How to Know When You’ve Made it as a Freelance Writer

Carol Tice

I got this question on one of my live events recently:

I think the hardest part of freelancing for me is knowing when I’ve “made” it. I know it’s a learning process and understand that it’s a lot of work, but I think fear and doubt are two problems that plague me the most.

So there it is.

When will we “get there”?

When will we arrive?

When will that nasty feeling in your gut that your writing doesn’t cut it go away?

When will you be able to earn a full-time living from writing?

Will someone tap you on the shoulder and let you know they’ve discovered you’re trying this writing thing, but that the Universal Editors Association have voted you out of the club and banned you from ever getting another gig?

I’ve got some news — only you can make that feeling go away. Because there is no red tape you will break, no party that will celebrate. There is no “made it” in writing.

My swimming pool dream

When I think about “making it,” I always think of this one dream I’ve been having since I was little.

I call it The Swimming Pool Dream.

In it, I’m at the bottom of a swimming pool. It’s my aunt’s swimming pool actually, where we spent many a happy summer day.

We didn’t own a pool, and in southern California, you need a pool. So we’d go to Aunt Bea’s.

The pool is familiar in my dream, and I’m a good swimmer.

I love to swim. I swim happily right up to the top.

But something’s wrong. I can’t see the sky or Bea’s orchard of fruit trees and grapevines and green lawn. I can’t break the surface.

I feel around, and I figure out there is a dark-blue, thick plastic cover on the pool.

Somehow, I’ve been left in the pool and someone came and put the cover on it. Odd.

I’m not panicked — yet.

There’s a small airspace between the cover and the surface of the pool, so it’s OK. I tread water and take a few breaths.

Then, I rip open the pool cover.

But instead of the sky, water rushes in.

On top of the pool, there is another pool, it seems.

I’m at the bottom again. I swim up to the top. Another pool cover. I rip. Water. I swim. I stop and breathe.

Again. Again.

I start to get tired. I wonder how long I can do this. But what else is there to do?

I rip. The gushing water again. I swim.

It goes on, until I wake.

I’m never able to get out of the pool.

The truth about your writing

This writer’s question, and my swimming pool dream, both came to mind again this week because a writer I really like, Jeff Goins, has written a book about making it as a writer.

It’s called You Are a Writer (So Start Acting Like One). (And no, I’m not affiliate selling it — just think you should check it out.)

Jeff recognizes a truth.

It isn’t the outside world that decides if you are a writer. It’s you.

Being a writer is something you are, in your soul. It’s who you are.

You aren’t going to make it. Like my endless swimming pool, you are in it, all the while.

You keep writing because You Are a Writer.

It’s a passion you have, a drive that won’t leave you alone.

You need to write.

When you aren’t writing, it’s painful, like a limb has fallen asleep.

Once you know this about yourself — that you’re a writer — the question is whether you will encourage that gift, or let it wither.

Whether you will act like a writer, or hide that talent under a rock.

What makes a writer?

The big problem is, too many writers are waiting for the outside world to give them the stamp of approval.

They want a big magazine article assignment, or to be the next J.K. Rowling.

You think there is some arrival point where you know you’ve got a career as a freelance writer.

Other people will tell you it happened — “You’re a writer now!”

But that’s not how it works.

Consider the life of Emily Brontë. She wrote poetry, and just one novel in her life — but it was Wuthering Heights. It was not published until shortly before she died, and didn’t win wide acclaim until after her death.

Was she not a writer?

Of course she was. No outside force ever said so. But do you doubt that she was?

A writer is something you know you are inside. No matter what. You can tell, because writing is what you do.

Once you own that truth — and start writing, and putting your writing out there — good things can start to happen in your writing career.

When you will “make it”

As someone who has a freelance writing career many people admire, I bet you think I can tell you what it’s like to make it as a freelance writer.

But I can’t. Because I think my career has just started.

After all, I just published my first print book. This is the path I always wanted to be on, writing great nonfiction books. Maybe fiction ones too, someday.

I’m at an airspace. There’s a little breathing room. I’ve swum to the top of one pool.

And ripped open the next pool and begun to swim into that new world of writing challenges.

But I’ve arrived nowhere. I immediately started writing on my next book contract. Deadlines loom. Pressure abounds.

Now that I’ve set a new high watermark of writing books, everything I write has to be at that level of quality.

I think our writers’ journey is more like that pool dream than like a race you run and then you cross the tape, and you finish, and you’ve made it.

