How a Freelancer Learned to Be a Hustler – Forbes.com

How a Freelancer Learned to Be a Hustler

 

Ah, the freelance life. You work from home. You set your own hours. You are your own boss.

It’s awesome, right?

It can be, if you know how to do it.

TIP #1: Ignore the experts.  

If you Google “how to be a freelancer,” you will get a range of advice. But most will fall into a single category. They will encourage you to impose a series of rules upon yourself that will make you productive, happy, and successful. Sometimes, these rules involve getting dressed as if you’re going to work, setting regular work hours, and pretending you’re at a “real job” while you’re at home.

What is the point?

I’ve been a freelancer for most of the last 15 years. Here’s how I do it. I get dressed if I feel like it. I work whenever I feel like it. I go for a walk when I feel like it.

If you’re what I would call a “true freelancer,” someone who freelances because they can’t stand to work any other way, you must honor your “true freelancer” nature and do it your own way. If I wanted a job where I had to wear a skirt to work, commute more than 10 feet from my bed to my computer, and discuss last night’s TV lineup at the water cooler, I’d have that job.

I don’t want that job. I’m a creative. I do what I want.

TIP #2: Hustle or die trying.

In order to be a successful freelancer, you must be a good hustler. Ideally, you should be a born hustler. My grandmother was something of a hustler, and I like to think she passed the hustler gene on to me.

For those who find self-promotion agonizing, who can’t stand the idea of negotiating payment on a regular basis, who aren’t sure if they have what it takes so maybe they should go back to that old job they hated, it’s best to avoid freelancing altogether.

According to Merriam Webster, the definition of hustle is (in part), “  to obtain by energetic activity <hustle up new customers>.” The enterprising freelancer must be good at the hustle in order to survive in today’s economy. He or she must get a perverse thrill out of finding new revenue streams, extracting payment from clients, and surfing the waves of gigs as they ebb and flow.

According to Wikipedia, the definition of hustler is (in part), “a practitioner of confidence tricks.” It’s always seemed to me that a good freelancer is one who can hustle oneself — hustle oneself into believing that one can make this work. Without that confidence, the freelance hustler will fail.

TIP #3: Diversify, diversify, diversify.

Here’s how I would never be able to survive as a freelancer: doing one thing. I’m able to support myself as a freelancer because I can do more than one thing. I’m a writer, a blogger, and an editor. But I also do things that fall into the category of marketing. I generate social media content for big PR companies working with big-name brands, and I work with big websites helping them drive more traffic to their sites.

I can do this because I am good at being a creative, and I am good at being a marketer. This means my clients get two for the price of one. This is what is referred to as a “deal.”

TIP #4: Work for free.

I do this rarely. I do this for certain reasons only. Those reasons may vary.

For example, recently I wrote this piece for Harvard’s Nieman Storyboard. I did it because I was writing about something I love, and that’s what I need to do more of: things I love.

If you don’t sometimes do work for love and love only, you’ll probably go insane as a freelancer.

TIP #5: Be an asshole.

The other day I asked my editor at Forbes if I could write a post entitled: “Why Being an A**hole Pays.”

Not long before that, I had written a post entitled: “Fire Me? F*** You.” That post was about how departing CEO Carol Bartz had gone out in a blaze of swear words. My “A**hole” post was going to be about Bartz, Deadline.com editorNikki Finke (who recently wrote a letter to a rival publication with which she is legally feuding that concluded: “Now get the fuck out of my face“), and Michael Arrington, the founder and now former editor of TechCrunch who is notorious for, among other things, being something of a jerk.

I ended up not writing the post because my editor didn’t care for the title, which, frankly, irritated me. But here is my point. The point is you can read all over the internet about how it pays to be nice, and it’s all about good faith, and why this sort of kumbaya approach to doing business is the best way to do business, and while I would like to agree, I would have to say after 15 years of freelancing — or hustling, whatever you want to call it — I do not agree.

This is capitalism, not a self-help party. Capitalism is not about holding hands, and sharing your feelings, and hugs. It’s about dogs who eat other dogs, and hustlers who play confidence tricks, and winning big. I’m not saying I live in this mentality all the time, but I have come to feel that the endless reams of advice given to people, women especially, to play nice is seriously misguided.

In one of the many posts on TechCrunch about Arrington’s departure, a commenter referred to him as a “controversialist.” I’m not sure I’d encountered that word before. According to the Cambridge Dictionary, thedefinition of a controversialist is: “a person who likes to disagree with other people and say things that make people angry or think about a subject.”

I like this idea. Of being a controversialist. I think this is important. I think this is the new, new thing. I think I am something of a controversialist, and I think this, maybe more than anything, is what has helped me survive as a freelancer. I think sometimes it’s hard for women to be controversialists. Although not always, of course. For example, there’s Madonna, and Ann Coulter, and Cindy Gallop.

