Tom OMalley Podcast Host

A Freelance Love Letter

Episode 1

In this debut episode of MMMW, I’m discussing what freelance means to me—and what it can do for YOU. I’ve been at this for over 15 years and can’t wait to share my story. If you want to make extra money building websites, my love letter to freelancing will get you hyped for what’s next! Let my journey from free work to 5-figure deals be your inspiration. Use my lessons-learned as a shortcut to success in your own creative side hustle!

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Links from the Episode


TOM O’MALLEY: Hey there, fellow freelancers. You’re listening to Tom with Making Money Making Websites and today I’m discussing what freelance means to me—and what it can do for YOU. I’ve been at this for over 15 years and can’t wait to share my story. Let’s get it going!


Welcome to triple-M W, y’all; a brand new podcast helping YOU create real supplemental income on YOUR terms. When it comes to freelance web design, I have plenty of experience, tons of advice (and lots of feelings). I thought it would be fitting for our first episode to dive into WHY I’ve stuck with my creative side hustle for as long as I have—and why I believe anyone with a computer and a PULSE should do the same…

Ok, first off, the barrier to entry is quite low here. Let’s be honest. Fact is, you do not have to be a web design wizard to get started. There, I said it. You don’t need a fancy degree or specialized training. As long as you know more about it than the clients who hire you, there is money to be made. No matter where you are on the learning curve, there is a business looking for your help. Now granted, you will hone your skills and refine your talent over time. You’ll get better with every new website you launch – and can increase your rates accordingly. I will be the first to admit I’m not even that great at web design (I wish I was) – yet I’ve somehow managed to turn this very accessible skill into a life-changing income stream for myself and my family.

You’re probably thinking, “if it’s so easy to become a freelance web designer, why doesn’t everyone do it?” Good point! I think they should! Get this: competition is irrelevant here! There’s PLENTY of work to go around. Every business needs a website. The pandemic proved that in spades. When the world was stuck inside, those who rose to the occasion and got creative online survived and thrived. The internet isn’t going anywhere and we are the architects making it all possible.

So maybe for some context, especially being my first episode and all, a bit about how I got in the freelance game. I was raised in a totally normal, lower-middle class family. My dad owned a couple restaurants but it was a rather unforgiving town for independent dining establishments. I blame / credit him for my entrepreneurial spirit. When I was really young, I showed some potential for drawing but never pursued it outside of art class. I suppose I had a creative flare but cared much more about skateboarding and video games at the time. I started working super young – like 14. Like the day it was legal for me to get a paycheck (maybe even before). I was a dishwasher at a golf course. Pretty brutal gig. Minimum wage, obviously. Not the healthiest work environment overall. Looking back, that must be what shaped my disdain for full-time employment. The scent of burnt pasta sauce and industrial-grade soap still triggers me to this day.

Toward the end of high school, something mildly exciting happened… My friends and I were watching a VHS called CKY for the 300th time. For those of you unfamiliar, these videos were 2 hours of skateboarding and mischievous antics by the dudes who later became “Jackass” on MTV. I noticed they included an email address in the credits so I reached out and offered to make them a website. Why? Cus I’m weird. To my surprise, they said YES! Now all that was left to do was learn how to make my first website! There’s obviously tons more to unpack with this story but let’s move ahead.

My parents did the best they could helping out with college tuition – but I was still buried in student loans and always short on spending money. There were times my meal plan ran out before the end of the month and I became a raccoon mooching off the cafeteria trays of my friends until the account reset. It’s always interesting to see the inventions born from desperation. I don’t know why but I decided to put what little graphic design experience I had to work and offer banner ad designs on eBay. Yes eBay! Mind you, this is before freelance marketplaces like Upwork and Fiverr. I was a dorm room trailblazer! I think I charged maybe $12 per banner and got a handful of orders each week – a lotta repeat business too. Hey, it was better than any of the campus jobs! More importantly, it was a first taste of using my creative skillset to change my financial picture.

After graduation, I moved to New York City—and this is where my freelance journey really starts to take shape. You see, I landed a pretty sweet job at a non-profit theater in midtown. In fact, it was so sweet, I ended up staying there for 10 years. Nice boss, cool coworkers, good location, manageable workload. Everything was ideal… except the pay. The salary was… pathetic. Definitely not enough to support life in Manhattan – that’s for sure. Most of the staff lived upstate, in other boroughs, or the outskirts of New Jersey to make it work. Not me. I didn’t move to NYC to commute from a different state. So I set out to bring in extra income through my side hustle of designing websites—and that’s exactly what I did. 9am to 5pm belonged to my employer and the rest was for me to make the best of. There were, of course, ups and downs – feasts and famine – but above all, it was proof that I could supplement my day job with freelance income and live the life I wanted (in Manhattan).

