22. Increase Your Awkward Tolerance

No one WANTS to feel socially awkward. But when we avoid awkwardness, we often avoid connection too.

There’s an assumption that connection should feel easy and comfortable—you’re supposed to just “click.” But what if connection is supposed to feel awkward, at least initially?

The same is true in workplaces. Meeting co-workers, building team connection, trust, and belonging often starts with small, slightly uncomfortable interactions.

What?
According to happiness expert, Tal Ben Shahar, one of the strongest predictors of long-term success—in business, relationships, and life—is how much failure or emotional discomfort we’re willing to endure.

We need to be able to do hard—and awkward—things. I call this building your awkward tolerance.

So What?
If we don’t experience—and survive—socially uncomfortable situations, we don’t build confidence in our ability to handle them. So we avoid them. And the more we avoid social interactions, the lonelier we get. In workplaces, that avoidance can look like staying quiet in meetings, eating lunch at your desk, and keeping conversations surface level.

What if we embraced the awkwardness instead?

When I feel awkward (which is often), it helps to remind myself that I’m building my awkward tolerance. That discomfort is part of path to the relationships and opportunities I care about most.

Meeting new people can be awkward. Meaningful conversations can feel vulnerable. Deep friendships require effort and emotional risk. (TV rarely shows this part).

Now What? Connection Practice: Build your awkward tolerance.
One of the most powerful ways to improve your relationships is to get more comfortable being uncomfortable. Practice in small, incremental doses—like exposure therapy. Repeated experiences build confidence that you can handle uncomfortable situations.

Try gamifying it by giving yourself a daily or weekly awkwardness challenge.

Kat Vellos, author of We Should Get Together, suggests you:

• Make a list of all kinds of social interactions, ranging from making a phone call, to speaking up in a meeting, to attending an event where you barely know anyone.

• Rate each activity on a 1-10 awkwardness scale.

• Choose one on the easier end and practice it regularly before gradually working toward harder challenges.Making a list of all kinds of social interactions, from making a phone call, to having a conversation with a friend, to attending an event where you barely know anyone.

Your workplace connection list might include introducing yourself to someone new, sharing something personal in response to “How was your weekend?” or inviting a co-worker to lunch.

Creating connection doesn’t require perfect social skills. It requires a willingness to take risks and engage in small acts of social courage.


What about you? Please share your responses in the comments—we love hearing from you!

What’s on the high and low end of your awkward activities list?
Have you ever been glad you moved toward — not away from — the awkward?