Here’s What Long-Term Freelancers Do to Stay Disciplined. You?

More often than not, when I tell someone (say, at some social or networking event) how long I’ve been a commercial freelancer, people are impressed, often saying, “I could never work for myself; I’m just not disciplined enough.”

Course, my standard answer (somewhere in my book as well) is something like: “Once you get a taste of how great the freelance life is, staying disciplined—at least for me—isn’t all that hard, because you’ll do anything to keep such a sweet gig going.”

Yet, thriving as a freelance commercial writer over the long haul—especially with the numerous economic ups and downs of the past several decades—ain’t easy. So, if you’ve pulled it off, for even the past 5 years (heck, especially the past five years), take a bow. You’ve clearly got strong stuff.

This whole idea of discipline came to mind again as I ran a tip in the November Well-Fed E-PUB last week, from Pittsburgh, PA FLCW Jeff Durosko, about what he does to stay disciplined. Jeff’s in that “strong-stuff” category of folks, having been at it for eight years.

A few of Jeff’s ideas for keeping the rigor in his business life, and most importantly, to treat his business AS a business:

I get up, get dressed (not dressed up, but not in sweats or pajamas either) and get ready just as I did when I worked in the corporate world.

I go to Starbucks after dropping off my daughter at school and head straight back home to my dedicated office where I work through the morning. Having a dedicated office with a door that closes is key to keeping one’s routine. While I may “reopen” that door late at night when the kids are in bed, I don’t let it consume my life.

I must confess, I DO work in my sweats, but then again, I didn’t come from the corporate world, so I’m not trying to emulate that setting. I’m not at my desk at oh-dark-thirty, being more of a 10:00-10:30-ish to 7-ish kind of guy (with a walk or sometimes a bike ride worked into the day somewhere; I intend to enjoy the “free” in “freelance” whenever possible). But, I’m serious about my work, and let my work earn me my breaks.

I could be wrong, but I suspect a lot of folks who say, “I’m just not disciplined enough to run my own business” say that, not because they truly lack discipline (heck, they’ve gotten up every morning and made their way to an office for years, which sure looks like discipline to me, though perhaps it’s just fear…), but because they just haven’t had much practice at it, nor the tools—many of them mental—to stay on track.

Something else I’d say to them: You’ll get used to anything. The idea of freelancing may be new and foreign to you, but once you do it for a while, if you enjoy some success, it’ll quickly ratchet up your belief level in the overall viability of the enterprise—and that’s a HUGE step to transforming that initial success into a more enduring variety. So much of success as a freelancer is mental.

Do you agree (that much of freelance success is mental), and that most people could pull it off if they shifted their thinking?

If you’ve had some long-term freelancing success, what would you tell someone who’s not sure they have the “right stuff,” to make it seem more doable?

When starting out, if you doubted your ability to make it work, but still made it happen, what changed for you?

What strategies, approaches or tips have worked to help keep you on track and thriving over the years?

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22 replies
  1. Joseph Ratliff
    Joseph Ratliff says:

    I challenge people who say what you pointed out in the article PB…

    “I could never work for myself; I’m just not disciplined enough.”

    I ask them a question…

    “Were you really that disciplined when you were working for someone else?”

    Most people aren’t. Let’s face it, we (those of us who have worked for someone else at some point) didn’t REALLY work a full, nonstop, 8 – whatever hours in a day… no… we screwed around a little, took some breaks, talked at the water cooler, whatever.

    But we were not that disciplined. At least most of us weren’t (I certainly wasn’t).

    And working as FLCW’s (at least, in my case) we still aren’t.

    It’s why your “corn flakes” story exists in Well-Fed Writer (you didn’t schedule the call that came in? tsk, tsk Peter 🙂 ), it’s why I don’t always write for the same amount of time each time I start writing.

    We’re human.

