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Lessons Learned From My Son

Last Saturday should have been beautiful.

It was the first summer weekend in Charlotte when I wasn’t out of town or it wasn’t raining. The skies were bright and the temperatures were in the mid-90s. It was the perfect day for soaking in a watering hole as so many Charlotteans do on hot summer afternoons.


A look at lessons I learned from watching my son develop that I’ve applied to my entrepreneurial career.


Friends invited us out on their boat for an afternoon of swimming and cooking out. I spent the morning catching up on missed freelance writing deadlines as I overextended myself during a period of heavy travel. All the while, I was looking forward to the afternoon – laughing with good friends, watching Deacon splash in the lake, and relaxing for a few of hours.

Yes, Saturday should have been beautiful, but I ruined it.


Even through my recent successes, I’m struggling.

As I described in my May Income Report, things appear to be moving in the proper direction. I launched an e-course, hired an assistant, and experienced my best month both income and traffic wise. Also, that same morning, I received an email from an editor of a major magazine expressing interest in a pitch I sent. We’re talking a number-one-circulated-magazine-in-the-country-within-my-niche kind of magazine.

Yet, I still wasn’t happy.

Even with all of this positive movement, I’m nowhere near where I feel that I should be at this point in my writing career. I left a six-figure job almost two years ago to pursue what is beginning to feel like a silly dream. Almost two years in, I’ve yet to even make a fulltime living as a writer. In fact, I could probably make more money, and work less hours, flipping burgers at McDonalds.


Two things are weighing me down to the point that daily I feel like mounting a failure.

First, I think of the sacrifice we made so I could pursue a writing career. Two years ago, we were working with a real estate agent to purchase a house. While we were comfortable in our townhouse – the mortgage is crazy low and it has wide-open spaces for entertaining – we dreamed of something bigger so my wife could have a proper garden and the family we were planning could have a yard to play in. Yet, we paused those dreams for my writing career.


A look at lessons I learned from watching my son develop that I’ve applied to my entrepreneurial career.


Today, I live in a neighborhood where I no longer know my neighbors. Most of our friends have moved out. They use words of “dump” or “ghetto” to describe a place where they once live and we still call home. Through my decisions, we are stuck here at least two more years.

Second, while I’m proud to be a father, I never desired to be a stay-at-home-dad. I didn’t earn my MBA and experience a lucrative career to spend my days changing diapers and putting away toddler toys. I feel like less of a man because of the recent addition of stay-at-home-dad to my title. It’s not something men do. At least this is the message society constantly tells me and which I can’t turn a deaf ear to.


Yes, I do realize how superficial all of this sounds, which is why I’m not happy that I snapped at my friends on Saturday.

As the afternoon waned on, conversation on the boat seemed to linger on real estate for way too long. The words “dump” and “ghetto” were included with “so glad to be out of there” to describe my neighborhood, my house. Prices of unaffordable to us new homes were tossed out.

I silently sat through the conversation, falling deeper into my depression.

Then, the conversation turned to stay-at-home-moms. “Why would she even bother getting an advanced degree if she was just going to be a stay-at-home-mom?” was uttered by I don’t remember who.

This is when I lost it and angrily retorted. “I guess that makes me a loser then because I have an MBA and am a stay-at-home-dad. Is that what you think of me?”

I don’t even remember what the reply was because I shut down. Behind my sunglasses, I was fighting back the tears. I retreated to the far side of the boat to play with my son since it was all I was qualified to do.


A look at lessons I learned from watching my son develop that I’ve applied to my entrepreneurial career.


Please don’t think that I’m mad at my friends or that they were being rude. They had no idea what I was going through. But it is a reality that most who pursue an entrepreneurial career experience at some point. There is a fair level of uncomfortableness as we give up things to pursue a life of freedom from the tentacles of corporate America. We sacrifice now so that at some point in the future, we can have even more than we are giving up in the present.


Right now, I’m trying to teach Deacon how to crawl.

I lay him on his stomach and place a toy in from of him to play with. After a couple of minutes, I move the toy out of his reach. At first, he tries to stretch his little arms out to grasp it. Then he kicks his legs and looks at me with an expression of “Daddy, why’d you move it?” on his face.

This is when I toss out a few encouraging words like, “You can get it Deacon! I know you can! You’re strong! You can crawl to it!”


A look at lessons I learned from watching my son develop that I’ve applied to my entrepreneurial career.


He typically buries his head in the carpet and starts to gyrate his torso back and forth, attempting to lift it off the ground. His legs then start to tuck under, and his butt pops into the air. I almost think he is going to crawl. Instead, he flops into a roll on his back and starts to cry.

I roll him back onto his stomach and begin to offer more words of encouraged. “Don’t cry Deacon! That negative energy will get you nowhere. Instead, turn that negative energy into positive energy! I know you can crawl to the toy. You need to know you can crawl to the toy. Transfer those tears into crawling. You can do this!”

He looks at me with determination on his face and tries again. Each attempt, he gets a little closer to crawling.


If I only I followed the same advice I give Deacon…

As entrepreneurs, it’s easy to get wrapped up in our struggles and to drown in our tears. To think that crawling to the toy will never happen for us. We want to roll onto our backs and settle for the easier to reach toy that we can have right now.

Is that the toy that we really want? A life where we take what is handed to us by someone else for our mediocre efforts?


A look at lessons I learned from watching my son develop that I’ve applied to my entrepreneurial career.


No, it isn’t. The easier to reach toy will never satisfy us. We’ll always think about the dream we gave up on.

As I watch Deacon learn to crawl, I’m learning way more from the process than he is. I, too, am learning to transfer negative energy into positive energy, that wallowing in what I don’t have now will never move me forward to what I want to achieve.

His determination helps fuel my determination. That someday, we’ll be playing in our own backyard, and it will be grander than anything I could have imagined. Better yet? I earned it all through my entrepreneurial efforts.


How do you manage similar struggles as an entrepreneur? 

 Life Lessons Learned From My Son