The Millennial Boomer Professional Shadow

Once in a while I get hit with a giant “duh, I should have thought of that.” Last night was one of those prized moments. During a 2AM business meeting at Denny’s in Santa Monica – apple crumble and two cups of coffee later – my partner looks over at me and asks: “So why aren’t you shadowing and writing about successful Millennial Boomers in your blog?”

I should have thought of this sooner: I’ve been doing the whole shadowing program for ummm, the last five years! At first, it was an effort to help my interns get ahead in their careers by pairing them up with a client or two and letting them have full access after the client Okayed it. I wanted my interns to get the full real world experience before I let my darlings go out into the big bad world. What can I say, I’ve been a mother practically my entire life.

After about my sixteenth intern it became abundantly clear how much value they garnered from the whole experience; but the model was off and something was missing; the whole idea needed perspective. I never really put my finger on it until 2AM last night – or is that this morning? I tell ya, Denny’s business meetings are just legendary in my life. So many breakthroughs happen between the fries and pie…

I realized the model needed to become more parallel. It needed a more seasoned perspective – more of a collegial learning experience. Now, for the first time I could easily answer the question posed by my partner in that late night impromptu meeting. “Why don’t you shadow successful Millennial Boomers?” Why the hell not!?

After all, I was the one that coached all the interns about how to shadow my executive clients for so many years: I’ve become THE Professional Shadow. So that’s what I’m going to do. Professionally shadow successful Millennial Boomers and tell you – my burgeoning Millennial Boomer readers – all about the experience. I hope you’re ready for this; because I do mean “all”.

Each month, for the next 12 months, I’ll shadow an executive Boomer that is living a Millennial Boomer life. I’ll spend time to understand his (or her) world; get the low-down on the good, the bad, and the ugly. Has their personal life become more strained in this new Business 2.0 world? How do they stay motivated when the media tells them they are becoming obsolete? What were some of the major pitfalls they would have planned to avoid? What were some great decisions and not so great decisions they made along the way and how did those decisions form the success they enjoy now?

I think you can agree there’s no better way to learn than from those who have been there done that. Sounds like a great idea to me and so does the shoe shopping trip I plan to take to celebrate. Ta!

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