Is your marketing problem a mindset issue or a systems problem?
Twenty years into freelancing, I still don’t have marketing completely figured out (will anyone ever have it fully figured out? I doubt it.). I’ve gone through stretches where reaching out to potential clients felt so daunting that I’d find almost anything else to do instead; the fear of being ignored or turned down was enough to keep me from trying.
And I’ve gone through other stretches where I felt confident and ready, but when the time came to write something for myself — an email, a post, a connection request — the words refused to come. I found myself scrolling through other posts and reading about how well everyone else was doing, rather than marketing myself.
Both of those struggles are real, and if you’ve experienced either one, you’re not alone. Believe me, I’ve been there. But they’re also different problems — one a mindset issue and one an action issue — that call for different solutions.
What helped me work through the fear of putting myself out there isn’t the same as what helped me finally build some consistency. That’s why it’s important to identify what’s holding you back before you try to force your way to a solution (which almost never works, if I’m being honest).
How to tell if it’s a mindset issue
A mindset block usually isn’t obvious at first. You might do a ton of prep to start marketing yourself: updating your profile, perfecting your website, researching companies you want to work with. But you never go further than that. You tell yourself you’ll pitch clients once your portfolio is updated, once you have more clips, once you feel more confident about your rates. But even when you satisfy those conditions, you add more conditions. The goalposts keep moving.
I do this too. I'll set up a webinar and then barely mention it until it's almost too late for people to sign up, telling myself I'd be bothering them. Somewhere underneath that is a fear that no one will show up — and by not promoting it, I get to avoid finding out. If people don’t show up, it’s because I didn’t market it, not because they weren’t interested. Raise your hand if that feels uncomfortably familiar.
Some questions worth sitting with (pay close attention to the last two):
Do you find yourself dreading marketing tasks in a way you don't dread the client work itself — the writing, the editing, the work your freelance business provides?
When you imagine sending a cold pitch or posting about your services, does it bring up feelings of embarrassment or fear of being judged?
Do you downplay your experience when talking to potential clients, even when you know you have relevant experience?
When someone says “no” or ignores your message, do you take it personally or assume the problem is you?
When you see other freelancers promoting their work or sharing their wins, is your first reaction self-doubt rather than inspiration?
Do you find yourself waiting to feel "ready" before reaching out to clients?
Is there a version of yourself — more experienced, more polished, more established — who you're waiting to become before you market yourself seriously?
Have you ever talked yourself out of sending a pitch, email, or connection request because you assumed the answer would be no before you even tried?
Those reactions point to something deeper than a missing strategy. Fear of rejection, imposter syndrome, discomfort with self-promotion; these are real and common, and you need to acknowledge them and figure out how to move through them or they will become self-fulfilling prophecies.
If it’s a mindset issue
The most important thing you can do is separate your sense of self-worth from the outcome of any individual marketing effort. Just because something doesn’t turn out the best-case scenario doesn’t mean you’re a failure. It’s possible the client had a full roster, or they needed a specialist in a different area, or they got busy and forgot, or the timing was off.
You won’t always know why, and that’s okay. What matters is that you keep trying.
I’ve found it helpful to reframe marketing into something a bit less emotionally loaded. For many freelancers, “marketing” carries uncomfortable baggage. It sounds pushy, salesy, or at odds with the kind of thoughtful, craft-focused work they got into freelancing to do. If it feels that way for you, try replacing “marketing” in your head with something more neutral: “creating opportunities,” “business development,” or “potential client outreach.” None of those phrases change what you’re doing, but they might make it feel less overwhelming to get started, and that might be all you need to get unstuck.
If your fear of judgment (or rejection or failure) runs deep, it’s worth examining where it comes from. Journalling, talking to a therapist or coach, or even just having honest conversations with other freelancers can help surface beliefs you didn’t know you were carrying. A lot of us absorbed messages early on about money, ambition, or visibility that don’t serve us now. Noticing them is the first step to loosening their grip.
One practical move: start smaller than you think you need to. If sending a cold pitch feels paralyzing, don’t start there.
Comment thoughtfully on posts by people in your target industry.
Follow your ideal clients on LinkedIn before you send a connection request.
Tell one person in your network what kind of work you’re looking for.
Send a follow-up message to a past client.
Ask for a testimonial from someone who you know loved your work.
Then build up to something more uncomfortable.
And always remember, the biggest threat to your business isn’t someone saying “no.” It’s not having enough clients to keep your business going because you haven’t told anyone you exist.
