Gary Vee and The Flamingos

Happy Flamingo Birthday to me!

Happy Flamingo Birthday to me!

 No, the title of this post does not refer to a 1960s rock band. Though, I suppose it could!

I recently had a milestone birthday. I won’t say which one, but I will tell you there were flamingos involved. Which was fun, because I LOVE flamingos! There is a post why here. Gosh I wish there were a flamingo emoji to type right here and now! But back to the point . . .


I have never been one to worry too much about getting older. Possibly because I didn’t start getting grey hairs until about 2 weeks ago. Thanks, Dad! Ok it was 2 years not 2 weeks ago, but still I won the genetic lottery with late onset grey hairs.

But the flamingo birthday did make me start to feel like I was running out of time. This feeling came only partly because I had so recently started a new career. For me, and I suspect for a lot of people in my demographic, this sense of limited time for making a meaningful contribution (not to mention build up retirement savings that will last another 40 years!) comes in equal measure from our youth centric culture and a societal message that we should be winding down when we hit a certain age.

Do you remember that ad campaign for a financial institution that promised Freedom at 55 for customers who invested with them? Even if you don't remember the particular advertisement, you are no doubt familiar with the concept because it has since made its way into our collective consciousness about what a successful life looks like, at least in North America.


I expect I am not the only one who internalized the message that being able to retire by 55 was a sign of a successful life. That message was strengthened for me by the fact my parents, and most of their friends, retired around age 55. They are in their mid 70s now and have spent the past 20 years travelling and living a very active retired life.

The reality for me is that if I were to “retire” at 55 I would not be able to sustain the lifestyle to which I have become accustomed (I was a late bloomer with regards to financial responsibility! (More on that in another post)  AND I would be bored out of my mind! I thrive on challenges and learning new things. Thus the creation of the Stellar Life Project! (I set up and operate this website almost entirely by my self. Except for the one time I broke it and had to get professional help!)

Ok. So, back to the flamingo birthday and my sense of diminishing time to make a meaningful contribution and build the life I want. (Yet another occasion when a flamingo emoji would come in handy!)

I changed careers in my mid 40s. Not because I was unhappy with my work, in fact I really loved my job as a high school English teacher, but as a result of events that were outside of my control. If you are curious about that story, check out the about me page.


I had this feeling like I was starting over, only with a lot less time than I had the last time I started. And it was true. I wasn’t 25 anymore. This awareness was a constant cloud over any success I experienced. I crushed it right away in my new career. I got the rookie of the year award in my first year of real estate and then by year 3 I had tripled my business and I was making more money than I ever had before. I was happy when I was working with clients and helping them make their housing dreams into reality.

And yet . . . I didn’t feel successful and I couldn’t shake the idea that I didn’t have much time to get this right. By this I mean life. What can I say? I am a hyper-achiever (not a good thing by the way) and so I am always looking at what I haven’t done instead of celebrating what I have accomplished.

 And then a (younger) friend sent me this clip by Gary Vaynerchuck:

Until I saw this video, I had never heard of GaryVee.

Now, I can divide my life into two parts: before and after GaryVee. Yes, the impact was that profound.

What I learned from GaryVee: I am better equipped than my younger self to do anything I want to do! And I have more time than I realized.

This idea of working only until 65 is outdated. We live in a very different world than our parents. My dad retired at 55 and he has been travelling and enjoying his retired life for the almost 20 years now. And that’s great for him because he didn’t love his job. But I still feel like there are things I want to do. I want to continue to help people in the work I do and I want to create things that bring me joy. That’s why I am motivated to create meaningful relationships with my clients. It’s why I write and why I draw (badly) in my bullet journal and share the results on social media! And Gary Vee pointed out that I have time to do those things and more.

Don’t get me wrong, I would love to spend my time travelling and playing pickle ball. Well, I actually have no interest in pickle ball. I would do yoga retreats instead :) But I do those things now and they punctuate the work I so love to do and they are an extension of the creativity I am trying to cultivate in my life.

The message in the above video was like a free pass to me. I have time to do what ever I really want to do. Not everything. But whoever has time to do EVERYTHING they want? But, we all have time to do the things we REALLY want to do. It’s not too late and it doesn’t matter how long it takes. Because I have time.

That’s why I started this blog and my youtube channel. I have always wanted to tell my stories. Teaching allowed me to share some of my stories with my students. But it left little time for actually writing. My business now also puts a lot of demands on my time and so I could continue to make the excuse that I am too busy or too tired. But when I asked myself earlier this year how much time I was spending in my Zone of Genius, the answer was NOT ENOUGH. So, with Gary Vee’s words in my head, I was determined to take action.

I am so grateful to be living in these times where anyone, including me!, can start a blog and a youtube channel and send her ideas out into the world. To be perfectly honest, I write because I need to write. And now that I have started writing again after many years of not writing, I feel like a desert traveller who has come to a magical life giving spring of water. I do hope that my words reach someone else and inspire them to choose a stellar life, but I am happy that by working on the various components of my Stellar Life Project (this blog, the youtube channel and my Instagram account), I am living my stellar life by being in a constant state of learning and by telling my stories.

GaryVee ends this video with these words: “Fuck winding it up. Start it up! You’re only 50.” I have been silent too long. Thoughts of not being good enough or not having something important enough to say have choked me to silence (yet another post to write on all of that!). But I have another 40 years in front of me. Maybe another 53 if I live to be 103 like my great-grandfather! So, I am going to tell my stories for anyone who cares to read them. Maybe it will only be my grand children. Good. I want them to know what I have learned about living a stellar life!


I want you to know too. Thanks for sticking with me this far. I don’t have it all figured out yet, but I have time. I have learned a few things a long the way and so, in hopes of saving you some time, I will continue to share what I have learned and what I am still learning. What I know for sure is that we are ALREADY STELLAR!

Deb Stellingwerff