What’s Your “Discomfort Threshold” for Growing Your Writing Business?

During one of my commercial writing group-coaching series a few years back I had a candid email exchange with a participant about a question she’d submitted to be addressed in session. It was:

What can I do to stay motivated during those periods when my business-building efforts yield nothing?

She then analyzed her question—rather dispassionately, I’m proud to say, writing:

I now realize that first question was something a lazy person who gives up easily (my past life) would ask. I’m fascinated by how a lot of what you and your book say dovetails with what I’m reading in one of those books on how millionaires think.

It contains wealth principles like: “If you are willing to do only what’s easy, life will be hard. But if you are willing to do what’s hard, life will be easy.” I guess our comfort zones have to expand to include taking more risks.

I thought it was a very…adult realization. Seriously, we’re all lazy, but if you want a life unlike that of most people—perhaps have a successful commercial copywriting practice?—you’ll have to do things most people aren’t willing to do.

As I’m fond of reminding people, this path isn’t easy, so don’t expect it to be. And if they’ve never built a business before—much less a commercial freelancing business—then building a successful one will entail doing things they’ve never done before in their lives.

Let’s get real: this is the crux of success in most businesses, and certainly ours. We all have our thresholds—the points beyond which we just don’t/can’t (as yet) go.

If your comfort level demands that, you only, say, prospect for commercial writing work by bidding on online job sites, and only communicate with prospects and clients by email, unless you’re a prolific marketer, your income will likely be limited.

Simply put, the better-paying marketing copywriting work takes digging to find and land. And, as a rule, its greater complexity (relative to, say, articles), demands a greater involvement/discussion with clients—by phone, in in-person meetings, etc.

And let’s face it, all that opens us up to having our skills be judged by those paying us—especially if we’re being paid well.* All fertile ground for some pretty serious discomfort.

(*If you started out being paid peanuts—or perhaps are still there—it’s less intimidating, isn’t it? After all, how much can they expect for such low wages? But making more money raises the stakes, the stress, and hence, the discomfort. Interesting, no?)

Hey, I hate being uncomfortable as well, but when I started, I knew that success was going to require stepping out of my comfort zone in a big way, for a certain period of time. But here’s the key: the discomfort I felt was really quite fleeting.

And how can it be not be, when suddenly, you discover, for instance, that cold-calling isn’t that hard after all, that people are actually nice, and that—imagine!– some of them are actually interested? Not to mention that they’re all unfazed by your call, when you thought it was going to be some big uphill battle to explain yourself.

Some writers will move past their blocks, realizing the discomfort not only is never fatal, it’s both fleeting and finite as well. In most cases, you’re left wondering exactly what you were so afraid of in the first place. And, it’s not going to stretch for year after year—unless you’re doing it very part-time, and in fits and starts.

Have you expanded your comfort zones since you started? How so?

What sorts of things scared you to death early on, but are now second nature?

What advice would you give someone still held back by their comfort zones, from making a truly good living as a commercial writer?

Any other thoughts or comments on the subject?

Want to be a guest blogger on TWFW Blog? I welcome your contribution to the Well-Fed writing community! Check out the guidelines here.

11 replies
  1. Joseph Ratliff
    Joseph Ratliff says:

    So, when I started in this business…

    I wrote a “sales letter” (crappy one), printed 300 copies of it along with 300 business cards … and handed that “marketing package” to 300 local small business owners (most of which were in, because they worked “in” their business).

    I did this in a random fashion, and learned the tough lesson about the need to target markets from this experience.

    It took a few days, but handed all 300 out. Got 22 initial responses calling into my “office” (my kitchen table). This was because I was offering a free 15 minute consult to start.

    Then, I called the remaining of them to follow up. Got about 30 more responses.

    Landed 4 projects totaling $22,000 worth of work (I came from a sales background).

    I also had a “database” that I worked from for about a year.

    Then that tailed off, and I made the HUGE, glaring error of NOT continuing to market myself while I was busy … and went into a “feast or famine” cycle.

    That was my “Starting Out” discomfort threshold. 🙂

    The rest has had its ups and downs … but nothing was quite as adventurous as the beginning.

  2. Katherine Swarts
    Katherine Swarts says:

    For a lot of us, “something we’ve never done before” includes accepting responsibility for the scariest thing of all: making our own decisions as to setting priorities and managing time.

  3. Jennifer Mattern
    Jennifer Mattern says:

    I know we have very different marketing strategies, so I won’t go into the cold calling side of things. But ultimately, no matter who you target or how you market yourself it comes down to the little successes. If you can stick your neck out just far enough to reach one of them (that first client who says “yes” to a higher rate for example), it’s often enough of a confidence booster to push you toward the next.

