The Great Recession morphed our language, but I still don’t know when it became cool to call yourself a hustler and to encourage a life of hustle.

In my life, hustlers are always struggling. They are broke. There is no long-term vision for their lives. Things move quickly for them because there’s no time to pause and reflect. They move from one job to the next, without a pot to piss in, and wait for the hand of God to intervene. God doesn’t look like God, however. God comes in the form of a scratch-off lottery ticket, a $20 bill on the sidewalk, or a cash contribution from a family member who just can’t stomach the bullshit for another minute.

I’m not the Oxford Dictionary, though, and hustle doesn’t always mean hustle in the way I’ve just described it. People who move swiftly use the word hustle to describe the way they’ve found a bridge between “passion projects” and income.

If you can meet your basic obligations in life, you can hustle and call yourself a hustler. What do I care?

But hustlers very rarely meet their obligations. It’s a woman who has “something in the pipeline” that will fund all of her dreams if you’ll only loan her $2000 so she can make rent and pay her overdue utility bills. It’s a guy who is following his dreams but can’t seem to understand that he’s stealing from your long-term dreams when you give him money.

I love agile and creative thinkers who attack the world’s problems with ferocity and passion. I love artists who cannot stomach the idea of doing anything but art. But to hustle is to fail. I think the hustle behavior we see from Gary Vaynerchuk and his ilk deserves a better name.

3 Responses to To Hustle is to Fail
  1. BZTAT


    an enterprising person determined to succeed; go-getter.
    Slang. a person who employs fraudulent or unscrupulous methods to obtain money; swindler.

    The Oxford definition that you referenced confused me. This one from is more in line with what I have always thought a hustler was. The first use of the word implies that a hustler is scrappy and fly-by-the-seat-of-one’s-pants, but intent on financial success; The second implies that a hustler is an opportunistic cheat who purposefully swindles money from others.

    Most artists fit neither description. Few are enterprising with solid financial goals (although we can be quite scrappy). And despite following the desperate patterns that you accurately describe, artists typically have more pure motives than to purposefully swindle others.

    Artists and creative people are quite often, by their very nature, anything but enterprising. For this reason, your continuous theme of “keep your day job” is solid. Those who implore people to follow their passions without helping them develop legitimate plans for doing so are the real hustlers

    Still yet, there is dissonance between the workplace and the workforce that leads people to seek a professional outlet for their creativity. We are told that the modern workforce needs to be creative and innovative in their jobs, yet most workplaces value compliance with external objectives over creativity. No wonder people are wanting to leave and follow their passions.

    Is the problem that there are too many wannabe entrepreneurs, and snake oil salesman taking advantage, or is it that the workplace is not evolving to the needs of society?


  2. Kelly O

    I’ve had two connotations for hustle until recently. One was basically a pool hustler – or the idea that you were doing the minimal amount or trying to con someone into giving you your way. You hustled them. The other was remembering a gym coach in junior high who used to scream at us to hustle up when my group of friends would inevitably get bored running in circles on the track and start walking.

    I think the first person I heard use hustle in a different context was Tory Johnson – I’d read her books and saw her start Spark & Hustle, and still had a bit of a qualm about that word, because it felt strange in my brain to make that a positive.

    Jon Acuff started writing about hustling, and I’m still in the 30 Days of Hustle, nearly a year later. I try to not get hung up on vernacular, and I know “side hustle” isn’t necessarily a bad thing.

    I just need to get Coach Pike out of my head, I guess, and remember I’m not a Greaser…

  3. David T.

    Hustler is a magazine…
    The hustle economy speaks to the increasing competitiveness that seems to be required to just get by anymore. Heck just out in public I about get run over in the stores. Everybody wants their piece of the pie and they’re happy to leave you without any.
    Hustling can refer to con artists and scams but it can also refer to pushy salesmen, job candidates who BS prospective employers, etc. If you can fast talk, outwit, outrun, and shove aside, you can do anything.
    I don’t want to be like that but I understand the desperateness that causes people to be like this.