That’s what I meant when I wanted to write, “Why Being an A**hole Pays.” It means if you want to be successful, you are going to have to do more than want it. You are going to have to be it, and weather the criticism, and do the hustle, even when that means being an asshole.

Stop taking no for an answer. Stop giving up. Stop playing nice and start playing hardball. Then you will start hitting home runs as a freelancer.

Read my Forbes blogEmail me. Follow me on Twitter. Visit my blog.

 

  • smallfarmersmallfarmer 8 months ago

    Good stuff. Definitely true about women over-buying into kumbayah. Nice has a role, but you have to be able to throw down as well. Too much kumbayah keeps women down.
    Surprised you didn’t mention Ms. Stewart in there.

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  • erichenaoerichenao 8 months ago

    I love you being an a**hole. It inspires me…thank you…AGAIN!

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  • hosedinamericahosedinamerica 8 months ago

    Totally agree. When I get up in the morning I look in the mirror and ask “What can I do today to be a bigger a***ole than I was yesterday?”.
    I’m not at work to run a popularity contest and I’ve always had to “hustle” for a job, I enjoy eating lunch alone and I could give a rat’s a*s if myo-workers like me or loath me. Afterall, business is a dog eat dog world.

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  • chiguy31chiguy31 8 months ago

    Its important to have teeth – and be known to have teeth (especially for women).

    Once you have nipped a couple of times, people become aware of this attribute and watch for the teeth. In fact once you have bitten publicly, you probably will not have to bite again.

    Robert Heinlein said: “An armed society is a polite society”. Holds true for having teeth in the business world.

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  • suicideblondsuicideblond 8 months ago

    “im a hustler baby… i just want you to know..its not where ive been..its where im ’bout to go”~JayZ

    i sing this to myself in the shower EVERY DAY…

    “namaste” is for hippies (ok ok or for AFTER work)

    im a BUSINESS person … so ill be over here… hustling…
    xoxo

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  • Author
    Susannah BreslinSusannah Breslin, Contributor 8 months ago

    Martha was here in spirit.

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  • Author
    Susannah BreslinSusannah Breslin, Contributor 8 months ago

    You inspire my assholery.

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  • Author
    Susannah BreslinSusannah Breslin, Contributor 8 months ago

    I can’t tell if you’re being serious or sarcastic, but if you’re being serious, you’re a bigger asshole than me, so kudos on that.

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  • Author
    Susannah BreslinSusannah Breslin, Contributor 8 months ago

    It’s a fine line, knowing who to bite, when, and how hard.

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  • Author
    Susannah BreslinSusannah Breslin, Contributor 8 months ago

    Word.

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  • kenhollykenholly 8 months ago

    Brilliant and humorous too. Most of the constructive criticism I received during my working years had negative value.

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  • Author
    Susannah BreslinSusannah Breslin, Contributor 8 months ago

    😀

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  • dsantodsanto 8 months ago

    I work as a consulting geologist. In my circle, if you are identified as a hustler you are doomed. It is one thing to market yourself and exagerate your abilities or your companies expertise, it is another thing to fail to back up your claims. Do not promise more than you can deliver.

    Business people are smart. They can smell a phony. This also applies to government Bureaucrats to a lessor extent. Bureaucracies are a major source of business at the present time.

    Maintain existing clients through outstanding service and product. Attract new business by demonstrating previous success. Establish a strong, aggresive, honest reputation. Integrity and character are your key to success. Also, value. Provide outstanding service and product at a cheaper rate.

    Maybe it’s different in marketing, but my advice to young business people is, do not identify yourself as a hustler.

    Doug Santo
    Pasadena, CA

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  • principlexprinciplex 8 months ago

    I have a different self-talk than “being an asshole.” Mine is, “Stay true to yourself and if it doesn’t come out as polished as you would like, you will learn as you go.”

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  • donblancodonblanco 8 months ago

    Susannah,
    After being out of the workforce for nearly two years, due to illness. Do you have any reccomendations on how to jump back into the workforce, head first?

    I’m in Detroit and the job market is very poor (Marketing/Graphic/Multimedia Arts.) I’ve been thinking long and hard on how to attack it. Do I go in as the bargain and get some clientele, or go in with a high price (get things done) kind of work? If I was in a larger Metropolitan area, I believe I could easily go for the bigger fish. Since I’m in Detroit, for the first time in my “Professional” life, I’m thinking about earning some clientele and a business base instead of going for the dosh right away. I’m thinking there are not enough “big fish” to go around to sustain myself? Not to mention, if I get enough work to hire some others to help build business.

    I realize that this is the complete opposite idea of your piece. That is exactly why I’m posing this dilemma to you! What is your advice?

    Thanks

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