10 Important Lessons From My 20s and 30s (Now That I’m 40)

I turned the big 4–0 this year. Yes — that typically dreaded milestone of FORTY.

For the last year, I have been a true digital nomad, working and living remotely while continuing to support my agency team. I have been very deliberate about doing something I neglected in years past when I travelled: connecting more with the local people than partying with tourists, basecamping and living for extended periods of time while learning about cultural nuances, myths and legends, the folklore of the people you're breaking bread with and learning, laughing and bartering with. This authentic immersion has become very important to me as a traveler.

Every year, I have a ritual where I mentally unpack key lessons insights I have learned, replaying scenes of my experiences in my head and taking notes. Perhaps because I have always been such a movie buff and lover of storytelling, I tend to mentally view my life from the perspective of a series of cinematic closeups, wider shots and establishing, contextual shots.

There are sometimes those life moments of victory, moments where we get exactly what we want.

Then of course there are the inevitable obstacles and challenges.

Life moments when we’re tested and pushed to our limits, moments that we often depict in the playback of our minds as failure — when in reality, they should more be looked at as lessons and learnings that can inform the journey ahead.

When I was 22, or 27, or even 35 — age 40 seemed so distant and far?away

I found myself thinking about writing this piece when I turned 39, marvelling at the passage of time and remembering how, when I was 22, or 27, or even 35, 40 seemed so distant and far away, as if it’s this sagely old age after which nothing good ever happens again.

But of course that is just some ageist BS.

While there is nothing like being young and coming of age — I’m also learning that there is much to be said about the age I find myself right now.

A friend of mine recently called it being “Young and Wise” — he was referring to the fact that we are, at 40, still relatively young but also having accumulated many scars from various life experiences.

Here are 10 lessons that I learned during the last two decades, tidbits that could help anyone coming up in the world of business, creative entrepreneurs, designers or artists — especially if you are a twenty or thirty something blissfully navigating the world around you and never imagining that one day you’ll have to gracefully share your wisdom with those younger than you.

Life Really Doesn’t Start Until?40

It’s so crazy that something so cliche, that I have heard so many times — and rolled my eyes at every time — is starting to unfold in my lived experience.

I feel mentally prepared for the future in a way that I have never felt before.

When I was 20, I had zero roadmap of what to do, what was going to happen, where life would take me or where things would end?up.

I also had zero strategy or tactics to deploy to chip away at trying to find the roadmap.

You really are a blank slate entering your 20s— and in some ways I really miss that decade, the innocence, the naiveté, the self-discovery.

If at 20 you have zero roadmap and zero strategy — at 30, you are beginning to formulate a strategy, informed by some of the hard and painful lessons you’ve learned in your 20s.

You’ve worked out some personal redlines, some boundaries, some guiding principles, the beginnings of an overarching worldview, and you employ some tactics that keep you securely and safely locked into your own particular flavour of self-delusion.

But you still have no clue what’s going to happen, or what exactly is currently happening, or even what you particularly want to happen!

Your strategy is largely one of avoidance — you have pretty solid ideas about outcomes you don’t want, situations and scenarios that you would prefer not happen. You are beginning to deploy a general life strategy but you still have zero (or very little) roadmap of what is to come — you still have harsh lessons to learn over the next decade

It’s really at age 40 I’m discovering that, for the first time ever, I’m now in possession of both of the roadmap and the strategy that I didn’t possess coming into my 20s — and this goes back to some of that developed wisdom that I referred to earlier.

At 40 you have a Roadmap AND you have a?Strategy

Your roadmap is becoming clear — the value you want to bring to the world, the politics and principles that you stand for, the concepts and ideas that bring you joy, playfulness and peace

Your strategy to accomplish and achieve the milestones on your roadmap is also much easier to locate at age 40, and involves a lot of meditation, mindfulness, reflection, reading — and strenuous exercise.

Ninety Percent of Things Don’t Matter in the?End

It’s usually when I find myself in the trance-like state that is brought on by a great cardio or weight training session that #2 on this list comes into view.

I’m talking about the fact that in the end, 90% of the things we worry about ends up not amounting to anything of significance.

It’s actually painful to calculate, to quantify how little so many of the things we get upset about end up mattering in the end.

Over time, you learn that its beneficial to zoom out as I mentioned earlier — this is where the camera that is in my brain starts to zoom into wide shots and establishing shots — and remember how relatively small and insignificant we are in comparison to the vastness of the universe.

