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How I went from project-based work to $8.5K+ in monthly recurring revenue

Table of ContentsUpdated May 18, 2015

For the first year and a half of my adventure into freelancing, I was primarily a web designer.

If someone needed a website, I would gladly design it for them. Sometimes I helped with some basic marketing work as well, but in general I positioned myself and was perceived as a web designer.

Eventually, this started wearing on me and I wanted something more.

I wanted to be strategic.

I wanted to make a bigger impact.

One day I decided that I was going to become a freelance marketing director, and the rest is history. Here’s how I did it:

Making the change

At first the idea of becoming a freelance marketing director seemed odd. I was afraid of wearing the hat because I had become so used to exchanging money for something tangible (a website).

The idea of charging for strategy and consulting seemed odd to me: I was afraid that people wouldn’t believe I was good enough to be a marketing director.

Doubt filled my mind, but eventually I made the jump.

In the course of one week, I went from positioning myself as a Squarespace Web Designer to a Freelance Marketing Director.

  • I changed my website.
  • I changed my LinkedIn.
  • I changed my email signature.

And just like that, I was calling myself a marketing director.

Talking the talk

Changing online profiles was easy, but the next challenge was actually explaining to people what I was doing.

I didn’t even have a single marketing client yet, so everything I was saying I could do was basically theory.

Here’s the polished version of what came out after quite a few pitches that totally flopped:

“I work with companies as their freelance marketing director. Basically when you can’t afford to hire someone full time, you can put me on retainer and I will help with strategy and execution of your marketing efforts. By having multiple clients it allows me to take things I learn elsewhere and apply it to helping market and grow your business.”

Each time I pitched my new position to someone, I began to believe it more. I began to believe that I could rise to the role and the occasion.

Walking the walk

The amazing thing is that it started to actually work.

Within the first month I had closed two marketing clients on freelance retainer.

My first client was a developer recruitment company called I had known these guys for a long time, but positioning myself as a marketing director turned them into clients from acquaintances.

The second client was a Squarespace web design business called Digify. This also was someone I had known for years. The CEO, David, constantly came to me for advice on building up a web design business, but I had never given him a framework to really hire me. This marketing director role was the tipping point for that relationship.

Then, within the next month I had closed two more.

As a project based web designer, I averaged between $8k–11k per month in project-based sales. While I was making good income, I was spending countless hours each month writing proposals and taking sales calls.

In two months as a freelance marketing director, I had secured $8,500 in recurring revenue.

  • I didn’t have to take any more sales calls.
  • I didn’t have to write any more proposals.

All of that clutter of jumping from project to project dropped from my life.

I was now able to focus on helping a few select clients grow their business. The work was more fulfilling and the stability of recurring revenue helped bring peace to my previously chaotic life.

Evolving your business

It’s not an easy thing to evolve your business. When you have identified yourself one way for a long time, it’s easy to get trapped in that mindset and believe you can’t do anything else.

The truth is that you can.

If you want to evolve your career or transition to something new, you can.

Reposition yourself in all of your marketing materials, and over time people will begin to catch on.

The act of transitioning isn’t hard, it just takes the guts to do it.

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Written by Jake Jorgovan

Contributor at

Jake Jorgovan is the founder of Content Allies, a B2B podcast production agency. He's been featured by global publications including Entrepreneur, Inc, and many more for his ability to start and scale a service-based business successfully.

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  1. Jake Jorgovan says:

    I just got an email about this post with some follow up questions. I thought i would post the questions and answers here for anyone else who is curious.

    How do you price the offer? Is it monthly payment that includes everything? Strategy consulting and developing the content for the strategies?

    I am transparent with the companies and figure out how much they can pay me. And then we work together under the agreement that if I can make them more money, I get paid more. Generally this is on a monthly retainer

    The retainer is rarely tied to any clear deliverable. It’s tied to the value that I am able to create.

    One of my clients i have been doing a lot for but the revenues have been stagnant. While I am helping them grow and investing a lot of time, I am realizing I have to fix more issues with the business as well to make revenue grow.

    I could get angry for not getting paid enough, but when my compensation is tied to their growth it keeps me grounded.

    How do you position your pricing versus hiring a full time employee?

