9 Marketers Who Successfully Transitioned to Full-Time Freelancing (Their Real Stories)

The transition from 9-to-5 employee to full-time freelancer can feel overwhelming. You've read the strategies, seen the success stories, but sometimes you need to hear from real people who actually made the leap.

That's why I reached out to 9 successful marketing freelancers and asked them one simple question: "At what point did you go all in on freelancing?"

Their answers revealed something fascinating: there's no single "right" way to make the transition. Some were fired, others moved countries, and a few just reached their breaking point with corporate life. But every single one of them is now making more money and living better than they did in their traditional jobs.

Here are their unfiltered stories – proof that the freelance transition isn't just possible, it's profitable.

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1. Steph Weaver - The Pandemic Plot Twist

"I went all in on my freelance business at the worst time possible -- at the height of the global pandemic in 2020. I had just been fired from a full-time job I loathed in November, 2019, and for good reason. I had mentally checked out. And that was the best thing that ever happened to me. I was on unemployment so I had some money coming in, and nobody was hiring full-time employees, so I poured all my efforts into freelancing.

I made a promise to myself that I would never, EVER work in a cubicle for a company I didn't respect again. I think being on lockdown during the pandemic gave a lot of people time to reflect and access their lives and goals. I took stock of what I wanted out of life, both personally, and professionally, and that was a career I loved and was passionate about.

It took about two years to get the ball rolling, but I am making 4x more money than I did working full-time, and I am the happiest and healthiest I have ever been. I'm even leaving for a two-month trip to Paris in three weeks because I have the freedom and flexibility to work from anywhere!"

Key Takeaway: Sometimes the worst thing that happens to you becomes the catalyst for the best thing. Steph's firing wasn't a failure – it was her liberation.

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2. Josiah Roche - The Strategic Agency Exit

"I made the move to full-time freelancing when my side work started bringing in more income than my agency salary. But it wasn't just about the money. It was also about having more control over the kind of work I wanted to do.

Clients started coming to me for strategy, not just execution. So that shift showed me I was on the right track.

Working at an agency taught me how to juggle multiple projects, manage client expectations, and stay organized under pressure. But it also showed me how much time gets wasted in bloated processes.

There were long meetings, endless revisions, and campaigns built more for internal approval than actual results. So I wanted to focus on the work that actually moved the needle. Things like increasing ROI, lowering CAC, and building funnels that convert.

Before I left, I had a few steady retainers, no major financial obligations, and more leads than I could realistically take on without burning out. So it wasn't a leap of faith. It was a calculated step.

Freelancing isn't easier. But it's more direct. You feel every win and every loss. And that clarity forces you to focus on what actually matters.

The tradeoff is that there's no safety net. No paid sick days. No IT team to fix your laptop. No one else to jump in when things go sideways.

But there's freedom in that too. You get to choose your clients, set your schedule, and define what success looks like for you.

If you're still in a job and not sure whether to go all in, that hesitation might be telling you something. Because once the upside of staying disappears and you've got enough steady demand to justify the risk, the decision becomes a lot more obvious."

Key Takeaway: The transition becomes obvious when your freelance income exceeds your salary and clients start seeking you for strategy, not just execution.

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3. Georgi Petrov - The Trust and Expertise Builder

"I decided to go all in on freelancing after working in an agency for several years. What pushed me was the realization that I had built a strong enough client base and skill set to sustain my own business. The turning point was when I reached a point where I was consistently earning more through freelance work than I did at the agency, but I was still working for someone else's goals and deadlines. The biggest sign for me was the flexibility I had when working with my clients and the ability to focus on projects that truly aligned with my expertise and passion. It wasn't easy to make the leap, but the trust I had built with my clients and the control over my time made the transition smoother. The biggest challenge in the beginning was managing the work-life balance, but it paid off as I became better at time management. If you have the right clients, skills, and a solid plan, going full-time freelancing can be a game-changer."

Key Takeaway: Success comes from building trust with clients and developing expertise that aligns with your passion, not just chasing any available work.

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4. Daniel Reparat Bort - The Local SEO Specialist

"I decided to go all in on freelancing when I realized the work I was doing on the side, not just creatively, but financially, was more fulfilling than my full-time remote agency job.

Even though I had the flexibility of working from home, I was still tied to someone else's schedule and priorities. I started picking up freelance SEO projects in my free time and quickly saw two things: first, I enjoyed the direct client relationships and ownership of results way more than being another cog in a remote team, and second, there was real demand for Local SEO, especially from agencies that didn't have in-house expertise.

The moment I knew it was time to go all in was when I had a few consistent clients and enough savings to give myself a runway. I wasn't replacing my full-time income yet, but the growth was steady, and more importantly, it felt like I was building something of my own.

The pro of going full-time freelance is being able to scale on your terms. The con is trading stability for uncertainty, at least in the beginning. But once I made the leap and launched Smarktek, I never looked back. Freelancing turned into a real business, it just took trusting the process and committing fully."

Key Takeaway: Specialization in a high-demand niche (Local SEO) combined with steady growth and savings created the perfect conditions for transition.

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5. Natalia Lavrenenko - The UGC Content Creator

"I went all in on freelancing after realizing I had more control and better income juggling UGC clients part-time than I did in traditional roles. I was creating Amazon videos and Instagram content during nights and weekends, and the demand kept growing. Once I hit the point where I had to turn down paid projects because of my day job, the decision made itself. Leaving gave me time to scale, test new formats, and work with brands I actually cared about.

