The Born Freelance on Advising Wannabees

This series of posts by the Born Freelancer shares personal experiences and thoughts on issues relevant to freelancers. Have something to add to the conversation? Your input is welcome in the comments. 


This is the time of year for greater social interaction, even among self-professed curmudgeonly writers. But with it also comes the greater likelihood of hearing those inevitable dreaded words: “I’d love to be a writer too. Could you spare a couple minutes”?

In such circumstances, freelancers have no corporate borg to hide behind; no phalanx of personal assistants to whisk us away. We are entirely on our own to face what can be, for some of us, a bit of a dilemma.

You see, most of us spend a lifetime on the other side of the equation. Our work is constantly being rejected or else arbitrarily subjected to the cruelest of philological indecencies by an ever-changing cast of editors, producers and publishers. Of course, if you’re very lucky, every now and then an editorial angel will also enter your life with understanding and support for what it is you do. It’s all called making a living.

To be asked to be the prime arbiter of what is good or bad by a rank novice unused to the rigors of the game can seem to some of us an onerous task.


Wish to be helpful and supportive

When approached by a hobby writer or novice wannabe it is far too easy to be dismissive. (It’s understandable when you’re on deadline, of course.) It’s important to keep in mind that we may be the first professional that they have ever approached. That means we can carry a powerful influence on their creative as well as psychological well-being. Never underestimate the positive power of a kind word at the right time nor the devastating impact of a thoughtless, unkind word when someone is feeling vulnerable. And all creative acts are acts of vulnerability.

It might be constructive to review your own past experiences. How were you treated when you first approached professionals about your fledgling work or future career ambitions? Were they kind, dismissive, sarcastic or supportive? (I’ve had all four responses, even on occasion simultaneously!) What impact did that have on you, creatively and psychologically? What kind of response do you wish you had received?

To know what level of advice would be most useful and how much time and energy you might feel is appropriate to invest in its dissemination it’s best first to identify your possible protégés.


Dreamers want to be writers or artists but rarely become one. They are identifiable by their lack of activity in their quest. They are very busy pursuing their lives but the dream usually stays just that, a dream. However, they love to talk about it; they can easily drain all your time and energy and goodwill with a smile. So once identified, I keep my contact with them upbeat but as short as possible. All they usually want from us is to simply not crush their dream. I always tread carefully.


These need to be taken more seriously. They may have already joined some groups, had work online and/or be published. Some may be talented enough to go semipro if they have the necessary drive. But many choose to stay hobbyists in order to keep their work as a happy creative outlet. Once identified, I try to focus in on what they need. Usually it is specific feedback; helping out with the practical nuts and bolts of technique. But they too have a dream. And because they have actually trusted you enough to share part of it with you it can be even more fragile. It is a great responsibility to bear in mind.

Potential Pros

These are broadcast or journalism students, novice part-timers, etc. A few may resonate with your younger self: to them I always try to say what I wish others had told me when I was starting out (or did in any number of roundabout ways.) Mostly they too want to know that their dream is possible but the advice they seek is usually more about how to get on in the profession and what to expect along the way. It’s typically philosophical “big picture” advice. I always listen to them very closely. They probably know the answers without knowing that they do! Sometimes the best advice is to just remind them of the blindingly obvious – to believe in themselves and to never take “no” for an answer. They’ll find out soon enough if they’ve got what it takes.



So now you’ve identified your wannabe. Assuming you feel so inclined (and not all of us do all of the time), you can now choose how to respond to their inquiries, with the appropriate level of advice, time and energy.

A three hour tour

“Can you spare a couple minutes?” If you have the time and energy to spare, great. But proposed short coffee chats can evolve into hours if you aren’t careful! I find a preliminary round of emails to set up an informal agenda can be an invaluable time saver. What specific issues would they like to discuss? What exactly do they hope to get out of the meeting? That and suggesting a firm time to end the chat ahead of time will mean you avoid the dreaded “three hour tour” of coffee chats.

Online resources

These are always useful to have at your fingertips to pass along. This site, for example, provides an informative window into the day to day experience of freelancing. There are many others. One of my favourites is by the multi-talented Canadian science fiction writer Robert J. Sawyer. It’s an awesome first-stop for most budding writers (and even non-budding ones too).

Writer groups

I keep an eye on my local library and community colleges. They often provide many different kinds of free writers’ groups. Many wannabes can benefit from interaction with other novices in such mutually-supportive group environments. There may also be useful creative writing courses available through the same accredited institutions.

Show me what you got

I find it more appropriate to take a Hobbyist or PP seriously when they show me something they’ve written. Not only will it give any future chat a focus but it also shows me that they are not just Dreamers. (Chats or conversations can be in person or online, on the phone or even by letter – or some combination thereof.) I ask them to limit whatever it is they send me ahead of time to about 1000 words. That’s enough to get a pretty good idea of what level they are at in their development and if I can relate to what it is they are all about.

If I can’t relate at all I try to curtail my contact as pleasantly and as quickly as possible because chances are my advice won’t help them much anyway.

When it’s very good

When a submitted work clearly demonstrates great promise or ability, it is a relief and pleasure to be able to share my honest opinion with its creator. I find it, on the whole, a lot easier to respond to something I like or think is good.

But when it’s not very good

I find it a whole lot harder to respond.

But I still try to find something worth praising. Whatever it is, I try to find it. I always start with that. Was it a character? A turn of phrase? An intriguing theme? Something. Then I ask myself, what is it they need? Is it specific advice? Or is it simple encouragement to keep at it and keep improving?

What did you hope to achieve?

I inquire more closely about their intentions behind creating their work. What did they hope to achieve? How do they think they could improve it? In many cases they already know what should be done. We are often only needed to act as referees for their own creative instincts.

Setting realistic goals, expectations

Sometimes, however, it is necessary to break reality to them. I do this not by ripping their work apart but by talking about generalities: how hard it is to get published, the agony of rejection, the hardship of making it a living, and so on. If they have talent and drive that you’ve failed to see they will rightfully ignore you and press forward. I never tell them that their dream is impossible or that they haven’t a chance because who can truly say? If I could see into the future with that level of clarity, I’d buy lottery tickets. On the other hand, should they already know deep in their heart that they aren’t so talented or motivated, well then, you might just have done them the favour of their lives.

Moving on vs mentoring

Most wannabes enter your life and quickly move on. But every now and then you meet one that resonates with your younger self; to them you may wish to offer a kind of mentorship. It doesn’t have to be anything elaborate. Just the invitation to keep in touch whenever a particular road block pops up. Such contact works both ways. They get your support and encouragement. You get a much needed reminder of your own dreams as well as a chance to pay forward all the support and encouragement you once received.



Dreams can be fragile, complex phenomena without which life is not worth living. Some of us, through a combination of talent, hard work, good luck and sheer bloody-mindedness make a living in one while giving substance to others. More than anyone else, we must never forget how difficult dreams are to nurture and how easily they and their creators can be harmed.

It’s also worth remembering that we all once started out as wannabes. I hope these thoughts might prove useful the next time one of them reaches out for help or encouragement.

And in this season of special good will, I wish you the strength and bravery to dream your own most cherished dreams. May you too run into mentors and fellow dreamers to help encourage you in your quest to make all the best ones come true.


Posted on December 5, 2014 at 9:00 am by editor · · Tagged with: ,

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