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Be Your Own Boss

Tips for starting a business.

Don’t go into debt.

I have never had a credit card; my business always subsisted on cash on hand. I borrowed money from parents exactly once to pay my rent three months after I started my firm. Later on, my dad gave me a short-term loan to buy a copy machine and pay my taxes. Both times, I knew how soon I could pay him back, and I did. I am the only person I know who has never had debt. If I had had a credit card at that time, I would undoubtedly still be paying it off at an extremely high interest rate. So if you decide you need more money than you can save for in the beginning, you might approach family and friends with a business plan and ask for help, or try to raise money on a site like Kickstarter, or go to a bank for a small loan—but keep in mind that many new businesses won’t see a profit for five years. Only lay out what you know your business can recoup, or what it needs in order to sustain itself. I never consulted with a financial advisor or lawyer, but many small-business owners do. I just knew that I needed to make a total of $1200 a month to survive, a number I arrived at by adding up my rent, all of my monthly bills, and the cost of groceries and coffee, plus $100. That was cutting it close, but I knew if I could earn that, I didn’t need to get another job.

Think “like a woman,” but occasionally execute “like a profesh dude who is kind of a dick and full of himself.”

Young women who are ambitious and energetic are perfect candidates for starting a business. I also think that women tend to be especially tenacious, and are often good at reading situations and understanding what other people need. Growing up in a patriarchy instills us with those skills, so why not turn them around to serve your business? Sometimes I would find myself being manipulated by a client or having to beg to get paid, and being way too understanding about what basically amounted to them disrespecting me/my business. You get afraid to say what you need, because you don’t want someone to think you are a bitch. But do you think any high-fiving corner-office bros ever think that? NIX THAT LINE OF THINKING! I was backstage at a music festival a couple years ago, and I was hanging out with a bunch of dudes in my line of work. Rather than casually conversing, the convos went like this: “Here is the genius thing I am working on and the next-level project after that.” I found myself (im)patiently listening and wondering: Why aren’t I bragging and hustling about my career? So the next time I was in a similar situation with my professional peers, I did that, and it got me a bunch of work. Occasionally, it helps to channel some super-assertive, braggy energy on behalf of your professional swagger. If you don’t want to emulate a cocksure dude, just be Beyoncé. Do you think she’s shy about getting what she wants?

Be cautious about your online presence.

A journalist friend suggests that you read all your potential tweets through the eyes of your boss’s boss. If you are self-employed, read them through the eyes of your clients. Or have a business-related account and a separate, private account. When you work for people, they may see what you do as an extension of your brand or company. Be mindful of how your comments/tweets/etc. might look to someone who doesn’t know you.

Do not be afraid of the phone.

Sometimes, long, impassioned emails are not the way to go. If someone is being a jerk, if you need to do some negotiating, or if a client is blowing you off about payment, get them on the phone. If you’re going back and forth for an hour, realize that a five-minute chat is time saved. Also, talking on the phone builds professional relationships in a way that a zillion emails cannot.

Get help when you need it.

I hired my first employee about three years after I started my business, but before that, whenever I needed help, I would hire a capable friend or acquaintance. Saying you are too busy to train someone else to help you, even though you are desperate for help, is usually just about control—you are afraid to let someone else do even a little. But being overworked is bad for your business. So if you find there is an aspect of your business that you cannot reasonably teach yourself—doing your taxes, building a nice-looking website—hire someone else to do it. Also, holler at the local colleges and get an intern to work for college credit. Give them some real work so they can learn to actually help you, aside from whatever small tasks you have for them. I wound up hiring almost every intern I ever had that did a good job—and they were great, because they knew the business from the ground up.

But remember that no one is going to work as hard as you do—and don’t expect them to.

In the last few years of running my company, I couldn’t have functioned without Dave as my right hand. One day, around 5 PM, Dave was packing up, and I said something about work that still had to be done—I was a little annoyed because it was our busy season, and I was working until 8 PM most nights. Dave looked at me and said, “Unless you are going to pay me for overtime, I am not going to work overtime.” He reminded me that this was my business, and as much as he loved working in my cold-ass basement with me and believed in what we were doing, for him it was a job, not a dream—and he would never let it take over his life. Don’t expect people to work more hours than you pay them for. Don’t expect people to pledge their souls (and/or free time) to your endeavors. Don’t expect them to care as much as you do about whether the business survives. Even if your business is casual and all buddy-buddy, conduct yourself in a professional manner or else the people you work with will not respect you, and they won’t stick around very long.