Agency life taught me speed, deadlines, and how to manage feedback. But freelancing gave me the flexibility to build around my kids' schedules and focus on projects that matched my style. The trade-off? Less stability and no built-in team. But the upside—creative freedom and direct client relationships—was worth it. If your freelance work is consistently paying more than your day job, that's your green light."

Key Takeaway: When you start turning down paid freelance work because of your day job, it's time to reconsider your priorities.

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6. Luke Matthews - The "Burning Boats" Strategy

"I first started freelancing online in 2016 on Instagram. I was a micro-influencer in the sustainable fashion space. My partner at the time and I started taking pictures and writing blog posts about sustainable fashion brands giving back to artisans in the third world or helping the environment in some way.

I did this until 2020 part-time while I was working in construction.

In 2020 I moved to the UK and went all-on on freelancing because I gave up all my construction income in Canada when I moved.

There was no choice but to make digital marketing work as a full-time job. I'd already been working 7 to 8 months of the year and then traveling winters for a long time so to make the leap form that to just fully working remotely online wasn't too big of a jump.

I just needed to burn the boats, fully move abroad and give myself no easy out to make cash when I needed it.

It's been 5 years and I haven't looked back!"

Key Takeaway: Sometimes creating a situation where you have no choice but to succeed is the push you need – but Luke had 4 years of part-time experience first.

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7. Nick Lafferty - The All-In Mentality

"I ran a successful consulting business for over two years, earning nearly $1M in revenue during that period. I helped B2B SaaS companies generate sales pipeline from LinkedIn and Google Ads. I also wrote a 2,000+ subscriber newsletter helping freelancers navigate all the challenges involved in running your own business.

I think the only way to succeed as a freelancer is if you go all-in. I've seen too many people try and keep one foot in the full-time door by applying for jobs and interviewing at the same time they're trying to grow a freelance business. It really hurts their ability to advertise and grow their freelance biz because they're not all-in and they feel like they can't post openly about it on LinkedIn.

I think there's a big mental benefit to the all-in mentality, it forces you to just get it done."

Key Takeaway: Half-committed freelancers get half-committed results. The all-in mentality forces you to make it work.

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8. Lauren Christiansen - The Strategic Narrative Builder

I was freelancing on the side for a long time, first while working a full-time gig and then while I was job searching. Even though I had interviews and even a job offer, I pulled the plug completely on interviewing to go all-in on my own business because there were compromises on the table for every salaried role that weren't there for my freelance work. In reflecting on what I wanted most out of my next role, I realized that the work attributes I most valued -- freedom to learn and explore, the responsibility of managing my own schedule, and the ability to pursue growth and projects that I found most interesting -- were simply more available as a freelancer.

To truly get those from freelancing, I knew I had to commit. Having done both part- and full-time freelancing, the biggest pro to full-time is that you can take more control of your narrative, marketing and opportunities. At the end of the day, it's hard to position yourself both as a full-time employee and as a reliable freelancer. You can't be as strategic about marketing your business, and clients questioning your commitment means you lose out on opportunities. Your employer may also be wary of letting you openly share your opinions and experience online if they don't align with your company. Because of that, I felt passive as a dual freelancer/salaried role worker. I was waiting for things to come to me rather than building my voice, business and marketing engine."

Key Takeaway: You can't build a strong freelance brand while hedging your bets with traditional employment. Full commitment enables strategic marketing and better opportunities."

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9. Gavin Tanner - The Simple Math Approach

"I knew I needed to quit my full-time job and go all-in on freelance when I was working every weeknight and every Saturday on my freelance work. Not worth it! I basically did the math and said "if I'm making $100k working ~15 hours a week on freelance work, then if I quit I feel like I could almost triple that". So I did, and then some :)"

Key Takeaway: Sometimes the decision comes down to simple math. If you're making great money in limited hours, imagine what you could do with full-time focus.

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The Common Threads

After analyzing these 9 stories, several patterns emerge:

1. Specialization Wins

Every successful freelancer became known for something specific – Local SEO, UGC content, B2B SaaS marketing, or strategic consulting. Generalists struggle; specialists thrive.

2. Proof Before Leap

None of them quit without evidence that people would pay for their services. They all had clients, income, or clear demand before making the transition.

3. All-In Mentality

The most successful freelancers committed fully. Those who kept one foot in traditional employment struggled to build momentum.

4. Timing Varies

There's no perfect time to make the switch. Some were fired, others reached income milestones, and a few just got fed up. The key is recognizing when the conditions are right for you.

5. Freedom Over Security

Every single freelancer mentioned freedom – freedom to choose clients, set schedules, work on interesting projects, and build something of their own.

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Your Next Steps

If these stories inspired you to consider freelancing full time, I encourage you to read my 3-Step Framework to Transition from a 9-to-5 Job to Full-Time Freelance Marketing.

Here's a summary:

1. Identify your specialization – What are you genuinely better at than 80% of marketers?
2. Start building proof – Take on small projects while employed to validate demand
3. Calculate your numbers – What income do you need to replace? How many clients would that require?
4. Build your safety net – Save enough to give yourself runway during the transition
5. Commit fully – When you're ready, go all-in. Half-measures produce half-results.

The freelance life isn't for everyone, but for those willing to build something of their own, the rewards – financial and personal – can be extraordinary.

Which story resonated most with you? What's holding you back from making your own transition?

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