Enough time has probably passed for me to qualify talking about the scars, lessons, and stories along the way. No matter where you are in your journey, I hope mine can give you some perspective.
Lesson #1: Pain Pushes Until the Vision Pulls
Some people might say, “If you told me back then what this journey would require—not just in terms of skill or strategy, but heart, soul, and sheer grit—I might’ve paused. Maybe even walked away.”
Not me, haha. This is not a boast, but it’s also not an exaggeration. I cannot overstate my hatred for being told when I had to do what, how much I could make, and what time I had to wake up.
That’s not to say I wasn’t grateful, this just wasn’t how I wanted to live. Obviously, there were responsibilities at the time. In 2015, I had already been married for ten years. My wife and I had just bought a home and she was studying to get into med school. The plan was for her to prepare for her exams while I worked. I really thought this house was where we would raise a family.
There were challenges, of course. I was in my late-30s, up to my neck in debt, had an undergrad degree I did nothing with, a bunch of church work experience, and absolutely zero business experience. I had no idea what I was going to do.
My hope is that by setting this context, you’ll see the reality of my situation and what it can sometimes take to really get things moving. Pain is often greatest catalyst for growth. Pain pushes until the vision pulls. The goal was to move from a present negative, then to a future positive. Once I attained enough “exit velocity” and could see above my immediate sight lines, vision started to pull me.
If you want to change your path, success demands more than you think. More work. More hours. More learning. A ton of un-learning. More of you.
Lesson #2: Honor Your Convictions and Make Decisions You’ll be Proud of Later
The online course industry was beginning to boom in 2015. Back then, the “laptop lifestyle” movement was everywhere (it still is) and people were promoting the idea of building a business selling courses, running ads, and watching the money roll in while you sit on the beach.
That didn’t really appeal to me. My preference was to work with people, live. I’ve always been this way. Even when listening to music, I almost always prefer live concert versions of songs over the radio version.
It also bothered me that online courses didn’t seem to be as effective in my industry. Some stats said the average completion rate was less than 5%, so that didn’t sit well.
I’ve also never told anyone this, but I knew I could have created a course on copywriting and made good money. I didn’t because it would have been a similar product to one of my early mentors, Ray Edwards. Ray never knew, so he never asked me to hold off on this… I just thought it was the proper thing to do. My relationship with him was more important.
If you buy, create, or sell online courses, that’s not a knock on you. I’ve taken a few courses that were really good. But my heart was in mentoring, guiding, coaching, and teaching –– so that’s what I did.
Looking back, I’m proud of myself for sticking to those convictions. Mind you, these were my convictions –– they don’t have to be yours. Neither do they have to be one or the other. That said, I’ve met plenty of people the past ten years that have stabbed friends and mentors in the back or sold a product they knew sucked and chose the money. (I don’t like those people.)
Lesson #3: Sh*t Happens… And It Can Also Be a Great Fertilizer for Your Future
In early 2016, six months after I went full-time in my business and was making the most money ever, my wife told me she wanted a divorce. That really sucked. Details will not be shared, but here are the big rocks you need to know:
- For me, it came out of nowhere
- I truly loved her, to the point I would have died for her
- Divorce was the worst experience of my life
- In retrospect, we never would have made it (I truly believe this)
- I was (and probably still am) co-dependent AF
- Eventually, it ended amicably
- I’m happier now (I hope she is, too –– she remarried)
- I no longer second-guess the decision (it was ultimately mine)
- Divorce was the greatest growth catalyst of my life
- Divorce sucked, but I am incredibly grateful for it now.
From 2016 to 2018, I hit the road hard. Conferences, masterminds, parties — if there was a room with the right people in it, I was there. The road became both an escape and a lifeline. The silver lining: I tapped into the power of proximity.
Many people who follow my work admire big names like Tony Robbins, John Maxwell, and JJ Virgin. Please consider that these folks do not rely solely on their online presence to grow. They show up in person because connection happens face-to-face. It’s why singers, bands, and comedians still go on tour.
If you’re anywhere around my age (I’m 46 now) you will never convince me that your business will grow if you don’t meet with people in person. You can’t hide behind your laptop forever. Sooner or later, you have to show up. That’s where trust is built. Deals are made. Partnerships are born. It’s why I believe so strongly in coaching programs, masterminds, and events –– especially in person.
I never expected that I’d have to rebuild my life while building my new business. My heart felt like it had been shredded into a thousand pieces. Yet, what shocked me most was how many people I met who had also been through divorce—and not just survived it but thrived afterward. Their stories gave me hope.
Yea, I drank and partied a ton and I should probably be dead. For awhile I shamed myself for all that craziness, but I’m ok with it now because that just meant the pain was that significant. Plus my college years were tame, so you could say I lived my 20s during my 40s (yes, it’s dangerous).
It’s been said that the grass is greener on the other side… because there’s more sh*t there. I would agree. I’d also add that the hard sh*t I experienced became the very fertilizer for my future.
Lesson #4: Know Thyself, Entrepreneurship is Full of Emotional Whiplash
In other words, the highs are high and the lows can be crushing.
