The Freelance Leap: How I Transitioned from a 9 to 5 to a Successful Copywriting Career

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One of my favorite things about my work is the way it opens doors to talk with brilliant and ambitious individuals. But it’s rare that the individual I get to talk to is an old classmate, and one who I’ve admired for years at that. 

That’s what made the conversation that inspired this article so special. I had the chance to sit down with a brilliant professional I used to go to school with and chat with them about my experiences as a freelance copywriter. They picked my brain about what prepared me for this career, how I got started, the challenges I faced, and how I made it sustainable. Me being me, I asked for prep questions before our call and answered them in a Google Doc so they’d have something to refer back to, which you’ll find here in near-verbatim form.

How I Transitioned from a 9 to 5 to a Career in Freelancing

Q: What went into your decision to go into writing as a career?

A: Stubbornness. Just kidding (kind of). I’d always excelled in English and the process of essaying, but was asked repeatedly what I would do with an English degree. Would I teach? Would I write a book? It was always framed as an absurd option; something that couldn’t possibly be sustainable.

But when I got into UC Berkeley–a school known for its poor student mental health and unforgiving grading curves–I knew that I wanted to do what I loved, and love my classes. My studies in the English department stood in contrast to my roommates who were all CS or Pre Med out of obligation and miserable.

Although I didn’t have a post-grad career in mind, I knew that the synthesis of ideas, leveraging of research, ability to form strong argumentation, etc,  implicit to the English major would be cross-applicable to practically every other field. That confidence freed me up to enjoy my coursework and immerse myself in all kinds of studies, including medieval and Celtic material, which pushed me to develop a literacy in fascinating and complex ideas.

This instinct paid off, as a marketing internship in the tech industry turned into a full time job offer before I’d even received my diploma. It was the first stepping stone for me in identifying my career.

Q: When it comes to time you’ve spent on learning your craft in the past, how much would you say came from school, on-the-job learning, and self-directed learning?

A: Higher education was, of course, incredibly valuable. It honed my tenacity and resilience in a highly competitive environment and shaped my mastery of the craft of writing (although no writer ever is finished mastering their art). More than any internship or job, I think that my writing was most strengthened when I was paving my own way. I pursued opportunities contributing to a major lifestyle publication, took initiative in developing professional systems that would legitimize my business, and found opportunities to build my portfolio, even when I was working full-time in marketing.

Q: Did you have a mentor when you started out?

A: I can’t say that I had the privilege of having a copywriting mentor, although I wish I did. It would have saved me a lot of time in the learning curve! However, there were clients I had who were inspirational and formative. The few that stand out to me are ambitious, poised, kind, and sharp as tacks. They are interpersonal and charismatic; they strive for excellence. And they taught me so much about how to run a business. I owe them a debt of gratitude, not only for giving me work when I was starting but for believing in my work. 

Now that I work with internal branding agencies for corporate clients, I get to work alongside senior copywriters whose portfolios put stars in my eyes. (Seriously, they are so cool.) I learn a lot from collaborating with them and reading their copy– they’re living proof that environments of excellence help drive our success.

Q: How did you decide what to put in your portfolio? Is there anything that almost made the cut, but didn’t? Why?

A: It’s worth noting that I’ve always had a portfolio of some kind with a personalized domain name and an up-to-date showcase of my work. It’s changed so much over the years for the better. 

When I was first starting out, a lovely and supportive retainer client pointed out that my old portfolio made my service offerings unclear. In an attempt to encapsulate everything I had ever done, I was confusing potential clients and missing an opportunity to define myself. 

I took that feedback and decided that I would design my portfolio solely around the work that I hoped to do more of. Rather than completely omit anything that fell outside of those parameters, I included them in short blurbs, enabling me to show my breadth of experience while still presenting myself as a specialist. 

I also minimized the emphasis on my published articles. Although I enjoyed the process and am proud of them, I don’t find feature writing to be lucrative or consistent, nor is it the kind of work my ideal client would typically hire for.

Q: Was there any one factor that ultimately pushed you to make the jump from salaried work to freelancing?

A:  Although my post-grad job in Silicon Valley marketing was a great opportunity and introduction to the corporate world, it wasn’t a good long term fit for me. I realized I didn’t love tech start up culture, and that the most interesting thing about my work was everything that had to do with writing. 

I decided to start freelancing on the side, slowly but steadily building a portfolio of work and made an effort to find opportunities to practice content writing and copywriting in my corporate role. Eventually, I was consistently making enough from it to afford my basic expenses. I put in my notice, knowing freelancing could at least bridge me to a new salaried job that emphasized writing more. But here I am, still freelancing almost four years later, and don’t plan on stopping!

Q: What did the first month or two of freelancing look like?

A: If I’m being honest, it was more like the first six months, and maybe even the first year. I look at where I’m at today–my client list, my income– and I am amazed. I’ve received so many comments from former classmates and colleagues who think that my career happened overnight, but it couldn’t be further from the truth. People don’t see the sacrifice, the zero-income months, or the self doubt. It took me about 3 years of freelancing to get where I am, and I wouldn’t change a thing.

For the first couple of months, I was still working full time and submitting proposals on Upwork for $40 here or $50 there per project, just to dip my toes in and build a portfolio. As I built my confidence, I started looking for larger contracted projects.  I received my first monthly retainer that had set expectations (a number of blog posts, and some social media captions). That was $500 a month for a year, and within a couple of months of that, this person referred me to another person for a similar type of monthly retainer. I continued looking for work and then landed another more expensive retainer, PLUS a set flat fee for providing website copy for that brand strategist’s creative entrepreneur clients. That was my first experience whitelabeling my services within a brand studio.  

I was very careful with my finances and was definitely not initially glamorous or in line with high-achieving Bay Area ambition, but it paid off.

Q: Has freelance copywriting panned out the way you thought or hoped it would so far?

A: I don’t think anyone realizes how long it takes to get up and running. However, there were a few things that kept me motivated through the difficult seasons.

  • I had enough academic and professional experience to know I loved copywriting and content writing
  • I knew I wanted autonomy and flexibility in my hours and projects
  • I experienced first hand that I didn’t enjoy a 9 to 5 nor was it conducive to the kind of life I wanted to cultivate for myself
  • I knew that had the ambition to take on the risk that freelancing brings in exchange for the autonomy I was looking for
  • I had a lot of passion and drive to take ownership of my work and forge my own path

All in all, I’m really pleased with how things have worked out. I have the autonomy in my hours and work that I want. I also have the consistency and fair compensation from corporate clients that makes freelancing sustainable and fulfilling.

Q: Do you have any tips for someone who is looking to explore freelancing?

A: There are so many I can think of off the top of my head. But in a hustle culture where there is so much clamor for work, and candidates are often just proposals submitted to a job board, I think I have one:

Who you know is everything. Every success I’ve had in my career thus far is because I was connected with someone who either gave me work directly or recommended me to someone who would. You never know when something will pay off down the line, so focus on putting your best foot forward and investing in authentic professional relationships. [Author’s note: I have so much more to say about this that it will have to be another article; stay tuned.]

Interested in more insider advice about freelancing and copywriting? Read the blogs here. And if you’re looking to collaborate with a copywriter who will be an asset to your corporate or internal agency team, connect today or drop me a line.

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Hi, I'm Hannah

Copywriter, content writer, and enthusiastic ally of passionate professionals and creative entrepreneurs. 

Through strategy-driven storytelling, compelling creativity, and a commitment to representing brands with excellence, I help businesses build meaningful connections with their ideal clientele.

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