#ICYMI Bullish: Three Career F*ckups I Made So You Don’t Have To

These days, I mostly feel like a pretty badass ladyboss.

But it wasn’t a straightforward path to get there. In fact, I declared bankruptcy after the failure of the company I started as an undergrad. After that, I moved to New York, lived in a series of sketchy little rooms-for-rent, and dissipated my efforts on dozens of random-seeming projects, gigs, and business ideas that didn’t pan out.

And yet – I throw this out there because I still get tons of letters from people who think that because they’re 26 and haven’t accomplished much that it’s too late for them – of course there was still plenty of time to find a few big things that worked and to set up the life I wanted.

Along those lines, here are some mistakes I’ve made that so you don’t have to!


1. Trying to seem big and official rather than personal and authentic

I was in a cab the other day, absentmindedly watching a commercial in which a diverse and muscled array of personal trainers offered their services. Come to our personal training company!

Hmmn. If you hire a personal trainer, you probably don’t care very much whether he or she is with a company. (In fact, you might prefer a solo practitioner so you don’t feel like you’re paying a middleman.) And you certainly don’t care whether the company is incorporated, or whether it maintains an office staffed from 9 to 5. You probably just want your trainer’s cell phone number.

Back when I ran an internet marketing firm (the one that sent me into bankruptcy), I thought people would really want to work with a Serious Company. I read a lot of business books that instructed me to assemble a board of accountants and lawyers and to put a lot of processes in place (see The E-Myth Revisited) before I even had clients.

Then, when I got clients, I would make sure they knew that I was the “CEO” of my company, and that the company had employees, and that our office was nice, and that the employees were actually on salary and not contractors, and that I was A Very Serious Person – so serious, in fact, that I never once actually hung out or went drinking with a client, but I did wear suits to the grocery store, just in case I ran into a client. Because, you know, that makes sense, right? I actually had one of those brass nameplates that sits on your desk – you know, with “Jennifer Dziura” engraved in it. I think it was a gift, but still. Gross.


Okay, so I was 22, and trying to pretend I was 32, which required keeping a certain distance. But now that I am in my thirties, and I regularly pay a web designer to design websites, I can tell you what I should have done:

• Be twentysomething. Most people are okay with young people designing websites. In fact, youth is often considered an advantage in fields related to technology or making things look cool.

• Actually hang out with clients. Let them establish a mentor/mentee type relationship with me if they really want. Deal with it. Ignore their life advice if needed; buy another round at the bar.

• Not rent an office. Let the employees work at home, on their own time, and pay them as contractors (see a lawyer/accountant on this score – the rules are confusing). Save tons on overhead! You know what all graphic designers already have? Photoshop licenses. There was simply no reason for a starving entrepreneur (Wal-Mart vegetable soup: fifty-four cents a can!) to give hundreds or thousands more dollars to the Adobe corporation. On the same score, I didn’t need to be paying utilities and worrying about how to weatherstrip the doors to save on heat.

• Share information. Let the clients realize that, by my working out of my apartment, I was keeping costs down, so they pay less! Then, buy another round.

These days, I have a web designer. Not a company. I don’t want to talk to a company. I really just want to send emails to Ximena. She lives in Argentina, where she works for a big corporation during the day, and freelances at night. She’s great. Done. End of story.

Playing it bigger than you are doesn’t necessarily help anything. Why not skip all the fancy “business stuff,” just do a really good job at what you do, and let people think of you as their awesome secret, like when you find one of those stylists who gives amazing haircuts in a weird basement somewhere, and then when you tell people about the amazing basement-salon, it’s like you’re actually giving people a gift by telling them about it.

And then if you have too many clients for the basement, or more work than you can do alone, you can think about all that other stuff. That can always come later.

Woman's hands holding coffee and the GetBullish Money Reset book on a cozy blanket


2. Thinking I could deal with sleazy people without getting sleaze on me

After I moved to New York, got a Director of Marketing job, and got laid off as the company slowly imploded on itself as a result of not actually having a product or service to sell to others (note to self: important!), I didn’t really want another nine-to-five.

I wondered, if I can make (for example) $70K full-time, why can’t I make $35K doing the same thing part-time, and then I could spend the rest of the time on my own projects? Well, as anyone who has had a baby and looked for such a work situation can tell you … hahahahahahahahaha. No. Not in this country. Not unless you spend a long time building up your career beforehand and making yourself so valuable that you can have or do anything you want.

I looked on Craigslist, and ultimately met up with a woman who was running this company that offered – okay, I have to fictionalize this – let’s say she was producing murder-mystery podcasts. It didn’t strike me as the most realistic business idea, but she had put a lot of work into it and we had a great first meeting over coffee and pastries.

