The Story of My History in Business – Part 11 – Getting Back on Top

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This is the next installment in an ongoing series where I talk about my history in business starting when I was a child to now in my late forties. Feel free to read parts zero, one, two, three, four, five, six, seven, eight, nine, and ten if you haven’t yet to get some context.   

-By Caleb Jones

I left off in 2002 where, after a fast expansion and hitting a six-figure income, my immature spending habits caught up with me. I lost my car, went into massive debt, and was forced to sell my house and move my entire family into an apartment. 

Early 2002 

Instead of a nice office, my new office was a tiny desk next to my bed. I still had a small staff back at my office, but I had to downsize there as well, so here I was working from home again. I hated it.  

Surprisingly, my wife at the time and my kids (my son was 11 and my daughter was four) didn’t seem to mind living in the apartment at all. They liked having the convenience of friends nearby and access to the apartment pool which they would often use while I was working back in the apartment. 

I floundered for a few months. It was around this time that I started to lose my motivation and my way. I had finally hit my big income figure of $100,000 per year (though at that moment I was making less than that because of my own incompetence) but… now what? 

I had no Mission, no overall meaning in my life. All I ever had driving me were those basic, Alpha Male 1.0 Societal Programming goals of a “real” business, a six-figure income, a cute blonde stay-at-home wife (who was rapidly gaining weight at this point but that's another story), and two kids. Since I had already accomplished all of those things several years prior, I didn’t really know what to do. 

What I did know was that I hated living in a apartment. I felt like a failure. Like I was going backwards. That became my new immediate goal: get the hell out of that apartment and back into a nice house. 

So, with that one goal, after floundering for a few months, I started to hit it hard again. I started marketing more, soliciting more referrals from clients, and presenting existing clients with possible new projects. This time around, the fire and passion weren’t quite there though. I was just going through the motions, robotically doing what I needed to do to get back to a nicer place to live.

I also started getting tired of computer consulting. In an effort to branch out, I started some other business activities, such as: 

  • Doing productivity and efficiency consulting, which I really enjoyed. I was also able to charge more for this using flat-fee pricing instead of hourly or retainer pricing. 
  • Doing time management consulting for businesses and time management coaching for business owners and executives. I didn’t like the coaching quite as much as the consulting, but it was still enjoyable and it was an easy, extra income stream. 
  • Doing public speaking. I joined my local Toastmasters group and started attending weekly meetings. I loved this. Even though I was an introvert (and still am), I was shocked at how enjoyable it was for me to speak in front of groups. It was a skill set I never knew I had. People assumed that I had a good deal of experience public speaking even though I was a beginner.  

This was at the beginning of the artificial real estate boom of the early 2000s, so my plan was to jack my income high enough so that I could sock away a hunk of money for a down payment on a shitty house, move the family into there, live there for one or two years, then flip it for a huge profit. This way the profit wouldn’t be taxed. 

Within a few months I had my income back up. Shortly after that, at around 2003 or 2004, I had cranked it to $135,000 a year, a number I thought was pretty impressive at the time. It wasn’t. I could have made much more. The problem was that my actions weren’t born of passion this time around. Instead, they were born of necessity. I just wanted out of that cramped apartment and back into a decent house so I could feel normal again. 

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I was back to where my income felt “successful,” but something was missing. Back then I couldn’t tell what it was. Today I know exactly what it was. I was missing a Mission. I was also living a life I never wanted. Deep down I wanted the life of an Alpha Male 2.0, not this confining traditional lifestyle. 

But I didn’t know any of this yet, so I just plugged on robotically.  

By the end of the year we were back in a house. It was a pretty lame house, but that was the point. Immediately I started putting money into upgrading the paint, carpets, and landscaping. Then I just waited until I could sell the damn thing and take my profits.  

At exactly the time frame where I could sell the house without paying any taxes on the gain, I think it was two years, I sold the house at an almost six-figure profit. I was only in my early thirties and this was the fourth piece of real estate I had sold at a massive profit. Added to my growing income, I was flush with cash once again.  

At some time around early 2004 I moved my family into a nice, five-bedroom house located at the top of the hill in one of the most expensive neighborhoods in the state. For tax purposes I put the house in my wife’s name (something that would really help me later during the divorce) since she wanted the house more than I did. I was back to my normal level of success. 

I started speaking more often, doing small seminars and conferences in the region. The more I did it, the more I liked it. My topics back then were productivity and technology. They were pretty rusty, but audiences seemed to like me and my speaking income, though meager, was starting to grow.  

Excitedly, I upgraded from Toastmasters and joined the National Speakers Association. To become a full member, you had to have a minimum number of paid speaking engagements per year or a certain amount of income per year purely from speaking. I wasn’t a “known" speaker yet so I wasn’t able to hit either of these numbers. Instead I joined their apprentice program and attended their meetings and national conferences as a paying non-member.  

Interacting with the speakers of NSA, talking to these guys, getting to know many of them, many of whom were idols of mine (Brian Tracy, Dan Kennedy, Alan Weiss, Randy Gage, Tom Antion, David Rabiner, Shawna Schuh, Patricia Fripp, Larry Winget, Nido Qubein  and so many others) opened up a whole new world of possibilities for me. Holy shit, I said to myself, these people are amazing. And I can do what they’re doing. 

Wheels started to turn. I still didn’t quite know what I wanted for my life, but I was much closer to discovering it.  

Little did I know I was about to change everything. 

To be continued. 

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