6 Things I Regret Doing in My 20’s and 30’s


Growing up on the Ballantyne family farm in Canada, I remember reading the newspaper almost every day as a child.

While I was mostly looking to see how badly the Toronto Maple Leafs had lost the night before (or as my dad called them, “The Falling Leaves”), for some reason I was also drawn to the stories about entrepreneurs striking it big and making their mark on the world.

I remember thinking to myself as a young man, “One day… One day, I’m going to be like them and have a big fancy house in Toronto and get Maple Leaf seasons tickets too.”

It wasn’t just the luxurious lifestyle that motivated me–although those things certainly didn’t hurt–it was the idea of creating an impact. Of being someone others admired. Of creating something that would help other people and that would have a lasting effect on their lives.

Today, almost two and a half decades later, I have achieved most of my business goals.

I’ve written multiple best-selling books. My YouTube videos have been watched over 13 million times. I practically invented a new way of using social media – specifically Instagram – to make money. And in 2011 I bought the business of my dreams, Early to Rise, from one of the biggest influences on my life, Mark Ford (aka Michael Masterson).

The good life I always wanted is mine. I have a luxury apartment with a view of the big city (where I live next door to a few of the Maple Leaf players, even though I no longer follow the team). I take 3-week vacations to Europe every summer. And most importantly, I have a brand new puppy dog (a yellow Labrador Retriever named Daisy).

But here’s something most people don’t know.

Along the way of my quarter-century journey from farm boy to businessman, I made nearly every mistake in the book.

I sabotaged myself at every turn, wasted years pursuing the wrong things in the wrong way, and threw away amazing opportunities that could have changed my life forever.

And today, I want to help you avoid making those mistakes so that you can live the life you want now instead of twenty-five years from now.

I’m going to share the six biggest regrets of my 20’s and 30’s to help you avoid falling prey to the same patterns and routines that hold so many of us back from the outcomes we desire.

If you’ll listen to what I’m about to share with you, I’ll help you save years of wasted time, avoid the biggest pitfalls to success, and live your perfect life sooner than you ever thought possible.

Let’s dive into my six biggest regrets…

1. Letting My Weakness Run (and Ruin) My Life

Let me tell you an embarrassing story.

Back in 2009, during the height of my social anxiety and introversion, I decided to attend a Dan Kennedy Super Conference in Chicago. And while I was checking into the hotel, I made an unusual request.

I asked for a room on the lowest floor and as close to the stairs as possible.


So that I could rush back to my hotel room during the conference’s intermissions and avoid having to talk to people while standing in the elevator…Yikes!

I allowed my biggest weakness – my introverted tendencies – to control me, and to this day, that pattern remains one of my biggest regrets.

For years I allowed my label lie of introversion to hold me back from achieving my goals and making the connections I needed to get to the next level.

Instead of pursuing growth at the expense of my comfort (something about which I’ll share more later) I chose to hide from the thing that would help me get to the next level. I stayed in my own little bubble and did my best to keep the rest of the world out.

The moment I made the decision to peel off my self-labeled introversion was the moment my business and life changed forever.

When I forced myself to bring more energy, joy, and enthusiasm to my interactions my business and lifestyle underwent an immediate change. I started making more sales, secured high-level partnerships, and grew my businesses at a speed that, to this day, still amazes me.

And if you want to achieve your big goals and dreams, you must do the same thing.

Kick your weakness to the curb. Attack it every day. Ask for help. Get direction. Chip away and get better every day.

Listen. We could argue back and forth all day about whether my being an introverted was a good thing or bad thing and whether or not you can control it.

But at the end of the day, success requires extroversion.

Notice I didn’t say success requires you to be an extrovert. It doesn’t and I’m living proof of that fact. But it does require you to develop your ability to be extroverted.

You can still enjoy spending time by yourself and prefer the company of your dog to the company of most people…But you must still put in the effort to develop your social skills and tap into your more extroverted side to succeed.

You must learn to make small talk, to shake hands, to say “hello” to strangers, to network and have engaging conversations with other high-performers and escalate those conversations to the point of partnerships, sales, or joint ventures.

You have to get out of your introvert box and stop using your label lie as an excuse for why you can’t succeed.

If someone like me can overcome my introversion and become a high-energy sociable person, then you can overcome whatever mental roadblock is in your way.

