People often ask me, “What’s the hardest part about freelancing?”
Ok, no one really ever asks. But if they did, I’d tell them unequivocally:
Self promotion.
Since I started my freelance and entrepreneur journey back in 2019, I’ve dreaded promoting myself.
I’ve tried every trick in the book to avoid it, but ultimately, there is no way around it when you are your brand.
In all that stumbling and fumbling, however, I discovered some strategies that made self promotion way less cringey.
I can’t say I enjoy it now, but I don’t dread it either. I am at peace with it as a necessary part of the job. If I want to maintain all the other benefits of the digital nomad lifestyle, it’s a small price to pay.
Something else happened when I made peace with self promotion. My business started growing. Each year, as I’ve found ways to promote my brand that don’t make me cringe, more business has come my way.
If you grit your teeth or break out into sweats when you think about promoting yourself, this article is for you.
I’m going to break down the psychology and stigmas around self promotion, then show you how I shifted my mindset and my marketing tactics to make self promotion way easier on my soul.
What is self promotion? (and why are we so weird about it?)
Self promotion is marketing yourself, your skills, or your business to others.
You have probably already practiced self promotion without even realizing it. If you’ve ever gone for a job interview, auditioned for a play, submitted to a competition, applied to college or a secondary school program, ran for student government—all of these require self promotion in some form or another.
In a more formal definition, self promotion is practiced by the self-employed. People who launched their own company, freelancers like yours truly, or folks whose names are synonymous with their brands use self promotion to reach new audiences and increase sales.
Self promotion encompasses virtually any marketing tactic you might undertake, from updating your LinkedIn profile to building an elevator pitch.
Your website, your social media pages, your newsletters, podcast appearances—all of these activities can fall under the umbrella of self promotion.
If you want some examples of self promotion, allow me to be meta for a moment and promote my own self promotion.
You can see how I promote myself on my primary marketing channels:
- My LinkedIn channel where I post a few times a week
- My website, the “home base” of my self promotion
- My newsletter, where my subscribers get the full brunt of my self promotion
See? That wasn’t so bad. I’m promoting myself right here in this article, but I’m doing it in a way that adds something of value. A lot more on that later.
For now, let’s take a closer look at why self promotion feels so icky.
Why self promotion is so hard
If you feel discomfort whenever you think about promoting yourself, you’re in good company. In fact, I would wager that the majority of people find it challenging if not impossible.
There’s a good reason for this. Society teaches us the value of humility. We learn early on that being cocky or braggadocious is irritating, and we are encouraged to reject those personality traits.
Women in particular are encouraged to practice humility, which explains in part why women are more likely to rate their own self-promotion abilities lower than men.
Self promotion flies in the face of this societal message. It requires us to talk openly about our skills, abilities, and successes—and that can feel a heck of a lot like bragging.
You don’t need to look far to find examples of self promotion that crosses the line into arrogance. (There are Reddit subs dedicated to them.) For many, the idea of coming off as a braggart is enough to stop them from self promoting at all.
On top of this, we live in a world where we’re bombarded with advertising at all times, from all angles. Once you open a browser or app, you’re guaranteed to see advertisements. Your inbox is likely filled with people trying to pitch you services you never asked for.
If you’re like me, the idea of adding your voice to the noise can make you sick to your stomach. That’s what prevented me from starting my mailing list for years—I knew I hated getting too many emails, so I assumed people would hate getting them from me.
All of this ties into the concept of imposter syndrome. It is easy to convince yourself that you have nothing worthwhile to add to the conversation, and being self promotional when you “know nothing” basically makes you a fraud.
I’m not saying any of this is true, mind you. I just know that’s how I felt for a long time, and from the many freelancers I talk to as part of my job, I know it’s a pretty universal feeling.
So, how do we overcome it? Here’s what I’ve found works.
Self-promotion strategies without the ick
After years of cringing every time I had to promote myself, I finally found some approaches that work. They’re not perfect—nothing about self promotion ever is—but they’ve helped me grow my business without feeling like I need to take a shower afterward.
The authenticity paradox (and how to deal with it)
Some people will argue with me on this, but I still believe it to be true: You cannot be both self promotional and 100% authentic.
The very act of promoting yourself means you’re selecting what to share and what to hide. You’re crafting a narrative, choosing your best angles, highlighting your wins, and playing down your setbacks. That’s not authentic.
But something else to consider: How often are you actually 100% authentic?
Do you act differently when you’re having dinner with your parents, versus when you’re alone with your bestie, versus when you’re talking to your boss?
Which one of those is the 100% authentic version? It’s not that black and white.
Being 100% authentic is something we reserve for our closest friends and family. So forget the idea of being 100% authentic when you promote yourself, because it’s not going to happen.
That doesn’t mean all self promotion is fake, however.
Instead of chasing perfect authenticity, focus on aligning your self promotion with your actual values and ethics. This creates what I think of as “sustainable authenticity”—the kind you can maintain long-term without feeling gross about it.
For example, one of my core business principles is radical transparency with my SEO clients. I am very clear about the work I’m doing, because it aligns with my ethics of providing honest, valuable information.
Of course, I’m not the only one who values honest and transparent info. My customers do too, especially because there are many other folks in my industry who prefer smoke and mirrors.
Promoting my transparency feels good, because I can stand behind it with my whole heart. It just so happens that it also appeals to my customer base.
And there you have it—my ethics and my self promotion are aligned. As a result, I don’t feel icky talking about transparency, and my authenticity shines through, netting me better results from my efforts.