Even if you don’t have a schedule, have a routine.

Being self-employed after having worked for other people can feel really weird. You are possibly at home all day, maybe not interacting with anyone; the demands are totally different. It’s hard for a lot of people—it was for me for a long time. Even if you don’t have an organized schedule, at least have a routine: get up, take a shower, get dressed, make some tea, and go sit at your desk or work space. Have a to-do list. I do my best work in the late morning and am creatively useless after about 3 PM, so I do all my errands and office-y tasks in the afternoon.

Take care of yourself.

Don’t run yourself ragged with the all-consuming task of starting your business. Rest, eat, take a break, and walk to the bodega for some gummy worms. Take off and go see a matinee. Skype a friend and talk about something other than business. Cook a totally involved lunch. Get a decent chair to sit in if your business involves being on your computer all day long. Do some yoga and stretch. Rest your eyes. One of the big reasons I have been self-employed for so long is that I can take a nap whenever I want to.

Some of these lessons I learned the hard way, and how you go about starting your business depends on whether you want to crochet bonnets to sell on Etsy, consult for Fortune 500 companies, or manage bands. The main thing I want to convey is that, a lot of the time, all you need in the beginning is ambition and ideas. You can start anywhere and at any age. Doing something you love as a profitable hobby now can very well turn into your radical adult-life career—so think about it. ♦


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  • purrr November 19th, 2012 7:19 PM

    Thank you so much for the “Growing up in a patriarchy instills us with those skills” line. I want to hug you.

  • christinachristina November 19th, 2012 8:02 PM

    Thank you, Jessica – this article is pretty perfect timing. I graduated with my BA in Graphic Design at the end of the summer, and my desire to begin applying to design firms is basically non-existent; my desire to work for myself and be a freelance designer is much stronger. But it’s hard! I don’t even know where to begin, really, and this article is very helpful. Not only are they great tips, but it’s also making me think, like “Hey, quit dilly-dallying and GET ON THIS already!” because I do love design and think I could do a great job by myself. So thank you!

    Also, this is totally unrelated, but I’m not sure where else to post it: will user profiles ever be a thing here on Rookie?

  • Olivia November 19th, 2012 8:21 PM

    love this. so valuable.

  • Rose November 19th, 2012 8:22 PM

    I also became finically independent, moved out and started my own business at 19!
    (without attending college)

    I’ve just passed my 1 year anniversary of making my living with my craft//art//make.

    This post is incredible, small businesses are more relevant & successful then ever but most kids don’t realize that it’s a very real option, especially with resources like Kickstarter


    • Tyknos93 November 19th, 2012 9:29 PM

      I remember you sharing your story months ago. You’re kinda awesome. This is not creepy is it?

      • Rose November 19th, 2012 10:12 PM

        Haha, not creepy =)

        Sorry if I’m a little repetitive, I’m just so passionate about this subject!

  • moonchild November 19th, 2012 8:45 PM

    This is awesome! My friend and I are starting an etsy in a about a week (we need the weekend to put the pictures and descriptions up) so this will really help!

    if you want to check it out, it will be called Whimsical Whiskers :)

    it’s raising money for us to go to leakycon (harry potter convention) :D


  • Tyknos93 November 19th, 2012 9:26 PM

    I have all of these tools and networking outlets and I talk alot about being a creator and innovator, but I sort of have no idea if people would be interested in what I’m selling. I’ve signed up on nearly every merchant site I can think of but I can’t drum up the gall to actually say “Here’s something I’ve made. I think it’s nice. Wanna spend money on it?”
    Gah this sounds weird.
    Thanks for this article.


  • spudzine November 19th, 2012 9:53 PM

    This is honestly really inspiring. I plan on selling artwork, and you give some really great tips on how I can accomplish doing so! Thank you!


  • justbouton November 19th, 2012 10:21 PM

    When I first read through the article, I thought it said “take off and go see a manatee” (instead of matinee) and just didn’t think anything of it. Manatees are obviously totally relaxing.