2. Numbness

In his book Turning Pro, author Steven Pressfield shares a concept he calls “The Shadow Career,” and it goes like this.

Most people know what they really want out of life. They know who they want to be, what they want to achieve, and the impact they want to leave on the world. They’ve known it since they were children.

Yet, the second they hit adulthood, they come up with an endless list of excuses about why it can’t be done.

You’ll hear them say things like:

“I’d love to write a novel but everyone knows you can’t make real money as an author.”


“I wish I could start a business helping other people live their best lives and achieve their dreams…but who I am to teach anyone?”


“I wish I could be a painter, musician, underwater wood welder, [fill in the blank]…but I can’t BECAUSE...”

And instead of doing the things they know they need to do, the things they feel called to do, they allow their fear of failure to hold them back from pursuing their dreams.  

They take on a shadow career–a job or business that pays the bills but is ultimately incongruent with their deepest wants and desires–and then numb their unfulfilling lives with a myriad of vices from television to drugs and alcohol to watching other people achieve the goals they’re too afraid to pursue.

If you look for them, you’ll see examples of this pattern in every industry and in nearly every highly successful person.

James Cameron spent years as a truck driver before finally embracing his calling to make movies.

Pressfield spent years taking on odd jobs (including driving trucks) before he finally decided to become a writer.

Samuel L. Jackson was numbing his pain with heroin and avoiding reality until he finally broke into Hollywood at the age of 43.

My friend Bedros Keuilian spent years working as a line cook at Disneyland before he finally decided to embrace his calling as an entrepreneur and start his first business.

And in my own life, I spent the first 15 years of my life numbing the pain of my underperformance by consuming a seemingly endless stream of travel blogs (without ever traveling myself), watching far too many episodes of The Office, and binge-drinking on the weekends.

Instead of being the executive and hard-charging businessman I wanted to be…I trained the executives and hard-charging businessmen.

I was bored and burned out in my own business, but instead of accepting the sacrifice required to break through to the next level and live the life I wanted to live…I numbed the pain and stayed exactly where I was.

Eventually, I couldn’t numb it anymore.

With debilitating anxiety attacks quickly becoming the norm and my life feeling like it was crumbling around me–despite having a 7-figure business and high levels of professional success–I knew I had to make a change.

I threw out my TV, gave up alcohol, and decided to live the life I wanted instead of reading about and watching other people live it.

And guess what?

It was one of the hardest things I ever did. The second I took away the emotional novocaine hit of binge drinking and television, the pain of my shortcomings and bad habits became sharper.

I was forced to confront my inner demons and make big changes in my life. But at the end of the day, this decision precipitated the personal and professional growth required to propel me towards the life I have today.

If you want to do big things in your life and push towards your peak potential, the first step is to stop numbing the pain of failure and inadequacy.

Listen. As you are today, you are not enough to achieve your biggest goals and achieve the life you want. If you were, then you’d have already done it.

To achieve your big goals and dreams and craft your perfect life, you must improve. You must face your faults and failures and do the work necessary to overcome them.

But you cannot do this if you are numbing the pain. You can’t use drugs, alcohol, tv, and other distractions to cover up the pain of not being the person you need to be. Regardless of your personal vice, it must be eliminated today to achieve the life you want tomorrow.

3. Ego

In 2011, I found myself at yet another Dan Kennedy Super Conference, this time in St. Louis, Missouri.

At the time, I was working on building out a Turbulence Training certification course that I hoped would be the ‘big break’ I needed to take my business to the next level.

Now, because I’d paid top dollar to attend this particular conference (a hefty 5-figure sum) I was privy to a special round table discussion in-person with Dan.

I’d been following Dan for years and, respecting his abilities as an entrepreneur, wanted to get his insight into my business.

So, when I finally got my chance, I told him all about my new certification program and how cool it was and how it was going to be the ‘next big thing’ that would launch my brand into the stratosphere.

His response was nowhere near as enthusiastic as I’d hoped for.

“Why would anyone buy this certification?” he asked.

And then… I froze.

Surrounded by maybe 15 other millionaires and high performers, I simply looked at Kennedy and said nothing, frozen in the most awkward silence you could ever imagine.

I couldn’t clearly articulate why someone would invest in my program, and, unable to overcome my own ego and admit that I didn’t have a good answer to Dan’s question, I simply sat there until he moved on to the next person.

