Being a digital marketing contractor is like tending a garden where every plant needs different care - some thrive with daily attention, others need space to grow, and occasionally you have to know which weeds to pull before they take over. After 15 years as an independent contractor,, I've learned how to help each client flourish while keeping my own business healthy and growing.
Let me be upfront about something first: everyone develops their own way of working. For instance, I've found I need actual breakfast in the morning - something with carbs because, let's face it, your brain runs on glucose, and mine definitely needs that fresh fuel to tackle complex marketing strategies… or those pesky wild HubSpot workflows. I also make it a point to get dressed in “work clothes” each day - no living in workout clothes or PJs for this gal… even though I’d really like to most of the time. But those are my quirks, and there are plenty more that we’ll save for a different blog. Your perfect routine might look completely different.
So instead of prescribing a one-size-fits-all approach, let's focus on what I believe are some universal truths about successful freelancing. These are the lessons that have consistently proven valuable, regardless of your personal style or specific niche in the digital marketing world.
The Real Deal: What 15 Years of Freelancing Actually Taught Me
Let's cut to the chase - you're probably juggling multiple clients right now, each convinced their project is the only one that matters (spoiler alert: they all matter). As someone who's evolved from general marketing strategy to becoming a full-stack digital implementation magicianne, I've got some truth bombs to drop.
1. Tools and Processes: Your Digital Marketing Safety Net
Remember when we used to track everything in Excel spreadsheets and sticky notes and note books? NIGHTMARE. Thank goodness those days are behind us. Today's arsenal of tools like Read.ai (which I’m still a bit on the fence about - I WANT it to work for more process, but still not quite sure), Monday project management, and HubSpot's CRM suite makes life infinitely easier. But here's the kicker - it's not just about having fancy tools; it's about creating bulletproof SOPs.
Your clients need to know exactly what to expect from you. When will you respond to their emails? How quickly can they expect deliverables? Setting these expectations isn't just professional courtesy - it's your sanity insurance policy.
2. Client Selection: Not Every Fish in the Sea is Your Dinner
Here's a revolutionary idea: you don't have to work with everyone who wants to hire you. I learned this lesson the hard way, but it was worth its weight in gold. My personal rule is - if someone pisses me off in our first 30 minute intro call, trust your gut, and politely decline. This isn't going to magically transform into a beautiful partnership - your work life isn't an enemies to lovers rom-com (looking at you Sarah J Maas).
3. Time and Value: The Eternal Puzzle
Pricing your services is about as straightforward as nailing jello to a wall. But here's what I've learned: start with your minimum viable rate - what you absolutely need to keep the lights on… the Kindle Unlimited subscription up, the Netflix rolling. Then consider your "happy number" - the rate that makes you excited to tackle even the most challenging projects.
Dia Bondi's "Ask Like an Auctioneer" approach changed my entire perspective on pricing. She teaches that negotiation isn't just about pushing for a higher dollar amount - it's about identifying multiple ways to create value. For example, when I'm discussing a new project, I might negotiate for:
Permission to use the project as a case study
Opportunities to co-author content that showcases our work
Performance bonuses for exceeding goals
Flexible project scope to better align with my expertise
These "increments of value" often end up being just as valuable as a higher hourly rate. They help build my business's reputation, expand my network, and create opportunities for future growth. Win, win, win.
4. Never Stop Learning (Because Marketing Never Stops Evolving)
I'm a regular at INBOUND, and you'll find me at weekly HubSpot Admin HUGs (HubSpot User Groups), soaking up knowledge like a sponge. Jay Schwedelson's "Do This Not That" podcast is my constant companion. In 2024, I even applied to speak at INBOUND about freelance HubSpot consulting. They didn't accept my talk, but putting myself out there? That's growth, baby.
5. Work ON Your Business, Not Just IN It
This is my current challenge, and if you're nodding along, you're not alone. We're all guilty of being the cobbler with barefoot children - spending so much time optimizing other people's marketing that we neglect our own. This blog post? It's me practicing what I preach. How am I doing?
6. Build Your Circle of Trust
Here's something they don't tell you when you start freelancing, or maybe they do, and I just missed that day of class: having trusted people who can review your work and challenge your thinking is absolutely crucial. Some of these relationships come naturally - like my partner Shane, who's become an invaluable sounding board (the perks being married and living together!). But others need to be cultivated over time.
Take Cecilia with Focused Momentum, for example. What started as a client relationship 10 years ago has evolved into both a lasting professional partnership and a friendship. She's exactly the kind of person you want in your corner - someone who won't hesitate to point out when you've forgotten to brand your HubSpot Annual Maintenance calendar (true story from just a few weeks ago - talk about a face-palm moment - who forgets to put their logo on their marketing ebook?!)
But here's the real secret: you need to be willing to be that person for others too. Recently, my friend Julie, a new freelance bookkeeper, was drowning in sticky notes and forgotten tasks… there are SO many deadlines in bookkeeping, gross. So what did we do? We turned a post-yoga brunch into a productive work session, setting up a Monday project management board to organize her client work. Sometimes the best support you can offer is simply sharing what you've learned along the way.
The Bottom Line
After 15 years in this wild ride of digital marketing contracting, I've learned that success isn't just about mastering the latest tools or staying ahead of algorithm changes. It's about building sustainable systems, choosing the right partners, knowing your worth, and never stopping your professional evolution. Think of it as a marathon, not a sprint - pack your water bottle, wear comfortable shoes, and don't forget to enjoy the view along the way.
Your journey might look different than mine, but these fundamentals will serve you well. In the ever-changing landscape of digital marketing, the only constant is the need to adapt, learn, and occasionally laugh at ourselves along the way. After all, we're not just building businesses - we're crafting stories that matter, and we're doing it better together.
Anne Fellini Bromley is the founder of Anneomaly Digital, an award-winning HubSpot agency, where she's spent over 15 years helping businesses transform their digital marketing operations. As a certified HubSpot expert and Most Promising HubSpot Solutions Provider (CIO Review), she's built her career on becoming a trusted extension of her clients' teams, growing from general marketing strategy to full-stack digital implementation. When she's not crafting marketing magic, Anne can be found at her home in the greater Denver area with her husband, and business partner, Shane and their menagerie of pets - three dogs and two cats, who serve as her unofficial "meeting management" team.