How I Went from Full-Time Employee to Freelancer
The career details you won't find on my LinkedIn profile
A year ago I quit my full-time corporate job. Since then, I’ve gotten a lot of questions about how exactly I transitioned from full-time to freelance. It’s a very fair question, and it’s important to acknowledge that while this journey looks different for everyone, the answer will almost always be: experience.
For me, that experience started in journalism and required a decade of lessons learned. And I wouldn’t change a thing. Because without all of the ups and downs, I wouldn’t have been in the position to (confidently) go freelance and ultimately achieve my career-long dream of being a CMO.
Whether you’re considering going freelance, or are, like me, just curious about career paths, this is what my professional experience has looked like over the last 10+ years.
Some Context: I went to college planning for a career in journalism or marketing or PR, nothing more specific than that. I majored in Communications knowing that it was my best bet for getting a job after graduation. I was also in school at a time when social media was still fairly new. None of my classes covered it and instead I was being taught the “Principles of Public Relations” by someone who had been retired for over 20 years… I often say now that my degree wasn’t useful for my professional life, but the jobs I had while pursuing that degree were invaluable.
It’s also important to remember that job titles are arbitrary and corporate hierarchies and politics play a major role in who gets promoted when, but that’s a post for another day.
Targum Publishing Company
Business Manager & Co-CEO, May 2014-May 2015
Managing Editor, Feb. 2013-Feb. 2014
My career started my sophomore year of college. I had a full-time job and an actual salary and I still maintain that nothing else throughout my four years of school prepared me for real life as well as my time with the Targum. I started working at The Daily Targum, the independent, then-daily printed, student newspaper at Rutgers University as a staff writer, then as an editorial assistant on the Opinions desk, before becoming Managing Editor, and for a time, acting Editor-in-Chief. I led an editorial staff of more than 100 people, created the paper’s staff social media policy, edited every article, covered breaking news stories, oversaw the website and social media accounts, and determined the layout of articles and ads within the paper. At the time, we printed and distributed 18,000 copies of the paper 5 days a week. I worked from 2pm-2am most days, staying in the office until the printer (an actual printing press 30 minutes away), called to confirm that the next day’s paper had finished printing.
And because I just couldn’t get enough, I spent my senior year as the Business Manager & Co-CEO of the publishing company that owned and operated the paper (it was required that a student hold this position). In addition to supporting the editorial side of the business, I led an additional team of ~20 people, some of whom were decades older than me, was responsible for a $1 million budget, oversaw all marketing, advertising, and PR campaigns, and was tasked with creating and implementing new revenue streams.
It was incredibly challenging work, and I loved every minute of it. It’s wild to think about the responsibilities, and frankly power, I had at the age of 20, but those few years were formative in so many ways.
University of Virginia
Social Media Associate, June 2015-May 2016
Because of the jobs I had throughout college I was lucky enough to get a job offer before I had even graduated. I had big dreams of working for a lifestyle brand, but I already had experience managing social accounts for higher education institutions—thanks to a few social media internships to fulfill credit requirements—which is how I ended up running the main social handles for UVA.
I have never been more depressed than the year I lived in Charlottesville. It was a combination of a lot of very human things, like living in a new town I didn’t like and where I knew no one, multiple breakups, the transition of post-grad, and the fact that I had yet to figure out how to really process any kind of change. But I also found myself so bored and unhappy at work. I spent each week in a cubicle, in an office building surrounded by nothing but other office buildings, and was making such a small salary that I spent my free time babysitting to make up the difference.
At the time, I hated this job, but looking back, it was one of the most important roles I’d ever have. It was at this job that I learned how to be the social media manager I ultimately became. I learned how to market a non-tangible product, how to actually use Google Analytics (one of the top 5 most important skills), how to develop a content strategy and plan for launching a new platform (I launched UVA’s official Snapchat account). I got to keep writing and led a few very fun campaigns.
stasher
Digital Media Coordinator, Aug. 2016-May 2017
You learn a lot when you’re in charge of all social and digital, including influencer partnerships and blog content, for two brands, have a budget of $0, and the company consists of only seven employees.
This job was 90% cautionary tale about how to spot red flags and how not to get taken advantage of, hence why I barely lasted a year. I won’t say anything more than that in writing, but this will always be the job that got me to San Francisco, and because of that, everything was worth it.
