Dear Joe: Where Do You Want to Be In Five Years?

I gotta concede: I dislike the headline and I dislike the question. Generally speaking, I can frequently look 12 to 18 months down the road. Anything further than that is so hard to predict. But when an old pal asked me where I want to be in five years -- at age 50, oh my -- I actually had a few answers. 

But before I share those thoughts, here's my bigger picture thinking:

  • I increasingly view my own milestones based on where my kids are in their lives. Sometimes that can be dangerous -- since predicting your kids' future isn't easy. But you can at least pencil in the big milestones -- high school graduation, potential college expenses, etc. Ultimately, you do need to organize your life (and finances) around those milestones.
  • I increasingly realize that businesses frequently last far longer -- or far shorter -- than I initially expect. Many of my former employers are now out of business or under new ownership. And yet, some of the brands Amy Katz and I have co-founded continue to march forward under different owners.
  • I'm now age 44. I'll be 45 in a few months. Somewhere in my late 30s, my "career" goal shifted from "make more money" to "pursue happiness" at all costs (well, within reason I guess).

Answer the Question

With those realities in mind, here's where I hope to be in five years -- the year 2020, at age 50 (again, oh my).

1. Right Here, But Reinvented: Over my 22-year career in IT media, I've bounced from big companies to startups to my own ventures. I've enjoyed each stage of the game for its own reasons. But ultimately, I enjoy charting my own destiny. And I think Amy Katz (co-founder and CEO of After Nines Inc.) has come to a similar conclusion. So I do hope to be chugging along at After Nines Inc. in 2020. The business may look quite different. My skill set may look quite different. But I hope to be "in control" of my destiny.

2. Physical Location - Anywhere: I live on Long Island. Most of my career has involved heavy business travel. More recently, my wife and I have focused on more family trips. Sometimes, I do have to work during family travel. But I enjoy it -- typically cranking away from about 5am ET to 8am ET before joining my family to start the day. And that day can start anywhere in the world. Anywhere.

3. Key Priorities: On the business front, staying close to emerging IT trends (no change there), plus mentoring kids who are graduating college and pursuing careers in IT media (whatever that means in 2020). On the family front, my two oldest sons should be out of high school by that time, and my youngest son will be in high school. Notice I didn't say I will have two sons in college. My wife and I do expect them to head to college. But as Chris Chase and I discussed during yesterday's podcast (Episode 12), college isn't for everyone -- especially as some skill sets move from colleges to trade schools. Ultimately, I just want my wife and kids to be healthy and happy. Everything else is gravy.

4. New Business Launches: Actually, I doubt I'll ever launch another business. I think After Nines Inc. is it for me (though I reserve the right to go back on that statement). We'll surely continue to launch a range of products and services under the After Nines banner. I think it's safe to say Amy and I have a few ideas for 2015 and 2016. But beyond that, we'll need to focus on course corrections for existing products before looking further down the road to 2017 and beyond.

5. Hobbies, Toys: I know I'm way late on this one. But I only recently rode a Segway for the first time. Way cool. I want one -- for about one-tenth the list price. Any sellers? I also plan to "buy back" a bunch of retro gaming systems from the 1970s and 1980s. Yes, I've already got the Atari 2600 -- actually, four of them are stockpiled in my attic, and one is in my home office. Next up: An Atari 800 and perhaps an Intellivision.

6. Time: The last but single most important item on my list. Time is the one commodity that I always want more of. More time with my wife and family, in particular. I'm starting to achieve that now. I've gone from an "F" in this area to mostly a "C" and perhaps even a "B" during some weeks. I know there are no guarantees in life. And that's precisely why "Time" isn't a focus that can wait until 2020.

And then one day you find ten years have got behind you.
No one told you when to run. You missed the starting gun.
— Roger Waters

Read that quote, and you begin to see why I dislike the headline ("Where will you be in five years?") Yes, long-term planning is important. But don't forget to live for the current moment -- every moment.

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