There are stages, and you get to the top, and take a breath. Then, it’s just time to take your writing to the next level. Time to swim in the next pool.

Our journey as a writer only really ends at the end of our lives. That’s when we’ve made it, to the only place you can make it in this life — the grave.

When we die, people will assess our body of work. Hopefully, it will live on and continue to inspire and uplift and help people, and bring them joy.

The rest is our path. Our journey. Our story. Our swim.

That writer was right — it’s a learning process and a lot of work. The part she missed is that it never ends.

For as long as our fingers can move. Upward we go.

Are you a writer? Leave a comment and tell us how you’re acting like one.

Swimmer: Morguefile


  1. Glori

    I’m just starting my own freelancing career. For me, it’s one of those decisions that you just take because if you don’t you may end up regretting you didn’t.
    I have many things to learn and a lot of experiences to encounter… I don’t know if I’ll be able to say “I made it…” someday, but I know I’ll be happy because I know I can say, even now, that “I’m doing what I love.”
    Thanks for the inspiring post Carol!

  2. Anne Baley

    You’re right, Carol, it’s a journey and not a destination. I don’t think we ever truly arrive as writers. Even Stephen King keeps coming up with more stories, and he could rest on his laurels if anyone can.

    Oh, and that has to be one of the scariest nightmares I’ve heard in a long time. I only hope it doesn’t pop up in my subconscious tonight. 🙂

    • Carol Tice

      I used to think that, that it was a nightmare. But with a few more decades of living under my belt, I think it’s just a metaphor for…life. We don’t arrive. There are times when we can kind of stop and take a breath, and gather strength for the next thing. Then we gotta keep going. Or we’re done.

  3. Lisa Baker

    I just had to say that this is my favorite post of yours ever. So wonderful. I have always written, but I don’t think I ever really felt like I HAD to write until I started blogging. I know I’ve found my niche because I can’t stand not writing. And I keep having new ideas, dreaming bigger dreams, and plunging into the next pool. 🙂

    • Carol Tice

      Wow, thanks! But really, it’s Jeff Goins, who inspired this post…I love what he put out in this new ebook.

  4. CMRoane

    You tapped into a universal theme and described perfectly my secret fear I’m a fraud, -despite the fact I’ve made a living writing for more than 15 years. Nicely done and congratulations on your book.

    • Carol Tice

      That was me, for so many years! Only you can look inside and realize…you are a writer. Nobody can kick you out of this club. And you’re making a living from it, too! That’s bonus points. You know how many people working in cubicles would kill to be you. Try to appreciate your awesomeness!

  5. Debbie Kane

    Great post, Carol. My biggest fear is that I’m not a “serious” writer because the majority of my work is copywriting, not journalism. This blog and being a member of the Writers’ Den convinced me that a writer is a writer and if you believe you are one, you are. Before that, my “live” writer’s group — all former journalists with major publishing credentials — had me second-guessing my sales-focused writing and desire to branch out into online publications and social media. BUT — I’m making a living doing what I’m doing — and they’re not any more! Plus, I’m having more fun.

    • Carol Tice

      Copywriting isn’t real? It’s amazing the complexes we can get, isn’t it?

      You should be laughing out the other side of your face with all your journalism writers, since you probably make more than they do as a copywriter 😉

  6. Christine

    Great article! How true! Whenever I am asked, what made you choose writing as a career? I always laugh and say, if you knew the road that lead me to here you would know, I didn’t choose it, it chose me. You’ll know you made it when you get to heaven and God has all of your pieces on display for all of eternity to see what you’ve done with the gifts that He gave you.

  7. Aisha from Expatlogue

    Thanks to both you and Jeff Goins for being great sources of inspiration for struggling writers. Having someone to turn to to “reset the focus” when things get blurry is invaluable and you two do this for me.

    I’ve been taking part in a research study into the use of mindfulness in depression relapse prevention and I’ve found I can apply what I’m learning there to my writing. Most of the pressures we feel are self-generated as we attempt to measure ourselves by other peoples terms of success. I wrote about it in my post yesterday Making My Choice – Mindfulness in Writing

  8. Lynn Hess

    What a vivid analogy! I can definitely see how the swimming pool dream represents the writing life — and life in general! I guess the challenge is to enjoy the swim, and to especially appreciate those sweet moments of airspace where we can relax for a minute while we prepare for our next swim.

