Walking away from a 9-to-5 job with a steady paycheck and health benefits to start your own business isn’t easy. To help you to take the plunge, we’re introducing a new monthly editorial series The Case for Quitting where we ask self-employed women all about how they successfully struck out on their own, from how they balanced their side-hustle with their full-time job to how much money they saved before handing in their two-week notice. This month we chatted with copywriter Rachel Leslie who quit her job as a digital copywriter at Nike to start her own storytelling studio. Read on as she shares how she broke into the field, when she knew it was time to leave her corporate job, and why she recommends saving up a six-month safety net before quitting.

What was your major in college and what did you want to do when you graduated? 

I majored in journalism and minored in business administration. When I graduated, I wanted to become an arts and culture journalist. Think, William Miller in “Almost Famous” going on tour with bands, covering the latest shows and album drops. 

What did you actually do after you graduated? What types of jobs did you apply to and what industry were you looking to break into?

I moved to Santa Barabara, California, for an unpaid internship at an indie newspaper called, The Santa Barbara Independent, where I was their arts and culture intern. In addition to my internship, I worked at a local restaurant as a host to pay the bills. 

Before getting that internship, I applied to any and all jobs and internships in writing for news publications, media organizations, and the list goes on. I was determined to write for a newspaper or magazine where they had a substantial section in music, events, art, and feature stories. It was a tough time to be applying for jobs in print journalism in 2013 as there were whispers that journalism was dying, print specifically. 

How did you get into copywriting?

When my internship came to a close in Santa Barbara, I started looking for other opportunities to continue writing. I contributed to the newspaper and got paid for my articles, but it was nowhere near enough money to get by, so I began exploring marketing and PR agencies. 

I was hired as a paid intern at a PR and marketing agency working with nonprofits and social impact businesses in the Santa Barbara area. I found this type of work interesting because I could still exercise my journalistic skills in a way, but on behalf of our clients. Plus, I could get behind what they were marketing as they were often community events, organic products, and so on.

My experience at that agency was my first foray into copywriting, and the rest is history; from booking a one-way ticket to Vietnam and working as a freelance writer for magazines and copywriting for five-star luxury hotels and businesses to moving back to the U.S. to join the agency world here in Portland, Oregon, and most recently, working at Nike as a digital copywriter.

What was it like balancing your full-time job with your side-hustle? Do you recommend starting a side-hustle while you have a full-time job? 

For as long as I can remember, I was always doing something on the side of my full-time job. Whether it was freelance writing for the indie newspaper on the side of my full-time internship or taking on copywriting projects here and there alongside agency work. It can be time-consuming if you let it. Like giving up your weekends and evenings to stay on top of your side hustle, but if the passion is there and you want to see if it’ll work, you’ll do it.

I recommend starting a side hustle while you have a full-time job because it gives you a chance to experiment with what works and what doesn’t as you work out the kinks and see if it’s really something you want to pursue full-time without the added stress of making rent.

How did you know when it was time to make the transition from side-hustle to full-time? What was your strategy for making the transition?

Starting my own business was something I always knew I would do. It was just a matter of when. I found this desire grew stronger and stronger to a point where I knew if I didn’t try now, I’d always regret it.

I was in two group coaching programs while in my 9-5 that gave me the tools, education, and resources to hone in on my copywriting service to expand that into a full-blown business. In addition to those programs, I began building up my client roster while marketing my copywriting and storytelling services to others online and through word of mouth. I wanted to prove that there was a demand for my expertise and services before saying goodbye to my 9-5. After juggling both for over a year, my business grew to a point where the time I was working in my 9-5 actually took away precious time from growing my business.

Another big part of this strategy was focusing on repositioning my mindset for entrepreneurship. Accepting and being open to the challenges, learnings, and failures that may come along the way while embracing them and keeping pressing forward is crucial to running a successful business. I’d have to say that this was (and still is!) one of the most challenging tasks in starting your own business. There’s a great deal of fear that comes with saying goodbye to what we’re taught to consider safe and secure (i.e., a stable salary, benefits, etc.). But once I realized that I’m in control of what happens and that I can do anything I set my mind to, that made the decision easy.

How did you prepare for the transition before quitting your full-time job? What, if anything, do you wish you’d done differently?

I spoke to my husband, who’s been my biggest supporter throughout all of this. We set a date and made it official! That felt so amazing to have a fantastic support system to back me up and to put a date in place.

Since starting my business, I kept track of my business’ income and expenses to see how much I needed each month to survive, and I did the same for my personal finances. I also hired an accountant for my business right before I left my full-time job to help me manage everything and have someone on hand I could turn to for questions as I navigated this new chapter. This helped put things in perspective for me as to what I needed not just to survive but to thrive in my day-to-day, as I had done before with a secure paycheck.