    This isn’t to say we don’t TRY to be disciplined… but it’s not an excuse to put off the opportunity to be a FLCW. 😉

  2. William Reynolds
    William Reynolds says:

    The real difference between freelancing and a salaried position, of course, is that you can’t expect a set amount of money regardless of your actual productivity. If you fail to secure the jobs and produce the writing, you can’t pay the rent and bills. When I think, “I don’t feel like working,” my next thought is, “Yeah, but how do you feel about starving?” Once that question really sinks in, I find that the self-discipline tends to take care of itself.

    The great savior is technique. If your writing chops are strong enough, you can fall back on technique and write through migraines, emotional upheavals, noisy neighbors, lack of sleep, and just about any other potential obstacle. The result may not win an award, but it will be professional quality, it’ll get submitted on time, and it’ll buy the groceries. That, to me, is freelancing discipline.

  3. Millie Lapidario
    Millie Lapidario says:

    I’m with you on looking presentable at all times—no excuses. I find that I even have better posture when I’m well-dressed with my hair brushed and makeup on. And better posture further reinforces my professional mindset!
    One other tip I can offer other freelancers working from home: Prepare your lunch the night before just as you would if you were going to work the next day. It’s made a big difference for me. I don’t end up wasting time looking through the refrigerator shelves, wondering what to eat. And I don’t waste time chopping or washing vegetables (which may only tempt you to wash the dishes for a mid-day distraction). I literally grab the tupperware out of the fridge, eat and go back to work.

  4. Peter Bowerman
    Peter Bowerman says:

    Great stuff, Joseph, William and Millie!

    Love your comment/observation, Joseph! So true. We aren’t always disciplined – it just appears that way to those on the other side. And just because you feel you’re not that disciplined (i.e., you’re a card-carrying member of the human race…) is definitely no reason to think you can’t make as a freelancer. Because…

    As William points out, if you start feeling lazy, you just have to ask yourself “How much do I like this life?” OR, even more powerfully, “How much would I like to go back to the 9-5?” And if the first doesn’t get your butt in gear, the second usually will.

    And great tip, Millie. Setting up proper structures is SO key to success. And if you take the guesswork (AND, more importantly, as you point out, the potential for distraction) out of the equation, the easier it will be to stay on track.

    Point being—and it truly is a powerful point, so read this a few times so you get just HOW powerful—it’s not about how disciplined (or not) you are; anyone can set up structures like these, and they will MAKE you more disciplined, by definition. Put the discipline in the framework; don’t leave it in your own hands.

    Anyone else?

  5. M!ke
    M!ke says:

    Shortly after I began renting desk space in a coworking office, it became easier to be disciplined about business.

    To Millie’s point, consider: we are conditioned to be productive after our morning routine at home. Brushing teeth. Getting dressed. Making lunch. All of these activities have been hardwired as precursors to ‘productive time.’ For me, leaving the house activates a deep well of discipline cultivated over my entire educational career.

    After spending my first two years freelancing from home (often from my bedroom. Blech!) I find the office setting immensely helpful for discipline. Not to mention cross-pollinating with other freelancers. But that’s a comment for another post.

  6. Princess Jones
    Princess Jones says:

    I agree with having a home office, having a routine, and getting dressed. Those all help me.

    But when they aren’t enough, I get out of the house. I can get work a lot of work done in the library or a Panera Bread. Why? People can SEE you. So if I’m sitting there eating soup and playing on Facebook for two hours, I know that the nosey person next to me sees me.

    Yes, I provide my own peer pressure to get the writing juices flowing.

  7. Anthony Carter
    Anthony Carter says:

    I’ve been working from home since 2007. I have managed to be very rigid in my daily schedule – almost to the point of being regimental. I think it’s the only way to get through a working day from a home office (with the distraction of family, postmen, delivery drivers, et al).

    I am at my desk by no later than 8.30 am. I go through my emails and social networking stuff and then by 9-9.15 I start work proper. I usually make my coffee around the same time each day as well. I take lunch from 11.45 until around 1 pm. I work through until about 4.30, at which time I may sort dinner out for the kids, etc. I am back in the office at around 6.30 pm until about 9 pm. And that’s my day.

