Making the Switch: 9-5 to Freelance


As I walked to my car one final time as a Product Specialist for a sneaker retail chain. I prepared to drive into the land of the unknown (while rapping along to Slick Rick’s “Children’s Story”). It’s funny how you remember the little things when getting ready to shake up your life.

I’m here to tell you that every heroic quest you’ve seen in a movie is nothing compared to the story of you leaving your job. Beyond the financial pressure, your confidence, faith, and discipline will be tested to every degree. Even getting out of bed will be unbearable some days. But I challenge anyone who’s looking for fulfillment to take the journey, because it’s worth it.

For me, the journey started in the barbershop in 2008, with stacks of dusty, worn-out magazines sitting quietly in the middle of the coffee table. As I impatiently waited my turn, I read anything that grabbed my attention.


I vividly remember digging for the GQ issues, which were usually on the bottom of the pile, and skipping directly to the “Style Guy” column written by the late Glen O’Brien. Every time I read O’Brien’s responses to the fashion questions he had received, the rest of the barbershop quieted to mute in mind.

I could hear O’Brien’s voice in the pages as I read—It was both comical and educational. From him I learned that I could use my writing to have a conversation with readers, rather than just to publicize my personal opinions. And, I liked that.

Prior to becoming a Product Specialist for a sneaker retail chain, I wrote for various menswear blogs; they loved my down-to-earth approach to men’s fashion. Every time I saw an article of mine posted on a home page or shared on social media, I felt confirmation that writing was something I was decent at.

Requests for my writing gradually increased. Some paid; some didn’t—but it didn’t matter; I enjoyed the opportunity more than anything. As I started contributing regularly to a few sites, the opportunity allowed me to create my own weekly style column with a publication called “the Stndrd”. Seeing my work in print helped raised my profile and confidence, but even with a few printed issues under my belt, I still never thought becoming a freelance writer would be possible. I wondered how writing could even be considered work.

By year three, my love of my corporate job had begun fading, and it was getting hard to ‘fake the funk’. Emotionally, I was less attached, less fulfilled, and more occupied fantasizing about life outside of those four walls. I knew something bigger was calling, but I like having health insurance, so I was torn. I was also about to get married, which wasn’t as frightening as the thought of becoming a husband who couldn’t provide. I quietly thought, “how do I write myself out of this one?”

I started sending my resume and editorial samples to every publication and online magazine with a contact page. I was hoping I could at least get a small writing gig to cover my half of the rent, but nothing ever landed. I finally received a small offer from an overseas menswear company that ended up contacting me about creating some preliminary content to launch their menswear website. The pay was decent, but not enough. Nevertheless, it was a start.  


While no words of wisdom will ever fully prepare you, I want to share some solid advice that will help you take the corporate leap of faith.


A month after getting married, I gave notice; two weeks later, I left my job with mixed emotions. My last day was met with heartfelt handshakes, emails from co-workers, and empty promises of keeping in touch, until I finally walked to my car and took one more glimpse. I then left quietly for home.

As I pulled out my phone, I was jolted by emails informing me that payments for my credit card, cellphone, and car insurance were all due in two weeks. Once I subtracted rent, I would only be left with $100 to my name. I knew it was time to stop dreaming and start working.

Today, I’m happy to report that I survived my first year of being a freelance writer with several writing gigs, some personal style jobs, and becoming a part-time tutor.

While no words of wisdom will ever fully prepare you, I want to share some solid advice that will help you take the corporate leap of faith…


One thing I can admit is that when I left my job to become a freelancer, it was not the perfect time. However, I will say that if I had waited for the perfect time to leave my job and pursue my passion, it would have never come. There will always be an excuse—or even a valid reason. My advice is to wait for the right time rather than the perfect time.



Anything new requires time and patience to learn and navigate. The more time you have, the better your navigation. That’s especially true when you become a freelancer. The first month, I was extremely hard on myself because I had expected my time to instantly be filled with new clients and writing gigs. Instead, I was met with a lot of lonely afternoons on the couch. In the early stage, don’t be afraid to contact someone who’s a seasoned freelancer to get some pointers and words of wisdom. Invite them out for coffee and soak up all of the information you can. I guarantee that it will be the most valuable cup of coffee you ever have.


One thing I learned fairly quickly was how slowly invoices get paid. Always be upfront with your services and payment arrangements, and always have a contract. The contract doesn’t have to be the size of a college textbook, but make sure it includes your job responsibilities, your pay rate, deadlines, and any late payment fees (always a good idea). I learned that even with a contract, your client will push the “how long can I wait until I’m forced to pay” button. In this case, kindly send them an email stating the agreement and your late payments fees.


You never know how much money you need until you need it — especially as a freelancer. This truth was something I had to address and figure out quickly after missing the due date on several bills. As an entrepreneur, the money shuffle is unavoidable, but having a budget will help you in the long run.


The most common (and hurtful) mistake new freelancers make is to wait until they leave their job to officially begin their freelance business; this trap is a bad idea. Start now. While still working my 9-5, I came in 30 minutes early to finish writing assignments and style orders; I dedicated my evenings after work to do even more. I encourage anyone who can balance working a 9-5 with their passion to do both until you outgrow your job and you can no longer juggle. Start setting time aside, even if only 20 minutes a day, to work on your craft. You’ll be surprised by how smoothly the transition goes when you get a head start.   

I took the leap and survived. Some call it luck, but I like to think it was God’s plan. Word to Drake. The struggle is definitely real, but your purpose is realer. I hope you enjoyed that coffee; now go write your story.

WorkTony Logan