In late summer 2005, I entered what would be the start of 14 wonderful years in the staffing industry. For those who aren’t familiar with the term “staffing,” maybe you know the term headhunter. I was the Chuck Woolery of Careers.

I spent my days on the phone with both candidates and clients to help make an ideal match - dream candidate meets dream job.

Every Monday morning, I’d grab my hot mug of coffee, sit down at my desk and fire up my computer, and prepare to start a new week of making job-seeker dreams come true. And most days, I did just that.

Most days, it didn’t even feel like work.

I loved what I did. And on the days when an offer was accepted - it felt like I was not only doing well at my job, but truly changing people’s lives for the better.

But that was most days. On other days, I kept seeing a situation play out - over and over - that I found incredibly troubling.

I’d work with a candidate who was so excited to take a new job, and at the very last second, they’d have a change of heart. They’d stay right where they were (even though something compelled them to look for a new role in the first place) or worse, they’d accept a counteroffer against their better judgment. One thing always happened without fail though: They’d come back to me within 6 months and say, “I made a huge mistake.”

Even when I was able to place a candidate successfully, there were still recurring themes in WHY they wanted to leave their jobs. It was usually some version of:

“I was passed over for a promotion… again.”
“I didn’t get the salary increase I wanted and felt I deserved.”
“I’m not getting picked for the types of projects I’d like to be doing.”

On those other days, it didn’t feel fair to profit from other people’s frustration.

Those disappointments were hurting them. It was hurting me too.

For a while, I couldn’t quite see what the relationship between all of those things was, until one day, after my 3rd unexpected, rejected offer of the week, I was on the phone with a candidate who gave it to me straight.

After a slow, audible inhale and exhale, she said to me,

“Henna. I really want to take this new job, and I’m ready to make a bunch of excuses to you as to why. But if you want the truth? I’m frozen. I’m scared to death to even bring this up to my boss. That conversation is going to be so awkward. I’d just as soon not do it at all.”

That’s when the pattern became crystal clear.

Despite all of the personal development talk, risk-taking was still clearly terrifying for most people.

They’d say, “I want to, but HOW?”

The desire was there, but the ability to take action eluded them. The awkwardness of trying something new would stop them every time.

I’d almost forgotten that feeling.

As a first-born child of immigrant parents, I stuck out like a sore thumb. I didn’t act, eat, or dress like most. A bit of an accent thanks to English being my second language. The smell of curry wafting from my lunchbox and through the cafeteria. Ill-fitting pants that were decidedly not in fashion, because fashion was low on my parents’ priority list as they acclimated to this country.

My parents also enrolled me into every extracurricular activity there was… and I stunk at all of them. But they had a rule: See it through, even if you feel awkward as hell.

So I got good at awkward. And it became my biggest gift, especially at work.

I’ll try anything once.
I pivoted my career twice.

And most of my professional colleagues would call me a risk-taker. These days, that title makes me smile.

I was the girl who always felt so out of place.

So embarrassed.
So uncertain.
So stumbly and fumbly and ungraceful and not brave.

The very idea that this girl would be now considered the “risk-taker” of her circle of friends and colleagues seems like satire.

But it finally makes sense.

Because the key to taking more risks is NOT to eliminate awkwardness, but condition for it instead — to get good at awkward.

Now that I know it… I have to share it.

Ambitious professionals deserve to know how to strengthen our risk-taking muscle.

I have an action plan to get us there. No dumbbells required.