*Insert face palm emoji*

As embarrassing as this story was, it was a valuable learning experience for me and contains an even more valuable lesson for you.

Everyone thinks they’re doing something amazing. Every entrepreneur out there believes that what they have to offer is the “next best thing,” a million-dollar idea, a disruptive force in their respective industry.

But guess what?

No. One. Cares!

I wasted years of my life pursuing dead-end ventures and doomed-from-the-start products because I thought I was a special snowflake.

“I’m Craig Ballantyne!” I thought to myself, “I’m the guy who founded Turbulence Training… Of course this is going to work out.”

And for years, I let my ego get in the way of my results and prevent me from living the life I truly wanted.

Listen, until you have a particular articulation of how your solution–whether it’s a product or service–will solve big problems and end pain for others, no one cares.

No one cares who you are or what you do or how great your mom thinks you are. Your big idea doesn’t matter. Your “cool” new app is irrelevant.

UNTIL… You can answer the only question your prospective customers actually care about:

What’s in it for me?

I let my ego hold me back from creating the products my customers wanted and instead I created the things I wanted.

And this arrogance likely cost me millions in lost revenue.

Let go of your ego and remember until you have a particular articulation of how you’re going to end pain and suffering for other people…no one cares.

4. Complacency

One of my greatest personal failings, and biggest regrets, is the way I showed up in my romantic relationships over the past two decades.

During my 20’s and 30’s I was a hard-charging, ambitious, and unstoppable entrepreneur by day–constantly seeking to expand, grow, and improve–and the most boring and lackadaisical romantic partner by night.

The second I broke through to a new level in my business or income, I was already looking up and trying to find another ceiling to smash through.

But my romantic relationships were a different story.

I would quickly settle into relationships that were fine…and then stay there.

My life turned into groundhog day as we did the same things over, and over, and over, and over, and over again.

The conversation was the same every Saturday night.

“Hey Craig, what do you want to do?”

“Takeout and a movie?”

“We did that last week…”

“Yeah, but I’m really in the mood for takeout and a movie.”

(Because God forbid we actually go out and, you know, do something … Especially with people that I didn’t know!)

And so the cycle went for years.

Because I was getting my most basic needs met inside of my relationships, I never bothered diving deeper and attempting to grow more.

The pain of vulnerability and authentic connection far outweighed the pain of “the same ‘ol thing” and for the better part of two decades, I allowed complacency to ruin potentially spectacular relationships.

If I’d simply been willing to apply the same energy and enthusiasm I had for my professional and financial pursuits to my relationships, my life would look much differently from how it does today and I could have avoided the years I wasted on my “Frat Boy” lifestyle.

I could have avoided the binge drinking the pointless parties and the anxiety-inducing escapism in which I indulged and would have moved faster professionally and financially because with a supportive partner by my side.

Thankfully, my love story turned around when I held myself publically accountable to meet the love of my life.

I made a goal of going on more dates (12 dates in 90 days), then I asked for introductions from trusted friends. My friend Vanessa introduced me to Michelle, who I eventually married! She and I now have a beautiful daughter and have another on the way!

It’s wild how life can change when you put forth intention, set process goals, and have accountability.

This wouldn’t have happened had I not overcome my complacency and held myself to a new standard.

Listen. Your business and career are undeniably important. But you must always remember that your life doesn’t happen in a vacuum.

Your personal life isn’t in one neat little box over here with your professional life in another box over there. They are all interconnected and the way you show up at home impacts how you show up at the office which impacts how you feel about yourself as a person.

So don’t make the same mistake I did. Invest in your relationships, both romantic and platonic, the same way you invest in yourself and your business.

Inject aliveness and excitement into your relationships. Try new things. Go on regular date nights. Take time off to explore the world and vacation together.

I promise, the rest of your life will only be better for it.  

5. Suffering in Silence

Did you ever see the movie The Green Mile?

If so, then you probably remember Michael Clarke Duncan, the towering protagonist who possessed the admittedly unusual power to relieve the pain of other people by taking it into himself before exhaling and releasing that pain.

For years, my dear friend and mentor Bedros Keuilian was a like Mr. Duncan, taking in the pain of his clients, friends, and family and bearing it himself–except Bedros struggled to exhale and let go of that pain.

