The Dark Side of Leadership

It was 3:47 AM when I finally admitted I had no idea what I was doing. Three files of code sat mocking me on the screen—three files that should have worked but didn’t.

The crushing weight of responsiblity bore down as I thought of all the lives, businesses and futures in my hands.

A battle raged inside my head as I argued with myself.

‘I’m already financially free. Why am I even doing this?’

“Is this even gonna work?”

“Am i makeing a HUGE mistake and wasting months of my life?”

That’s when I began to understood the true cost of leadership.

The Leadership Illusion

Most people have a distorted view of what it means to be a leader.

This is especially true in the home business profession.

Most of us equate “Leadership” to “The good life.”

The money, freedom, fame, popularity, etc.

But these are external fruits, and what most don’t see, are the roots that create those fruits.

When I got started in my home business, I had this picture of having all the money I wanted, with all the freedom i wanted.

This dream picture of “The Good Life.”

No worries, no stress, no problems.

Residual income = Easy peasy life

For a long time, I made no money. I realized I needed to work very hard and hopefully “become a leader” if I wanted to reach my goal of financial freedom.

Now that I’m ‘retired‘ and have plenty of residual income, I should be kicking back and enjoying the “easy peasy” life right? 🤔

ummm….

“With great blessing, comes great responsibility.”

Reality Check

This image is from the book “Developing The Leader Within You.”

Wait, so you’re telling me that as I grow in leadership, I actually have less ‘rights’ (freedom) and more responsibilities (things to do)?

Yeah, sort of…

That’s not what they said in the business presentation is it?

What about all the beaches, cars, vacations and free time?

Well those are there too and don’t get me wrong, building a business from home CAN give you gift of waking up in the morning a blank slate of a day.

It can give you the ability to ask the question “What do I want to do today” instead of the dreaded question “What do I have to do today.”

No where you have to be, no boss breathing down your neck or making you feel small, no office politics to deal with, no suit or horrible commute.

It can put you in a space where you work because you want to, not because you have to and what a gift that is…

But, with all things in life, there is a day and there is a night…

And that leads us to “The dark side of leadership.”

As I grew in leadership and experienced more success, I found myself using a metaphor to describe my experience to others.

The 2 sided coin

Success is like a 2 sided coin, one side is freedom and the other is responsibility.

You can’t have one without the other.

Financial freedom is the reward, responsibility is the price.

When you lead, you assume responsibility for those who follow you.

You have a responsibility to set an example for them.

You’re responsibe for serving them, inspiring them and making sure they have what they need to succeed.

You’re also responsible for problem solving.

A great entrepreneur once said…

“When you’re a leader, all the worst problems that everyone else can’t solve, get sent to you.” 😬

What Makes It Worth It?

For me, the choice to become the best version of myself and serve people in the best way I could, has been the right one.

The financial rewards are incredible and do relieve much of the stress and problems that existed before, relating to money.

And I do have a TON of freedom to go where I want to go, and do what I want to do, when I want to do it, which is SUCH a gift, especially compared to that old cubicle prison I used to be stuck in.

My family doesn’t want for anything.

I can go out to eat and not give a thought to the bill at the end.

The debt-free feeling is priceless!

So the upsides are worth it.

But what about the dark side?

Has that been worth it?

A recent example…

Picture this: Me, at 46 years young, watching YouTube tutorials on code while my family sleeps. Staring at error messages in a language I barely understood. MONTHS of early mornings, mind bending problems, and more work than any other time of my life.

In march of this year, one of our developers told us he was no longer going to help us with one of our key products so i was faced with a choice.

Find someone else and keep dealing with the same programmer problems we’d been dealing with for years, OR – do something bat shi* crazy and learn software engineering so I could build a more solid foundation for the future of our community.

I chose the crazy path.

This stretched me to my limits, 3:00 AM mornings, and 10 to 14 hour days, the sacrifice of hobbies, and yes, even some family time.

I’m financially free, so from a personal standpoint, none of this was even necessary.

But I knew that to secure our companys place in the future, it had to be done.

The night before we were scheduled to release it, live at our event, we had data migration issues and were up late in the night, only to not get it solved in time.

But we were committed and decided to release it anyway.

After our presentation, when everyone got access, the cheers rang out and we broke for dinner..

“I LOVE this.”

“This is soooo cool.”

“This is AMAZING.”

These were comments that made me smile.

Then…

“The app’s not working.”

“The site is down.”

“Oh, noooooooo…” I said as – I began to work through dinner to get it fixed.

Actually getting to eat during lunch and dinner can sometimes be a rare treat for my business partner and I because we’re responsible for making sure everything is working the way it’s supposed to work at the event.

Long story short, we got the app back up within a few minutes, and in the coming weeks solved the final data migration issues.

Now our customers are using the new app and loving it.

Our processes are MUCH smoother and we’re able to enhance things on demand as we see value we can add.

It all worked out for the best but it wasn’t the easy path.

It was the hard one.

And that’s what leaders often do.

They do what’s worth doing, not because it’s easy (many times it’s the more difficult route) but because it’s worth it.

But even the dark side of leadership has a bright side.

Through this whole programming journey, I learned that I was capable of more than I ever thought possible.

My faith was tested and re-forged in the fire of trial, to come out stronger on the other side.

I became more and I grew from my service.

When we showed our community what we’d built, the notes of gratitude and the sincere love and appreciation filled me with something money never can.

The sense that my life and efforts are mattering and making a difference in the lives of others.

And at the end of the day, isn’t that the point?

Leadership isn’t a light switch—it’s a dimmer.

Every time you choose responsibility over comfort, you turn it up a little more.

Every time you solve the problem no one else will touch, it gets a little brighter.

The dark side of leadership? It’s just the shadow you cast when you finally start standing up straight.

The question is: How bright are you willing to shine?

Thanks for reading,

PS: This is a picture of my business partner & I at the event we launched our new app & system at.

You see that little peanut butter ball on the desk?

That was a protein snack Amy, one of our top affiliates gave us because she knew we hadn’t eaten much. To be loved and cared for, and to feel that people love and care for you, is one of those gifts you get when you choose to lead in your best way.

PPS: The dark side of leadership has also taught me: Your external success is directly proportional to your internal foundation. Those 3:47 AM battles weren’t just about code—they were about the mental and spiritual resilience I’d built through years of daily practice.

The “Magical Morning Formula” is the exact 7-step system I used to retire at 40 and that continues to fuel me through the hardest leadership challenges.

It’s what gave me the power to learn software engineering at 46, push through those brutal 14-hour days, and stay centered when everything seemed to be falling apart.

Leadership doesn’t start when you face the crisis—it starts in those quiet morning moments when you’re building the version of yourself that can handle what’s coming.

Ready to develop the internal power that makes external leadership possible? Get the complete Magical Morning Formula here – completely free