Wish We'd Known: The Art and Etiquette of Being Your Own Boss

We can all figure out the pros and cons of being your own boss without too much thought but making working for yourself actually profitable is often another order of magnitude because... it takes work. Here are some tools of the trade-off from people who've figured out how to make having a home business work for them:

I am writing this article (for inadequate pay) from my sunlit living room couch. I’ve got the obligatory Law & Order repeat playing in the background and my dog Ziggy at my feet (fine, on the couch next to me). I did shower and dress for you people but, let’s face it, I could be sitting unwashed in my mismatched jammies and you’d be none the wiser...because I work for myself with a living room for an office. I don’t don panty hose and I also don’t get paid vacation.

I don’t have to stand wedged in a subway and I don’t get my metrocard comped by any benevolent employer. I have to pay for my own insurance but I can write that and everything else remotely work-related off on my taxes.

Sound like the dream job to you? We can all figure out the pros and cons without too much thought but making working for yourself actually profitable is often another order of magnitude because… it takes work. Here are some tools of the trade-off from people who’ve figured out how to make it work for them:

Sell Thyself

Marketing your product and hustling for work is a big part of self-employment, which is probably why I suck at it because just the thought of self promotion makes me want to hurl. So, how do you strike a balance without seeming shameless? Or does that even matter?

Ashley Stetts, a full-time model whose sideline is giving out pithy, kind of awesome financial and cost-saving advice on her blog, the Frugal Model knows how to sell herself like a pro.

Stetts’ advice: plug away. As long as you’re honest, it won’t be shameless. “You are going to be your best marketing tool, so if you don't believe in yourself, who else will? You have to believe that you're going to be successful and set goals that might sound crazy but that you commit to anyway.”

Set up a website, a Facebook page, Yelp, Linked In, have a business card made up even if that seems old fashioned. Network wherever you are.

Get Your Butt Out of Bed

Jay Heinrich, a writer and corporate consultant on the art of persuasion, advocates making yourself a morning person. “Yeah, I know. I'm not either. But I get to my home office early so I have a distraction-free several hours, before everybody but my European friends start making noise on the Internet. No phone calls, no Skype meetings, just me and a whole lot of coffee.”

“The one thing that I have enforced for myself is to get up, take a shower and get dressed right away,” said Stetts. “Staying in your PJ's just puts you in a laid back frame of mind. You have to realize that you are still in a work environment.”

Maintaining Focus

Anybody who works for themselves and at home knows the many temptations and distractions that lie in wait: families being a biggy.

When I interviewed my far-more-disciplined husband Mark Pennell about how he runs his successful residential design/build company from an office in the corner of our apartment, he advised “get a door and close it.” You don’t want to turn around from your desk and immediately enter your personal world: “kids screaming, diaper changes, somebody wanting something…It gets easier when the kids get bigger.”

Rug rats and a load of dirty dishes aren’t the only distractions. As Stetts has found, that computer you work on has that magical place called the internet that’s really just one big rabbit hole. “It is so easy to get sidetracked into looking at your friend's Facebook wall, wondering what the hell she did to look so good in that bikini. Then googling diets. Then going on pinterest and looking at pictures of food.”

Her advice? Have a separate work area that is nowhere near distractions like the TV. Also, putt aside time slots devoted strictly to working, allowing yourself breaks for self-indulgence. This way, there’s a structure for the day. “At the end of the night I create a list of tasks and goals to be completed the next day so that I can stay on track.”

Working for yourself means you are your own manager, and you have to be able to take that role seriously.

Give Good Communication

One hallmark of the self-employed is that you can never really escape your clients. But you can set boundaries. At this day and age, turning off your phone and not checking it all day is just a no-go for anybody. But “I’ve learned to set some clear boundaries so I’m not run over by needy clients. Just because my client is calling me at 10:25 pm and on Sunday morning doesn’t mean I have to answer it instantaneously,” said Pennell.

Rosemary Tator, author and freelance management consultant, concurs. “Clients will be clients. You turn cellphones off when you go to the movies or church. The same goes when you’re in business for yourself. After work hours, set an alarm to chime for an email from a particular person if need be but make sure to shut the work off at times by turning off your ringer and not answering every call as it comes in.”

Have Pride, Not Ego

Anybody who works for themselves these days has to be able to wear a lot of hats and play receptionist/peon as often as the glamorous bossy parts. Don’t check your pride at any door but do check your ego, advises my husband. “I am the boss and the errand runner. I love working construction alongside my workers and I love designing buildings. When you’re working for yourself, you have to be prepared to get your hands dirty and do the grunt work.”