Chairish
Senior Social Media Manager, Jan. 2021-Apr. 2021
Social Media Manager, Mar. 2018-Jan. 2021
Social Media Coordinator, May 2017-Mar. 2018
For the most part, I loved my time at Chairish. I worked with some really wonderful people, got to be a manager, and had the chance to grow into a leadership position. I got a crash course in design and travelled to some of the country’s best and biggest flea markets. I created and curated endless amounts of content, got to keep writing, was in charge of the brand’s digital identity, saw the company through a rebrand and the acquisition of a competitor.
Ultimately, I hit a ceiling, which is the unfortunate reality for a lot of folks working in social media. I was chasing a “Director” title I was told I “didn’t qualify for” (despite managing a team) and I was so burnt out from being online (what felt like) 24/7 managing brand accounts and responding to nasty DMs from customers. I also realized that in order to be a VP of Marketing or CMO at any point, I still had so much to learn. I was very well-versed in all things organic media, but had virtually no hands-on experience in the paid side of marketing, especially when it came to performance marketing and media budgets.
Procter & Gamble, Native
Senior Manager, Digital Content & Integrated Marketing, Nov. 2023-May 2024
Senior Integrated Marketing Manager, Dec. 2022-Nov. 2023
Integrated Marketing Manager, June 2022-Dec. 2022
Influencer Marketing Manager, Apr. 2021-June 2022
For better or worse, my time at Procter & Gamble is, at least, 50% of the reason I was able to go freelance. As you can imagine when working for a global corporate conglomerate, I learned more than I ever could have imagined and was exposed to many invaluable facets of CPG marketing. And it certainly doesn’t hurt to have such a recognizable brand on your resume.
When I joined the team, I was in charge of a multi-million dollar influencer marketing budget and launched Native’s creator presence on TikTok. For the first time I got to work with agency partners and plan campaigns that supported both DTC and retail strategies. Getting a bit bored with managing the influencer program, I had begun taking on larger projects, like planning omnichannel campaigns for Earth Month and Pride, which at such a large scale, were often planned 6 months to a year in advance.
Before I joined P&G, I’m not sure I even knew what integrated marketing was. It wasn’t until Nicole Landberg joined the team, and so kindly pointed out that integrated marketing was the name for the extra work I was already doing, that I had any real understanding of what the future of my career could look like. Nicole was instrumental in helping me finally achieve the career growth I knew I was capable of and was ultimately looking for. For the first time, I felt like I had a leader who was genuinely in my corner. She ensured that I was constantly doing the work I needed to in order to move forward, allowing me to lead ecommerce projects and site merchandising, sales and promo strategies, and retention efforts across email and SMS, all while still overseeing the influencer program and managing a team.
If you’re wondering why I quit, this post pretty much sums it up.
Skylar Allen Consulting
Digital Brand Strategist & Marketing Consultant, June 2024-Present
It’s really important for me to mention that in addition to all of the above experience, one of the biggest things that allowed me to go freelance was that I finally felt some sense of financial security. Having worked in corporate positions for so long I was able to increase my salary year over year, which also helped me figure out what I could realistically charge for consulting. When I quit P&G I wanted to give myself time, first to rest and take care of myself, but also to build my business, rather than feel like I immediately had to be matching my corporate income.
Combining all of my skills and experience, I now work with a variety of DTC brands, supporting them in various ways across the marketing funnel. I support clients, like Binto, by stepping in as their Fractional CMO. I provide day-to-day guidance and help build integrated marketing strategies across paid and organic media channels. I help improve customer journeys and acquisition, hire and resource marketing teams, craft brand storytelling, and provide qualitative and quantitative analysis. Freelancing has opened so many doors for me, both personally and professionally, and I have zero plans to go back to a full-time role.
I could talk about all of this for hours, but for now, I’ll stop there. If you ever have questions about your career journey or want to pick my brain about any of my experience, feel free to leave a comment below, book a 1:1 session, or email me at hello@skylarallen.co.
Thanks for reading Room to Grow! You can follow along on Instagram, connect with me on LinkedIn, or shop my favorites. If you’re interested in partnering with me or Room to Grow, you can email hello@skylarallen.co or fill out the form on my website.
Thank you for sharing your career story. I loved reading it and being a part of your journey. That college photo is priceless!!