    You have no idea how you (and Jeff Goins, too) have contributed toward my having the confidence to call myself a writer and to actually swim forward instead of spending my working life treading water. I just quit my job to freelance full-time, and can’t wait to see where this adventure takes me. I am a writer!

    Thanks, Carol!

    • Carol Tice

      Congrats, Lynn — it’s all upward from here.

  9. Tania Dakka

    I’m acting like one by making it the second most important thing in life (after my family). I schedule time to do it. And I get it done. 🙂 When we live according to other’s approval, we’ll never “make it.” We have to love and believe in ourselves and our work and move on with what we know we can’t NOT do. Thanks for the awesome post!

  10. SuzanneG

    Okay, this is the second time in the last half hour I’ve been slapped in the face with the fact that I’m still carrying around a desire for others to approve of what I do. I just commented about that over at Jeff Goins’ Day Four of his 15 Day Writing Challenge. It’s time for me to stop waiting for that stamp of approval. I write because I have to. Thanks for giving me that additional push, Carol.

    • Carol Tice

      You know, approval from others is…nice. I know when I won my first major national writing award (a SABEW Best in Business Award — I know, dorky!) I felt very validated.

      But all great writers also have a stack of rejection letters. You can’t let outside forces drive your writing career. Where it’s going needs to come from within.

  11. Linda Hamilton

    This post says it all and it’s true. But true writers never die, they just transform from a physical body that walks and talks to a mental and print body that resonates their thoughts and stories forever. How many writers do I read about that passed while in the middle of their next novel or essay or article? We’re writers. It’s what we do. It’s a drive to speak through our writing to millions globally who find our work rewarding, entertaining, educational, inspirational and all-encompassing.

    Funny you write this today. I just told a group of friends last night that I had arrived as a professional freelance writer… reaching a dream to write and be paid and be published. It’s my second phase, one that’s more rewarding because it’s rebuilding. Like all writers, I’m still in process honing my skills, building relationships with editors, and seeking new endeavors that allow other writing juices to flow.

    Great post. Says it all and so true! Here’s to another pool, a stronger swim, and another book on your “just published” bookshelf!

    • Carol Tice

      Yeah, sounds like you caught that breathing space…you built a client base and you’re getting paid and published. Now, on to the next pool!

  12. Early Conner

    Good Day,
    Thank you for being inspired to write this and sharing your dream to summarize the fear even successful writers seem to hold onto at the back of their mind or the bottom of their gut.
    I have wanted to write fiction since I was a child but always allowed “blocks” to stop me time after time.
    I am just recently facing those blocks and searching for the tiny doors that are always there to be found. I will drink my potion to fit through the doors, even if it means ending up in the swimming pool.
    Thank you again:)
    Early Bird

    • Carol Tice

      It’s so funny you reference Alice…my daughter was in a musical version of Through the Looking Glass yesterday!

  13. Liesa Malik

    How true your words! I do not consider myself a writer even though I’m going to have my first book published in about a year. I do not read enough. I do not work on my next novel daily. My marketing customers are unimpressed with the articles, brochures and other copy I write for them. My critique group is full of writers who put words and ideas together much better than I.

    Then I realize I am listening to that horrid critic voice in my head that wants me to give up, grow up, and go do something boring for a living.

    Now show me a blank sheet of paper and I will fill it quickly with doodles and oodles of words. My heart soars when I can put something on paper. I land in the clouds when someone says they like what I’ve done. Maybe, just maybe, I’m and artist and a writer after all.

    • Carol Tice

      I think you know the answer there.

      And congrats on the book! It’s amazing how sometimes, no amount of achievement erases our doubts. Only we can make up our minds to do that.

  14. Susanna Perkins

    Carol, what a terrific analogy! It really does describe the ongoing process of starting, breaking through, starting again at the new level, breaking through, etc. “I’m a writer” is always a journey, never a destination!

  15. Laura

    Thanks Carol, this is a really beautiful and poignant post. It’s amazing what the right mindset can do for people (and how it can work against us). It’s funny how this seems to affect writers so much more than other professionals. Sometimes I wonder if it’s because we’re in a fairly artistic field. Even though there are proven ways to sell to someone in copywriting, even though following the right grammatical rules in journalism and fiction writing help–you’re still developing your own style which will never perfectly mimic someone else’s. We can’t memorize a specific formula or study at a trade school that will say we’ve become “master writers” like getting certified to be a healthcare practitioner.

