct, and train you.
  4. Figure out who your ideal reader is. Who are the people who respond to your Facebook posts? Who follows you on Twitter? Who honestly compliments you and your work? What do they love and hate? What are their hopes, fears, and dreams?
  5. Build your audience. Of course, use media native to you. Do you prefer audio podcasts? Enjoy chumming it with people on Google+ Hangouts? Need to argue in print? Do you design your way into hearts? All of the above? Whichever media you choose, create something people actually enjoy watching, reading, or listening to.
  6. Build a personal media brand. Few people know Matt Inman. Everyone, however, knows The Oatmeal — that infamous cartoon site. Matt makes about half a million a year. In merchandise. Same story (roughly) with Darren Rowse, Seth Godin, James Altucher, Marie Forleo, Ramit Sethi, and Gary Vaynerchuck. They built an empire on media … and fueled it with merchandise, speaking, and consulting.

In case you haven’t noticed, the Internet is about direct sales rather than advertising. And building the audience is the crucial thing.

You can do that with the right kind of hustle. Especially on the Internet, which gives you an unfair advantage built on the age-old principle of attracting and engaging an audience.

What to do next

Want to learn more about becoming a rainmaker? Building a personal media brand? Then subscribe to the Rainmaker podcast. It’s our new (and free) educational resource for 2014, with a “media first” perspective.

And the first podcast is not your usual audio fare. Check it out for yourself (it’s only 22 minutes long), and let us know what you think.

Look forward to hearing from you.

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Reader Comments (43)

  1. says

    Go Demian…… The Digital Hustler/ Rainmaking Jedi Master.

    That’s quite a mouthful. Love the 6 point lesson. I jumped on the internet train 6 years ago and it was the best decision I ever made. It’s been hard trying to commit to a cause, the internet offers so many possibilities.

    For the first time this year the picture has gotten clearer since joining authority and teaching sells. These are great tips, I wish I knew a lot earlier on.

    • says

      I think it was in the text: “In fact, about eight months in as a freelancer I decided I did not want to do it for the rest of my life. What I wanted was to put my weight behind a meaningful culture and cause. I wanted to be part of a team.”

      • says

        Thanks Michael. Yes, I saw that paragraph. Guess I was just wondering if Demian was able to expand on that. No pressure to reveal more – the explanation he gave is totally sufficient.

        • says

          Hi Ian,

          On top of what I wrote in the article (the part about being part of a team was a lot more important than this introvert thought it would be) I just wasn’t interested in the business side of things … the accounting, pitching new clients. I realized I wasn’t an entrepreneur … I wasn’t interested in building a business, I wanted to write, research, experiment … you know, just focus on my craft. I also didn’t like the run up of having to meet new clients, build that relationship. That’s just more emotional energy that I wanted to invest. I found myself latching on to the clients that I liked and trying to get them to hire me. πŸ˜€

          • says


            I can so, so relate to this. It’s what I’m dealing with now. Just trying to streamline the process to make it less daunting, but it’s hard, especially for us more introverted types.

  2. says

    Finding out who you are – it evolves, right? Who I was ten years ago isn ‘t the personI am today …. and am likely to change in the next decade. I agree that it’s the place to start though.

    Know thyself – perhaps the most difficult of them all…

  3. says

    You made it through, man!! I’m glad you did. Can’t tell you how many priceless lessons I’ve learned from your work that have aided on my journey of rainmaking.

    Love the New Rainmaker vibe. So happy I’ve made it through my share of crappy jobs and mind numbing periods of outright confusion and doubt that brought me here to find this community of fellow misfits. Here’s to the year of the rainmaker.

  4. says

    Great post Demian. I lived that life for about 11 months too. Great benefits, mind numbing, soul sucking work. I’m on the road to recovery and will definitely be following your advice. Here’s to rainmakers!

  5. says


    Thanks for your thoughts on finding out who we are and what we really want to do. I also have had many offline jobs and have never stayed in a job I didn’t like. I’ve never understood how someone can stay in a job they hate for years and years just so they can retire and hopefully be healthy enough to enjoy it after all the stressful years of working at a job they hate!

    I’ve always loved working with animals, but now as I’m getting a bit older, I’m trying to also find a way to use my other love of writing. It’s a little less physical!

    It’s seemingly difficult to compete with all the bloggers and marketers out there, but really, with the internet, you’re not talking about a limited parameter. The potential for finding an audience is limitless. We just have to figure out how to develop that audience and I thank you for all the info provided here on Copyblogger that will help do just that.

    Still trying to find my voice and become a Rainmaker, Karleen

  6. says

    A great post and a real eye opener. Thank you! I guess I might even print this one out and use it to motivate myself. I could do with a good move! Off to the printers it is.

    What I like about this post most of all is tip number two. And I agree with you, Demian, that it can be pretty scary. Especially for someone who seems to enjoy criticizing others in a very blunt way most of all. Like I do. In private. For now. Pherhaps I should give it a try. Seeming as how correcting stuff is what I like. And laying it on them might just be the trick of getting their attention! :-)

  7. says

    I enjoyed reading this article. Discovering one’s gifts is a lifelong process. It’s amazing how many people try to discourage writers based on it not being “realistic”. It’s also funny – when you tell people you are a writer, many act like you just said you are the tooth fairy. Writing is not as magical as most people think it is. For many of us, it’s the one thing we’re good at. It’s also interesting to discover that introverts don’t want to be alone all the time. We all need the energy of working with others. It just looks different depending on your gifts.