It didn’t happen overnight. In the beginning, I think I was charging something like $300 for a full website build. A few hundred bucks a month soon turned into a couple thousand. Over time, the money became more steady and substantial—in the neighborhood of $60-80,000 each year. As I sit here today, I just filed last year’s taxes on nearly $200,000 in freelance revenue alone.

So here we are – 15 years later, starting MMMW—a virtual love letter to freelance. Why? Not because maintaining a side-gig is a ton of fun or because I’m filthy rich as a result. But because it has afforded me a lifestyle on my own terms. THIS is what I was made for.

The benefits of freelance web design look different for each individual person, but I believe three common pillars make it all worthwhile in the end:

First, there’s Freedom. This is a big one for me. The feeling of being tethered or tied down professionally makes my skin itchy. With a regular job, you are expected to be in certain chairs at certain times. What kinda life is that? Freelance offers independence – the freedom to work wherever you want, whenever you want, with whomever you want, on whatever you want. Your work/life balance is in your hands. Even more so if you take the leap to full-time like I did recently.

Next is Finance. For me, freelance means having a day job that makes me happy while bringing in the money of one that wouldn’t. It’s also a financial insurance policy. What if you lose your full-time job? Hey, I did! Luckily, I had a thriving side hustle to catch my fall. Virtually all financial experts recommend diversifying your income streams and investments. Well, freelance is your chance! When we talk about the money side of web design, I always come back to this: it makes your future happen faster. Everyone has different financial goals. Some look forward to a cushy retirement while others just want to drive the new Tesla. No judgment here. Whether freelance pads your vacation fund or fills your shoe closet, it brings you closer to your dream – beyond what your fixed paycheck may otherwise afford.

Last but perhaps most important is Fulfillment. It’s all too common to find ourselves in 9 to 5 jobs that pay the bills but deflate our soul. Freelance web design is a much needed creative outlet – one that comes with a sense of pride and accomplishment in mastering a lucrative craft. Speaking of, how many of you don’t feel as though you’re paid enough for the value you bring to your employer? Well, in the world of freelance, YOU determine your own worth—not some stuffy board of directors. This is also your opportunity to scratch the entrepreneurial itch that keeps you from fully immersing yourself in a standard career path. Sometimes, a little side hustle provides the personal fulfillment and professional worth we’ve been searching for all along. Let’s not discount the good feels that come along with making an impact for other small businesses and cool brands. In many ways, you’re changing lives—while improving your own.

Alright, friends, I just threw a whole bunch at you in a short time. Before we wrap up here, let’s recap our Mind-Blown Moments:

  1. Getting started in web design is way easier than you think. You can always learn more (and charge more) as you go.
  2. Freelance offers the freedom to work on your own terms and achieve a healthy work/life balance.
  3. Relying solely on a bi-weekly paycheck and meager annual raises puts your future goals in the distance. Generating supplemental income brings them closer.
  4. Don’t be a drone if it’s not in your DNA. You can be a company man during the day and find personal (and professional) fulfillment with your freelance side gig on nights and weekends.

Now instead of promoting a sponsor for today’s episode, I would much rather encourage you to visit MMMW.CO right away and join my mailing list. It’s on every page – you can’t miss it. Many of my most lucid thoughts and valuable tidbits are sent via email. Totally free, tons of value, and never too often. You will not regret it! Go to MMMW.CO and subscribe today.

Thanks SO much for listening. Episode one over and done! Let me say, this podcast has been a dream of mine for some time and I’m excited for everything we have in store for you. Follow along for some epic rants about the in’s and out’s of freelance web design as well as interviews with real people who are killing it on both the business and creative side of things. For notes and extras of today’s episode, head on over to Until next week, fellow freelancers!


About the Podcast

Embrace the freelance life and make your future happen faster with expert insights and deep-dive interviews about the business side of web design.

Meet Your Host

Tom O’Malley is a successful freelance web designer based in Charleston, SC. In nearly two decades of building websites, Tom has proudly served clients big and small across dozens of industries—earning over $1 million with his creative side hustle.

Making Money Making Websites

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