    That confidence didn’t come easy to me in the beginning. But I was determined not to end up being one of those $5 web content writers (all the rage at the time on the buyer side). When I decided to move more into writing for the web, a colleague recommended me for a gig with an online publication. She told me she was making $.25 a word from that client. So I said “what the heck,” and pitched $.35 per word instead. That was far from typical for web articles at the time. They said “yes” without hesitation. I should have asked for more. 😉 Ever since I’ve made it a point to take a similar approach. Sometimes the most difficult person to convince of your worth or value is you. But once you can do that, it only gets easier from there. Not easy. But easier.

  4. Princess Jones
    Princess Jones says:

    I’m not a natural salesperson. I’m fortunate that I got that out of my system before I started working for myself. When I was an insurance agent I would quote people and say “Sorry” before telling them the price if I thought the amount was too much. I was uncomfortable telling people what things costs and automatically devalued what I was selling with that.

    I had a decent boss and he fortunately introduced me to the perils of “counting the money in other people’s pockets.” You have no idea what they think is expensive. He also taught me that we could make deals with people quoted high but we couldn’t go up from quoting low. It was a light bulb moment for me and I brought it with me into my writing business

  5. Cathy Miller
    Cathy Miller says:

    After a 30-plus year in healthcare/employee benefits, it was easy to stick with that industry. However, in the beginning, I found myself doing non-writing work that I had done in my corporate life and hated. I also found it difficult (in the beginning) to turn down gigs that did not pay me my asking price. No, I didn’t go to the $5/article route but it was still less than what I was worth.

    Your statement, Peter, that the discomfort is fleeting is exactly what I found. I have no problem walking away from those who are unable to afford my services.

    Another outside my comfort zone step I took was writing for another industry. I was very uncomfortable outside my niche but a client who had changed companies (and industries) asked me to write for her – for a logistics management company. I think it was some of my best work. Who knew? 😉

  6. Peter Bowerman
    Peter Bowerman says:

    Great stuff, everyone. Funny how off-the-top-of-my-head topics like this one seem to resonate quickly, while some of my more-thought-out posts languish. Useful to notice…;)

    Thanks, Joseph. Yes, BIG discomfort when suddenly things get very very quiet. Why do we somehow think the phones/email in-boxes will continue to light up in the absence of any sustained effort on our part to ensure it happens?

    Great point, Katherine. For many used to the corporate teat, having to run their own show, while what they want on some level, is very…discomfiting, at first. Every coin has its flip side.

    Love your comment, Jenn. Such good stuff. Sometimes, the best way to get comfortable is with baby steps. Just a little beyond what you’re OK with. Do that enough times, and one day, you wake up in a place completely unrecognizable from where you once were.

    I remember selling books door-to-door in college for two summers. Talk about building one unsettling, discomfiting brick on top of another. But because their training was so good, and we were surrounded by others doing the same thing, we were carried along on a wave of seeming normalcy. It’s all about paradigms.

    At the end of the first summer, I remember looking back completely blown away by how far I’d come in shifting those comfort zones. I truly could not believe I’d done the things I’d done. And as Jenn points out, each step gives you the confidence to take the next. But you have to start.

    Princess, that’s a golden nugget your sales manager passed on, “Don’t count the money in other people’s pockets.” SO true. Never apply your own standards to others, especially when it comes to fees. If you’re used to making $5 an article or $10 an hour writing, then of course, $75-$100 an hour is going to induce sticker-shock in YOU.

    But, think about it. Assuming you’re going after decent-sized companies with budgets, that perception is completely irrelevant. No, it’s not easy to think like that, but it’s the truth. And all it takes is one time of delivering (while cringing) a “higher-than-comfortable-for-you” quote to a client, and have them say, “Sounds fine to me,” to rewire you forever.

    And Cathy – exceptionally useful revelations. If we’re smart and flexible in our thinking, we’re capable, as writers, of far more than we think we are. Sure, if a subject is highly technical, I will likely steer clear, but if it’s not, so what if we don’t know a lot about it? If that client is ready to hire us, go for it.

    And sometimes, as I’ve found from plenty of experience, NOT knowing much about a particular subject can make us an ideal person to write about it. Why? Because unlike someone who IS familiar with it, we’re unlikely to assume a lot of knowledge on the part of the prospective reader (a concept discussed in this post), and as a result, our work will be clearer and more effective.

    Thanks for all this!


  7. Lori
    Lori says:

    Great post, Peter! I love that your coaching student came to the realization on her own. It’s tough to look into your own actions and find fault. Good for her.

    I have expanded beyond my comfort zone since I began. I was sending out queries to magazines, but quickly realized how limiting that was, especially since I wrote for trade magazines in a specific niche. That’s when I started taking on press releases, brochures, ghostwritten article and books, and white papers.