    I also work Saturday’s, but they are my ‘special’ day, whereby I do not have a ‘fixed’ schedule (as the workload is not so heavy on a Saturday). I work on most public holidays (apart from Christmas) and haven’t had a holiday for three years. Would I change it and go work for someone else? Not a chance.

  8. Peter Bowerman
    Peter Bowerman says:

    One thing that doesn’t get mentioned too often, especially in relation to the early days of our businesses is how lonely, grueling, tedious and seemingly unproductive the business-building process often is. The early days (or when we’re in the process of rejuvenating a business gone fallow…) can be very tough.

    And it’s in those times that we need to be most vigilant because it’s only natural that we’ll want to escape from that grind into any number of distractions at hand (fridge, bed for a nap, load of laundry, Facebook, etc).

    Great comments Mike, Princess and Anthony. Love reading how different people set up their day—and their space—to support their commitments. And I agree that getting out of the office—whether on a permanent basis through an outside office, or from time to time as needed to get things done, can be a great strategy (certainly has been for me!).


  9. Karen Wormald
    Karen Wormald says:

    I’m well into my 12th year of freelancing and it’s become more habit than discipline. M-F, clients know I’m reliably at my desk from about 9-6. I take about 15 minutes to fix lunch, and another 15 to surf the Net for fun while I eat it.

    Job One each day is the paying work that maintains cash flow. After that, I do extracurricular writing projects that interest me. I NEVER have the TV on during the day.

    My home office is visited only by cats. On workdays, I do no housework, but save laundry and cleaning for weekends, just as I did as a cubicle drone. Occasionally, if things are quiet, I’ll slip out for an hour or 2 to run errands. Every month or so, I take a Friday afternoon off to lunch with a friend or see a movie.

    I just returned from 2 weeks on a transatlantic crossing by ship with no cellphone or Internet. I deliberately gave clients no way to contact me because I needed a break from the work.

    It’s having the freedom to schedule my life on my terms that makes me love freelancing. Sometimes I’ll work weekends if a client who appreciates it really needs my time, but it doesn’t happen too often, and it’s my choice.

    When people tell me they don’t have the “discipline” for what I do, I agree with them. If they think just showing up merits paychecks, whether they produce or not, they’d starve freelancing. In return for the steady income and benefits, they SHOULD have to beg the boss for time to get their teeth cleaned. It’s a tradeoff.

  10. Cathy Miller
    Cathy Miller says:

    I’m an infant in my 5th year of freelancing. Where does the time go?

    My aha moment came early in my career. I put together a panel of speakers for an organization I belonged to. One was a writer who owned his own business. He made a comment that when he started, he figured, worst-case scenario, he could go back to corporate life.

    I had to control the urge to gasp. I felt my heart lurch and knew I could never do that. It was at that moment that I really began looking at my freelancing as a business-an important distinction as others have pointed out.

    I’m on the fence about whether most people could pull off freelancing. I think many on the corporate treadmill may say they hate it, but they want that connection to the machine. It’s security (as much as any job is secure these days). Could some get off that treadmill & succeed. Of course. Most? I’m not so sure. I agree it’s a mind thing, but some are unwilling to make that shift in thinking for many, many reasons.

    I think if you find the balance in your personal and professional lives, the resulting satisfaction is a major motivator to keep focused on freelancing success. At least it is for me. I spent over 30 years on that treadmill. Isn’t it funny how freelancing has brought me to a much healthier state without the treadmill? 😉

  11. Joseph Ratliff
    Joseph Ratliff says:

    Peter said:

    ” is how lonely, grueling, tedious and seemingly unproductive the business-building process often is. The early days (or when we’re in the process of rejuvenating a business gone fallow…) can be very tough. ”


    People who are new to the business sometimes ask me “Joe, why do you blog?”

    What Peter said above is one reason why I’ve been blogging since 2006. It helps in the tough, early days of really building this business to have something where I can go to and say “Look, I accomplished SOMETHING at least.”

    (blogging is sometimes one of the 5 things I do each day to market myself)

    This business can be tough in the beginning. But that weeds out those who aren’t truly committed to building a FLCW business.

