Success at Any Age: The Baby Boomer’s (and Gen Y) Guide to Becoming an Overnight Success

by / ⠀Personal Branding Startup Advice / April 4, 2012

If only I could go back to my twenties and know what I know now, at age 57. I have screwed up more times than anyone ever had the right to, and here three decades later I am finally getting my act together. There are lots of Boomers out there that have the one thing you Millennials really need: experience. The good, the bad and surely the ugly, has given the Boomers a very tough skin and we want to give back; to you. You, who are more brilliant and more technologically savvy and eat, breathe and sleep social media that to us, is like a foreign antibody that we know we need to embrace, but scares the crap out of us.

I’ve been “self-employed”

All my life I have been an ‘entrepreneur,” and highly unemployable, but years ago that term was seldom used. We were just “self-employed” which came with all the perks- and the baggage- that it does today. Business was surprisingly simple back in the pre-PC days and technology was as innovative as the dinosaur-like fax machine, which is on the endangered list as we speak. For decades, from about the fifties to the eighties, the world of business pretty much moved at a snails pace, especially by today’s standards. The “rules” remained fairly intact and what worked last year, or five years ago, or even last decade, was probably still OK. In today’s post 2000 world the rules are so inexact and malleable that they should be written in pencil or on a dry erasable board, since you can be sure that by the time you embrace today’s rules, they are gone, just like yesterdays “fastest processor” becomes obsolete.

The three phases

Over the past three years and long past it’s due, I finally began to understand myself. I put aside my inflated ego and became humble and started to really truly, with 100% conviction, “give back.” The number of times I failed is embarrassing, but when I reached my deepest deep, my lowest point of pain, I wrote a book and poured out my failures in the hope I could help others. And I looked for other Baby Boomers to learn from and share their stories. I broke down the life cycle of business into Phases One, Two and Three. Phase One is from 20-30 (Gen Y), two is from 30-50, (mostly Gen X) and the Boomers in Phase Three. As I interviewed dozens all across North America some surprising results showed up. Of the many Millennials I spoke with I was shocked and amazed at what they- and you- have done, and that is you have been able to create business success 90% faster than most Boomers ever did. There were more similarities between the Boomers that mostly shun social media and the Ys that embrace it, than I expected to find. The Boomers were raised in a tougher, harder, much different world than what the Millennials have been raised in. For Boomers, we were not all “winners” and did get all the wonderfully awesome tools and support and accolades that you may have gotten all your life. The Boomers “lost” many times, so we got used it and learned how to learn from it and bounce back. I guarantee you that if anyone under 30 speaks with a Boomer lifelong entrepreneur, you will hear stories and learn much more than you expected.

Coming together

So rather than have that happen randomly I am creating an intentional outcome, and that is mentorship classes between the Gen Y and the Boomers. The program is NOT exclusionary and everyone can play, regardless of the Generation they/you are in and regardless of age, sex, nationality, religions or any other identifying biases anyone can carry.

The United States is getting their (our) asses kicked by cheaper labor, more focused and highly educated students and a host of different factors coming at us from different countries. My conviction is that America may never and probably will never be The Economic Superpower it once was, BUT what other country can tap into the educational brainpower and experience of 73 million Boomers and mix that in with the collective technological and social media skills of 80 million Millennials? Can you imagine the innovation we can create; the new businesses- and jobs- we can create by focusing our talents and energies? I call it the New Economic Paradigm.

So that is my mission, my goal, my lifelong commitment and I will be teaching and speaking and training towards that end. Much of these concepts are described in my book along with the mentorship program, so the question I have for you is:

Would you like to play??

You can fail alone, but you cannot succeed alone, and I wish to engage all the Millennials as well as the Boomers to create this reality. With the greatest of respect I am your willing partner in this new economic stimulus program.

Bio: A bio may be redundant as this concept pretty much shares my experiences and can only hope that your path is less bumpy than mine was. I welcome any and all social media wizards that would like to partner with me to launch this nationwide program. Visit for more information.

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.