9 Habits: Act Your Age

Years ago, I wrote a bestselling book called 9 Habits of Highly Profitable Writing. I’m assaying a second edition now, and that process includes posting each of the habits here for you, for free. 

This habit is the scourge of freelancers of all stripes, but especially creative types like writers, web designers, musicians, and artists. If writing nonfiction is the habit that’s the most important, this is the one that’s most commonly missing among the people I coach.

The thing about freelancers is we fired our jobs for a reason. We went out on our own because we were sick and tired of being told what to do. We all thought we were smarter than our bosses, and we knew for damn sure we were better looking. We may even have been right, but do you know what we’re all worse at than our old bosses?

Being A Boss.

And that’s where so many writers get into trouble. We’re great at writing. Some of us are even good at planning long-term projects, but as a group we’re pretty terrible at following through on our plans. The sad truth is that if we were good at the daily grind of getting stuff done, we’d be happy punching a clock for full-time work with benefits and paid vacation. The result of this is a host of obstacles between the average writer and the freelance income you need.

Common symptoms of a Third Habit Deficit include:

  • Turning in assignments late
  • Working until 2 in the morning to turn in something on time
  • Having no clear budget, and no solid idea of how much money you made this month
  • Forgetting to invoice clients
  • Showing up late
  • Having to leave early
  • Not sticking to a budget you create
  • Slow or frustrating communication with clients
  • Constant worry about if you’re forgetting something
  • Constant worry about money
  • Having to miss family commitments to finish work
  • Taking on more work than you have time for
  • Finding yourself with insufficient work to fill your time
  • Disorganized time
  • Looking for key materials in your office, files or hard drive when you should be writing
  • Taking basic requests for change personally
  • Working poorly with editors
  • Knowing about solutions to your problems, but never having time to learn how to implement them

Don’t judge yourself too harshly if you resemble the above remarks. They’re epidemic among freelancers and consultants. Most of us are constitutionally challenged when it comes to professionalism and organization. I resemble those remarks more days than I care to admit. 

The good news is this is true of nearly all of us, which means if you conquer this disadvantage by building a contrary habit, you’ll have a competitive edge over all the competition who haven’t.


A couple weeks ago I was visiting friends and family out of town during a long-planned trip. By chance, I also had two huge assignments due by the end of the week. I mentioned this to two literary agents, a film editor, and a professional writer.

All four of them made noises about how turning in a week late was still considered on time, or even early. They made it clear that industry-wide, deadlines are these porous concepts that nobody takes very seriously.

Which is good news for those of us with a Third Habit deficiency…but even better news for those of us who turn in on time regularly. When I made noises back to the effect of I know, but being on time is kind of my thing, they looked surprised and impressed.

Be Polite, Even When You Don’t Want To

A few years back, I did a series of blog posts for a medium-sized business in Los Angeles. As we were wrapping up the deal, my client told me I beat out 150 other applicants to get the gig. I asked him if he’d mind telling me how I floated to the top of that heap. He said that 98 percent of the applicants obviously hadn’t read the entire job description, done basic research into his industry, provided work samples or even bothered to spell-check their cover letters.

That goes beyond basic professionalism and into the realm of common courtesy. It’s not okay to ask somebody for money while simultaneously demonstrating no regard for or interest in that person. Professionalism starts with being polite, whether it’s this kind of research or simply thinking about how your decisions impact the time, stress or success of the people you do business with.

The Solution

We’ve established that we freelancers are bad at this, and that being bad at this keeps us from making the living we want. You’ll not I don’t say “the living we deserve,” since maintaining unprofessional habits means we don’t deserve to make any more money than we’re already making.

So how do we fix it?

We find a boss.

I don’t mean going back to a regular job. That defeats the whole purpose of having a freelance career. I mean find somebody who will hold you accountable for your success, and who you’ll listen to when you make them kick your ass. Whoever you choose needs to be able to:

  1. Make you commit to timelines and deadlines for finishing your projects.
  2. Touch base with you on your progress in a way that encourages you to stay on schedule.
  3. Chide you as gently or firmly as you need when you fail to keep your promises to yourself.
  4. Encourage you when you don’t feel like doing something important.
  5. Do all of the above without the kind of drama that leads you to rebel and sabotage your own success.

When I mention this to coaching clients, a lot of them immediately think of a spouse. That’s a natural idea, but in most cases it’s also a mistake. There’s too much emotional baggage, and too much ignoring of one another, in most marriages for this to succeed. Instead, try

  • A parent
  • A sibling
  • A former co-worker
  • A former boss
  • A writing group
  • A random friend

If you’d rather not work with somebody you’re that close to, my Iron Writer Community on Facebook provides some basic accountability to people, along with a group of freelance writers who commiserate and give one another advice when needed.

You can also take advantage of the burgeoning mobile worker community, which has meetups in most cities where work-from-home professionals of all stripes get together for companionship and accountability. Sometimes a like-minded stranger is a better person for giving this kind of advice than even your closest friends.

Exactly who you choose to hold you accountable is up to you, but you must have somebody. I meet weekly with a friend who owns a small motorcycle accessory business. We act as one another’s accountability partners – him for my writing, me for his shop. That works for my business writing. For my fiction projects, I meet with a writing group every other week…and they give me static if I haven’t delivered the chapters I promised.

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