In these moments, I find it useful to remember the famous picture of the Pale Blue Dot — and these famous words by Carl Sagan:

"... if you look at it, you see a dot. That's here. That's home. That's us. On it, everyone you ever heard of, every human being who ever lived, lived out their lives. The aggregate of all our joys and sufferings, thousands of confident religions, ideologies and economic doctrines, every hunter and forager, every hero and coward, every creator and destroyer of civilizations, every king and peasant, every young couple in love, every hopeful child, every mother and father, every inventor and explorer, every teacher of morals, every corrupt politician, every superstar, every supreme leader, every saint and sinner in the history of our species, lived there on a mote of dust, suspended in a sunbeam. The earth is a very small stage in a vast cosmic arena. Think of the rivers of blood spilled by all those generals and emperors so that in glory and in triumph they could become the momentary masters of a fraction of a dot. Think of the endless cruelties visited by the inhabitants of one corner of the dot on scarcely distinguishable inhabitants of some other corner of the dot. How frequent their misunderstandings, how eager they are to kill one another, how fervent their hatreds. Our posturings, our imagined self-importance, the delusion that we have some privileged position in the universe, are challenged by this point of pale light. Our planet is a lonely speck in the great enveloping cosmic dark. In our obscurity -- in all this vastness -- there is no hint that help will come from elsewhere to save us from ourselves. It is up to us. It's been said that astronomy is a humbling, and I might add, a character building experience. To my mind, there is perhaps no better demonstration of the folly of human conceits than this distant image of our tiny world. To me, it underscores our responsibility to deal more kindly and compassionately with one another and to preserve and cherish that pale blue dot, the only home we've ever known."

Treat People?Well

The futility and pointless cruelty of human strife brings me nicely into the 3rd lesson I have learned in my 20s and 30s: treat people well.

Reputation ends up being everything. People have long memories for those they remember as being assholes, abusive, self-absorbed or cruel.

There is that famous quote that at this point has been attributed to 400 different people in history, but whose basic premise is:

People will forget what you did, people will forget what you said — but they will never forget how you made them?feel.

Makes sense, right?

We are emotional beings, living in a world of emotional stimuli — positive, neutral and negative.

Of course you can’t be perfect, and most of us can definitely say we have committed all of the aforementioned sins — but generally, these are attitudes I would pay attention to.

Let’s just say the ROI on reputation — being at least perceived as good and kind to the people you come into contact with — in the long run this perception turns out to be astronomically in your favour.

Always Be?Honest

Important, but the most painful because we all want to be liked.

History has taught us that oftentimes, you will not be liked when you tell the truth.

There is a famous Malcolm X quote that I have come to love over the years. It has turned into a personal mantra of sorts:

I'm for justice, no matter who it is for or against.?I'm a human being, first and foremost, and as such I'm for whoever and whatever benefits humanity as a whole.”

The true essence of who Malcolm X was.

Or, at least, who I perceive him to have been.

It’s a tough standard to uphold, and at times it places you at odds with those you love. Strangely, at other times, it may even cause you to share opinions with those who are usually your enemies.

But the truth is the truth.

I hold an unwavering loyalty to it. To always try to at least be on the path to discovering it, because let’s face it — many aspects of our modern lives are set up to enable us to routinely lie and be untruthful with ourselves.

Think Critically

Which is a perfect segue into the 5th lesson on this list, and that is to always defer to being a critical thinker.

Read beyond the headlines.

Read between the lines.

Always seek deeper meanings, observing how things connect or link to one another — relationships between thoughts, ideas, groups of people, hierarchies and power structures, making note of who ultimately benefits from certain outcomes.

Modern life has made it very attractive to outsource our critical?thinking

I have become especially aware of how many blind spots, logical fallacies and cognitive biases we all carry around with us on the daily.

Modern life has made it very attractive for us to outsource our critical thinking faculties, to relinquish our individual power and autonomy, and instead have a litany of social and political structures, institutions, authorities and thought models do our thinking for us.

You’ll separate yourself from the pack, elevate from where you are and reach escape velocity on the path to where you want to be — the sooner you focus on this truth.

I can’t emphasize it enough. Think critically.

Give Love

This is a really important lesson, one of the most important on this list, arguably the single most important one.

It’s one that I find myself having to learn over and over again.

