One problem contractors often mention is the lack of paid sick leave or vacation time. When you work for yourself, your boss tends to be a harsh taskmaster. But we all get sick, want time off, have emergencies. There’s no getting around that. A freelancer needs time off without suffering financial hardship.

The trick is to treat your leave just as an employer treats an employee’s leave. Employees don’t get paid for not working – they get paid extra when they do work, and that extra is held back until they take time off.

As a freelancer, you accomplish this by working ahead. Do enough work to amass a savings account from which you can draw your weekly or daily nut while you’re not working. When you return to work, schedule in additional hours until you’ve refilled your bank of leave money.

This can be a problem for the less disciplined among us. With no boss or time clock to make sure we work, it’s easy to take time off when we don’t have any banked time to cover it. The only solution to this is personal discipline: don’t take the time unless you have it. If you have an unavoidable emergency or serious illness with no time, you will need to scramble for extra work until you’re caught up.

Planning, discipline and organization are important traits if you choose to take this approach to scheduling time off as a freelancer. If you don’t have them, you’ll need to practice them until you do – or get an “accountability partner” to bust your chops for you on a daily or weekly basis.

Thanks for listening.

I’m a professional freelance writer, and have friends who freelance as artists, web designers, coders, financial consultants and bodyguards. Freelancing can seem like a dream: set your own hours, charge more than the daily “wage slaves,” live with your work ethic as the only limiter to your earnings. On the other hand, nobody guarantees you a paycheck. If you do it wrong, you wind up not just broke. You’re broke with an embarrassing gap in your employment history.

Freelancing successfully requires a different formula for different people, but one rule remains true. This rule serves as a warning to many – but for those who do it right, it defines the fastest route for setting yourself apart from the pack. The rule is simple:

People who want to go into business for themselves are often the least suitable people to do so.

Traits that support success for freelancers include attention to detail, sweating the small stuff, working well with multiple bosses, being consistent in communication, and making decisions that help your team over decisions that support you the most. Most people who want to freelance have trouble with one or more of these categories – otherwise, they wouldn’t mind working a 9 to 5 job.

Because this is true, the degree to which you treat your freelance career like a regular job is the degree to which you will rise above the freelance herd. From talking with my freelance friends – both the successful and the struggling, I’ve identified eight habits for remaining professional while working from home in your underwear.

• Observe a maximum one-day turnaround on emails and phone messages unless you’ve notified a client you’re unavailable.
• Keep all your deadlines, from turn-in dates to promised communication.
• Take your lumps with a smile. Some clients will behave in ways you find unreasonable. Working “for the man” means playing nice. Working for yourself means playing nice with more people, more often.
• Set working hours: time when you’re “at work,” and times when you are not.
• Remember marketing. In a regular job, you have to work to their specs. While freelancing, you need to spend some time every day finding your next assignment.
• Observe business communications etiquette. Just because you don’t have an HR inquisitor looking over your shoulder doesn’t mean you don’t need to be polite.
• Have a professional website, professional business cards and professional letterhead.

The majority of freelancers hit the market with a strong skill set and a bad attitude. Don’t be that guy. It might cost your ego a little from time to time, but it’s the price of admission for success. This isn’t the only key to making it as a freelancer – there are many, many (Many! MANY!) other requirements. But if you can’t see yourself observing these rules, you’re probably better off sticking with your day job.

