My favorite read of the week is "The Biggest Money Mistakes We Make—Decade by Decade," an in-depth piece from The Wall Street Journal. As I read the piece multiple times, I began to compare and contrast the article's lessons to my own life. Here's the blow by blow.

Life In Your 20s

The Journal Says: You're likely playing it too safe -- especially with investments and retirement accounts. They should be weighted toward higher-risk growth stocks rather than low-risk income investments. Your money will have plenty of time to recover amid a market correction, pundits assert.

ChannelE2E says: When I landed my first job out of college with InformationWeek, it was July 1992. The twist: My employer required me to be "on the job" for a full year before allowing me to make 401K retirement contributions. At first glance, that pushed my 401K participation out until July 1993. But I couldn't enroll until the first of the year. That pushed me out again -- until January 1, 1994. Bummer. That was 18 months of lost contributions as well as lost matching contributions from my employer.

  • My dumbest financial move of the decade: Buying a used car that had a bad reputation. It died with 75,000 miles on it.
  • My smartest financial move of the decade: Marrying my wife. Amid all the perks of marrying a wonderful person there was a huge bonus: She's a great saver. That allowed us to buy our first house. And we lived below our means during most of our 20s.
  • What I'd tell my 20-year-old self today: Max out your 401k contribution -- at least up to the maximum for the company match.

Life In Your 30s

The Journal Says: You'll get overwhelmed by complexity. You're having kids but still trying to live the high life like in your 20s.

ChannelE2E Says: I suffered my first layoff at age 31 during the dot-com implosion. I was out of work for about four months. It was humbling. But we had a few dollars put away from our 20s. So we ultimately banked a portion of my severance check.

  • My dumbest financial move of the decade: I got addicted to Disney World vacations. Our family grew and we soon had three young sons. We went to Disney World every year for the first few years of my 30s. One year, we went twice. That particularly year was the first year we didn't save any money while married... Not smart.
  • My smartest financial move of the decade: This is a three-parter. First, we purchased a bigger house --- using the appreciation from our first house along with some savings from our 20s. The result was a larger home without a larger mortgage. The second smartest financial move involved incorporating my first business (JCP Media). Purely freelance in nature. But it at least taught me to watch cash flow, chase payments, meet deadlines and deliver customer service. This  set the stage for my smartest financial move -- co-launching a business with Amy Katz in 2008. We bootstrapped the business rather than taking out loans.
  • What I'd tell my 30-year-old-self today: The bad career days are part of a journey and not a permanent destination. On the financial front go find a financial advisor to start building your retirement plan now.

Life In Your 40s

The Journal Says: You're set to misjudge big expenses. Instead of paying down your mortgage you stretch it out for decades to come. You also get "sandwiched" between expenses for your kids and potential expenses for your aging parents.

  • My dumbest financial move of the decade: Trying to manage investments and retirement planning on my own. I'm not talking about huge sums of money. But just the basics -- how much to put aside and in what types of investments -- requires time I didn't have. I finally corrected this error around age 43.
  • My smartest financial move of the decade: This is another three-parter. First selling our business in 2011, then exiting that business in 2014. Selling wasn't a life changer financially. But it ensured my life savings wasn't tied up in a single investment (i.e., a company). And second, exiting the business allowed me to recharge and reprioritize my life. And that set the stage for ChannelE2E's launch in 2015. I was 45 at the time.
  • What I'd tell my 40-year-old self: The long hours of a startup can be worth it -- if you have a true plan to scale the business and/or exit.

Life In Your 50s

The Journal Says: You're now in a difficult catch-up mode. On the one hand, you want to live a good lifestyle now that your kids are likely out of college. But on the other hand, a growing number of folks want to start their first businesses while in their 50s. And that can involve a risky drain on your savings.

  • My dumbest financial move of the decade: Too soon to say. I'll soon turn 47. When I push into my 50s, I suspect a major financial mistake may involve emotions vs. dollars and cents. My emotions say my wife and I want to put each of our three children through college, and that can be $60,000 per year. Multiply that  (3 kids X 4 years) and the total cost is $720,000. And that's just if college costs hold steady. Hopefully, my wife and I will avoid emotional decisions and out-of-control loans. Instead, we'll strive to focus on the dollars and cents of it all. State colleges  here in New York cost closer to $20,000 per year (or $240,000 total cost for three kids). And some private schools award merit scholarships, which can slash college costs by roughly $20,000 per year or more. Plus, there are financial aid options.
  • Warning: During this decade I think many entrepreneurs will make a fatal or near-fatal mistake. They'll have no feel for their business's value and no potential exit plan. HTG Peer Groups CEO Arlin Sorensen calls this the massive Valuation Gap that awaits many MSPs and IT service providers.
  • My smartest financial move of the decade: Hopefully, it involves something with ChannelE2E. Amy and I don't plan to sell this business. Rather, we're running it in a cost-effective manner to keep paying our bills while putting money into our respective retirement plans.

Life In Your 60s

The Journal Says: Most people fail to delegate important tasks and financial decisions as their capacities diminish—potentially leading to bad financial moves.

  • My dumbest financial move during this decade: Far too soon to say since this decade won't start for another 14 years or so. Hopefully, my wife and I can avoid "emotional" big ticket items like the dream retirement home that really isn't within our reach.
  • My smartest financial move during this decade: At this point, I don't think I'll be a business builder or true entrepreneur anymore. Perhaps I'll be consulting in some form. Again, it's too soon to say -- especially since two of my core long term interests (IT and media) are volatile markets.

No doubt, many entrepreneurial journeys can stretch on into your 70s and beyond. The Journal didn't look that far ahead. Neither will I because bedtime is calling.