Surviving A Mid-Life Jog, And the Road Ahead

After a four-month jog to clear my head, I'm back -- co-launching After Nines Inc. with Amy Katz. But I'm not necessarily the guy you knew before. Raw statistics suggest I'm entering the second half of my life, when experience -- rather than raw, youthful energy -- will increasingly guide me forward. Clearly, it's time for a few changes. Here's the rough game plan.

Back in May 2014, Amy and I both exited our previous employer, Penton -- which has successfully transformed into a professional information services business. Amid that business transformation, Amy and I reached personal inflection points as well. After 22 years in the IT media industry and a successful business launch/sale to Penton, it was time for me to regroup, recharge and rethink life. Ditto for Amy.

Symbolically speaking, we each went out for really long jogs to clear our heads. During the four-month self-imposed "retirement," I dropped out of the business world -- other than attending a few Golden Seeds angel investor events and popping up on Tech News Today each Tuesday. I wasn't sure if, how or when I'd fully "come back." I had no destination in mind this past summer, other than joining my wife to watch our sons compete in lacrosse, track and football camp.

Yes, I checked in with Amy pretty regularly. The conversations were always about our families. Our kids. Good memories from our business journey together. But for the most part, we danced around the elephant in the room -- did we want to get back into the game? And if so, would we do so together? Frankly, I don't think we broached the subject because we were having too much fun... doing "nothing" other than focusing on family.

But at some point, we both knew we needed to do something creative. Something fun that wowed customers. And of course, something profitable to pay our respective bills. And we also knew we loved building businesses together. Yada, yada, yada (sorry, I've got to skip some of the best details and strategies): After Nines Inc. has launched.

New Rules of the Game

Still, the game plan this time around is quite different vs our 2008 business launch. There's now a voice inside my head that reminds me every day: I'm 44 years old. Basic statistics suggest my life is more than half over.

Note to self: I'm not going to spend the second half of my life blogging 18 hours a day just to get a few thousand extra page views per month. Ditto for Amy -- a few years younger than me -- on the business development side of the house.

Past, Present, Future Priorities

During that extended jog away from business, I began thinking about my life in 22-year chapters.

  • Chapter One (ages 0-22) was all about goofing off. And in some ways, underachieving.
  • Chapter Two (ages 23-44) was all about hard work and pursuing "success," even if it meant sacrificing time with my family. I overachieved in some ways, but also got a lot of things wrong.
  • Chapter Three (ages 45-66) is to be written. I turn 45 early next year. But I share some ideas below.
  • Chapter Four (ages 67-88 and beyond): The bonus round. There's no guarantee I'll even make it out of Chapter Three and onto Chapter Four. But I hope to have a plan.

Chapter One, Ages 0-22

I goofed off. A lot. I had a good brain and natural athletic ability but wasted a lot of that talent in my youth. But I got some fortunate breaks along the way -- a great family with great parents who pushed me toward college. While there, I met my future wife -- Annemarie. She gradually made me realize there's more to life than partying. In order to hold onto her, I started getting serious about a career focus. Fortunately, I spent a lot of time writing and programming early PCs in my youth... which set the stage for Chapter Two.

Chapter Two, Ages 23-44

I married the love of my life -- Annemarie. Our family grew to include three awesome sons. But I worked. A lot. It's a safe bet you did, too. It seems like all of us have been asked to work non-stop since the PC, LAN and Internet booms started, and even harder since the dot-com implosion and more recent cloud wave.

Fortunately, hard work and friendships opened doors to some huge career breaks. I landed a job at InformationWeek right out of college -- a great weekly IT pub from a great company (CMP Media). As my relationships grew in the industry, I moved up the ranks at CMP, Ziff Davis, Microcast Communications (thank you Al, Mike, Gary) and other career stops. But I was always working. Always. (Then again, just about everyone in IT is always working.)

Late in this chapter, a friend (Amy Katz) and I worked on a few projects together at Ziff Davis, Time Inc. and more. We clicked on business fronts at Microcast Communications. We shared similar family and financial values. We co-founded a business by 2008, built it, and sold it to Penton in 2011 -- a business parent that could ensure the brands we created (The VAR Guy, MSPmentor, Talkin' Cloud) could stand the test of time.