    It really does remind me of being a song writer or a painter; there’s no “wrong” way to do either, and you’ll always have people who will love your work along with those who simply don’t get it. I struggle with wondering whether I’m good enough, but at those times I just remember that I’m being paid to do what I do, and if I didn’t have any talent for writing it’s unlikely I’d have been hired in the first place! Your biggest critic is definitely yourself, so I just keep setting goals and going after them.

    Love that you mentioned the Brontës, by the way! Wuthering Heights is one of my favorite books and Jane Eyre isn’t too far behind.

  16. J. Delancy

    One more metaphor: We don’t do our best swimming until we get thrown into the deep end of the pool. I’ve been writing speeches for ten years plus and will still procrastinate and freak myself out trying to write a 500 word post. It’s always hard to believe what mental barriers other people have and it’s even harder to climb over your own.

    • Carol Tice

      Oh, you should see me any time I’m writing the first thing for a new client. Massive complex. M A S S I V E. And of course, it’s all in my head.

  17. Miss Britt

    It’s kind of strange how often writers get into discussions about whether we are or are not writers. I don’t imagine cable installers sit around and wonder if they are or are not cable installers.

    Are you writing? Congratulations, you’re acting like a writer.

    Is someone paying you money in exchange for words you’ve written? Congratulations, you’re a paid writer.

    Does the bulk of your income come from writing? Congratulations, you’re a professional writer and when people say “what do you do for a living?” you can honestly answer, “I’m a writer.”

    I think the only true questions that remain are:

    Are you a good writer?
    Are you doing what you love?

  18. Joanne

    Oh my goodness Carol. What a wonderful post. Thank you so much for sharing – especially the dream. Wow.

  19. Jeff Goins

    Thanks for the shout-out, Carol. Kind of you.

  20. Rob

    I make a distinction between freelance writing as a career and writing as a creative endeavour*:

    Recognition and compensation are my two benchmarks for success in my freelance writing career. It’s a bit like climbing a mountain: you can stop and take in the view at stages along the journey, but need to keep on going if you want to reach the top (or a comfortable chalet you are happy to call home).

    As for writing as a creative endeavour*, I have to agree with Charles Bukowski:

    “unless it comes unasked out of your

    heart and your mind and your mouth

    and your gut,

    don’t do it.”

    * I spelled endeavour right!

  21. Ken

    I’ve always wanted to be a writer. But I only started to be serious when I started a blog a year and a half ago. I still feel that I’m not worthy to be called one until, you’re right, the time that I get accepted to write for a magazine, newspaper or a book deal. Or I get a thousand readers in my blog everyday. For now, I use my blog to express my thoughts and my faith. I’ll continue to write whenever I feel like it; writer or not.

  22. John McDuffie

    I love this blog. The approach to writing and freelancing is not as stale as most blogs I read. I pretend to be a freelance writer daily. So far my clients are buying into my disguise. I think I have made a career as a writer, but I don’t think I have “made it.” I have 3 goals that i wrote down the day I sold my first piece. I have not achieved any of those goals. One goal is crazy, but we all need someplace to reach right? I think if I can accomplish 2 of the 3 I will call it a win. Until then, I’m just faking it and hoping no one finds out.

    • Carol Tice

      I want you to read the post again, John — you’re a writer already.

      That feeling of being a fraud is just in your head. Everyone else thinks you’re writing for clients! It took me Y E A R S to figure that out. Save yourself the stress and just look in the mirror and say it now: I’m a writer. You don’t have to check off any goals, create world peace, or nothing. You write, therefore…you’re a writer.

  23. Philip Mboya

    Very inspiring! I have to admit, i struggle myself with the ” i have reached” mentality. For me it has always been a 4 figure monthly income and now i realise that stopping because of reaching one goal can be likened to suicide. Just like in your dream, had you stopped when you got the first cover out who knows what would have happened. I guess the most important thing is to keep on going.

    Thanks for sharing!

Related Posts

LinkedIn Round-Up

LinkedIn Round-Up

Successful freelancers use LinkedIn daily. After all, it's the only social media where it's socially acceptable to talk about work. In honor of our upcoming bootcamp, LinkedIn Profile Mastery, we wanted to give you a round-up of all our posts on the topic of LinkedIn....

9 Journalist Interview Tips from a Successful Freelance Writer

9 Journalist Interview Tips from a Successful Freelance Writer

Have you been struggling to interview sources for your freelance articles? Then these 9 interview tips are for you. These journalist interview tips will help boost your interviewing confidence and make you better prepared to take your freelance article to the next...