    I tell them to think of me like an employee except I am not full time. I want them to think about me as a long term investment and not just paying me to get something out of me.

    One client I had to dropped because they couldn’t get into this mindset.

    I want to be part of their team and that is how I position myself and act.

    Do you keep them on a month to month basis and they can stop anytime they want?

    Yeah, it’s casual. There are no contracts or anything. They can stop whenever they want.

    The thing is the relationships with my clients are so tight that I don’t really need to worry about them walking.

    Have gone for a niche market?

    Yeah, in a way I am niching. My goal has been to align my clients with my personal brand at

    The alignment isn’t perfect right now but they are pretty close.

    1. Preston D Lee says:

      Thanks for adding the extra insight, Jake! Really top-notch.

  2. Dean Scholey says:

    Great article Jake, I am going through the same issue at the moment.
    My question is, has changing your title and the way you position yourself, change the actual services that you offer. Meaning are you still designing website, and doing graphic design. Have your service offering changed with your new market positioning? I have come to the realisation that when client hire me for branding or graphic design services. I end up helping them explore and develop their market positioning especially small businesses who only have time to work in the business not on it.

    1. Jake Jorgovan says:


      Yes, changing how I position myself has drastically changed the services I offer. It was an odd thing to start charging for consulting and strategy, as opposed to a clear deliverable like a website. But the positioning worked and soon people started hiring for my brain and not just what I made.

      Changing the way you frame yourself changes how people will interact with you.

      I hope this helps.


      1. Dean Scholey says:

        Yes I totally agree, Only recently have I started thinking about where my value lies with the client. I soon came to the conclusion that skills come cheap ‘5r’, but ideas, concepts and business acumen are where the value lies for the client.

        Reading your blog and website has inspired me to reposition myself.
        Thanks you and keep up the great work.

  3. Jerome Tanibata says:

    Great article, Jake! It’s always interesting see how someone can re-invent themselves as you have. As I read through your article, you make it sound easy but I’m sure there were a lot of challenges. That could probably be another whole article, but briefly, what were a couple of the biggest hurdles you had to overcome in order to get to where you are now?

    1. Jake Jorgovan says:

      Hmmm, the biggest hurdles would probably be in the mental shift to making this happen. I had a lot of imposter syndrome going on where I felt wierd to be charging.

      It was also a challenge to make the transition. When I started landing this recurring revenue clients, they wanted my full attention right away but I still had to close out project based work. At one point when I had my first two retainer clients on board, I still had about 5 web design projects open. It was a bit overwhelming and stressful. I just had to put my head down, crank out the websites and move beyond them.

      But now things are much better 🙂

      I hope this helps.


  4. Teja Yenamandra says:

    As CEO of, I can say that he’s worth every single penny. Proud to call him a friend and consultant.

    1. Jake Jorgovan says:

      Thanks a ton Teja. I appreciate that!

  5. Stanley Straughter says:

    Nice!! I’m curious as to how you were averaging between $8k–11k per month in project-based sales, I need that in my life right now… 🙂

    1. Jake Jorgovan says:


      I wish there was an easy answer but that amount of income came from doing a lot of stuff, and a lot of marketing.

      Here is a post explaining the various different ways I was going about getting clients:

      It also took learning how to charge right and attract the right types of clients.

      I explain more of it in my book The Creative’s Guide to Freelancing. You can download a free sample at

      Hopefully this helps!


      1. Stanley Straughter says:

        Thanks Jake, I will definitely look over the information and purchase the book when it’s released, thanks for the info!

  6. dsreyburn says:

    Food for thought. Good food at that. Thanks for sharing Jake.

  7. Amy McKinney says:

    Good article! I hadn’t thought much about repositioning myself, but I do find myself doing a lot more marketing strategy with my clients than what they originally hired me to do. When is your book releasing?

    1. Jake Jorgovan says:


      Thanks a ton. I probably could have done this a year ago but I just didn’t even think about it.

      The barrier to making this shift was completely mental and not in skill set or portfolio. If you want to make the change, just do it!

      The book is already released and you can buy a copy at Use the promo code gdb10 for a 10% discount.

      Thanks a ton Amy!


      1. “Website Expired”

        Did the freelance marketing fizzle out?