When we launched that business back in 2008, my three sons were ages 10, 8 and 2. I barely saw them. But I was having a blast. Amy was, too -- even as she and her husband Larry were busy raising a daughter and son, too.

Somebody Hit Reset

A brutal reality check arrived by 2010, when my wife's brother died of cancer. He was age 44. We were close. He was even closer with my wife and kids. Amy also had her unfair share of family loss during our business journey together, including the death of her mother in law. We started as business partners, but evolved into friends who supported each at all times.

October 2014 will mark four years since my brother in law's death. I am now 44.  I'm keenly aware that each day I wake up, it's a bonus day -- a day my brother in law didn't have. His illness, courage and death made me realize that my life-work priorities were out of whack. It was all work. No life. It was fun on the business front. But neither healthy nor sustainable. IT industry peers like Arlin Sorensen kept telling me: "It's not work-life balance. It's life-work balance. Get a life. Enjoy your family."

Chapter Three, Ages 45-66

I will turn 45 early next year. Amy and I are busy building After Nines Inc. We're striving to cover new ground -- rather than retrace our previous footsteps.

We're jogging forward with eyes wide open. I realize there's no guarantee that I get to complete Chapter Three. Nor is there a guarantee that I get to move on to Chapter Four (ages 67-88). Based on my life experiences to this point, I'm now focused on a few core values and/or life learnings...

  1. At some point, you must go home: I completely disappeared into the business world the past six years or so. My kids are now ages 16, 14 and 9. My wife, Annemarie, has done an amazing job as CEO of our household and family. Her unwavering support allowed me to pursue the entrepreneurial dream. The story is similar for Amy and her husband Larry; he freed Amy to pursue business dreams that were otherwise not reachable. But at some point you NEED to go home before it's too late.
  2. Money can buy freedom, but not happiness: America's culture teaches us to consume -- non-stop. Get a new smartphone every two years. Lease a new car every three years. Buy more house than you can afford TODAY because your salary will "grow" to support the lofty mortgage TOMORROW. In many cases, it's perfectly fine to consume those "wants" -- but too often as a culture we consider them "needs." The true power of money, in my mind, is the ability to buy freedom and time. Of course, we've all got limited time. My goal is to shift as much of that rare commodity -- time -- toward family. I'm finally doing a decent job at that.
  3. Never stop taking risks: Ironically, playing it "safe" is actually the riskiest move of all. Thousands of editors "played it safe" at newspapers as their industry collapsed. Thousands of folks sit on cash because they're too nervous to take a long-term view of the market -- and that cash has less and less buying power every day due to inflation. Thousands of businesses ignore their own inventions (Xerox and the GUI; Kodak and the digital camera) because they don't want to cannibalize existing revenue streams. But rivals always move in for the kill. Always. With those realities in mind, you've got to take calculated risks instead of sticking with the status quo.
  4. Gambling and risk taking are not the same: When you gamble on something -- a penny stock, a football game -- you typically have no control over the outcome. When you take a risk, you're using multiple first-hand knowledge points (your business experience, your market expertise, your industry relationships) to push the odds toward your favor. And very often the best "risks" in life involve "betting" on yourself and those whom you trust most. Like my wife, Annemarie. And my best friend, Amy Katz.
  5. Yesterday's achievements don't count: As the CEO of a software company once told me: What if Steve Jobs stopped at the Mac? What if Walt Disney stopped at Mickey Mouse?
  6. Life gets complex. Simplify everything: As a culture we're always striving for more. At some point, you've got to strive for less. When you focus on less and boil your life down to two or three really important things -- for instance: faith, family, friends -- the path forward becomes clearer.

With that bullet list in mind, I'm working hard to ensure Chapter Three (Ages 45-66) is truly balanced. I may get the priorities mixed up from time to time. But I'm making progress. Amy is, too. Life-work balance is in our business plan. And its hard-coded into our tagline: "Timeless IT guidance. From 9:01 daily."

We're focused like a laser on our clientele. But please don't blame us if we steal an extra minute to be with our families.