Get the FREE Freelancer’s ToolkitGet the free toolkit!

I Found Freedom: Devon Smiley

When you’re itchin’ to make the leap into full-time freelancing, there is nothing more inspiring than hearing stories of people that have done it themselves.

The ‘I Found Freedom’ Series is all about telling those stories.

Everyone prepares for the leap in different ways, but often we go through the same ups and downs to make it happen.

Here’s Devon Smiley’s story.

I Found Freedom: Devon Smiley

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

My first day of full-time entrepreneurship was February 2nd, 2015. That week was definitely full of emotion. Excitement over what was to come, bliss at not having to get into the car for a snowy commute, and more than a little anxiety as I pondered the question: “Am I really ready for this?”

What kind of freelancing do you do?

I’m a Negotiation Consultant. I work with entrepreneurs and corporations to help them get what they need in business.

I love the variety – I’ve helped stylists send surefire proposals, dog walking businesses raise their rates, and have even provided guidance to pizzeria owners on negotiating with their vendors. It keeps me on my toes!

How long have you been planning to make the leap?

The idea to launch as a consultant was planted over 2 years ago. At the time (and up until this February) I was working as a full-time negotiator for an aerospace company. I enjoyed my work, but the confines of corporate bureaucracy (and cubicles!) meant that I wasn’t able to have as big of an impact as I wanted. It become more and more important to me that I flex my skills in new, creative ways – and that I use what I’d learned to help the ‘little guy’ in business too.

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

I did!

During a rough patch earlier in 2014, I’d set my computer password to ‘Freedom34’. At the time, I laughed, and figured it was a bit of a day dream that I’d be out of my day job by my 34th birthday.

Manifesting + working my buns off meant that I could give notice on January 19th – the day after my 34th birthday.

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

I’d been blogging and cultivating my business on the side for almost a year, so I had a website, social media, and a small but loyal group of subscribers/followers by the time I gave my notice. I’d started working with a business coach in the months leading up to my departure because I wanted to make sure I could hit the ground running.

Of all of the prep work I did, I think that it was the blogging that paid off the most. I’d taken time to experiment with formats, find my voice, and practice my consistency before it became my ‘job’. I can’t imagine facing that learning curve on Day 0.

Did you have a savings or buffer fund?

One of the feelings I struggled with the most in quitting my corporate job was the idea of the ‘Golden Handcuffs’. I’d been working my way up the ladder and pay-scale for a decade – so replacing my salary as a freelancer seemed (and still seems!) daunting. I was limited in how much side work I could take on because of how important it was for me to avoid conflicts of interest with my employer. I also had a lot of panic related to being a homeowner…those mortgage and tax bills add up!

When I went full-time into freelancing, I had a buffer of 6 months of expenses saved. Which, if I watch my pennies, I think will stretch to 8 months. It’s not as much as I would have liked, but I’m quite conservative, so I don’t truly think there ever would have been ‘enough’.

What was the hardest part of making the leap?

I thought that hardest part would be the financial issues, but those take the 2nd spot.

The most difficult adjustment has been figuring out what to do with all of this time I now have to work on my business.

I feel the same way I did after finishing my MBA. It had been 2.5 years of taking classes at night while working full-time. Every moment was accounted for – just as it was when I was building my business foundations on the side. When I graduated, all of a sudden there wasn’t a stack of homework that had to be done. It’s the same now – I wake up each morning and can fill the day with whatever work I want to do. It’s hard to be confident you’re making the right choices all of the time.

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

IMG_1390Waking up and filling my day with whatever work I want to do! A blessing and a curse in these early stages I guess.

It’s wonderful to know that when I decide to dedicate time to a project, or hit publish on a new post, that I’m very purposely working towards helping others. I get to use my powers for good, have an impact, and be absolutely 100% myself while doing it.

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

My two biggest pieces of advice are to start early, and write your own definition of freedom.

Doing the foundation building work before you’re a full-time freelancer will take a bunch of stress off your plate once you’ve made the leap. Play with ideas, practice your craft, build your network.

A big part of that foundation is to define what freedom looks like for you. Not everyone wants to be working remotely from South East Asia (I burn like a lobster, so there are no beaches in my Freelance To Freedom plan!). It can be tempting to buy into someone else’s idea of what being a freelancer looks like – but resist. Make it your own.

How did you celebrate?

My former colleagues and friends took me out for a nice dinner the week I left the company – we raised a glass to ‘new adventures’.

My quiet, solo celebration was on my first morning as a full-time freelancer. I went to the cafe near my house, ordered a double long espresso and a raspberry danish. I sat in the window with my journal and captured my thoughts. How happy I was. How scared. How eager I was to get back home and start working. I look back on that entry when I feel overwhelmed, or I question my decision to leap. It’s like the perfect touchstone for how I want to feel as an entrepreneur. Giddy.

In one short sentence, what does freedom mean to you?

Thanks Devon!

Devon Smiley is a Negotiation Consultant who believes that no one is ever ‘too small’ to negotiate. She helps entrepreneurs build the confidence and skills to ask for – and get – what they need in business. Knowing that figuring out what to ask for is half the battle for entrepreneurs, she’s created the 3 Must Do Business Booster guide to give them the kickstart they need to bring their business to the next level. Connect with her on Twitter , or Instagram.



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.

+ get the FREE Freelancer’s Toolkit including:
✓ From Last Corporate Day to a Month of 5k
✓ How to Get to Steady
✓ 4 Steps to your First (or next!) Passive Income Stream Workbook
✓ Daily advice, tips & inspiration

Yes, please!

{ 0 comments… add one }

Leave a Comment