I can still remember walking through the San Diego Convention Center after one of my biggest talks back then, at Social Media Marketing World (great event). About 700 people were packed into my session. I earned really high marks on my talk and afterwards, people came up to thank me, tell me how much my talk resonated, and even asked for selfies. It should’ve felt incredible.
But then I walked back to my hotel room, alone. No one to talk to, no one to process the experience with. No wife to text. I got to my room, plopped onto the couch, and felt the weight of it all crash down. I went to dinner with my friends Chris and Trivinia later that night (they were there for me in such big ways) and got an email for the divorce settlement while at the table with them, three hours after I crushed it on stage. Damn.
You don’t have to go through a life-changing event like divorce to experience something like this. Webinars used to kill me. You pour your energy, creativity, and heart into it for weeks — maybe months. The webinar goes live, people are engaged, the sales roll in, and for a moment, you’re flying high.
But then it ends. The audience logs off. The thank yous fade. And you’re left sitting there in a room by yourself with your laptop closed. Honestly, think about how weird that is! You just presented to a ton of people from all over the world in your pajama pants and business top, and now you’re sitting in your office alone.
For a long time, I tried to avoid these ups and downs to the point that I stopped hosting webinars for over a year. But avoidance doesn’t work forever. The dip isn’t something to run from, it’s something to navigate.
I’m wiser now. After a big webinar last December, I didn’t stick around to stare at the sales dashboard or refresh my inbox. I closed my laptop, grabbed my coat, and went to Central Park to go ice skating with friends.
The whiplash is real, so you need to know yourself and recognize your patterns.
Lesson #5: Relationships Are Rocketships but Also Safe Havens
Looking back, the most meaningful things aren’t the big milestones or the stage time, they’re the relationships.
In You Are the Brand, I wrote that relationships are rocketships — they can propel you to new heights. An addendum: not every relationship is supposed to take you somewhere higher. Some relationships need to be places you can land –– safe havens where you can relax, let your hair down, and just be.
During my toughest seasons, my friends and family helped me celebrate the highes, navigate the lows, and kept me grounded. They didn’t need to understand my business or my industry; they just needed to understand me.
In a world where the online space increasingly feels fake, real relationships remind us what it means to be fully seen. To be fully accepted. To be fully loved.
My gallery of friends is pretty balanced. Some are like octane-fueled espresso: Type-A, all the time. These are the people you conquer the world with, but I can only take them in short bursts. Others are like a warm cup of tea: steady, calming, and comforting. Both are great, but sometimes your crazy self just needs to sit with tea.
Lesson #6: You Can’t Always Play 100% Through Pain
This shouldn’t surprise you, but I’ve often compared myself to others over the years. I’d see people building huge businesses and wonder why I wasn’t further along. The gift of hindsight has shown me how different my circumstances were, and that you can’t compare apples to oranges.
Many of these successful entrepreneurs had strong bases — great partnerships, supportive marriages, or other things to anchor them. While no situation is perfect, that kind of foundation is invaluable. Meanwhile, I was wandering the earth, trying to rebuild my life while my word was completely upended. Building a business is tough enough, but doing it while your personal life is in turmoil? That’s hard.
If you’re going through a really tough personal challenge, give yourself grace and space. Think of a wide receiver coming off an injury—you wouldn’t expect them to sprint at full speed right away down the field. You can’t expect yourself to be 100% while playing through pain.
I have wondered what I could’ve built if my home life had been more solid back then. Maybe having kids would’ve thrown all my plans sideways, but they also could’ve lit a fire under me that nothing else could. Many of my friends with kids have said as much.
But alas, my life is my life now. The past cannot be changed, but the future is yet to be written. Friend, keep things in perspective. Run your own race. And if you’re in pain, take the time to heal.
Lesson #7: The Way Out of Your Head is Through Your Heart
I’m in my head a lot, so much so that I used to gauge relationships through a lens of “season, reason, or lifetime.” I would wonder what role someone was supposed to play in my life and for how long. Looking back, that was more about protecting my own emotions than building genuine connections.
It also occured to me that I built a lot of connections because I’m co-dependent AF (see #5 in my list earlier) and wanted to please people. Maybe you can relate to that and you’ve swung the pendulum the other way, shutting everyone out. If so, let me encourage you — take it one day at a time and stay open.
No one is coming to save you, but that doesn’t mean you shouldn’t let people surprise you (or let yourself surprise them). If you only give your time, energy, and presence to people who benefit you, that says a lot about where you are right now.
I’ve tried to pay this relationship thing forward by curating my own communities. It still astounds me that I never would have met these people had I not started a business. I am so grateful for the people who have been in my world and allowed me to be part of theirs. If you’re one of them, thank you.
This year, I’ve downsized my groups across the board in an effort to go deeper with fewer people. Numbers don’t impress me, depth does. I’m making less money, but will be wealthier for it. My experience has shown me that money finds you when you honor this kind of prompting of the heart. I don’t think it will take me ten more years to look back and be proud of this decision.
***
There are many more lessons from the past decade, and I plan to dive deeper into them throughout the rest of this year. My hope is these reflections encourage you to look at your at your life with a little more intentionality. For me, success isn’t just about what you build –– it’s about who you build it with and how you build it. It’s been hard but absolutely worth it.
Here’s to the next chapter—and to building a business (and a life) worth celebrating.