The Confidence Conundrum: How a Newbie Writer Builds Enough to Succeed…

In my first commercial freelancing group coaching series, one of the participants said: “I think my biggest problem is uncertainty. I prefer feeling confident about what I’m doing – to be able to do it with authority, and I just haven’t been able to reach that point so far. I’m always afraid I’ll do it ‘wrong.'” Welcome to the human race.

Not at all surprisingly, that statement resonated with all the other “coachees,” and the same issue has been brought up by many folks in every series since. When you’re starting out in a new field, and often, as one’s first foray into self-employment, to boot, it’s easy to get mighty wigged out by this Big Unknown (a.k.a. commercial writing).

Sure, I’d like to think that commercial copywriting resources like my book can demystify the business-building process quite a bit, and it no doubt does. But still, until someone takes those steps for themselves, everything they read about in my book (or any other) is still untried, unproven – to them – and hence, still theoretical.

So, how does one develop the confidence necessary to make it as a commercial freelancer? How do you know you’ve got what it takes to succeed? How do you get yourself to a place where you can boldly go where you’ve never gone before?

Well, the bad news is if you’re a newbie, chances are, you’ll have to deal with this. But, that’s also the good news: most commercial copywriters starting out deal with this. Sure, if you’ve left a corporate position, and carry experience, clients and work from that industry – or ex-employer – with you, you’ll likely have an easier transition. But, that’s not the norm.

I see the confidence-building game as three-fold. Arguably, a lack of confidence is driven by a lack of mental adjustment, a lack of experience and a lack of knowledge. The mental side? Get comfortable with the fact that you likely won’t be comfortable for a while (one reason this field pays so well…). Just the nature of the beast, and knowing that’s the case should make it easier to deal with.

The experiential side? Self-evident. You gain confidence by doing. Every new commercial writing experience you have, every copywriting project you work on and complete successfully, is a brick in your own personal Confidence Wall.

You learn a little more about the commercial freelancing process, you understand a little more about copywriting clients – what they expect, how they are to deal with, and how to make their lives easier (your goal, by the way…). Sure, all situations are a little different, but there are always some commonalities in every scenario.

String enough successful commercial writing projects together (translation: growing respect, competence, portfolio, testimonials, and bank account), and one day you’ll wake up and realize that this gig is for real, and so are you. That’s where confidence is born. But it takes time.

The knowledge side? Along the way, of course, you can hasten the process by reading books on copywriting, marketing, sales, etc. The more you know, the more tools you have at your command when talking with clients about their challenges. In addition, study the work of fellow commercial freelancers. Visit their sites, see how they position themselves, look at their samples (starting with mine) to get a sense of the required skill sets.

How did you build confidence in your abilities when you were starting out?

Was there one particular project that stands out as a big confidence booster for you?

Do you remember the moment when you realized you had what it took to make it in this business?

18 replies
  1. Donna
    Donna says:

    I’m still a newbie, Peter, but I do remember the “moment” I thought I have what it takes to make it as a commercial freelance writer. One of my ezine articles got picked up by BBC. “That” BBC. I figured if I was good enough for BBC, I was good enough.

    I appreciate and enjoy your blog, Peter. Thank you for your work.

  2. Beth Carter
    Beth Carter says:

    In the beginning, I just read everything I could. In particular, I was very worried about *how* to submit a project to a client — how it should be formatted and what it should look like, that sort of thing. I was faking it until I was making it, but I was terrified that my work wouldn’t look like a copywriter’s work is supposed to look like, which would give me away as a newbie. Your book helped a lot, as did Nick Usborne’s online copywriting guide — both have lots of nuts and bolts and really walked me through my first year.

    I’ve been doing this for several years now, and I still read a lot. It never hurts to keep reviewing the basics.

    But boy, do I wish I had a good BBC story like Donna!

  3. Roxane B. Salonen
    Roxane B. Salonen says:

    Peter, I always look forward to your posts, but this one in particular could not have been more timely. My business has launched — this is it. This is the real deal, the thing I’ve been preparing for for the past year (if not my whole life). And I’ve now stepped into that zone of wondering, do I REALLY have what it takes? While I fully believe that I do, you’re right that each project is different, and therefore, the job of a freelancer means constantly starting over, redefining one’s work, and taking risks. That’s not a comfortable place for most human beings, but to recognize the normalcy of it, and even realize it’s what makes the job exciting and not so hum-drum, really helps keep my motivation at a high. Thanks for reminding me that we all feel a little uncertain now and again, even if we KNOW we’re in the right place. 🙂

    And Donna, amazing story about the BBC. Congrats!

  4. William Reynolds
    William Reynolds says:

    We learn by doing. The more we exercise our writing muscles, the more we recognize our own strength. And the more projects we finish, the less fear we have over whether we can do the next one that comes along.