I also utilized my network of mentors and coaches during this pivotal time. As you can imagine, lots of what-ifs, thoughts, and fears came up in making this transition, and they were crucial in helping me get through this rollercoaster of emotions.

Lastly, I continued to market myself, show up and serve my online community every day. I had a few ongoing client projects in the works and a few lined up for the following month, so I knew I had some guaranteed income coming in for at least a few months after quitting my full-time job.

Were you worried about money? What advice can you share for people who are worried about leaving a steady paycheck to start a new career? 

Of course. As I was making the transition, I had many fears and worries about money, like, What if I don’t get any more clients after leaving my job? What if I don’t make any money next month? What if I fail? 

That is where that mindset work came into play again! I had to focus on rewiring my scarcity mindset to one of abundance and assurance. Instead of focusing on the what-ifs, I began writing affirmations and mantras like, “Clients come to me with ease,” and “What I focus on grows” and so on.

Journaling also helped me work through these fears and feelings about money. By asking myself, what do I need to feel safe and secure and what do those words mean to me, I was able to address these thoughts. 

On the more technical side, proving that my service was in demand before leaving my 9-5 and signing clients for future projects helped alleviate those worries about no money coming in. 

Did you save up first or did you just jump in headfirst?

I had a six-month safety net in place before I quit my job. This reassured me that if I didn’t make any money in my business, I had six months of savings in place to keep me going. So what I did was calculate my existing expenses to understand how much money I needed to make each month to pay my mortgage, bills and get by each month. 

What's the most important thing you have learned from making a big change in your career life?

I’ve learned that I’m in control of what I want to do in my life and in what makes me happy. And that there’s no point in waiting for something to tell you what to do next. It’s up to you. When I was making the transition from my corporate job to building my own business, I kept waiting for a sign. For something or someone to tell me, “Rachel, it’s go-time!” But I kept waiting, waiting and waiting and that sign never came. I realized that I just needed to take the leap and do it because there would never be a “perfect” time. 

It’s easy to celebrate the wins, but how do you handle failure or when something hasn’t worked out for you?

I treat it as an opportunity to learn and grow. As an entrepreneur, I’ve realized that things don’t always work out as planned, and that’s okay. When something doesn’t work out, I try to understand why and where I could have done better so that when I’m faced with a similar situation, I know how to approach it and hopefully, there’s a different outcome. 

What’s the biggest mistake you’ve made and learned from along the way?

When I first started, I created too many copywriting services. I quickly realized I was trying to do too many things at once. I overcommitted and under-delivered and I wasn’t able to produce top-quality services. I realized I could better serve my ideal client by focusing on what they specifically need and how my one or two niche services could best serve them.

When you look back and reflect on your previous career do you have any regrets or are you still really happy with your decision?

Every step of my career has prepared me to do what I’m doing today. I’m immensely grateful for the opportunities I’ve had and the people I’ve met along the way because it’s all shaped my values, beliefs, and my vision for the future of my studio.

Going after what you deserve in life takes confidence and guts. Does confidence come naturally to you or did you have to learn it? What advice can you share for women on cultivating confidence and going after their dreams? 

Funnily enough, I have a fraternal twin sister, and she’s definitely the more confident and outgoing one! So no, confidence did not come naturally to me. It took me a while to learn it and to embrace it.

One aspect that helped me gain confidence was surrounding myself with other leaders, mentors, and coaches who embodied the confidence I wanted for myself. Being around these people lit something inside of me that I could tap into and infuse in my own business. I also journaled (a lot!). A helpful exercise that helped in embracing my CEO mindset and imposter syndrome was writing out all of my accomplishments onto a piece of paper. It helped me realize that I was a skilled entrepreneur and that there was no reason why I couldn’t do this. I still go back and look at that list when I’m having an off day. 

What is the #1 career or money book you always recommend and why?

I love” You Are a Badass At Making Money” by Jen Sincero—especially the audible version! This book is raw, real, and eye-opening as to what is genuinely possible not just in your career but in your life. It gave me a whole new perspective into the power of your mindset and money and how the two can be truly life-changing.

What advice can you share for someone who is thinking about leaving their current gig to pursue their side-hustle or passion?

As my former employer’s tagline says… Just do it. Give it a try! And do your due diligence beforehand. First, determine if there’s a demand for your product or service; then, rally a community of mentors and friends you can lean on for support and get your finances in order so you can understand not just what you need to live, but to thrive, too (because if brunch with the girls makes you happy that should be factored in, too).

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