5 Stages of the Freelance Journey

I’m a full-time freelance web designer. I don’t have a boss. I get dressed (kinda) and drive to my leased office space every morning to work on projects I prospected, courted, and landed myself. 100% of my income is directly attributed to client work. My freelance journey, however, may not look exactly like yours.

Timing, personal circumstances, market trends, and even luck can influence the trajectory of your freelance journey. If we look at it from a general perspective, though, the steps along the way are fairly common across the board.

No matter where you are in your own journey, I thought it might be encouraging to visualize what could be ahead if you stay in the game and continue to grow.

1. The Hobbyist

Perhaps you took an Intro to HTML class or maybe you’re checking out a free trial on Squarespace. Regardless, something is clicking for you here. You’ve got the web design bug! It’s challenging but fun; frustrating but rewarding—you’re eager to learn more. At this early stage, it’s more important to sharpen your sword than monetize your talent. You have a lifetime to cash in on what you learn today. Enjoy the untethered innocence of your new hobby, my friend!

2. The Helper

After some time learning the basics of building a website, you will eventually (inevitably) find yourself being asked to help someone else with theirs. Client #1 may very well be an auntie, cousin or neighbor—and you aren’t likely to charge them much, if anything at all. That’s okay. This is still a priceless stage; to experience the dynamic of creating a project under the direction of someone else’s needs. You get to learn which of your new skills go the furthest and which ones are falling short. How valuable is that!? Of course I hope you’re able to snag some walkin’ around money here—but try to remember there is plenty of that in your very near future!

3. The Side Hustler

So you’ve launched a few websites and probably been asked to dip your toe in a handful of other creative services as well. Who knows, you may have put some bucks in your pocket while honing your digital craft. This stage is when things really start to take shape, though. A true side hustler maintains their day job while earning every dime they can on a freelance basis. Nights, weekends, lunch breaks, holidays—when your coworkers and friends are relaxing, you’re raking it in. Their paycheck is a black & white, matter of fact, unwavering absolute. Yours is merely a piece of the financial pie now. No longer do you have to wait for grandma’s $5 birthday check to earn extra income. Now, the sky’s the limit for your dreams. Freelance web design is making it all possible!

4. The Full-Time Freelancer

The cash you bring in from your side hustle is pretty cool… until it becomes really cool. Before you know it, you find yourself in a bit of a conundrum; is it time to jump ship on my J-O-B and go all-in on freelance?

Personally, my freelance workload was commonly too much to handle while holding another job. As you know, work leads to work—and I was working my tail off! I started asking myself what my tipping point was. Something had to give. Either slow down my side gig or quit my real gig. Luckily, my boss at the time made that decision for me.

I’ll be the first to admit this stage is a BIG, scary step up, but I haven’t looked back since. Never again will I work for another human being. I’m eternally grateful I had the foundation of clients and years of experience to make my transition a smooth one.

5. The Agency Owner

Although I placed this at the end of the rainbow as the final stage of the freelance journey, I myself am not certain I want to go there. You know I’m always game to debate the difference between a freelancer and an agency. For today’s purposes, I’m strictly talking about a big headquarters employing several people working on projects for major brands, tons of white boards, ping pong tables, cold brew on tap—the whole nine yards.

There is something exciting about the fantasy of having a bustling office filled with creative staff all working to further my company’s growth and success. However, I suspect some of that is pure ego. Is it practical? Is it necessary? I’ve already proven to myself that I can meet my own financial goals by being a solopreneur. Do I want to muddy the peaceful waters here? Maybe someday…

As you climb the rungs in your own freelance journey, take a moment to appreciate where you are and how far you’ve come. Most people have their paycheck and that’s it. You, on the other hand, have created a stream of supplemental income that can make your future happen faster. Whether you’re at stage 1 or 5, someone out there wishes they were where you are. Celebrate your success and always work toward the next step.