Think Like a Boss for a More Successful Freelance Writing Career

Think Like a Boss for a More Successful Freelance Writing Career - Freelance Writing Pros

Some of us went into freelancing at least in part because we wanted to be our own boss. Maybe, like me, you were sick of office politics and not having enough of a say. Maybe you thought you could do better on your own. Or perhaps you grew tired of micro-managers looking over your shoulder. But since starting your freelance writing career, how well have you handled that role of being your own boss?

When you freelance, you have immense freedom. And that can be a great thing. But it can also breed complacency if you settle into a routine you deem “comfortable” rather than pushing yourself toward that better thing you might have originally envisioned.

The solution? Think like a boss.

This doesn’t mean you have to become the thing you despised about a traditional work place (if you did). It doesn’t mean you have to be completely rigid.

But when you “think like a boss” as a freelance writer, you’ll take more control over your career, your earning potential, and even your general wellbeing.

Let’s look at how you might do that.

Set Goals & Milestones

Your freelance writing business might as well not exist if you don’t have goals. In business you have to always be working toward something, even if that’s just a specific income target for the year.

Go further than your big, long-term goals. Consider setting milestones as well. For example, you might have monthly milestones when working toward your yearly income goal. If you don’t reach them, it’s time to re-evaluate things and figure out how to make up for lost time.

Goal-setting is fundamental to being in business because it’s about where you’re going. Give yourself plenty of freedom in how you get there. But don’t leave yourself feeling directionless by ignoring goals altogether. And go beyond goal-setting to actively tracking your progress, just like an external boss would. That’s how you find out where time and money are wasted and where they would be better spent.

The more efficiently you can reach your goals, the more time and money you’ll have left over to enjoy outside of your business.

Set Deadlines

Along those lines, set deadlines for achieving your goals. If a boss assigns you a project, they probably also tell you when they want that project delivered. Act like a boss. Don’t wait around on clients to set deadlines for you. Set them yourself too.

You might set stricter deadlines than what a client demands so you can deliver early and impress that client. Or you can set deadlines on work for your own business such as redesigning your website, updating your LinkedIn profile, posting to your blog, sending queries for the month, or drafting a new case study or other marketing materials.

There’s more to freelance writing than delivering client projects. And when you control your own deadlines, you never have to worry about making time for the basics like attracting even better clients. When your clients are the ones setting all of your deadlines, it’s easy to de-prioritize areas of your business you can’t afford to ignore. You might get so caught up in a rush of projects from one client that you don’t leave enough time to secure gigs for when that contract ends.

When you think like a boss, you take care of your customers, but you don’t do it at the expense of your broader business.

Stick to a Schedule

Another way you can think more like a boss is to create a strict or semi-strict work schedule and stick to it. That doesn’t have to mean a 9-to-5 schedule.

Pretend you’re applying for a new job, and your potential employer is open to negotiation on your schedule. What hours would work best for you? You can work around your kids’ schedule. You can work around your most productive hours. You decide. But decide.

It’s easier to stay on course when you know what you’ll be doing, and when, each day. Write it on your calendar. Pretend you have to clock in. If your schedule says it’s time to work, then get to work as if you had a boss waiting to reprimand you if you showed up late. An employer would treat your work schedule seriously, and as a freelance writer it can help if you do too.

Having a set routine makes you think harder about the times you decide to change it.

Track Your Working Time

When you work for a traditional boss, they’ll usually keep track of your working hours. Consider doing the same for yourself if you don’t already, whether with a simple time log or an app like RescueTime. You’ll identify trends like when you tend to slack off (if ever) and when you’re pushing yourself too hard with overtime.

Even better, you’ll get a better idea of how you work at different times of the day, or different days of the week. For example, you might find you work best in the very early morning hours (like I do) or that your productivity peaks at a different time of the day.

We all have times of the day we prefer (such as a self-professed “night owl”). But that doesn’t mean our preferences or when we feel like we’re at our best reflect the reality of when we actually work at our best.

When you get in the habit of tracking your working hours and productivity in this way, you’ll be able to optimize your schedule moving forward. And when you schedule tasks in the times when you’re best equipped to tackle them efficiently, you can get more done in less time.

That “work smarter, not harder” approach helps you increase your billable hours or enjoy more time off without sacrificing income.

Hold “Meetings”

Well, you can’t hold meetings in a traditional sense because as a freelance writer, it’s just you. But still, consider scheduling some time alone with yourself to “discuss” progress on current projects and what’s coming up.

I’m not talking about client calls about specific projects, but rather “meetings” related to your overall business.

I like to treat these as planning sessions, and I hold at least one each week, usually on Thursdays (my main administrative day). It’s when I hash out next week’s work plan / to do list, and it’s when I evaluate and re-prioritize projects if necessary.

For example, I like to operate with 90-day plans.

I hold quarterly “meetings” with myself to review goals and make new plans for the next 90 day stretch. I hold somewhat shorter sessions or meetings with myself monthly to review progress and figure out how I’ll use the next month to get closer to those 90 day goals. Then I hold weekly “meetings” to flesh out the task-by-task schedule so I know what I’ll be working on next to keep moving forward.

And every day before I start work, I ask myself three questions:

  • What do I want?
  • Why do I want it?
  • What can I do today to get one step closer to that goal?

This helps me keep my to-do list in perspective so I never lose sight of the bigger picture. And it reminds me that all the little things I do that day are about getting me somewhere that matters to me.

