The Fine Line Between Self-Promotion and Bragging: A Freelancer’s Conundrum

Self-promotion is a task that I presume I need to do as a freelancer. When cycles of little to no work become the norm — sometimes, unfortunately, lasting for weeks on end — I have two options, as all freelancers do: wait for work to come to me or find ways to take on more assignments and projects. The first strategy (well, not really a strategy, more of a dim hope) is not reliable. It’s great when people reach out to me with writing projects, or I get a referral, but this doesn’t happy very often.

In general, when work dries up, I tend to rely on a few strategies: mostly apply for freelance jobs listed on remote/freelance job sites, reach out to old or existing clients if they have any assignments I could do, and self-promote. When it comes to self-promotion, this usually takes the form of trying to be active on Twitter and blogging more frequently.

But to be honest, I’ve got into the habit of self-promotion when I’m busy as well; again, trying to maintain an active presence on Twitter and in the blogosphere. I view self-promotion as a natural part of freelancing life, a way of mitigating the lulls of worklessness, as well as better my chances of getting work (and work I actually want to do) when I need it.

Self-promoting as a freelancer, while it sometimes feels fruitless, does pay off. Through sharing work and blog posts on Twitter, I’ve connected with people in industries I’m interested in, and gained lasting freelancing gigs. Self-promotion benefits networking, opens me to new opportunities, and gives me a sense of maintaining an online presence that I feel needs to be maintained.

So self-promotion is kind of second nature by now. But even though it’s habitual, it doesn’t always feel natural. Often it doesn’t. I was thinking recently about how it’s sometimes hard to distinguish between self-promotion and bragging. Do I need to self-promote as much as I do or do I just want to brag on social media about something that I want to make me appear a certain way (i.e. productive, intelligent, thoughtful, interesting, original)?

Maybe it’s impossible to self-promote, by definition, without ego involved; which isn’t necessarily a negative since some level of ego is needed to function in the world and in work specifically. Part of me, however, sees bragging as egoistic in a negative sense. (A relationship to a work-influenced ego can be positive and healthy so long as that relationship serves a positive aim and isn’t too clingy.)

I’m sceptical of bragging (including humble bragging) in myself and try to look out for it. Bragging is annoying, first of all (and humblebragging is actually more likely to make people dislike you than regular bragging, according to a study published in the Journal of Personality and Psychology).

Bragging might come off as pretentious and insincere, as an attempt to make yourself seem superior to others by constantly showing off your achievements. I find the urge to brag is also strongest when I feel less secure and self-confident. During times like these, bragging, whether online or in-person, might cause a temporary alleviation of these feelings, but similar to any quick fix, there is a danger that achievements and boasts become a crutch for feelings of inadequacy. And neither are reliable foundations for a stable, healthy self-image.

However, with self-promotion or sharing good news, it’s hard to know if I’m letting bragging tendencies creep in. When is sharing a piece of writing a form of self-promotion or excessive, ‘look at me’ kind of pride? When does sharing become self-indulgent oversharing?

Social media makes it especially attractive to brag since there are rewards (approvals) for it from potentially many people. And the fact that posting and online interactions lack the physical presence and cues of others makes bragging more likely and frequent, I think. In real-life situations, if we bragged as we do online, it would be easier to sense the social consequences.

As a freelancer, not wanting to be a social media braggart is tricky because some level of self-promotion is clearly useful. It is understandable to not self-promote, or self-promote very sparingly, if you’re humble and modest by nature and you find self-promoting just to be out of sync with your character, making you cringe and feel a pang of guilt or embarrassment whenever you do it.

At the same time, there’s nothing wrong or self-obsessed about regular self-promotion, including on social media. The relevant question here is not if you should self-promote as a freelancer but how. I don’t have any set recommendations for this, as this isn’t really an advice-giving post.

My own personal experience, nonetheless, is that I find self-promotion lacks the quality of bragging when my intention is to share something of (potential) value (to at least some people); and it has the quality of bragging, conversely, when my intention focuses on pride and the wish to impress others. I also find being brief and matter-of-factly helps to keep self-promotion from veering into the territory of bragging.

To self-promote as a freelancer can take some getting used to at the beginning. The next challenge is to then know the difference between promoting yourself and promoting an inflated ego in yourself and annoyance in others.

Originally published at https://www.samwoolfe.com on October 11, 2021.