The Path to Freelancing – Is it Accidental?

Today, as I write this, I reach a milestone in my journey as a part-time traveler.  

Seven years ago I received a job offer after completing an internship while still a student, and I began working just two weeks after I graduated from college.  Since then I’ve worked with avid determination to fit travel into my life — amongst career demands and within my 3-4 weeks of allotted vacation time.  I remain passionately convinced that for working professionals, time to travel is not only possible but, for many of us, highly necessary.

Yet at present my life has taken on a completely different shape.  I ask myself as I realize — it’s true!  When did I become a full-time writer?

how to start freelance writing

One year ago I decided to take the leap of faith into freelance work — and the lifestyle that comes along with it.  Though it took longer than that for me to really own it, and though I still have days where I question my choice, I’ve finally grown comfortable with the fact that I’ve carved an actual career path for myself.  

I’ve spent countless hours researching, debating, and searching for what feels something that arrived suddenly.  Isn’t it funny how that happens?  Months of small efforts, enlisting new habits, and planting the seeds…and then one day, all of a sudden, you’ve got something to show for it.

By no means has it come without sleepless nights and panicked grasping — but waking up excited to face the day and itching to get to work is something I will never again take for granted.

Today is also my half-birthday.  I know it’s not much, and that it’s a bit silly to even celebrate a half-birthday at all, but I take the opportunity to reflect and take stock of where my life is headed.  

As I approach twenty-nine (read: almost thirty) I feel more than ever the pressure to walk the traditional path — you know, the one we’re all supposed to want without question, the one it feels everyone is following but you.  

I’m the girl who always planned, who often succeeded, and the one probably least likely to deviate from said path.  Yet here I am.  At time it feels awfully self-indulgent, yet at other times it feels like a no-excuses necessity worth fighting every day for.

It kind of feels like dancing without music, literally marching to the beat of your own drum.

All of this leads me to wonder: if we’re dancing without an audible soundtrack, at what point do we rock on, and at what point do we realize that we look ridiculous?  Does it matter if no one else hears the music, as long as you’re enjoying the dance?

what if i fall

(Image source: Pinterest)

< I learned to ask myself this daily when traveling, and it helped me be okay to ask it at home. >

The road to freelancing hasn’t been smooth, as anyone will tell you.  How does one even start freelance writing?  I admit that it took years of working in a job I dreaded daily and making sacrifices to create a safety net to be able to take a chance on myself.  I think, however, just as a small part of me knew that my personal life would never be the same after traveling, some part of me knew that perhaps a less traditional path was what I needed to walk (or, fly!) on.

I applied for “real” jobs here and there, and I’ve been disappointed  — but I refused to apply for a job I wouldn’t be ecstatic to accept, just as I won’t continue to date someone I’m not dying to see again (read this for a wake-up call on that…)  It’s scary, having no one to answer to but yourself.  Self-employment —  being in the business of “you” — is a daily adventure in itself.

For me, it’s worth it.

Perhaps the biggest benefit of freelancing is built into the word itself — being free. What really is freedom?  I don’t think of myself as a person who fears commitment — if anything it’s the opposite: I throw myself wholeheartedly into anything I pursue.  I’m all in.  To me, having freedom, at least at this point, is choosing for life to be a blank canvas.  I decide what goes on it, what doesn’t, and I choose the colors that suit me.

If your life was a blank canvas, what would you paint?

Realizing that what was once a tiny flicker of a flame is now a legitimately burning (albeit small) fire — that I write for a living, that I get to write about what I love, and that I love what I do…

It seems almost accidental that I’ve arrived here.

Yet this…this is what I’ve learned:

It’s anything but accidental when it’s something you’ve always dreamed of.

For what it’s worth, some helpful words I’ve gathered that I offer now to you:

  • The greater the risk, often the greater the reward.
  • The quality of your life is in direct proportion to the amount of uncertainty you’re able to deal with.
  • Almond macadamia lattes on a foggy day in San Francisco are a gift from God.
  • When at a loss for words or ideas — get out of your desk chair (and maybe your pajamas) and go engage with the world around you.
  • Learn to go with the flow of life — and refuse to settle as you do.

“Trust that when the answer is no, there is a better yes waiting for you down the road.”

And finally….

“Trust the timing of your life.”

anne in handwriting

P.S. Did I mention that I’m a professional writer? Hire me?

Freelancing is just one path on the road to balancing life and travel.  Is it something you desire?

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  1. So proud of you!! You’re one of the best writers I know, and you deserve this so, so much. You’re journey’s been so inspiring, and San Francisco’s so lucky to have you settle down and write in it!

    • Thank you, lady! That means a lot coming from one of my favorite writers… 🙂
      Can’t wait to have you back in SF writing with me again!

  2. Outstanding and inspiring! I’m on the path to starting freelance writing and it excites ne everyday. I’ve come to realize too that I am the only one that put pressure on myself to be on the traditional path. Thanks for the inspiration. 🙂

    Also, I certainly need to try an almond macadamia latte! That sounds amazing.

    • I’m so glad the post spoke to you! It can be tough to openly share pieces of our journey like this, but hearing that it helped you is exactly why I do it.

      The “traditional path” is a weird pressure, isn’t it! It can be stronger at some times more than others. I like your point that we are the ones who are in control of how much we let that pressure affect us.

      P.S. The almond macadamia latte is from Saint Frank on Polk!

  3. Jessica

    Hi Anne! Beautifully written. I am starting a travel writing class to do the same thing. It is scary to leave my traditional job because I have made it pretty far in my career. I live in San Francisco and would love to grab a coffee with you sometime!


    • Hi Jessica – so great to hear from you. I’d love to chat more with you about travel writing and life. Send me an email? Look forward to connecting. 🙂

  4. Excellent, Anne. As I’m more than ten years older than you (!!) and walking that traditional path, I say, “Fly, Anne! Fly!” I have every confidence that you’ll fly high and far.

    • Francesca, thank you for the comment. I appreciate your confidence in me!

      I have to say though, you are far from walking the traditional path of most, being that you not only manage to blog but continue to travel! Your daughter wanted to write a travel blog and you got business cards made for her… You are an inspiration to me and so many others. Whatever path you’re flying on…I say soar on.

  5. This was such a great post! I’m so happy for you that you’ve found your way.
    I love your closing quotes too, especially about the quality of your life related to the uncertainty you’re able to deal with. I need to tattoo this on my forehead lol.

    • Thanks, Kristin 🙂 I’m glad you liked it! I have to admit, I’m always sharing quotes that I also need stamped on my forehead. Love that.

  6. I wholeheartedly agree that nothing is accidental and you were destined for this path! Can’t wait to buy your first ebook! Happy writing 😀

    • We all find our way, somehow…right? Thank you for reading and for the well wishes! 🙂


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