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I Found Freedom: Maisie Smith

Continuing on with the “I Found Freedom” series, Maisie Smith is here to tell us how she decided to make the LEAP after realizing that her 7-years advertising career wasn’t giving her the freedom she knew she needed.

I remember Maisie telling me her quit date in the FTF community on Facebook earlier this year, and I was so excited when she made it happen.

Here’s her freedom story:

Maisie Smith

When did you make the leap exactly and how does it feel?

My last day in the world of cubicles and 2-week vacations was May 27th. It’s been an exhilarating ride since then. When I wake up in the morning, I’m excited about all of the possibilities each day carries with it. I’d not experienced that previously, so each morning of freedom is a blessing in my book.

What kind of freelancing do you do?

I am a freelance writer. My main focus is on content creation for small businesses. Stories are my life and I’m good at digging for the “weird”… that’s where the magic happens… and turning it into compelling content.

How long have you been planning to make the leap?

I became disenchanted with my advertising career after about 7 years. Everything seemed so surface-skimming. There was no real depth to any projects and the fast pace wore me down to a nub of apathy. I floated along for 2 years, trying to figure out what I should be doing with my life. I read book after book on “finding your passion” and “chasing your dreams”, but nothing really stood out as a path that I wanted to journey down. I was a scattered mess.

In July of 2013, I was at the World Domination Summit in Portland, waiting for a workshop by Pam Slim to begin. She’s the enchanting author of ‘Escape From Cubicle Nation’ and ‘Body of Work” (two books that I highly recommend). About 2 minutes before she took the floor, I was hit by this burst of energy that completely cleared my mind of the fuzz. And then my soul clearly said, “You need to be a writer. And your company will be called Audacious Muse Writing Studio.” Right then and there, with 30 seconds to spare, I opened up a browser on my smartphone and purchased the domain.

When I returned home, I got cracking on building my business.

Did you choose a quit date and how did you choose it?

I chose May 31st as my quit date. There was no rhyme or reason to the date. It just seemed like a natural month and day to quit. It also gave me the time I needed to plan for my exit.

Maisie Quit Date BoardI made a colorful 5-31 sign to keep at my desk as a reminder of my goal. I posted cryptic pics of it to social media with a note “something big is coming” and would leave people to speculate. I began telling family and friends about the date. Accountability is HUGE for me, so actually announcing the May 31st date created a sense of urgency and a “no going back” attitude.

I’m proud to say that I beat my deadline by 4 days. My last day of working in the corporate world was May 27th.

In which ways did you plan/prepare for the transition?

You can’t just say, “I’m going to be a writer” and bam… you begin a career writing. I had to decide what kind of writing I wanted to do and niche it down to what I was best suited for. With my background in advertising and other creative careers, I knew that I wanted to help businesses be more fearless with their writing. I knew that was where I could make the most difference.

I began working on a website for my company, Audacious Muse Writing Studio, as well as sharpening my writing abilities through journaling and other exercises. I read voraciously.

Most importantly, I started telling people about my plans. I began networking at local small business events. This helped me to line up clients ahead of time.

Did you have a savings or buffer fund? If so, how much?

I would like to say that I saved a ton of money for the transition to freelancing. However, in the name of transparency, I have to admit that I only had $1500 in the bank when I quit my job. This definitely put the pressure on me to begin earning money right away. I couldn’t fail.

In some ways, I think this was a good thing. It forced me to approach others with boldness, learn how to ask for business and get seriously lean with my lifestyle.

If I had to do it over? I’d definitely try to save more.

What was the hardest part of making the leap?

Towards the end, right before making the leap, I experienced a dizzying amount of resistance. What if I’m not good enough? What if people don’t see me as qualified? What if I fail? I began comparing myself to successful freelancers (people who had been doing this shit for YEARS), feeling like I just didn’t have what it takes to succeed. I was standing on the entrepreneurial cliff, toes dangling over the edge. And while I should have been looking out at the horizon and all of the places I was going to soar, I instead found myself looking at the ground like a frantic pilot scouting out a place to crash and burn.

Luckily, I have a wonderful man in my life to help me sort out my fears. He gave me the courage to launch off of that cliff and hold tight to my dream.

What’s the best part of finally freelancing full-time?

I love that I get to call the shots. All decisions are mine. When I throw the covers off in the morning, I have the ability to plan out my day however I want it to be. Feel like reading? Great. I’ll start with that. Want to stare out the window for 15 minutes and just think? Cool. Drink a beer at my desk at 3 p.m.? Right on.

What is your advice for others wanting to find freedom through freelancing?

Many people wait until conditions are perfect before they make the leap into freelancing. “I need to wait until I have more money. Until my skills are better. Until I have the perfect headshot. Until I know without a doubt that this will work.” I can tell you this: that will never happen. Perfect timing is an illusion. You just have to jump sometimes and trust that you will not allow yourself to fail.

How did you celebrate your LEAP?

Fargo, baby! Weird, right?

Fargo, North Dakota is actually a super-cool city for entrepreneurs and oddballs like myself. I attended the Misfit Inc. conference there at the end of May that served as my reward for “giving the finger to the Man.”

Maisie SmithMaisie Smith is a freelance writer, storyteller, blogger and lover of geeks and craft beer. Her bold little company, Audacious Muse Writing Studio, inspires and supports small businesses wanting to give the finger to the status quo through creative content and telling better stories. Connect with her on Facebook or Twitter.



Leah Kalamakis Leah Kalamakis is the founder of The Freelance To Freedom Project and a web designer/developer for brilliant entrepreneurs. When she’s not hanging out in the FTF Community, you can find her people watching on the streets of NYC. Come say hi on Twitter, Instagram, or Facebook.

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{ 4 comments… add one }
  • Great interview with Maisie! Love it… “giving the finger to the Man.” I can totally relate and I gave myself a quit month rather than date. I could feel that March would be my month and my last day at my corporate job was actually in the last week of February. It feels AMAZING!!!! Thanks for sharing.

    • Maisie

      Katie! Isn’t being a “quitter” glorious? I can’t believe I waited as long as I did to make the move to full-time freelancing. 🙂

  • Love it, Maisie! Could really relate to your story! Love the entrepreneurial cliff metaphor … keep looking up, girl!

    • Maisie

      Thanks, Beth! There are quite a few similarities between freelancers and I am so grateful for this space that Leah created where we can share our journeys with one another.

      To freedom!

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