He suffered in silence for the better part of half a decade and kept all of the pain, frustration, and struggle to himself because “That’s what real men do.”

It wasn’t until a few years ago, at the peak of his anxiety attacks, that I was able to coach Bedros through his pattern of suffering in silence and get him to reach out for help.

And I was only able to help Bedros because I spent years of my life struggling with the exact same pattern. I suffered in silence every single day–not because I was taking on the pain of my friends or clients–but because my introversion was so severe I had no idea other people were experiencing the same struggles and challenges as I was.

I didn’t know there were other people out there who had overcome the exact problems I was facing–and had a specific solution they could share to help me do the same–because I didn’t want to face the discomfort of opening up to friends or strangers.

Instead, I chose to suffer in silence, feeling like an island and facing my challenges alone.

And the second I made the decision to break out of my introversion and ask for help, to be vulnerable and real with my friends and mentors, and to let go of my own ego…everything changed.

I no longer felt alone and had access to individuals who were able to help me overcome my biggest obstacles and achieve my biggest goals.

I realized that I was not alone and that there were thousands of other people facing the exact same challenges as me. And better yet, that thousands of people had already overcome those challenges and could help coach me through the process of doing the same thing.

If you are facing challenges that seem insurmountable and you feel like no one else understands what you’re going through, you must surround yourself with other high-achievers and top performers.

Join a mastermind, hire a coach, attend a live event.

When you open up about the reality inside of your life and bring other like minded individuals along for the journey, you’ll quickly realize that you are not alone. There are other people facing the same challenges as you and there are other people who not only can help you…but want to.

But it all starts with you.

You must be willing to take that first step, admit that you can’t do it by yourself, and ask for help.

And the second you do, I can promise your life will change forever.

6. Self Sabotage

Throughout my entire life, the one pattern I regret more than any of the others was self sabotage.

For nearly two decades, I knew who I wanted to become. I knew the man I needed to be, the habits I needed to develop, the business I needed to build, and the results that I would enjoy as a result of these changes.

And for nearly two decades, I sabotaged myself at every turn.

I avoided challenges and pain and did whatever it took to stay comfortable and complacent.

Instead of embracing discomfort, surrounding myself with people playing the game at a higher level, and acknowledging my failures and shortcomings (so I could take action to resolve them) I rigged the game to serve my ego.

I refused to be a small fish in a big pond and instead, did whatever I could to keep my environment small so I could feel big and important.

And this perpetual self-sabotage cost me years of progress and stopped me from becoming the person I needed to be sooner.

Sure, I now have the business I always wanted, am plugged into a network of elite entrepreneurs, and am proud of the person I’ve become.

But it took me almost twenty years to get here. I could have moved faster, impacting more people, generating more income, and living the life I wanted sooner if I’d just had the self-awareness to acknowledge my shortcomings and end my self sabotage.

Whatever your goals and ambitions, the first step to achieving them is to eliminate your self-sabotaging tendencies.

Maybe you quit the second things get hard and jump to the next shiny object, hoping things will be different this time.

Maybe you indulge in workaholism and pursue financial and professional success at the expense of the things that really matter.

Or maybe you’ve allowed your fear of failure to hold you back from ever getting started and you continually lie to yourself saying, “When XYZ happens…then I’ll finally be ready to take action and move towards my dreams.”

Whatever excuse you’re using, whatever self-sabotaging habit you’ve adopted, it must stop today.

To break through to the next level and build your perfect life, you must get out of your own way and stop being the bottleneck to your own success.

And to do this, you need a mentor and a coach by your side who can call you out on your self-sabotaging patterns and give you the strategies and tactics you need to succeed.

If you’re interested in having one of my coaches help you overcome your biggest challenges and guide you through the same steps I took to achieve success, email support@earlytorise.com with the subject line “Coaching” for more details.

Craig Ballantyne

If you want to double your income, work less, and become the ambitious millionaire you've always wanted to be... Craig Ballantyne is the coach who will help you do it. With more than 20-years of experience as an entrepreneur and five 7-figure businesses under his belt, he specializes in helping "struckling" entrepreneurs get out of the mud and build the business of their dreams. To see if you qualify for Craig's "Millionaire Coaching Program" send an email to support@earlytorise.com with the subject line "Millionaire".