To try this out, I suggest writing down a list of your non-negotiables. What practices make you roll your eyes when you see other people doing them? What values do you refuse to compromise on? This list will be your guideposts for authentic self promotion.
Lead with value, not sales
Want to know my golden rule for self promotion? Be helpful first, promotional second.
If you start every post bragging about your wins or making a hard pitch for your products and services, you’re going to alienate your audience and make yourself feel super gross.
Instead, focus on sharing something that’s actually helpful to your audience. Think of something they can use, even if it’s just something small. Giving away free and helpful advice feels a lot better than pushing sales.
Here’s an example of what I mean. In the LinkedIn post below, I share a step-by-step process for finding and updating content that needs refreshing for 2025. The post provides real value—anyone could take these steps and implement them right away.
The bulk of the post is pure education. I’m teaching people exactly how to solve a problem, with clear steps they can follow. This positions me as an expert while actually helping people.
Only at the very end do I include a small promotional pitch about my upcoming training and one-on-one services. By that point, I’ve earned the right to promote because I’ve already provided value.
This approach works because it flips the traditional self-promotion model on its head. Instead of leading with “hire me,” you lead with “here’s something useful.” The promotion becomes a natural extension of being helpful.
Do this often enough, and people start to see you as “that helpful person who always has good tips.” This makes them want to follow you, subscribe to you, and eventually, hire you.
Own your channels (and let the unfollowers go)
Here’s something that helped shift my mindset: Your marketing channels belong to you. Your website, your social media accounts, your newsletter—these are your spaces to promote yourself.
When someone visits your website or follows you on social media, they’re choosing to engage with your content. And just as easily, they can choose to leave.
It may feel uncomfortable when you see someone has unsubscribed, but trust me, it’s actually a good thing. Every unfollow or unsubscribe is someone self-selecting out of your audience. They’re making room for people who actually want to hear what you have to say, and you no longer have to worry about annoying or offending them with your self promotion.
Once I accepted this concept, self promotion got a lot easier. I stopped worrying so much about “bothering” people with my content. After all, they can always hit that unsubscribe button if they’re not interested.
This mindset shift is particularly powerful for your newsletter. I used to agonize over sending emails because I hate getting too many myself. But then I realized—everyone on my list actively chose to be there. As long as I’m providing value (see above), I’ve earned the right to show up in their inbox.
For more tips on developing and owning your marketing channels and personal brand, check out these articles:
Building genuine connections (aka networking without selling)
Self promotion gets awkward fast when you’re putting yourself out there to people who don’t know you—and whom you don’t know either. It feels unnatural, like walking up to a stranger at a party and listing off your accomplishments.
But isn’t that what networking is?
No, but that’s why a lot of people dread networking. They imagine walking up to strangers, shaking their hands, and making a pitch. In reality, most networking events involve conversations about weekend plans, the quality of the food being served, and the best places for bubble tea as much as they involve making sales pitches.
If you walk into a networking event and refuse to talk about anything but your sales, you’ll be remembered by everyone—and not for the right reasons.
That’s why I always recommend warming up your leads first, whether they’re in person or online. Take time to build genuine connections with people who might need your services down the line.
Building genuine connections means taking real interest in other people and their work. Subscribe to their newsletter. Read and comment on their social posts. Check out their website and the content they’re creating.
Better yet, meet them in person at networking events. Have a real conversation about their business, their challenges, their goals. Practice active listening. Don’t try to sell them anything—just connect as humans first.
When you build these genuine connections, something interesting happens. These people become part of your network naturally. And when they need services like yours, you’re already there as someone they know and trust.
If you want more guidance on how to do this, check out this 20-minute mini-course I made to help people with this:
This approach takes more time than traditional cold outreach, but it feels infinitely better. Plus, it works. People are much more likely to work with someone they’ve already connected with than a stranger sliding into their DMs with a sales pitch.
And once again, I’m going to be meta-metareferential and point out that this video is an example of the helpful self promotion I use—and if you watch it, you’ll find self promotion examples tucked throughout like easter eggs.
If possible, delegate the ickiest tasks
I’m a professional writer, currently writing a memoir.
So why is it that when I have to write about myself for my own website, I contract the worst case of writer’s block?
For a long time, I used to beat myself up about this. I would tell myself I was a fraud, because what kind of copywriter couldn’t write his own copy?
Then I talked to a bunch of other copywriters, more experienced than me, and found out all of them felt the same way. And most of them hired other people to do their own copywriting, so they could focus on their clients.
I have had to learn this lesson a few times over the years.
I spent hours and hours agonizing over my website, before I realized it would be more cost-effective just to pay a talented freelance web designer to make it look as good as I wanted it to look.
I made a total mess of my email marketing streams before I gave in and hired someone to untangle what I’d done and make them work like a well-oiled machine.
There were a few reasons why I didn’t reach out for help sooner. Some of it was financial—though typically, what I spent in time and anguish was more expensive in the long run. But more than that, it was pride—it was a fear of looking helpless by asking for help.
The truth is, behind every successful freelancer and entrepreneur, you’re likely to find other talented freelancers and entrepreneurs who helped them get where they are.
They learned to outsource the parts of promotion that gave them the ick, and I recommend you do the same.
Self promotion isn’t going away anytime soon, but it doesn’t have to make you feel gross. Focus on being helpful, own your channels, and build genuine connections. Most importantly, align your promotional efforts with your values. When you do that, self promotion stops feeling like a necessary evil and starts feeling like a natural extension of who you are.
