Why I Went (and Stay) Freelance

Before I get into why I am a freelancer today, I want to share a little background on how I arrived here. Over the last 10ish years I have worked for tech companies, big and small, in some kind of full-time marketing role. Most of the companies were B2B and most of them sold complex software that was always a little beyond my marketing brain’s comprehension.

I started my career as many eager Marketing undergraduate students do — I got an internship at a Boulder-based tech company as a field marketing intern. From there, the roles I took on evolved as the way we communicated and conducted business online evolved: things got digital.

My roles progressed from field events and conference sponsorships to running digital advertising campaigns, producing webinars, writing demand generating content, social media strategy, lead gen and nurturing, website messaging, sales enablement, and the list (of digital things) goes on.

I always felt fortunate and very grateful to have a “good,” secure job that provided me with health benefits, workplace safety, learning opportunities and development, the ability to try new things, and the chance to work with some really talented marketers and intelligent founders. But something was always missing…

The companies I worked for were not my babies, not my dreams. So ultimately the work I accomplished didn’t fully feel like mine to celebrate.

Most recently, prior to freelancing, I held my most senior role to date: Director of Demand Generation for a cool marketing software startup. I was super pumped to take on a leadership role, share all my demand gen experience and ideas with the team, and drive sales.

Then COVID hit. Oh! And did I mention this cool martech company primarily served large-scale, live events? Yep. A big chunk of the growing startup was laid off. After that, I saw two options for myself:

Either start applying to full-time positions like a mad woman, hope some cool company hires me and begin the whole full-time employee onboarding process again

OR, use this as an opportunity to start something new. Something of my very own. Go freelance baby!

Now that you have a feel of where I am coming from, here’s a little bit more info on why I went (and stay) freelance.

The opportunity to be consultative

When I think about the times that I was most lit up while working full-time, it was when I was sharing my learnings, tried and true best practices, providing a new way of solving a problem, or discussing all the new, cool tools I learned about at a conference. In this way, I really enjoyed acting as a consultant to my colleagues. Being of service in the form of a consultant gave me energy and motivation to keep doing a good job at work.

I find some much joy when I get to”act as a consultant” (or just do my actual job) with my clients. Because I am outside of the organization, I have the unique privilege of seeing my clients from a different perspective than they do. I can help them see through their blind spots and push them to try new approaches or uncover efficiencies. To me, being of service to my clients means communication and collaboration with every step.

Flex my muscles across multiple business types

During my time as a full-time employed marketer, I remember holding team brainstorming sessions that felt unsatisfying because the “ideas well” had run dry. It’s easy to get stuck in doing things the way the marketing team has always done things.

Working with multiple clients across different industries is beneficial for both my clients and my professional growth.

How this helps my clients: they get access to proven, successful strategies and campaign ideas. I grab what’s been a hit for one client in industry A and then repurpose and tailor it to another client in industry B. I partner with other awesome marketing and creative contractors that offer a diverse set of backgrounds and experiences (more to come about this later). The exchange of information and ideas I gather, by working with clients across business types, is really inspiring for me as a freelancer.

How this helps my professional development: I get to collaborate and learn from smart, passionate founders that have built their businesses from the ground up. I learn from both their successes and failures. Working across multiple industries pushes me to think creatively about my own freelance business.

Spread the love

This one is short and sweet. Winning and succeeding is really fun. By being a freelancer, I get to work with multiple clients and win multiple times! Some may call that really, really fun.

Helping clients accomplish success, no matter if it’s launching a brand new website or posting a Facebook ad, is one of the most gratifying parts of my job as a freelancer.


During my days as a full-timer, I occasionally had to work on projects or tasks that I did not fancy. Sometimes I had to swallow my pride to get the job done just because my boss asked me to.

As a freelancer, I consider myself lucky to now have a lot more choice in terms of the kind of work I take on. I recognize more choice in my work across:

  • Clients — I’m no longer locked into working for one type of company. I can now be choosey with the types of companies I work with (and the people who run them).
  • Projects — I do the work that I am hired to do and don’t have to worry about the rest.
  • Marketing Disciplines — As a seasoned digital marketer, I have dabbled in lots of facets of marketing. I am better at and enjoy some disciplines over others. I now get to lean into the skill sets I want to pursue (content creation) versus the ones I can do but don’t necessarily love (new software implementation).

Collaborate with other kickass marketers and creatives

As with many creative professions, it’s important for practitioners to keep their skills sharp and continuously learn. One great way to do this is collaborate with others in your field aka your marketing team.

This was actually one of the fears I had with going freelance — the lack of learning from others. Boy was I wrong!

I joined , a Collective of marketing talent from across the US and a Fractional CMO. I get to collaborate on client projects with executive-level marketers and crazy talented creatives on a daily basis. Working with other marketers and creatives from diverse personal and professional backgrounds helps me stay sharp and uncover new skill sets.

No more meaningless meetings

Ok, this reason may sound a little harsh but it’s true! Any former or current full-time employee can attest to the fact that they’ve sat through some meetings that were not a good use of their time. Am I right?

Sitting through meetings that didn’t pertain to what I was currently working on (at all) or didn’t provide an opportunity to share feedback and collaborate was one of my biggest pet peeves with working full-time. Especially during the time of COVID, people don’t want to be forced to sit in front of their computers for another hour just because it’s a recurring, weekly meeting. As a freelancer, I am only invited to meetings that I need to be a part of.


My fiancé is a crazy talented animator. Needless to say, the man works long hours. For the last six years of our relationship I have informed him a handful of times that I believe “I’m just not cut out to work a full-time job.” He never really understood what I meant and you might not either. So let me explain my reasoning.

It’s not that I’m afraid of hard work or don’t want to put in the necessary hours to complete a project. I simply think the 40 hour work week is B.S. Why is this structure, which was conceived 100 years ago, still widely adopted across businesses of all kinds? As individuals, we all have different energy levels at different points throughout the day. Some people are more creative in the evenings and task-oriented in the early mornings.

As a freelancer, I have a lot more control over my schedule. I work until the project is done and don’t feel pressure to stick around until 6pm because everyone is still working in the office. I strive to be as efficient as possible. More time = more freedom = more happiness!

Wrapping it up

This year, the world has seen a massive shift across many facets of our daily lives, including how we work. When COVID hit Los Angeles, I initially felt overwhelmed with not only figuring out my next career move but also figuring out how I can support others. I took a leap of faith into the freelance world, I trusted my gut and couldn’t be happier.

As a freelance marketer, I experience two clear wins:

  1. I get the opportunity to help clients make real impacts in the world
  2. I have grown professionally. I’ve been able to hone in on what I’m best at and refine my offerings. The more I grow professionally, the better-suited I am to serve my clients… it’s all connected!

If you’re a startup company looking to grow your business online, feel free to check out my digital marketing services here or you can drop me a line by getting in touch with me here .

Originally published at https://www.jackie-rebrovic.com on October 27, 2020.

Freelance digital marketer on a mission to help b2b startups grow. Based in beautiful Santa Monica, CA.