The common denominator, say all my experts, is to work your butt off and work to satisfy your own toughest customer first: yourself. It’s that work ethic that separates the wheat from the chaff when it comes to making self-employment work.

As Stetts puts it, “If you are not dedicated 100% to what you're doing, you're never going to just "get lucky.” Unfortunately life just doesn't work that way.

Manage Your Money

Cash flow is inconstant in self employment. It can be feast or famine with a surplus of work one month and an unwanted vacation the next. Per Stetts, the most important financial advice she can give is to live below your means. “Especially when you work for yourself, you never know when your financial situation can change, so it's important to always be prepared and build an emergency fund of at least 3 to 6 months salary while you can.”

Or, as freelance photographer JR Deila puts it: “Money doesn’t exist before it’s in your bank account.” His advice: don’t buy anything you can’t afford to replace, don’t put everything on a credit card. Keep it real.

In praise of delegation, hire an accountant!

They know all the ins and outs of sending 1099s, writing off anything and everything permissible, setting up business accounts and LLCs. As Russ Kolbert, my indispensable tax man, puts it: think tax avoidance, not evasion. Russ makes sure we save every receipt and reminds us that we can write off not only the protective work clothing, for instance, but also the laundering. Who knew?

Per Rosemary Tator, “I’ve gone back and forth on this but this is a good thing to deputize. I wouldn’t clean my own chimney, after all. And I hate doing my taxes.”

Partner Up

“You can only be great at so many things, so you can't beat yourself up over not being able to do it all,” said Stetts. Beyond the taxes, as your own boss, it is very important to choose what you’re not going to do in general. That can be just as important as what you are doing.

Stetts has found that it’s helpful to have a good network of people in the same field to be able to get input and assistance from when you need it.

Pennell advises reaching out and finding somebody you like and respect to partner up with. Don’t find your twin, he says, but somebody with complementary skills. “I find I like what I do more and I feel less stressed that I have to do everything. It’s not only better for me but it’s better for the business since I started working with my partner.”

Keep Track of Time

Staying on top of your schedule and billable hours is essential to working for yourself. All my experts keep a calendar and a log or diary of some kind that they use for scheduling and also as a guide for time management.

As Heinrichs said, “The first thing I do is write in my diary, jotting anything that comes into my head. It's a warm-up, stretching my stiff, blood-poor brain. I write down anything that occurs to me and then list the tasks I have for the day. For long-term work and keeping track of clients, I use productivity software (Omnifocus). But the diary gets the momentum going.”

Rosemary Tator couldn’t agree more. It’s her business to teach business people to be more effective with their time. She likens keeping a detailed calendar to setting yourself up like a dashboard and being able to move and shift as needed. “Living from a schedule gives you the most flexibility.”

Indulge the Benefits of Working for Yourself

Heinrichs has a little visualization exercise for whiners: Apply for a 9-5 job, buy a commuter ticket, some mold-resistent Tupperware and see how you like the life. He says to take advantage of the freedom of working for yourself with regular indulgences. “My home office has a basketball net, balance ball, climbing blocks, and other toys. I wear athletic clothing, keeping a nice shirt available for video meetings. I take a half-hour nap every afternoon. Why? Because I can. That's the whole point of working at home: you're not in some cubicle! There is no dress code! No one laughs when you fall off your balance ball or whiff a basket or snore loudly! This is awesome!”

My partner-in-crime adds that being his own boss allows him freedom to be an active part of his kids’ daily lives. “I may not have the assurance of a Friday paycheck and I may work a lot of hours at unorthodox times, but I feel so lucky to be doing what I love and not missing my kids’ childhoods. I wouldn’t trade the flexibility of being able to help coach my kid’s ball game and walk my daughter to school every morning for anything.” Aww.


Ready to take your career to the next level? Join our Take Charge of Your Career Community Challenge! You’ll get daily emails with expert tips and tools from TheLadders’ Amanda Augustine to give your career a boost in just 4 weeks. Sign up now!

Like this? Want more?
Connect with Us
Follow Our Pins

Yummy recipes, DIY projects, home decor, fashion and more curated by iVillage staffers.

Follow Our Tweets

The very dirty truth about fashion internships... DUN DUN @srslytheshow http://t.co/wfewf

On Instagram

Behind-the-scenes pics from iVillage.

Best of the Web