  12. Lori
    Lori says:

    Oh, I agree totally on freelance success being a mental victory. It’s strategy — if you can create strategies and follow through with them, you have what it takes to rock the job, in my opinion. Most people working for an employer is involved in some form of strategy, be it for a better position, better pay, or as part of a team trying to complete a project. In freelancing, we’re a team, as well. We partner with our clients to get the job done.

    I’ve told people who balk at the idea that it’s about making sure you market yourself daily. Be in front of potential clients. Don’t sell to them 24/7 (I think a lot of freelance fear comes from thinking we have to push ourselves on clients), but create a bond, a name recognition, and as you’ve said in your book, Peter, stay in touch so that they call you first when they have a need.

    It takes just a few minutes a day, too. Nothing complicated, just hello.

    I think when I started out, I didn’t doubt I could do it. I just didn’t know how I was going to get where I wanted to be. It all clicked for me when a writer friend saw me struggling between temp work and freelance work and said “Treat this like it’s your only option.” That shifted my thinking instantly. I started throwing all my might behind the marketing side, and soon I no longer needed to supplement the income.

    What has kept me on track and thriving has been a heavy focus on creating more client contacts. I network every day. If I have three regular clients, I look for the fourth. I keep the one-off gigs to a minimum and make sure I connect with clients that have ongoing needs. For me, having a bunch of regular clients isn’t job security. I’ve had an instance where two regulars disappeared within days of each other. The feeling of scrambling to find more work did not appeal, so I’m always working to avoid it.

    Plus I think it goes without saying that I do my best to create repeat business. I give them what they want. I use tape recorders in phone meetings to make sure I get exactly the nuances they want. Then I deliver on their requirements. Plus, it never hurts to give them more than they expect.

  13. Star
    Star says:

    After 35 yrs of this, I am not sure everyone can do it. At the moment, even scruffing together enough jack is hard. But I do it (1) because I am disabled and cannot go to a real job, which I don’t feel like anyway, and (2) because I still think it’s sort of fun. I get up at 6:30, feed the cats, try to second-guess the dog who has decided being housebroken is a bore, totter around on my hurting legs, watch morning news (the paper was too expensive–$300 a yr for a pamphlet largely of AP stories), and finally put on make up and my uniform of comfy pants and some cheerful top (eBay), jewelry, and makeup. Have to have some war paint. What if in the course of the day I see myself in the mirror–the horror! I work from 7:30 to 10:30, eat ramen (no decisions), then work until 1 or 2 or whenever my vision gives out. Then I watch more news, listen to audios, and watch recorded shows, always with an eye on the darned dog looking suspicious. It pays to keep hours. That would be my advice. And get dressed. This bunny slipper myth is making all freelancing look dorky.

  14. Peter Wise
    Peter Wise says:

    A great post as usual, thanks Peter.

    Yes, much of freelance success is mental.

    I sometimes find that due to distractions, errands etc, and maybe if I don’t have a tight deadline to meet, that it gets to be quite late in the day and I realise I haven’t done as much productive work as I should have. I always make myself work late and get a decent return on the day, otherwise I know that in my mind I’ll regret it.

    Even if it’s a fallow period workwise, any good freelancer knows that there is always stuff to be done – adding to your website, boning up on the market or industry trends, doing paperwork. And yes, checking out relevant forums and blogs like this one.

  15. Melzetta "Mele" Williams
    Melzetta "Mele" Williams says:

    Peter, I LOVE your comment about that period of time when you’re starting out or breathing life into an existing business:

    “… the early days of our businesses is how lonely, grueling, tedious and seemingly unproductive the business-building process often is. The early days (or when we’re in the process of rejuvenating a business gone fallow…) can be very tough.”

    Each letter in that quote is dripping gold! I’ve always had trouble remaining disciplined in marketing my services.

    Years ago, when I started my sole law practice, marketing was easy — other attorneys sent me the cases they didn’t want (messy divorces, dicey custody cases). So I was busy!

    I disliked practicing law, and had always planned that career 2, would be as a writer. But when I started my FLCW business, things were different. I didn’t expect it to be easy, I just didn’t expect it to be THAT challenging.