  • Domenic November 19th, 2012 11:08 PM

    definitely reminds me of a version of Forbes that I can relate to because I am not like really corporate and don’t know who king Abizubabai is.

  • SweetThangVintage November 19th, 2012 11:50 PM

    I was just talking to my mom about quitting my job and starting a personal grocery shopping business! IT’S A SIGN!

  • Yani November 20th, 2012 12:41 AM

    God. This is great,

    I wish we were friends. x

  • caro nation November 20th, 2012 1:16 AM

    My dad has worked in the music business for years, and even though we sacrificed hippie private school and a really drafty, dark tutor house for his continuing on, it feels worth it to me. I love having all those records downstairs.

    Also, reading this I couldn’t help but be reminded of “J&H Productions.”

    • Zebbie January 18th, 2013 1:18 AM

      I was reminded of “High Fidelity.” Funny movie (and John Cusack <3). The record store he owns is a total bust, in large part due to product obsolescence. The novel was released in 1995 and the movie adaptation in 2000, and even though vinyl is sort of making a comeback now, nobody was buying it in the age of Napster. (MP3s are still #1 of course, but vinyl still hasn't exactly gone the way of the eight-track.) He's going broke as a result. But he actually ends up getting better entrepreneurial advice from the techno punks who steal from his shop and release a demo tape than he could ever have come up with otherwise.

      Oh, and of course he gets a little help from Jack Black who adds some hilarious erratic "character" to the otherwise calamitous record shop. (Would you expect anything less from Jack Black? :-D) Another big reason for his near-failure is because his girlfriend has left him, and he doesn't have a passion for the store anymore — maybe worth a tip of advice for this article, don't let your personal woes hamper your business. Otherwise you won't ever have Jack Black sing Marvin Gaye's "Let's Get It On" at your first big gala event. ;-)

  • VivaViviana November 20th, 2012 1:23 AM

    This is so awesome because I was JUST wondering what the heck I’m going to do with my life. I’ve so seriously thinking about starting an online shop slash blog or a serious fashion website ever since I was 18.

    I mean, seriously, I HATED working in retail, and I don’t miss it one bit, but maybe I learned a lot from it too.

    I was thinking I could be a freelance stylist or personal shopper, yet also design an accessory line, run a fashion blog, AND also somehow help make the world a better place. I need to tackle this dream.

    This article helped SO much, like I need to start planning right away!

  • Lillypod November 20th, 2012 5:07 AM

    i am 18 and run my own business. my parents have definitely been my inspiration…they have always been self-employed!

  • 062131 November 20th, 2012 8:47 PM

    Ahh, this is inspiring. This business stuff is so scary sometimes.
    I don’t know if anyone is still going to read and comment here, but I really wanted to find out more about how to sell clothes/accesories in stores!

  • Melissa @ WildFlowerChild November 21st, 2012 9:11 AM

    These are wonderful tips. Thank you so much for sharing! This is very useful.

    <3 Melissa

  • rockslita November 21st, 2012 3:49 PM

    The title caught my attention immediately. I am very interested in starting an own business. This helped me very much, thanks!

  • Kaila November 24th, 2012 9:31 PM

    needed this. :D

  • mynamesambertoo December 10th, 2012 10:26 AM

    Thought about some tv shows that are related to the topic of starting your own business/working for sum1 u know that has. Might watch them to get inspired to move forward with my own ideas. In no particular order

    1. Bob’s Burgers
    2. True Jackson V.P.
    3. Unfabulous?
    4. Clueless TV Show (episode where Cher and Dee start their muffs business)

  • mynamesambertoo December 28th, 2012 10:03 PM

    I noticed M.I.A.’s song Paper Planes can relate to business and money somehow, especially the video! At least for me, I have to try to find a version without the gunshot sounds for now…..

  • Nomali March 4th, 2013 8:33 AM

    Such great advice! I finished high school when I was 16, did a two-year diploma and started working right after I graduated at 19. I’ve been toying with the idea of starting a freelance type of thing and working on my online thrift store on the side. To see if I’ll be happier. Dunno.

    Thank you Jessica, thank you Rookie for always knowing just what I need.

    x Noms