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 insecurity and find confidence—even when things are rough. We’ll talk about the confidence to raise your prices, come back after considerable time away, close deals with giant corporations, craft a new lifestyle, and more.

But before we get to those stories, I wanted to share what I’ve been working on personally when it comes to rediscovering my confidence—or, maybe, finding it for the very first time.

Like I said, I’ve often confused the special feeling I get from earning some arbitrary status with real confidence.

Knowing that I get to use a special line at the airport or that the airline is going to take care of me when there’s a heinous delay gave me a sense of confidence.

  • Running a 6-figure product launch gave me a sense of confidence.
  • Getting singled out in class for an exceptional paper gave me a sense of confidence.
  • Climbing a certain difficulty grade at the gym gave me a sense of confidence.
  • Entering a conference hall with a name badge that says “Speaker” gave me a sense of confidence.

It’s not just what I’ve achieved. It’s the fact that I belong to a secret club… and that membership means I’m good enough, smart enough, and work hard enough.

Turns out, I substitute status for real confidence.

And that’s the problem: I seek out status because I lack confidence.

These arbitrary markers of status don’t actually give me real confidence. They just pacify my anxiety for a while.

I’ve been driven by a need for status my whole life.

I want to prove that I belong. That I’m worthy.

I desperately want to be recognized.

I want to be seen as smart, hard-working, successful, and strong.

And because I lack the confidence to make this known on my own, I’ve tried to let my status do the talking.

It works—sometimes. Status has often given me the little boost I need to feel comfortable speaking up or meeting someone new.

Unfortunately, status is ephemeral.

And when I no longer qualify for the status I’ve been leaning on for confidence, I can find myself in a free fall.

In 2018, I lost my status.

For the first time in 7 years, I didn’t qualify for status with my airline.

For the first time in 9 years, my company didn’t generate more revenue than the year before.

I only spoke on 1 stage. I didn’t teach in front of thousands in a fancy video production studio. My husband went back to work.

To me, these all felt like serious defeats—like something important was missing from my life.

Now, can I tell you what’s really obnoxious about this though?

I chose those things.

I decided to pull back from speaking last year so that I could focus on building our community from the inside out.

I decided to stop teaching so that I wouldn’t dilute our community-oriented value proposition.

I decided to focus less on revenue and more on creating an exceptional product first.

I decided to not fly so much and take more time at home.

They were all good decisions. But the loss of my status as a frequent flyer, a keynote speaker, a solo breadwinner, a bestselling teacher…

…it rocked my confidence.

I questioned my own worthiness, value, and credibility. I just didn’t know if I had what it takes.

A few months ago, I finally started to make the connection between these arbitrary marks of status and my self-confidence.

I started to see how status gave me a false sense of my own confidence.

I thought I felt secure in my own abilities and confident in my potential—but it was just an illusion made possible through random achievements.

I needed to find a true sense of confidence in order to move forward.

The truth? I do not have this figured out yet.

I have a feeling that confusing confidence with arbitrary markers of status is going to be something I deal with for a long time.

What I can tell you is that I’m learning to put my energy and attention into things I truly want to achieve instead of chasing whatever version of Double Diamond status is currently in front of me.

For instance, while Sean and I still want to visit every United States National Park before 2027, I’m learning to let go of rigid benchmarks for how many new parks we need to visit in a year…

…and learning to enjoy whatever park is in front of us right now.

While I do want to get stronger, I’m learning to let go of arbitrary goals I set in the gym just to be able to say I can climb hard enough or squat enough weight to join an imaginary club.

While I’m committed to connecting 10,000 small business owners inside The What Works Network, I’m learning to let go of membership goals that might take me away from creating an exceptional experience for the members we have.

I suppose I’m finding confidence in presence, habits, and intention.

I’m paying attention to where status drives me instead of meaning or my own deepest desires.

I know not everyone is driven by status. And, I know not everyone confuses status for confidence the way I have.

And, I also know we live in a very status-driven society.

So even if you couldn’t care less about being Executive Platinum for Life at your favorite hotel chain, you might find yourself thinking that achieving a certain status with your business might make you more confident to level up with your business.

I’ve heard so many small business owners over the years tell me that things will be different when they hire a virtual assistant, get 1,000 subscribers on their email list, or generate 6-figure revenue. They believe they’ll be taken more seriously, that they can think bigger, that they’ll finally have confidence in what they’re doing.

Of course, the truth is that none of these arbitrary small business status symbols mean anything other than what’s on the surface. They don’t make you more credible. They don’t give you permission to think bigger. And they certainly don’t supply you with true confidence.

I’m learning that no achievement is a substitute for real confidence.

And, I’m learning what real confidence is to me—slowly, but surely.


Over the next month, we’re going to be exploring confidence from every angle as part of The Candid Confidence Project.

We’ve got 8 in-depth interviews—each with an entrepreneur who found the confidence to level up their business or their life and how they did it.

But that’s not all! There’s more to The Candid Confidence Project.

In between our podcast episodes, we’re sharing personal essays from successful small business owners on how they navigate insecurity and level up.

To get the whole Candid Confidence Project delivered to your inbox—that’s one email each weekday in August—go to explorewhatworks.com/confidence

Of course, we also want to include your stories and reflections in this project. We’re hosting a public conversation about confidence on our Instagram handle, @explorewhatworks.

Each day, we’ll post a prompt based on the interview or essay we publish. Share your thoughts in the comments or make your own post and tag it with the hashtag #candidconfidence.

As we kick off the project today, I’d love for you to share a time when you thought achieving a certain status would give you a much-needed confidence boost.

Maybe you were chasing a big revenue goal. Maybe you were making a big hire. Maybe you wanted an invite to speak at a major conference.

What’s your own version of the elusive Double Diamond status? And how did achieving it—or not—play out in your own sense of self-confidence?

Click here to share your thoughts or story.

Next week, you’ll hear from Jamie Varon, who found her way to redefining her idea of satisfaction and discovered a new level of confidence in the process. You’ll also hear from Michael Karsh, who went from starting a business to signing production deals with billion-dollar corporations in his first year.

Stay tuned!