    Then there were those emails you mentioned. I was the Queen of Email Marketing (in my own head only). But I knew from my days as editor that I needed face time. So I bit the bullet, paid the bucks, and went to trade shows. Since I knew a few people already, I started there. Nowadays, I have plenty of contacts from those shows. One just called me two weeks ago to discuss projects. The last show I saw him at was three years ago.

    What scared me was starvation/not making enough to cover the bills. It’s amazing how that becomes a great motivator. 😉 But seriously, I was scared of taking on something new and not doing a good job. Nowadays, I look at the project and decide if there’s enough familiarity in it for me to get the job done. Almost always, the answer is yes. Since I’ve learned to stick my neck out and try new things, I’ve increased the types of projects I’m able to handle. And these days, I love a challenge more than an easy assignment, so I seek out the new things much more often. I showed up at a finance seminar and made a few new contacts. I’m hoping to penetrate that industry a bit more. It’s because I want to do new things — that kind of thinking has helped me succeed more often than any other focus.

    My advice to someone hiding in the comfort zone — give yourself a “what the hell” moment. Just say to yourself “What the hell, I’ll try. If I fail, so what?” That thinking landed me a job as senior editor. It landed me several interviews/job offers. It gave me the courage to do the things I hadn’t done before.

    I’m not a fan of the cold call, but I’ve done it. When one way is getting you only so far, you have to try something else.

  8. William Reynolds
    William Reynolds says:

    I recently blogged on how shyness/introversion can lead some business owners to hold back when it comes to self-promotion. Essential tasks such as “blowing one’s own horn” in marketing content or making the rounds of networking events can easily take people out of their comfort zone. But without taking those essential steps, it’s all easy to remain invisible to the big, indifferent world out there.

  9. Peter Bowerman
    Peter Bowerman says:

    (Sorry for the delay in responding; was out most last week and weekend…)

    Great stuff Lori (as usual!),

    And yes, it’s fun to be in a position where you can say “Yes” to new projects far more than “No.” It’s the kind of deep knowledge that naturally comes to those who stay in the game long enough AND keep moving beyond their comfort zones.

    And it’s also the thing that’s hardest to convey to someone starting out when they ask you what tips you can give them to get started in the business. Too often, those requests come from a place of wanting a short-cut, but that kind of “deep knowledge” leading to the confidence to say “Yes” can only come with time.

    So, I guess the advice to that questioner would be: “Keep doing it for a long a time, and keep stretching.” 🙂

    And good for you for trying cold-calling, even if it’s not your preferred way to market yourself. There’s a BIG difference between not doing something because you’re deathly afraid of it (because you’ve never done it, and anything we’ve never done and don’t want to do, will always loom larger and scarier than it actually is) AND because you have done it, but choose other methods that are a better fit for your temperament.

    How true, William. One of the biggest challenges of working for yourself is to go against what most of us grew up believing: that it’s arrogant (or “prideful” as they say in the South…) to boast on yourself.

    But, if you indeed have a valuable service to offer, something you’re good at, and which can benefit others in the ways that matter most to them, then it’s not boasting we’re talking about; it’s simply letting the world know you’re out there and ready to serve them.

    Not that it’s easy to come to that way of thinking, but any resistance to thinking that way takes nothing away from the fact that it’s the truth.


  10. Star
    Star says:

    “If you are willing to do only what’s easy, life will be hard. But if you are willing to do what’s hard, life will be easy.”

    Sorry–but aphorisms like this don’t move me anymore. I also used to believe in the book Think and Grow Rich until I read Napoleon Hill never had any money. I came to prefer Normie (Vincent Peale) who said, among thousands of other things, if you get sad, think about the Sun. Yes, you have to persevere, but you also have to dump losing approaches sometimes. Other times, timing is everything. You may hit! The other day my daughter wanted to take some papers someplace and said, “Do we still have those silver folders?” I said, “No–that was 20 years ago, we don’t do paper much anymore.” I am always accused of being a dopey fossil for expecting return emails, politeness, a back and forth on projects. It worked then and it works now! I was told adapt or die–I did neither. Now I am screenwriting again after a 20-yr break–timing. What would I do to “grow” my writing business–well, not buy kneepads, not work for $5 a story and try to cobble up 20 stories a day, not be treated like someone’s insignificant “help.”

    Do we still do mass mailings, go to freelance fairs (loved those in DC), place classifieds, join things like Wash Independent Writers…or are those the silver folders of memory?

    But I do go on.

Trackbacks & Pingbacks

  1. […] article refers to Peter Bowerman’s post, What’s Your “Discomfort Threshold” for Growing Your Writing Business? He talks about how becoming successful isn’t comfortable. Barbara Stanny who helps folks […]

Leave a Reply

Want to join the discussion?
Feel free to contribute!

Leave a Reply

Your email address will not be published. Required fields are marked *

Optionally add an image