You might even consider holding a yearly “meeting” to give yourself a sort of personnel review. Have an honest conversation with yourself about where you’ve excelled, improved, slipped, or failed in the previous year. Then use that assessment to find ways to capitalize on new strengths and improve current or recent weaknesses.

Think of solo “meetings” as virtual guide rails to help you stay on track.

Measure Results

A boss is going to look for results from their employees. Are admin workers getting tasks completed in a timely manner? Are members of the sales team converting enough leads? Is the marketing department bringing in enough leads? Employees have to continually earn their keep. And they do that by achieving measurable successes tied to their goals.

Are you not seeing the results you’d like? Don’t be afraid to “fire” yourself from job roles you aren’t a great fit for. You can’t always do everything yourself — at least not well.

That might mean hiring help such asย  virtual assistant, developer, or designer. But it also might mean dropping strategies and tactics that aren’t working for you now and substituting them with another option that can help you reach the same end.

Some measurable things to keep an eye on would include:

  • income (yearly, monthly, weekly, daily, or even your average hourly);
  • visitors to your professional website;
  • search engine rankings for your target keyword phrases;
  • the number of clients you land during a set time period;
  • which pages on your site get the most visitors, and which see the highest bounce rates;
  • trends in followers and engagement on social media (just don’t get too caught up in vanity metrics);
  • how well certain pages or email newsletters convert.

To move forward, you have to know where you’ve been. Measuring results of past efforts is how you get that information.


Along those lines, learn how to delegate. Sharing responsibilities is a key element of growing a freelance business. Sometimes that means delegating work responsibilities to an employee or contractor. And sometimes it means delegating personal responsibilities so you can make more time for your business.

For example, you might hire a babysitter or nanny to watch the kids for a few hours each day. You might have a house cleaner come in once a week or get your spouse to help out more around the house. Think about how much you earn per hour worked. If you can hire someone for less than that and put that extra time into your business, then you come out ahead financially. And you’ll be less likely to burn yourself out in the process.

Don’t be afraid to ask for help.

When you think like a boss, it can help you think of your freelance writing business as something distinct from yourself. That isn’t always easy as a freelancer where you essentiallyย areย your business. So I want to challenge you to think more like a boss and embrace at least one idea shared here that you aren’t already using. It might not drastically change your business overnight. But it will hopefully give you a fresh perspective and new insight into what comes next and how you’ll get there.

This post was originally published on September 30, 2014 at All Freelance Writing. It has since been updated and expanded for Freelance Writing Pros readers.


Get more content like this in your inbox.

Subscribe to the Freelance Writing Pros newsletter to get notified of new blog posts and receive subscribers-only content.

Newsletter - Main

Jenn Mattern is a professional blogger, freelance business writer, consultant, and indie author. She runs numerous publications, a few including Freelance Writing Pro's sister site All Freelance Writing, NakedPR, and Kiss My Biz.

Jenn has over 20 years' experience as a professional writer and editor, 20 years' experience in marketing and PR, 18 years' professional blogging and digital publishing / web development experience, and around 16 years' experience as an indie author / publisher.

Jenn also writes fiction under multiple pen names and is an Active member of the Horror Writers Association.

11 thoughts on “Think Like a Boss for a More Successful Freelance Writing Career”

  1. Great advice, Jenn. I love the idea of doing evaluations every few months. I know I get into bad habits, and could be working more productively.

    Pinned and tweeted.

    Great image, BTW, makes it easier to pin and share. ๐Ÿ™‚

    • Thanks Angela. ๐Ÿ™‚

      I tend to slide into some of the same bad habits as well, so I need to get better about evaluations. I do quarterly evaluations related to my long-term goals (it’s that time again!), but I need to start adding personal evaluations into the mix. If I have time today I’ll put together a sample self-evaluation checklist and release it as a free download. If not, I’ll make sure it’s released by tomorrow. ๐Ÿ™‚

  2. My life is a bad habit…

    I really need to sharpen my pencil and get to work on my business/hobby/business…I have been getting a lot more work without any marketing whatsoever…

    Have to decide if I can take the plunge with both feet or keep testing the waters.

    This is a great motivation and test to see if you are really serious or just playing a game with your hobby.


  3. No wonder the updated list you shared on the Five Buck Forum the other day led me to ask how many years it covered!

    I guess I have trouble with long-range planning. In high school I never applied to colleges or took the ACTs (thanks to a lousy counselor who probably assumed I wouldn’t go to college because I was from a single-parent family & dad lost his job in a recession). I went to a community college and figured things out as I went along. I graduated college without a job lined up and fell directly into freelancing. Planning more than a month or two ahead is difficult for me, which makes your accountability thread all the more impressive.

    • I used to be much less focused on planning. But I’d go batty if I didn’t have a solid long-term plan now. I have more immediate lists planned out too. But if I don’t see the end game in what I’m doing today, nothing’s going to get done. If there’s no end goal, it’s almost impossible to reach the best possible outcome.

      But a month or two is perfectly fine! That’s more than a lot of freelancers plan for. ๐Ÿ™‚

  4. This article is a great read. I knew you have to do planning and stuff, but it never occurred to me to treat my business like I was the boss and employee. It makes sense though.

    Just going to warn my wife I’m going to be conducting an employee review for the next while ๐Ÿ˜‰

    • I have a post on the calendar specifically about 90-day planning and 90-day challenges. I’ll consider bumping that up to this Wednesday’s post if I can work in time to create the worksheet / tracker I’d like to release with it. ๐Ÿ™‚


Leave a Comment