  8. says

    Damian: “Dad, I want to write.”
    Dad: β€œBe practical, son.”
    Years later
    Dad: ” So, what’s new, son?”
    Damian: “I plan to use my writing to help make it rain.”


    Dig your writing, as always.

    • says

      Something like that. I recently ran into this with a young man who’s a talented illustrator. He’s going to school to become an electrical engineer because his father views his drawing as a nice hobby. Wanted to scratch my eyes out.

  9. says

    Just the inspirational story I needed today! Thank you!

    I’m also starting to grow particularly fond of blogging and advertising as a means to an end. I also agree with your point about “hustling.” If you’re hustling in the wrong disciplines, you’ll wear yourself out fast. But if it’s for a cause you believe in, the hustle makes perfect sense.

    Glad to know I’m not the only one who felt that way a while ago. Thanks again for the inspiration, Demian!

  10. says

    I am so happy for you, Demian…your journey continues to inspire and educate.

    Love you like another mother’s son who is my brother.

    But one thing you forgot to mention about that former job is losing all those lunch break Galaga games.

  11. says

    Spot on :-]

    What I didn’t know about writing when I was young: that I could. And so, in true “if you believe you can or you believe you can’t” fashion …

    Re finding your tribe, I wholeheartedly agree. Don’t choose your friends, choose your environment (community) for your friends will come from within that environment.

  12. says

    This is great stuff, Demian. Thank you. It comes at a perfect time for me, too. Working through the items on that list right now, and this post and the Rainmaker podcast are awesome. Looking forward to the next one.

  13. says

    I signed up for a journalism class in high school. I had wanted to write full-time since grade school. Worked on the school newspaper–it was a blast. Our sponsor had been a reporter for the Dallas Morning News and she was very smart. The whole experience was thrilling. I shared my dream of working for a newspaper with my Dad. A few months later he told me that we needed to go for a ride. We climbed into his gold Sedan d’Ville and off we went. He proceeded to tell me that he didn’t want me to be a writer because, “All writers are alcoholics and low-lifes”. This from a guy who never had time for me unless it was to “rain on my parade” or be disgusted with me for non-specific worthlessness.
    And it did appear that one couldn’t really make much of a living at it unless one cooked up a bestseller.
    Two years ago I discovered Copyblogger. It was revelatory. Thanks, you guys(and dolls). Can’t wait to get going with Authority.

  14. says

    So you think this internet thing will be around for a while…?

    Seriously the web has opened up so many opportunities for people to be who they really are and let their natural talents come through. Sometimes it does take some soul searching.

  15. gracezylb says

    I think this goes out to all introvert writers, like me. Thanks Demian! Thank you, Internet. πŸ˜€

  16. says

    Demian – this sentence really hit home with me…

    “In case you haven’t noticed, the Internet is about direct sales rather than advertising.”

    I agree – but I’m coming to a crossroads with my site where I need to make a decision. Curious about what you think – or anyone else at Copyblogger.

    Certain advertising platforms have contacted me – including ones that promote “sponsored content” from other sites at the bottom of each article.

    In general, I’ve always believed in keeping my site ad-free. (I’m trying to build a hyperlocal site that offers sponsored stories). But right now I’m working a day-job while still getting this site off the ground.

    Do you think SOME advertising is an okay way to generate passive income I can re-invest in the business? Or would I be selling out?

  17. says

    I genuinely, genuinely hate posts like this. It’s nothing personal, I’m really pleased that you went on your journey and found your personal niche in the world. But this was exactly the advice that I got from people who were being paid to help me find work. Real work, to supplement the small amount I could earn as a playwright and script advisor.

    Hustle is not in my nature, and though I really tried hard, I couldn’t parlay part time wages into full-time earnings. But all people would tell me was “Hey. lay out your dreams here, and then GO FOR IT!”

    After a year of unemployment, I got a job in the library. It’s great, a lovely place to work, and with three shifts a week, I make just a little more than I earn at the same time from writing. My life is balanced again, and best of all, I can pay the bills. That’s important to me and my family.

  18. says

    I never minded the hustle…as long as I was doing it for someone else. I worked in the “corporate” world for a decade, mainly in sales and marketing, and I could hustle with the best of them but on a personal level, if I was the “product”, I’d completely shut down and couldn’t sell water to a man dying of thirst. I still have the same problem.

    And unlike you, I had no idea that I wanted to write, nor that I was any good at it. I fell into it by accident when I lost my job in 2009. I had to find a way to make money, so I started freelancing. So, pretty much the internet saved my life as it were. Now I’ve just got to get out of the rut of impersonal writing and learn to use my voice to make it rain. I might be on the right track, though, seeing as it’s snowing like crazy here, but I obviously need to work on the “temperature” of things LOL…

    Thanks for the great post Demian.

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