It’s ok to be vulnerable

Ian Yip
5 min readDec 15, 2019

This is a multi-part series sharing the lessons I’ve learned on my entrepreneurial journey thus far. Here is the sixth lesson. Read the intro, first, second, third, fourth, and fifth lessons, if you haven’t already done so.

From where I’m currently sitting, running a startup makes the challenges I used to face in my various corporate roles seem about as stressful as sitting by the pool of a five-star resort worried about getting sunburnt.

Photo by Chris Greenhow on Unsplash

I don’t mean to make this about stresses in the corporate versus startup world. There are definitely challenges in the corporate world that we’ve all had to deal with. And if you’re currently struggling with them, your battle is just as valid as anyone else’s, including mine.

My reality right now however, is this…

Deadlines. Sales. Revenue. Renewals. Profitability. Conversion rates. Churn. Quality metrics. Customer satisfaction. Utilisation percentages. These are but a few of the measures of success I’ve had to deliver on in my previous roles.

If I missed a few of them in the corporate world, company performance suffered slightly, as did my performance rating (only sometimes, if I’m being honest). But it wasn’t a huge deal in the grand scheme of things. Miss just one or two as a startup however, and it’s lights out.

The duck

One of the most overly-used-and-abused analogies is the one about how ducks always look calm on the surface, but are actually paddling furiously underwater. But it’s appropriate in this instance, so I’m going to use it.

Photo by Joe Cox on Unsplash

I’ve had people say to me over the past few months:

“We’re concerned that you’re too calm, because it makes it seem like you don’t care enough.”

“There are some concerns over the fact you’re too polished, and that you’re not ‘start-uppy’ enough.”

While it’s tempting for me to tell anyone who says these things to go F*&$ themselves, I can see their point.

Typically, I’d prefer to be measured and calm, even when I’m not feeling that way. But what’s the alternative? Should I run around like Taz?

Source: GIPHY — Looney Tunes Attack GIF By Looney Tunes World Of Mayhem

Turns out, what’s been lacking in some interactions I’ve had, is a sense of vulnerability.

I’ve been conditioned over the years to always look confident, have everything together, and never let anything phase me. Some of this is cultural, some of it personality, and the rest is simply the business environment.

These are qualities I’m proud of. But when used in the absence of vulnerability, you risk coming across as inauthentic.

Authenticity is critical in most aspects of life. But it is particularly important in business and in leadership; any business person or leader who lacks it, ends up sounding like a bad advertisement whenever they open their mouth.

One key thing I’ve learned is that in a startup, people expect a large dose of vulnerability because every startup is inherently vulnerable. If the team doesn’t align with this expectation, a little bit of that authenticity is lost.

So, by all means, be the graceful and calm duck. But don’t forget to remind people:

“Hey, I’m paddlin’ really hard over here, and sometimes I feel like I’m sinking.”

Mental is everything

In business, everything, it seems, is everything. You can pretty much take any important trait of an individual or a company, and someone (or some article) will tell you how it’s “everything” or how it’s the number one key to your success.

But without your mental faculties, all the other “everything” items you obsess about, mean nothing. Beyond the benefit that injecting a dose of vulnerability has on maintaining authenticity (as outlined in the previous section), lies the need to acknowledge vulnerability for more personal reasons.

There is no shortage of literature talking about the mental health of professionals. And it’s clear that the constant need to “put on a brave face” is unhealthy, particularly as a startup founder.

Photo by Sydney Sims on Unsplash

While it’s true that to be successful in business, one needs grit, determination, and resilience, we forget that we don’t always need to look gritty, determined, and resilient.

The incessant pressure to look and be a certain way is unhealthy. I don’t have all the answers. But I do know that I need to be dealing with it instead of pretending everything is awesome. It’s not.

Catharsis

I don’t sleep much anymore. Prior to my current startup journey, I needed to be woken up by my alarm every morning. Now, I’m wide awake well before it sounds because I find it difficult to shut my mind off.

Photo by Ales Krivec on Unsplash

An ex-colleague I was having coffee with the other week observed that I’m very different now; he could see in my eyes that my mind was constantly thinking through a multitude of different things, despite the fact we were having an actual conversation.

I know these aren’t good things; I’m still working on it. More than that, I’m actively acknowledging it.

If you’ve ever had a highly-stressful role, I’m certain you can empathise. You can’t help but spend every thinking cycle trying to figure things out. Because there’s always lots of stuff to figure out.

Talking to your family and friends is cathartic. Speaking with a mental health professional is cathartic. Writing, can be cathartic. Whatever works best for you, do it. Stop pretending you’ve got your crap together at all times.

For me, writing this article has been cathartic, and a deliberate act of vulnerability that I hope some of you can learn from. That in itself, is rewarding.

And very selfishly, it makes me feel better.

Read on for the next lesson.

Ian Yip is the CEO of Avertro, which brings science to cyber story-telling by providing a simple, yet sophisticated executive and board cyber platform that helps organisations tell a compelling story, right-size their cyber program, and understand their cyber-why.

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Ian Yip

Cyber Risk. Cybersecurity. Business. Tech. Entrepreneur. CEO at Avertro. Former CTO at McAfee Asia Pacific.