The importance of failure as explained by the venture capital industry

How a meeting about win rates taught me that winning isn't everything

Although failure can be difficult to deal with, it likely means you're taking important risks.

Three years ago, I attended a venture capital firm’s annual meeting—an event where the company updates partners and portfolio companies on their investment and management strategies moving forward.

One of the meeting’s portions was on win rates, which represent the number of deals a company successfully secures (or “wins”) when competing with another firm in a funding round.

Given this, you’d think every company would strive for a win rate of 100 per cent. You can probably understand my confusion, then, when the venture capital firm stated they were targeting a win rate far below that.

However, as they started to justify their reasoning, it finally clicked. If you’re winning every single deal, it could mean you’re the best. But what it more likely means is that you’re not aiming for competitive enough deals.

A margin of failure implies that you’re taking risks. I think this margin is critical across all aspects of life for a successful career and fulfilling life. As such, failure should be celebrated, not feared. It means you’re trying new challenges outside your comfort zone.

Last summer, amid third-year internship recruiting, I started to see how deeply the fear of failure is ingrained in our systems. I watched my friends and peers retract from their social lives, stop eating, sleeping, and exercising, and even half-joke about self-harm.

I feel extremely fortunate to have grown up in an environment where the effort exerted, as opposed to the outcome achieved, was celebrated. It’s largely thanks to my parents, as well as mentors along the way, that I’ve learned the following strategies for coping with failure:

Come to terms with Plan B while in the process of Plan A

Let me use a plausible example. It’s exam season, and finals are right around the corner. You haven’t had enough time to sufficiently prepare for one class in particular and you’re panicking.

Well, what if you did fail the exam? What would you do? Chances are, there’s probably a lot you could do.

Depending on the situation, you could try to boost your marks in another course, defer your application for graduate school, or work something out with an academic advisor.

Regardless, if you can go into your exam knowing (a. you’re probably not actually going to fail and (b. if you did, there are ways you can work around the issue, then you’ll likely feel a weight lifted off your shoulders.

Maintain perspective

When viewed in isolation, anything can seem like a big deal.

Remind yourself of how insignificant your failure will be in the next five, ten, or twenty years. Think of how irrelevant losing that tennis match, case competition, or job is in the context of your life—and the world.

Try for as many things as possible to mitigate the risk of coming up empty-handed

Time permitting, the best way to ensure you have options is simply to apply to everything (within reason).   

If you’re interested in holding an executive position in a Queen’s organization, apply for multiple positions that interest you, or different teams. This way, you have a higher chance of securing a role in an area you’re interested in. The same goes for summer jobs or scholarships. The more you put yourself out there, the greater your likelihood of success is.

Build up your identity in as many ways as possible

I find that it can be disturbingly easy to become enslaved by your own archetype. If you’ve ever felt that people brand you a certain way (e.g. the over-achiever, the artistic one, the ‘quant,’ the mom), then you can probably relate.

It can be a dangerous self-fulfilling cycle that leaves you fearful of what people will think if you do something uncharacteristic or don’t get a certain offer, position, or result.

Regularly remind yourself and others of all the different things you care about, skills you’ve developed, and support networks you have. That way, if you fail in one area of your life, you’ll be able to remember all the other ones you can rely on.

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When you look at someone’s resume or list of accomplishments, it’s easy to have tunnel vision. That’s because it’s exactly that: a list of accomplishments. We’re used to only promoting our wins and successes when, in reality, that doesn’t show the full picture.

I think about this now when I look at my own achievements: I landed first-year executive positions (after being rejected from eight other clubs), won a national scholarship (after applying to over 25 and interviewing for five), and secured first- and second-year internships (after cold-emailing over 120 companies, being ignored by 70 per cent of them, and rejected by another 25 per cent of them).

The point is that failure is a good thing. It’s a natural part of life and an indication of your effort—a metric we don’t track often enough.

Whether it’s a job, certain mark, extracurricular, or even a sports team that you’ve been gunning for, it can be easy to become all-consumed by the stress and fear of rejection. It’s so easy to become consumed by that fear that it can distort your self-worth and shake your identity to the core.

But times like these make it important to remember that no one has a perfect win rate, nor should they be striving for one. 

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