I opened my email and saw the message that brightens the spirit of any cross-country traveler: my upgrade was confirmed.

Even better, this upgrade included my daughter.

Lola has always loved flying but this was her first First Class flight.

Of course, she had no idea what to expect when we boarded the plane.

She was 6 at the time and small enough to sit quite comfortably in economy so she was dwarfed by the faux leather lounger she buckled into. She was thrilled.

An hour later, the captain announced we’d be waiting at least another hour before we could take off.

We were going to miss our connection to Portland.

I was stressed and anxious. Lola had already fallen asleep while watching a movie on my iPad.

I grabbed my phone and called the special hotline for United MileagePlus premium status holders.

A cheery man answered the phone almost immediately. He already had my flight info and agreed that there was no way I was going to make my connection.

He said, “I can see you’re sitting in first class right now. Why don’t I go ahead and confirm your upgrade to the first flight up to Portland tomorrow morning?”

I thanked him profusely.

When I hung up, the flight attendants were coming around to get beverages.

I asked for a gin and tonic.

The flight attendant replied, “I make them strong. That okay?”

Of course, it was okay. I was stressed and, while my conversation with the agent had made me less anxious, a little self-medicating wouldn’t hurt.

Self-medication is one of the perks of First Class travel.

Eventually, we did arrive in San Francisco. We proceeded to the customer service desk.

We bypassed the long line of people waiting for help rescheduling their flights and entered the area designated for premium status holders. There was no wait.

They gave us a hotel room to sleep in for a few hours and a stack of meal vouchers—and sent us on our way. We made it to Portland the next morning, tired but care-free.

This kind of service is why I value frequent flyer status. The upgrades, the shorter lines, the extra perks.

But it’s not the only reason I crave it.

Receiving that kind of service, achieving that kind of status… it makes me feel special.

Like I belong to a not-so-secret club full of those who have been deemed worthy by the powers that be.

It gives me a little boost of confidence every time I enter an airport.

But not just there. My status as a woman who uses a barbell gives me confidence at the gym. My premium status as a speaker gives me a confidence boost at conferences. My status as an employer or a multi-6-figure business owner gives me a confidence boost when I’m interviewing or facilitating.

Feeling special is often a feeling I confuse with confidence.

This month, we’re looking at confidence. Not so much the confidence to start a business but the confidence to grow one, to deal with unforeseen challenges, to level up yourself and your goals and pursue something bigger than you ever imagined.

Throughout the month, I’ll be sharing conversations with small business owners about how they navigate insecurit...

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