I was pretty clear about what I wanted – I actually said, “If I can make $70K full-time, why can’t I make $35K doing the same thing part-time?” We worked with the numbers a bit and came up with something that worked for both of us – let’s say, 10-15 hours a week for $25K a year, something like that. I started the next week.

So, I went to her apartment, where she and her husband lived with their toddler. The first warning sign was when she told me that she had hired a flyer distributor on Craigslist – for $5 an hour. That’s … illegal. And ridiculous for such a physical job – putting up flyers around a city for more than twenty minutes is kind of exhausting. She wanted me to go down to her lobby and meet the flyer distributor. I did. I apologetically handed her a giant stack of flyers – when she had posted them all, she was supposed to come back and get paid.

What happened? She never came back, of course. So my sleazy boss was out $15 for the copies, and had wasted a trip to the copy shop – all to save a couple of bucks at the expense of an eighteen-year-old CUNY student.

When I expressed skepticism at the $5 an hour flyer position, this woman gave me another HUGE warning sign. She said, “Well, I’ve got a kid.”

Seriously? Probably the majority of bosses (being generally older and all) are parents. So, if you’ve “got a kid,” you can exploit people? “Sorry, minimum wage law! I’ve got a kid.” Um, no. But, moral arguments aside, no one gives you their best work (or necessarily any work) when they know they’re being taken advantage of.

That evening, I went home, and she finally emailed me a contract. Now, in our coffee shop meeting, she had been perfectly clear on the arrangement – I would work 10-15 hours a week for $25K a year. You have to be reasonably good at math to be as sleazy as this woman: she took $25K a year, divided by 52 weeks to get $480 (the amount she was supposed to be paying for 10-15 hours), and then wrote in the contract that, “Contractor will work 10-15 hours per week. When 40 hours are reached, contractor will submit an invoice for $480.”

That is, instead of paying $25K for part-time work, she was going to consider it a $25K a year full-time job, and then pay me less than half of that.

When I called her on it, she disappeared. I never got paid for that day’s work. Weeks later, she emailed me furious that I still had a software CD of hers that I thought I’d be using in my new “job.” I returned it to her.

She’s a sleazebag. While I might have wasted my time, I did learn a lesson I’ve had repeated a few times since: don’t do business with obviously sleazy people, thinking you can manage the sleaze. Probably not. It’s hard to even “just stay in it” until you get paid. Sleaze is infectious and all-encompassing. Filling up your business or social calendar with sleazy people will just result in introductions to more sleazy people, or introductions to nice people who will assume you to be sleazy by association. Run, do not walk. Run.


3. Dismissing natural talents (the myth of “new is better”)

I’m a big fan of exploiting your natural gifts. I think the ideal formulation is something like “Natural gift + hard-won, less natural abilities that form a penumbra around that natural gift, allowing you to make money.” But let’s get back to the part about fucking up.

In my current career, I sometimes laugh at how I am getting paid for things I have been able to do since high school (although I’d never have been able to negotiate the gigs, deal socially with people in order to get along, or even dress myself right). For instance, I strongly believe that I have authored the finest 1,000 GRE vocabulary flashcards in the world (you can get them on Amazon, published by Manhattan Prep), and I pretty much learned all those words in the ‘90s, because acing the SAT was pretty much my plan for escaping my hometown.

But somewhere in between then and now, I did a lot of things I was really, really bad at. For example – don’t laugh – I tried out for some kind of Maxim magazine modeling competition. While waiting in an interminable line of heavily made-up women, I tried to strike up conversations about wasting time and how the casting call could’ve been better organized. Others didn’t seem to mind, though.

And then someone from the magazine condescendingly told us that the girls who weren’t selected for the photoshoot would receive a consolation prize – free entry to a party where celebrities might be! I basically tried to unionize the other models at that juncture, pointing out that admission to a party isn’t a prize; standing around someone else’s party looking hot is a job. As modeling goes, it’s totally work and should be paid.

As it turns out, I was just in the wrong place. Plenty of models or wannabe models do enjoy free admission to parties where little-known rappers and film stars stop by briefly out of contractual obligation. I was wrong, and bad at everything I was trying to do. (Similarly, I once did a pretty mediocre job as tenth grade class president, due to the fact that I simply didn’t believe that homecoming floats or pep rallies were important. Those things were the job. I was in the wrong place).

Repeatedly, out of fear of being trite (WTF?), I made the mistake of disregarding my “old” skills as something I needed to move beyond. Instead, I was asking myself questions like, “What could I be a total beginner and also totally awkward at?” (I can’t even keep my eyes open in direct sunlight! I mean, swimsuit modeling? What?)

I finally came back around to … well, the way I had always been. But that natural core of skills – the small number of skills that allow me to run circles around other people – had to be bolstered by a hard-won arsenal of networking, marketing, financial, and communication skills that allowed me to figure out how to turn those skills into a thriving career.

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