When I first started writing songs, I was inspired and fearless. I was so deeply immersed in my creative process that I didn’t give any real thought as to how the rest of the world felt about what I was doing. However, when I decided to start thinking of songwriting as a potential career, I began to realize that taking risks was necessary to achieve the rewards that the industry had to offer. To that end, I’m going to cover a few of the important risks songwriters should consider taking and the rewards that often come as a result.

Risks and Rewards for Songwriters

1. Co-writing

The Risks

It will “mess up” the good thing you’ve got going when you write alone.
-By the way, you can always go back to writing alone.
Your collaborator will think you’re not talented.
-It might help to remember that there’s no accounting for chemistry and ultimately someone else’s opinion is just that.

The Rewards

You’ll be exposed to different styles of songwriting.
-You’ll come up with something better than either one of you could have written alone.
-You’ve got twice the number of people pitching/promoting the finished song.

2. Playing out/putting your music up online

The Risks

Your ideas could get stolen.
-This scenario is extremely rare. In my twenty-five years in music, the only example I’ve ever seen was with a song that was already a radio hit. I’d worry more about making sure your songs are so great that people want to steal them.
A publisher or music supervisor won’t be interested unless the song has never been exposed.
-There are countless examples of songs that have been around for years (or even on the radio) before getting re-cut and re-released.

The Rewards

There’s no better way to see if a song is working than to gauge the reaction of a live audience.
-Good things can only happen once your music is out in the world. Nothing good can happen if no one ever hears your songs.

Risks and Rewards for Songwriters

3. Getting your songs critiqued (either professionally or by your peers)

The Risks

Your songs will get trashed.
-Critiques are always a mixed bag. This is art. Take what you find helpful and discard the rest. You might want to pay particular attention if the same comments come up over and over.
You’ll get so discouraged, you’ll throw out a song that had potential to be great.
-You can always make sure you’re in a decent place with a song before you get it critiqued.

The Rewards

-You’ll learn to take criticism and develop a thicker skin.
-You’ll learn the art of rewriting.
-Most importantly, in time you’ll learn to believe in your own voice as a writer.

4. Meeting with a publisher

The Risks

They won’t like your songs/sign you to a deal.
-There are lots of publishers out there and not everyone will love what you do. You’ll be no worse off than if you’d never gone.
They want to hear more songs and you don’t have anything else written/demoed.
-You can always wait to schedule until you have at least a few songs and, by the way, if a publisher likes what they hear and want to hear more, they’ll wait.

The Rewards

The publisher might like what you do and even if they don’t sign you, they might ask you to write with their signed writers.
-Remember that nothing happens quickly.
They can point you in the direction of other publishers who might be looking.
-At the very least they might also offer valuable advice on how to make your songs more commercial.

Risks and Rewards for Songwriters

5. Pitching your songs yourself

The Risks

You’ll get rejected.
-Again, this is no worse than never trying and even the most successful songwriters/songs get rejected more than they get accepted.
You’ll get taken advantage of since you’re not an experienced publisher.
-You can – and should – consult with an attorney before anything is finalized.

The Rewards

Even if your song isn’t cut, you’ll be networking and meeting more people in the industry. You never know how that relationship might bear fruit years down the line.
You WILL get the cut and, since you pitched it yourself and don’t have a publisher, you’ll own your publishing which equates to twice the royalties.

6. Making the decision to pursue a career in music

The Risks

It’s scary to admit to yourself that your art is important to you because if it’s only a hobby then it’s ok if you’re not great at it.
-You’ll never know how far you can go until you try.
You might be taking time away from more “lucrative” professional work.
-If ultimately that work is unfulfilling, then maybe a little less money for greater happiness is a fair exchange.

The Rewards

There is no greater feeling than putting your music out in the world and reaching people with it.
You’ll find that all of that hard work and treating your songwriting as a business actually begins to pay off financially, too.


My experience has been that in songwriting we miss more times than we hit. The key isn’t avoiding risks but, rather, it’s getting back up after getting knocked down and taking more chances. I can safely say that without taking risks, you’re almost guaranteed to miss out on the rewards, too. Take a chance and see what happens. You might just surprise yourself.

Learn how to navigate your songwriting career.

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7 responses to “Six Calculated Risks for Songwriters”

  1. Gary says:

    Good stuff as always Cliff. Thanks!

  2. Great points, Cliff.

    I’m a big fan of critiques… a good critique can give you an unbiased opinion (not emotionally attached to the song) that can help you improve the song!

    The risk is to your songwriter’s ego, the benefit is a better song if you use the advice….

    Cliff, do you know any reputable song critiquers online?
    (Wild guess, but I am assuming you are too busy with all that you do to spend much time critiquing songs!)

  3. Great stuff.The choice is simple…either one develops the skill-sets to become a “”craftsperson”…and can hone a musical narrative with great skill..and, possibly reach a large audience and make a ton of money…or…one takes it further and takes great risks to dare to create something truly unique, despite the demographics of the marketplace…lwhich requires being self-validating and setting your own standards)…then one is an “artist” (a term highly abused in the music biz)…the end result may be a groundbreaking body of work and world acclaim…or, it may mean toiling in anonimity…….take your pick (or fingerpick it, as the case may be).

  4. Great advice, Cliff. I love your blog. So practical.

  5. Edwin Hendriks says:

    Hi Cliff. Awesome advice as usual and your passion for what you’re doing is evident. Key themes from this blog article – as usual there are a number of different approaches one can take, risks will be there, weighing up the risks and living with the consequences are necessary and ultimately, even if in a small way, one will get rewarded for your efforts.

  6. Think my favorite moments include 1. When someone is inspired to join my set in any manner or 2. When they ask who’s song that was and I wrote it. My covers reflect great artists that may not be familiar now, so the reviews are interesting.

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