40 is the new… Well, 40.

The subject of age is a perennial one. I’m too old to… That’s a young man/woman’s… If only I was in my 20’s I’d… But I have good news for you my friends. Studies show that in the immortal words of Aaliyah — Age Ain’t Nothing But A Number.

Everyone over 30 is guilty of this — and let’s be honest we were complaining by 28 — that oh, how we long for our youth. There is a perception in this country that aging is somehow a curse, not a gift. Of course there is the usual, just be glad you’re alive thing. I’ve been on Instagram, I know. It’s everywhere, and there is a place for that. But not in this article. The problem with simply being grateful for life is that it means you’re good if you stop trying. Your cousin’s kid who hasn’t left the sofa for 3 months because of an acute Fortnite addiction is alive — and probably stoked to be — but that’s not the sort of insight I hope to leave you with.

“Oldies” but goodies

A recent article I read written by Ryan Holmes, was actually the one that inspired me to say something. Ryan, outside of having a powerful first name, is a serial entrepreneur and founder of Hootsuite an online social media management platform which I’m happy to report we’ve been using in my company since 2011. The article was called The average age of a successful entrepreneur? Nope, think older and it is a great and inspirational tale from an experienced boss citing studies indicating the lion share of successful entrepreneurs aren’t the Gates and Zuckerbergs they are in fact the Noyce, Hoffman, Wilson and Marcus types. Average age 43. (Bernie Marcus was 50 when he started his little “side hustle,” Home Depot.)

That is great and refreshing news for a lot of 40-somethings, or nearly 40-somethings who I’ve been meeting with recently who are feeling insecure or inadequate for not having “made it” by now. But in the words of my friend Cenk Uygur “of cooooooursseee!”

How else could it go? There is a disproportionate amount of time and energy being spent on the 20-something up-and-comers by the best and brightest minds in business while an entire segment of those on the cusp with age, experience and maybe a little dough is being largely ignored by the business/life coach elites — to their detriment I say. While I do agree that it is wildly important to work on the farm-team, if you’re going to play in the big leagues you should pay some attention to the current roster, right?

This is a common mistake but its expected right? So its easy to understand the why. Everyone likes best the new car, the new puppy, the second wife, the latest K-Swiss/Gary Vaynerchuk sneaker collab and so on. The latest and greatest is always desired, of course, but there is little that can be done that trumps life experience.

An example of this lies in the recurring themes that come up time and time again on YouTube from business guy du jour. One such topic is failure. There is no shortage of content out there on failing and why its ok. Hell, I’ve even piled-on myself in another article. But to my previous point about life experience, when these guys are speaking to an audience of 24-year-olds the concept is simply too foreign for them to fully understand. They’ve barely had opportunity to try let alone fail. A person who has taken a couple runs at different careers, businesses, marriages or relationships however, is infinitely more likely to have experienced failure and only then is the advice of forgiving yourself for it practical.

Now don’t get me wrong, I love, love, love a lot of the content being produced by a lot of these dudes — the GaryVees, Tony Robbins and Keir McLaren’s of the world — much of their advice is helpful, and at a minimum inspirational for entrepreneurs of all ages. But the point I’m trying to make is that much of what these guys espouse is being directed at an audience who is arguably less capable of doing something with it than those who’ve been around the block a couple times.

The issue here is not that its problematic to inspire the next generation with entrepreneurial energy, that is needed and necessary. It is that the same advice when ingested by the previous generation — now in their 30s and 40s — can leave them with doubt and insecurity. After all, if this content is meant for 20-somethings then I as a 38-year-old may have been doing the wrong things for 15-years or more. Shit. Look at all that time wasted. Shame spiral. Frowny-face emoji.

The best way to overcome these doubts however is to take stock of the many benefits of age and life experience and do your best to ingest all the rah-rah, inspirational content through that lens. Not that it will be easy but that it can be done. I too regularly fall victim to listening to some successful guy ranting on YouTube about what I need to do to find my way. I am often met with inspirational fire — then post-afterglow biting insecurity. The real moral here is be confident! Trust in yourself and be proud of your journey. Knock off that 40-is-the-new-20 bullshit and be proud of all you’ve done and what you’ve accomplished so far. After all, it took a whole lifetime of decisions — good, bad or otherwise — to get you here, so own it already!

There‘s more work to do…

This is a huge topic worthy of exploring and I will continue do so in subsequent articles. In the meantime what are your thoughts as entrepreneur or human being — young or old — on the topics of success? Aging? Motivational speakers? Who are your fav’s? Leave comments below!

CEO at R2. Founder at Teammate Apart. Remote work advocate. Consultant. Writer? TBD.