How to Know if You’re in Your Cavern Club Season (and Why It Matters for Leaders)

Sep 22

Many leaders secretly wonder: Am I doing all this work for nothing?

The late nights. The invisible projects. The one-on-one conversations no one else sees. The meetings where you put in effort that doesn’t show up on any scorecard…and maybe never will.

If you’ve ever felt that way, you might be in what I call your Cavern Club season.

And as hard as it is? That season might matter more than any other.

What Is a Cavern Club Season?

Before the Beatles filled stadiums or broke records, they played nearly 300 shows in a sweaty, cramped Liverpool basement called the Cavern Club.

They weren’t famous. They weren’t glamorous. And most nights? They were just another scrappy band grinding it out while the crowd half-listened over their pints.

But in those years, they built the thing the world couldn’t see.

Timing. Rhythm. Stage presence. Stamina. Unity.

That season shaped them. It didn’t look big, but it made them big.

Every great leader I know has a Cavern Club season. In fact, every PERSON I know has them – they’re a very human experience as we grow and evolve in life.

It’s the time when you're putting in reps that no one’s clapping for. These times are when you’re showing up for YOU…for your FUTURE you…doing the work to level up.

These are the days when your work feels invisible, but something inside you says, This matters.

My Own Cavern Club Years

Mine looked like six years of teaching inside an ICF coaching program. Thousands of hours, around 5,000 to be exact, both face-to-face and over Zoom.

Some sessions landed. Others…well, let’s just say that when the pandemic forced virtual classes, I worked 9 days out of l0 in a row…10 hours on Zoom each day, facilitating, teaching, being in the flow of the class. By the final day, I was toast.

Nobody was clapping. No one was tracking my “metrics.”

But I was learning.

How to listen better. How to adjust on the fly. How to read the room, even through a frozen screen.

I didn’t know it then, but that was my Cavern Club. And it’s the only reason something wild happened this past weekend:

Three little books I wrote quietly in the past two weeks suddenly dominated the Top 3 spots in two separate Amazon categories.

And each one held a #1 spot in separate categories.

It felt surreal.

And then it hit me: This was my 1964 moment.

The same way the Beatles stunned the world by holding the top five spots on the Billboard Hot 100 that year. Those rankings didn’t come from nowhere.

They came from every gritty Cavern night that came before.

So did mine.

3 Signs You’re in a Cavern Club Season

Not sure if you’re in one? Here are some clues:

1. The work feels repetitive, but you know it’s sharpening you.

You're doing the same things, meetings, emails, conversations, but with more depth. You can feel the mastery forming, even if the outcomes aren’t flashy.

This is the season of one-step, not quantum leap.

2. You’re testing and refining constantly.

Some things land. Others flop. You’re gathering real-world data, adjusting your voice, figuring out what actually resonates.

If you’re not making mistakes, you’re not exploring new territory and growing.

3. You’re shaping who you are as a leader, in private.

You’re building confidence, clarity, and resilience away from the spotlight. These are the years that teach you what kind of leader you’ll stay when the lights do come on.

If that sounds like you, you’re not stuck. You’re in training.

What you pay attention to here will stick for years and decades to come.

Why This Season Matters for Leaders

Too many leaders measure success by size:

Landing the next title
Getting the big project
Crushing the quarterly target

But some of the most meaningful “Beatles moments” in leadership are quiet and unseen:

A team member says, “You helped me believe in myself.”
You hold a team steady through a hard quarter, and they trust you more, not less.
You start shifting culture, one hard conversation at a time.

These don’t show up on LinkedIn.

But they are the compound interest of leadership.

They are why you’re ready when the spotlight finally finds you.

A Question for You

Let me ask:

Where are you in your Cavern Club season right now?

What’s the quiet work you’re doing, the part no one sees, that might just be forming something essential in you?

Because one day, you’ll look back and realize…

This was the season that shaped you.

This was the basement where you found your rhythm.

This was where you became the leader you are now becoming.

Ready to step out of the cavern and onto the main stage? Let’s talk.

If you enjoyed this article, you might also like The Confidence Gap: Why You Feel Behind When You’re Actually Right on Time

Daniel Olexa, MCC, CIHt

Daniel Olexa, MCC, CIHt has been a coach all of his life. He started his 'official' coaching career in 2017. In less than 7 years, he earned his MCC credential, coached hundreds of clients, trained over 3,500 individuals around the world to become coaches (teaching nearly 5,000 hours of classes), and mentored more than 100 coaches to achieve their credentials with a 100% success rate. He is the founder of Transcendent Living, and believes in everyone's ability to live beyond normal outcomes (the definition of transcendence), if they are committed to changing their being through examining their stories of worthiness and self. Daniel is a 3x Amazon bestselling author, corporate trainer and keynote speaker. His motto is: "Extraordinary people do extraordinary things. (Re)Awaken to your gifts.”

https://www.transcendentliving.com