Why self-promotion feels so uncomfortable — and how to get better at it

Apparently, there is such a thing as being too proud of yourself. Or at least, that’s what we’ve been taught to believe. We’re perfectly happy to commiserate over a bad day at work, complain about a difficult boss or confess that we’re just trying to figure life out. But tell everyone about something we did really well? Suddenly, we’re worried about looking arrogant, braggy or like we’re trying too hard.

When Elizabeth Tan, 33, got a promotion, she found herself caught in this exact conundrum. Despite being excited about it, she hesitated to update her network publicly, choosing to confide only in her closest friends.

“I was afraid of people questioning why I needed to update my Linkedin profile with the title change. I didn’t want people thinking that I was performative or fake,” the external communications manager at Prudential admits. She worries that celebrating her successes publicly might come across as boastful. So, she usually only mentions her achievements when asked – and even then, keeps it to a line or two.

Kaylie Kam, 29, manager of social media and communications at Singapore Kindness Movement, also admits that she’s always excited to celebrate even the smallest wins of the people around her, but when it comes to her own, her first thought is always: “It’s just part of my job. I’m just doing what I need to. It’s nothing.”

Case in point: In June, she was invited to be on the jury for The Drum Awards Festival, an international award festival to celebrate works in marketing and media. The organiser had created a social card for jurors to share on their social media platforms, but Kaylie has procrastinated doing so.

“I know that it’s something I should be proud of and celebrate, but there’s another part of me that goes ‘Is this really worth sharing?’ It feels like I’m making too much of it by sharing,” she says. Hesitating to talk about one’s achievements is a habit many women – like Kaylie and Elizabeth – can relate to, and one that can be difficult to shake.

Humility becomes second nature

So why does celebrating ourselves sometimes feel so... embarrassing? According to Annabelle Chow, founder and principal clinical psychologist at Annabelle Psychology, part of the answer may lie in the culture we were raised in, where humility is deeply valued.

“When someone praised us as children, the adults around us might have dismissed the compliment with ‘No lah, nothing special’, quickly changed the subject or pointed out what we could still improve,” she explains. “The intention might have been to keep us grounded. Over time, however, we may learn that accepting praise is conceited, or that acknowledging our strengths risks making other people uncomfortable.”

The discomfort may also stem from our innate fear of rejection as humans, according to human connection specialist Simone Heng. Achieving in a big way can make us feel like an outlier from our “tribe”, while the extra attention can inadvertently cause us to be socially rejected.

On a more personal level, imposter syndrome could deepen this discomfort, where people doubt their skills or success, adds Annabelle. This may cause them to attribute an achievement to luck and discount the effort behind it, worrying that they would not be able to repeat their success. Some might also be reluctant to celebrate too soon, fearing they might tempt fate or “jinx” what they have achieved.

Annabelle is quick to point out that this feeling isn’t exclusive to women. The difference is how we may experience and express this shame. Some men may feel pressured to appear confident and capable, disguising their discomfort as humility, rather than openly acknowledging that insecurity. Meanwhile, women may become self-conscious of being perceived as aggressive or unlikeable when they promote themselves.

The career double bind

At work, Annabelle says women can find themselves caught in a particularly tricky situation with this shame, where they’re expected to appear both humble and confident at the same time.

“Understandably, some women respond by minimising their contributions, giving all the credit to the team, or trusting that good work will simply speak for itself,” she says. Unfortunately, this does not always pan out well.

It’s also why Simone took the opposite approach when she was working at a radio station in Dubai, laying out her achievements and opportunities on social media, despite her bosses’ remarks about how frequently she posted. For her, making sure people knew about her work came from a “deep survival fear” of being able to provide for herself.

Your wins deserve to be seen

If women give in to this shame, however, we may hesitate to negotiate for the appropriate recognition or pursue an opportunity unless we meet nearly every requirement, Annabelle cautions. We might overwork to prove our value, support others at the expense of our own capacity, or struggle to maintain boundaries between work and personal life, resulting in exhaustion, resentment or burnout.

Narrow assumptions about how a leader should look or sound – for instance, being assertive, outspoken or commanding – make it harder for women to see themselves and be recognised by others as credible leaders, she adds.

The answer, then, may not be to shout every win from the rooftops, but to stop treating our achievements like something we need to hide. After all, there’s a difference between being boastful and simply giving yourself credit for a job well done.

The trick, according to Simone, is knowing how to celebrate your wins publicly while thinking: How is the information you share also going to serve the other person?

How to own your wins without the brag

Find people who make celebrating feel easy

Celebrating your wins also becomes a lot easier when you’re surrounded by people who make it feel safe to do so. Annabelle says that when recognition is given fairly and people can acknowledge their contributions without being mocked, resented or penalised, we’re more likely to develop a healthy relationship with success. For Elizabeth, that support comes from her close friends. “I am extremely grateful to my girlfriends, who constantly remind me that achievements should be celebrated, and we deserve credit for our efforts,” she says.

Share the journey, not just the win online

Talk about your achievements on social media more than in person, Simone suggests. But balance those success stories with other insights like what you’ve learnt from your experience, thought leadership pieces, tips and advice that would add value to the people hearing you.

For Kaylie, she couples her achievement announcements with details of the process of getting there and challenges she encountered – takeaways that might be useful to someone else. It’s also content that she finds more interesting to read.

Let the conversation come to you

In person, prioritise connecting with people to hear their stories first, Simone says. That makes it easier for them to ask you about yourself, before you jump in to tell them about what you’ve accomplished.

She adds: “That works a lot better because they’ve opened the opportunity to want to hear more about me. I think in person, that’s a much more elegant way to build long-term social capital.”