One problem with taking on any profession is that it begins to taint how you look at the world. Cops and social workers probably get the worst end of that stick. On the other hand, spending a decade as a professional martial arts instructor gave me a new level of appreciation for film choreography and fight sports. I find the same thing is now affecting how I read. I just finished the newest Virgil Flowers thriller by John Sandford: Bad Blood. Sandford’s books – and he’s certainly written his share – can be a mite formulaic, but I love the heck out of them. He’s not saying anything important, nor is he bucking for a Pulitzer or Nobel Prize for literature. He just turns out good stories year after year. Sandford (and, yes I am aware that’s a pen name) uses some very specific techniques to make his pacing tight and engaging even though he’s really telling us the same story over and over again. Structure Sandford presents the story in chunks: short sections of just a few paragraphs that hop from viewpoint to viewpoint. Readers never get a chance to be bored because we’re moving around as much as the characters are. He does this more often in is Lucas Davenport novels than with Flowers, Kidd and his other protagonists. Point of View He examines key points from multiple views. He’ll describe eight seconds of a gunfight from one point of view, then review four of those seconds from an additional point of view. This builds suspense by delaying our gratification while simultaneously giving us further compelling exposition on what’s already happened. Inevitability Sandford often shows you the bad guy from early in the first chapter. You know what he’s about, and – if you know the protagonists – you have a guess as to what’s going to happen when they clash. Anticipating the train wreck is half the fun. Twists By far the most common plot twist Sandford uses is something going wrong. It might be bottoming out a pursuit car in a ditch, or the weather ruining visibility. A great example was a dead headlight in a surveillance car that tipped off the bad guy to the fact he was being watched, throwing a kink in the progress of the cops and the story. It’s a bit of deus ex machina, but Sandford uses realistic problems and loads them with so much emotion that they feel natural, right and tense. Characterization, dialog and word choice are other well-used weapons in Sandford’s arsenal, and I’m certain he uses others I’m not good enough to notice yet. But these are the insights I drew tonight. Thanks for listening.

My wife and I reverse the traditional arrangement. She has a career-type job, 40-50 hours per week, and brings in reliable income and insurance for our family. I work from, writing. At this point, I do bring in a respectable income. I also take care of the house, the kids, the cooking and our budget.

I love it. There are days I don’t love, full of sick kids, frustrating repairs and tight deadlines. But my time is my own and I go to work each day with my baby in my lap. In another post, I’ll go into detail on work-from-home tricks that aren’t scams – ‘cos seriously, this is awesome and you should try it. Today, let’s talk about a few ways to make full-time daddy and full-time work not add up to full-time crisis.

Act Like You’re at Work

I don’t mean stand by the water cooler and make passive-aggressive remarks about the other people in the house. I’m talking about setting goals and holding yourself accountable the way your boss and team would in a work environment. Without this in place, you will not make enough money to sustain your work-at-home lifestyle.

Organize, Organize, Organize

I came to this lifestyle after years of running a small business, so it’s possible I’ve gone overboard on this. I have job descriptions for my cleaning tasks, profit and loss sheets for my budget and a pretty solid schedule organized by week, month and year. You don’t have to get that detailed, but the more systems you put in place, the less energy you’ll spend on figuring out what to do. Energy is at a premium as a work-at-home dad, so do what you can to save some.

Get to the Gym

Make a workout every day or two a priority. There’s a host of research indicating this will make you more productive, resourceful and patient. It doesn’t matter if you run, lift weights or play some pickup ball – but it does matter that you get out there. Most health clubs these days have a child care room, so you can get a short break if your kids are under school age.

Go to Lunch

The hardest part of being a work-a-home dad is the sense of isolation. Sure, you’re with your kids, but you need to interact with other adults. Make plans to grab lunch with friends – especially working friends on their lunch breaks – two to three times each week. This will keep you grounded and hedge against the depression that often hits stay-at-home parents.

Take a Day Off

For me it’s Thursdays – a day I found myself tired and frustrated during my business management days. This doesn’t mean you actually take the day off from responsibilities. Just avoid scheduling any tasks for one day. This gives you a chance for guilt-free relaxation and provides a window for catch-up on any projects that ran long.

There are hundreds of other little tricks for managing home, kids and time. These broad-stroke guidelines form just an introduction. I hope somebody, somewhere found them helpful

Thanks for listening.

Library

• The Four Hour Work Week by Tim Ferriss
• The Seven Habits of Highly Effective People by Steve Covey
• Getting Things Done by David Allen