  5. Derek Rice
    Derek Rice says:

    Like Donna, I’m still a newbie (just got my third writing project today). I still regularly wonder whether or not I’ve got what it takes to make it. While I haven’t had one, defining moment, I’ve had a collection of itty-bitty ones that build my confidence. For example, when I was meeting with my client today, and as she was describing her business, and what she was looking for, I was offering suggestions and completing her thoughts in a way. The look in her eye and smile told me I was “getting it,” and she was excited about it. That was a big boost to my confidence today. I think confidence comes from repetition. Until you’ve done something once, you have no idea how long it’ll take you to do it, which of course can cause some hiccups when quoting fees.

    But until I can build up a portfolio with some nice examples of my work, it’s going to have to be a “fake it till you make it” business. I think the best thing I’ve done so far is to network, network and network some more. Getting connected with as many people as possible (other writers as well as marketing and content folks) has helped me too. I’m trying to surround myself with as many people as possible who can help me as I redefine myself, and my career.

  6. Peter Bowerman
    Peter Bowerman says:

    Thanks to all who’ve weighed in so far. There’s nothing mysterious about confidence building. Heck, the first time we rode a bike, I’m guessing few of us were very confident, but once we “got” the whole balance thing, our confidence soared.

    Derek, I love your story about the the reaction you got from your client. No better feeling than when they’re smiling, nodding, leaning into the conversation, and giving you all the “yup-you’re-trackin'” signals… 😉

    And just so you know, no kidding, I’ve been at this 17 years, and whenever I start a new project, I STILL get that twinge – that moment of totally irrational fear: “Wonder if this’ll be the project where I lose whatever’s worked for nearly two decades.” Ridiculous, I know, but true. Good thing, it doesn’t hang around for too long. And I say it’s presence isn’t a bad thing. it can keep you on your toes, and keep you from getting too complacent or arrogant about your skills.

    Just KNOW that no matter how long you’ve been doing this, you’ll still have those feelings of doubt. And you’ll absolutely feel them ANY time you get some critical feedback from a client. You can have finished hundreds of projects with flying colors, a veritable tsunami of amazed and happy clients in your wake, and the first time someone says, “You didn’t get it” (and it’ll definitely happen; don’t fool yourself about that), you’ll forget aaaaaaaaallll the successes and fixate on this one failure. Just so you know – THAT’S normal too. 😉


  7. Star
    Star says:

    Do you guys get the USPS’s hard copy mag DELIVER? I like it! I don’t know how to get on the list–does anyone? It’s free. Anyhow, it’s hard to have confidence with these shifting sands. Is writing mail still a moneymaker? Do people go to offices with a briefcase of samples anymore? Do some clients and editors answer respectful, detailed correspondence anymore? I see fewer of those. Shifting, shifting. A friend of mine and I say we don’t even know what we do any more.
    More revenue streams? Too many half-baked streams (AdSense, that’s you, babe). Still…a magazine about direct mail..a magazine! Can that last? I hardly get any mail in my box these days. I am trying to get established as a govt contractor. It’s crazy-hard.

  8. Melzetta 'Mele" Williams
    Melzetta 'Mele" Williams says:

    I consider myself a newbie as well. But, I’ve had two, “I think I can do this thing” moments.

    The first came after a video producer told me my script made things a lot easier in shooting a promotional video.

    The second moment came just the other day. This week I am on the set of a kids t.v. program (my husband is one of the actors). I was sitting in the director’s truck with the producer who was trying to come up with a slight change in dialogue. She just needed to change one word, but was stuck. I threw out a suggestion and she used it!

  9. John Jordan
    John Jordan says:

    Thank you for this column and my thanks to everyone for the comments. This is the most confounding issue I’m dealing with right now.

    I spent 19 years in magazine publishing, mostly working as an editor doing occasional writing assignments until I lost my job in one of many rounds of layoffs. With very little severance offered, I felt putting all of my eggs in yet another company basket would be a mistake so I started reading all I could about freelancing–Of course TWFW and TWFW:BFS were at the top of my list. Although I had some freelance writing and editing experience, it was many years ago, in what seems like a different world. Bills must be paid however so I took a job writing proposals in response to government solicitations. I should have listened to my gut because this job is not a good fit. The work is interesting but the management of the process makes me cringe every day.

    I want to be free to choose my assignments but my fear about getting “it” wrong sometimes gets the better of me. That’s why I greatly appreciate this entry’s message–all the reading in the world won’t get it done. It’s good to be reminded of that. I take comfort in knowing that first steps were difficult for other people as well.

  10. Chris Delker
    Chris Delker says:

    I’m a newbie, too — still wondering if I can make this FLCW thing work. New clients have been few and far between.

    But I have had a couple of those “I can do this” moments. (I’ve had some “ain’t no way this is going to work” moments, too — but that’s another topic.) One was recently during a job with a new client. The job was to provide the copy for a sell sheet (first one I’d ever done). Required an interview (first one I’d ever done) with the chief engineer of the product development team. A real gee-whiz grown-up copywriting project!

    The sell sheet was a hit. In fact, my primary contact at the company told me that one of their distributors – someone who had been affiliated with the company for more than 30 years – declared my sell sheet to be the strongest copy ever to come out of the corporate office.

    Definitely qualified as an “I can do this” moment!

    I’m a first-time poster here, so just want to add that I really appreciate this blog and the WF books. Great sources of information and inspiration.