    I thought I was the ONLY ONE experiencing those challenges/feelings Peter described and that somehow that meant I wasn’t ready to build THIS kind of business. So I floundered. Stopped and started. Changed marketing tactics too many times.

    Someone quoted you the other day, Peter… apparently you said something about building a FLCW business is more about a process than a personality. Diamond-encrusted letters in that one!

    Now, I understand that implementing a process takes patience, and confidence in your abilities. Understanding that makes it easier for me to remain disciplined in marketing.

    Thanks, Peter, for reminding us of what it takes to secure this lifestyle, and than we CAN do it!

  16. Peter Bowerman
    Peter Bowerman says:

    Thanks to all for weighing in… Sorry I’ve been a bit absent from the thread, but quite a bit of traveling in November and then a TON of work when I got back, has kept my nose to the grindstone. There are worse things…

    I’d have to agree with several comments questioning whether, in fact, anyone could succeed as a freelancer. Some folks are, in fact, so risk-averse that they’d likely not want to take the chance. Though one could make the case that those who continue to stay in salaried jobs are the real risk-takers in many ways. But I still do believe that anyone who did want it badly enough (vs. just thinking it’d be a “neat” way to work), and had the writing chops to pull it off, could make it happen.

    Thanks for sharing your routine, Karen. This woman’s serious – and I’ll bet it shows in the results you get. You could follow far worse models.

    I’m with Cathy in gasping at the notion that one could always go back to the 9-5 if freelancing didn’t pan out. Sheesh. Just the thought of having to do that would have me working 22 hours a day and napping the other two if that’s what it took to keep away from the corporate “clutches.” Shudder. At this point in my life, I am completely (and proudly) unemployable. 😉

    Thanks Joseph, and yes, the toughness of the business will indeed weed out the faint of heart. As I’m fond of telling anyone considering this business, it’s NOT an easy business, and it’s precisely because it’s not an easy business that it’s a true bona fide opportunity. If it were easy, it’d be fleeting.

    Great stuff, Lori, especially underscoring what freelancing is and isn’t (relationship-building, not constant selling). And Star, I was smiling and chuckling as I read your comment. The freelance life indeed looks different for everyone, and you can craft it in the way that works for you.

    And thanks, Mele, for the kind words. Keep it up and my swelling head’s going to start bumping off the ceiling. I DO still assert that success in our field is more “process than personality,” but then we’re back to the mental part of the equation, and whether someone would spook themselves from having that success.


  17. Don Sadler
    Don Sadler says:

    I couldn’t agree more with this. Having spent 24 years in the corporate world before going full-time freelance 5 years ago, I also kept the same routines when I went self-employed: Got up at the same time, got showered and dressed, and got to work in my home office by 8 or 8:30 every day. Heck, I had an extra 45 minutes in the morning because I no longer had a commute!

    I still maintain these disciplines, and keep careful track of my work time every day, week, month and year. Sure, I have the flexibility to take long lunches or breaks during the day if I want — and sometimes I do. But they’re the exception, not the rule.

  18. Mike Sweeney
    Mike Sweeney says:

    Lori, I like your thought about job security in the freelancing world: “For me, having a bunch of regular clients isn’t job security. I’ve had an instance where two regulars disappeared within days of each other.” Having regular clients might seem like job security, but the concept reminds me too much of a regular corporate job. So do strive for repeat business, but always be looking & reaching out to people.

  19. Lindsay Pevny
    Lindsay Pevny says:

    I’m still pretty new to freelancing, but until lap-chihuahuas are a standard in office buildings, I’m always going to feel motivated to work for myself at home.

    It’s more than that, too – I have so much control over how much money I make, what services I can offer, what new skills I can try out – it’s just so worth it.

  20. Peter Bowerman
    Peter Bowerman says:

    So true, Lindsay. We have a lot of control over many things (far more than in the salaried world, where your fate, on many counts, is largely in the hands of others), though with that control comes enormous responsibility… I wish you the best!


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