The Promise and Peril of the Road Less Traveled: Why I turned down big money to pursue my dreams

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The Road Not Taken
by Robert Frost (from the collection, Mountain Interval)

Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth;

Then took the other, as just as fair,
And having perhaps the better claim
Because it was grassy and wanted wear,
Though as for that the passing there
Had worn them really about the same,

And both that morning equally lay
In leaves no step had trodden black.
Oh, I kept the first for another day!
Yet knowing how way leads on to way
I doubted if I should ever come back.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I,
I took the one less traveled by,
And that has made all the difference.

My sister sent me this poem after I told my family that I was turning down a handsome signing bonus, salary, and benefits package with a tech industry giant in order to stay in Nashville and work in the music industry with no security and a freelancer’s salary that at its best would be a shade above the poverty line.

Despite the shock and bewilderment my decision caused, I was quite proud of myself.  In my mind, I was taking the good and noble path and was sure that with my qualifications I would have no problem making a name for myself in any industry.  Arrogantly, I thought that a year or two down the line I would be making even more money on my own than I would have at any corporate job, no problem.

Well, I was about as wrong as wrong can be.  As it turns out, nothing comes easy or free, especially if you’re trying to live out the life of your dreams and fulfill your purpose on this earth.  I had believed that as long as I was honest with myself and lived my life as such, money, success and fame would rain from the sky like frogs (see P.T. Anderson’s masterpiece Magnolia for the reference).

The truth is, taking the first big step toward living life on your own terms is the easy part.  It might not seem that way, after all, quitting your job, turning down a great offer, packing up and leaving town, none of these are easy decisions to make.  If you’re the type of person who fears uncertainty and instability, these decisions can be paralyzing.  Still, it’s nothing compared to what lies ahead.

I don’t want to discount any of the great thinkers who have written about the importance of taking control of your life by making changes and taking risks.  I’ve benefitted a great deal from this guidance and am an advocate of making these kids of changes myself.  Thing is, most of the blog posts, TED Talks, and “Top Ten Reasons” lists that I’ve seen on the subject focus entirely on why you should take the jump, seeming to imply that once you do, everything will fall neatly into place.  It doesn’t and it won’t.

In my case, I started working long hours in the music business for little pay, building up debt on the side and nearly surrendering my passion for music itself for the goal of making music make money.  When all the cards were down, the big money never came, not because we hadn’t worked our asses off to do everything right; sometimes things click with the right audience at the right time, and sometimes they don’t.

This wasn’t the way it was supposed to unfold of course, I had already taken the road less traveled, and against great opportunity cost.  What do you do when it leads you to a place that eerily resembles what you were trying to avoid in the first place?

Everybody only talks about the first spot where the roads diverge because there’s no map for where the road not taken leads.  I can tell you that if you do choose this path, up ahead you’ll see tracks leading back to the main road about every twenty feet, and you’ll run into more than a few junctions where both directions are scarcely traveled.  It’s tempting to turn around, and explain the whole thing away as a brief soul-searching expedition.

The key is to remain constantly and resolutely aware of why you chose this road in the first place.  Living life intentionally is never going to be as easy as following rank, and the failures and dead ends will often outnumber the successes.

Henry Ford famously failed in several business ventures before founding the Ford Motor Company, and Colonel Sanders’ first chicken shack went under without turning a profit.  The only way to achieve the life of your dreams is sharpen your grit at each turn and keep trying until something connects.

I may not have the answer yet, but I’m going to keep pushing on until I do.  That’s why I started One Week Without in the first place, to reevaluate everything taken for granted in my life and seek self-actualization and self-improvement at all costs.

The good life is out there waiting to be uncovered.  We will find it, with our heads down and feet trodding forever forward out into the unknown.

may we all get better together.



  1. Chris says

    I love this article and can relate completely. A lot of the motivational speeches you can find on youtube romantacize and glamourize working hard until you succeed, but it isn’t until you’re down in the trenches do you realize just how tough it is. Sometimes there just isn’t a light at the end of the tunnel. And when it gets this scary, it is VERY tempting to go back onto the “main road.” But you just have to keep on truckin’…

    • says

      Thanks so much for your thoughts Chris! You’re exactly right about how we romanticize and glamorize making the jump, I hope everyone out there who’s considering it can just know that everything isn’t going to go up at a 45 degree angle the whole time. There will be peaks and troughs, but the people who make it keep at it in the good times and the bad.

  2. says

    “The key is to remain constantly and resolutely aware of why you chose this road in the first place.” This, though. Seriously.

    I’m with you–just finished an unpaid internship in the music industry (now working as a usually unpaid music “journalist”, but which I LOVE but ugh some days), independent blogger, all that creative-y stuff. It’s hard. But a friend said something to me one that really stuck:

    “You know, if you do stuff you don’t want to do, then you’ll only be qualified for other stuff you don’t want to do.”

    Nothing has proven more true in my life. If at worst you’re preparing your resume for a career you will probably enjoy, and at best you’re preparing yourself for [insert superstar dream here], I think you’re doing it right.

    We just have to root each other on 🙂

    • says

      Hey Shauna, this comment has been one of the most inspiring things I’ve seen in a long time. This in particular: “if you do stuff you don’t want to do, then you’ll only be qualified for other stuff you don’t want to do.”

      I’m actually going through one of those times in life where I’ve got to make some tough choices, and those wise words are resonating very heavily in my ears. Thank you, thank you!