How to tell if it’s an action problem
An action problem looks different. You feel reasonably confident about your work and your value, but your marketing is inconsistent or, honestly, nonexistent. You know what you should be doing. You’ve read the advice. You’re not particularly afraid of putting yourself out there. You’re just not doing it. The time comes to market yourself and you’re too tired or too busy or just not feeling it today.
Ask yourself:
Do you have a clear sense of who your ideal clients are and how to reach them?
Do you find yourself procrastinating on marketing because “there are just too many decisions to make”?
When you do market yourself, does it tend to produce results but you do it too sporadically to build momentum?
When you do have time to market yourself, do you spend most of it figuring out what to do rather than actually doing it?
Do you tend to market yourself intensively when work dries up, then stop completely once your pipeline fills back up?
Have you ever had a stretch of consistent marketing that produced good results, but still couldn't sustain it long-term?
Do you have a general sense of what your marketing should look like but struggle to sit down and actually do it on any given day because there’s something else you’d rather be doing?
Is marketing always the first thing to fall off your plate when client work gets busy?
I know for me, when I get busy I immediately stop marketing. It’s the first thing that goes when my brain feels overwhelmed. It’s also the first thing to go if I’m cranky, tired, hungry, cranky, disheartened or down about freelancing, distracted, rushed, happy, cranky, or anything other than 100% committed to marketing.
If that sounds familiar, the issue probably isn’t your mindset. It’s your habits and systems. Marketing without a routine is easy to skip and relying on motivation is about as helpful as relying on magic to win you that lottery.
If it’s an action problem
Motivation is unreliable; it shows up when things are going well and disappears when you’re underwater with client work, exhausted, or disheartened during a slow period. In other words, we’re often the most motivated only when all conditions are perfect. But as soon as there’s a grain of sand in the works, our motivation disappears.
A system runs regardless of how you feel on a given Tuesday. That’s why having specific rules “I always market on this day at this time,” or “If X happens, I always respond with Y” is so helpful. It’s not about whether you feel like it, it’s about following your set guidelines.
Start by deciding how much time you’re willing to dedicate to marketing each week, and block it on your calendar like a client commitment. Even two or three focused hours can make a real difference if they happen consistently. The goal isn’t to do everything; it’s to do something on a regular schedule.
From there, narrow your focus. Freelancers with action problems often stall because their marketing to-do list is enormous and undefined. Pick one or two channels that make sense for your niche and go deep on those rather than spreading yourself thin. If your ideal clients hang out on LinkedIn, spend your marketing hours there. If referrals have been your best source of work historically, invest that time in nurturing relationships with past clients and colleagues.
If you’ve been freelancing a while, look at where your activities have had the most success and build on those.
It also helps to reduce the friction involved in each task.
If pitching feels like a production, build a pitch template you can customize quickly.
If posting on social media takes forever because you’re starting from scratch each time, keep a running list of ideas so you’re never staring at a blank screen.
If the whole process feels like it takes forever, break it down into steps and devote one day of each week to each step. At the end of the week, you complete the cycle and start over again at the beginning of the next week.
The less friction you face, the more likely you are to take action.
Finally, track what you’re doing. Not obsessively — a simple spreadsheet or even a notes file works fine. But having a record of pitches sent, posts published, and conversations started makes your marketing feel real and cumulative rather than like shouting into a void. It also shows you, over time, what’s working.
Webinar: Is Your Marketing Problem a Mindset Issue or a Systems Problem (or both)?
If you read this article and found yourself nodding along to either section (or both, if you’re like me) you’re not alone. II’ve let fear of rejection talk me out of pitches I should have sent, and I’ve had plenty of stretches where I felt confident but still couldn’t seem to market myself consistently. There’s no magic cure for either one, but there are ways to manage them well enough that outreach becomes something you can do regularly, even if it never feels completely comfortable.
In this one-hour session, we’ll go deeper into both the mindset and action sides of the marketing struggle — what’s really driving them, and the specific strategies I’ve used to work through both. You’ll leave with a clearer sense of which problem you’re dealing with and some practical tools to start tackling it.
Thursday, March 26 | 11:00 am Pacific | 1 hour
Free for paid Happy Freelancing subscribers — just reply to this email to register. Everyone else is welcome for $24.00 CAD. Register here
I have research, I have lists, spreadsheets but actually selling myself…🤷🏻♀️
As a marketing consultant the last thing I often want to do is market myself!