  11. Peter Bowerman
    Peter Bowerman says:

    Thanks to the new commenters… And yes, John, confidence-building truly is a one-day-at-a-time proposition. You just keep doing it, and once you get enough people telling you you did a good job, even your worst nay-saying side (and we all have it) can no longer deny the reality of progress and accomplishment.

    I was thinking of one of my “moments” – when I realized that I might just have what it takes. I’d done a small project for an agency early on in my career – probably year 1 or 2. It was a little introduction for an awards ceremony for employees for one of their clients and it had to hit just the right tone.

    I turned in my copy and promptly proceeded to start chewing my nails waiting for the feedback. I go out, come home and there’s a message on my answering machine (remember them?) My agency client says, “They loved it. And you’re not going to believe this – they didn’t change a single word.”

    I think I re-recorded that message onto a mini-recorder, and for the next few months, every time all those old doubts and insecurities would creep in, I’d turn it on, listen to it again, and say, “I can do this.”


  12. Eileen Ludwig
    Eileen Ludwig says:

    Loved your International Freelancer presentation. Came here to see what you do. Your presentation was from someone doing it NOT selling it like many who are coming into these fields. It was nice low-tech but knowledgeable.

    These newbie articles are inspiring. This is now the 3rd one in two weeks. Understanding and hearing about someone else’s process makes it doable. I have started four blogs which now I call Websites and have been digesting tons of information in the last two months. Of course, I want everything to go faster and quicker especially income.

    You reminded me how many years ago, I would say I was getting comfortable with being uncomfortable. When I panic, remembering that is important. Self-confidence left in my 20’s but I can see how your strategy of just getting out there and accept uncomfortable is a good thing.

    Maybe that type of confidence of a twenty something will never come back. Moving forward to succeed and stay out of a cubicle and 9 to 5 are great drivers for finding a way to make this work. The other way does not work for me, not in the long run. I adapt. I learn to live with it.

    I much rather be out and excited about new things.

    Thank you again for the best presentation and for this colorful and fun looking website. This is what fun looks like.

  13. Sharie Orr
    Sharie Orr says:

    Since I’m just getting started, I have little to go on. But it just occurred to me that I “kind of” have one of those moments.
    My daughter just started working at a new fitness facility. I went to the open house, which didn’t seem as successful as it should’ve been. Since I was already planning to see if there would be any work there for me, I took what I’d gleaned from my visit, what my daughter had told me, and from the company website and came up with a slogan that I thought fit the facility’s particular slant, as they weren’t “just a gym.”
    So I wrote this up, just for fun 🙂 , and a few days later when I actually read the only piece of marketing materials they’d had there (a brochure which I’d misplaced), I found it was so similar that it was almost uncanny. Even the format was the same. So that gave me a little boost in confidence. 🙂


  14. Peter Bowerman
    Peter Bowerman says:

    Thanks Eileen, for the kind words on my talk at IFD (and my web site). Glad you enjoyed it – I try to be realistic and straightforward about the opportunity, and so far, it’s paid off. I wish you the best as you move forward… And yes, it CAN be fun – why shouldn’t it be? 😉

    And good for you, Shari – definitely sounds like a good confidence building moment. Hey, maybe you indeed have what it takes… 😉


  15. Amanda
    Amanda says:

    I haven’t started my copywriting adventure yet, so I’m as green as anyone could be. My biggest fear keeping me from taking the first step is being turned down because I haven’t completed college yet. It’s hard to convince employers of your talents without that “badge of approval” (so to speak). I know I have the abilities I need — it’s just a matter of proving it.

  16. Peter Bowerman
    Peter Bowerman says:

    Hi Amanda,

    Thanks for weighing in… And just an FYI: In 17 years, I’ve never once been asked about a college degree – if I had one, or where I went to school (except, perhaps, within the context of casual conversation). That’s actually one of the nice things about our field: it’s exceptionally democratic in the sense that you’re not, as a rule, judged on age or education. You’re judged on results – your ability to get the job done. So, I’m telling you right now – if that’s the main thing holding you back, don’t let it. It’s a non-issue. Hope that helps!


  17. Star
    Star says:

    It’s hard to convince employers of your talents without that “badge of approval” (so to speak)

    Honestly, I think people are so inexperienced at BUYING creative services these days that you could talk yourself into an appropriate assignment–“I saw your ad and I did my senior thesis on social marketing–here is what I would include in your program…” Make it short–and general enough that only a contract will make it all clear.

  18. Doug Jenner
    Doug Jenner says:

    Strategic alliances can do wonders for your confidence.

    When I started out I was landing small gigs for micro-businesses, and they could be tricky (business owners not knowing what they really wanted, no budgets, etc). But networking paid off (so right, Derek) and I got to know a brilliant -and highly experienced – graphic designer.

    He started chucking me work and vice versa. Then one day he pulled in a meaty newsletter job (16-page quarterly internal comms) from a contact at a major transport network here in the UK. So guess who he got to do all the interviews and write all the stories? Little old me.

    That project was a real confidence (and bank-balance) booster. The designer and I have been working together ever since, and we’ve just started on another internal comms NL for a major security firm.

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