It can be so easy to get bogged down in the daily humdrum of life and forget that, whatever it is — and the it i’m referring to is the concept of love — is the lifeblood that powers our known universe, responsible for virtually everything good and positive about our existence.

Love is the lifeblood that powers our known?universe

Everything around you at this moment — the room that you are in, the piece of furniture you may be sitting on, the objects and products you see in front of you — remember that they are all labours of love, the results of an initial vision that some may once have thought silly or unnecessary or even unachievable.

Love can be many things.

Love can be a beautiful relationship that lasts the test of time. A marriage, partnership or friendship that enriches and empowers all involved to create amazing things together.

Love can be that kinetic frisson between certain people, spurring them to keep in touch with each other over many years, and even long distances.

Love is every amazing work of art, or book, or invention, every breathtaking statue or building you have ever seen.

These are all the results of love.

At least, this is what love means to me. Some people may have a different definition, so I’m curious to hear from you in the comments what the true meaning of love is to you.

Whatever love is, if you allow it, it feels really good when you give it, and it feels downright awesome when the feeling is mutual. After all, are we not all just a bunch of mirrors walking around, reflecting back the rays of energy that others beam at us?

Stay Curious

Question everything!

Assuming that you already know everything — or that you are beyond learning, that nothing is new under the sun — is not only really unattractive, cynical and myopic.

It’s also not a lot of fun.

I see this happening especially to some of my friends who are 80s born millennials like myself.

They forget that they are not yet old and wizened— they are still young, and there is much to be learned, and re-learned and — unlearned.

As Gary Vaynerchuk loves to remind his audiences — life is long!

You might not kick the bucket until you’re in your 90s or even older. So become dedicated to life-long learning, to thinking of yourself as a perpetual student.

You simply have no business becoming jaded and cynical at 30 or 35 or even 50 like so many people I know.

But easier said than done. It’s a struggle, one that needs to be grappled with daily. It can be frustrating to amass years of experience, knowledge, know-how, capacity and ability — and yet be constantly reminded that if you want to stay competitive and relevant — you must forever be learning new tactics and strategies, new languages, modes of communication and schools of thought.

Stay Humble

This one is on par with the Give Love lesson:

Humility is paramount.

I have learned this lesson the hard way, the easy way, the in-between way. From mentors I look up to. From books I have read. From heroes that I take example from.

Hell, I’m still learning this lesson every single week. And if we’re lucky, we live about 4000 weeks in our life.

So for me it’s been thousands of times learning this same lesson.

You’re not better than anybody else.

Everyone deserves to be heard, to have the freedom to pursue their dreams and ambitions, to hone their capacity for growth and expansion.

I’m reminded of several times in my 20s and 30s where I found myself starting from scratch, learning some new craft for the first time, and realizing that there will always be someone younger and more prodigious than you.

There will always be someone younger and more prodigious than?you

You can choose to check your ego at the door, learn from them, encourage their passion and celebrate their prodigy.

Or you can choose to do what I see a lot of people do: be stubbornly arrogant, refuse to acknowledge the expertise and experience of someone younger, and have their pride and insecurity block their absorption of necessary insights.

Always be prepared to reinvent yourself.

One instance I can vividly pinpoint is when, despite being a seasoned creative and marketing executive at age 36, I made a public pledge that I would spend the rest of my life crossing the mental chasm to becoming a creator.

I began earnestly learning digital storytelling, videography and film editing for the first time, sharpening my life skills — while also adding value for my agency clients.

Another instance is this past calendar year when I decided to deep-dive into crypto investing, DeFi and NFTs, getting involved with NFT projects and products, becoming familiar with the protocols, frameworks, networks and standards that make up the digital stack we refer to as Web3.

Do It For More Than?Money

Admittedly, I had this epiphany when I was already well into my late 30s.

But it feels great to finally be here, to have once and for all rejected the mental slavery that comes with building a life solely based on external optics, trying to impress people who don’t even care about you all that much anyways.

If I was airdropped 100 ETH right now, or several million dollars — what would I do differently with all of this new?wealth?

One morning, I asked myself this question: if I was airdropped 100 ETH right now or several million dollars — what would I do differently with all of this new wealth?

What would I wake up and do differently the next day?

When I realized that I would for the first time ever wake up and do the exact same things, a sense of ease washed over me.

It’s a critical place that I wish you all have the opportunity and capacity to arrive at.

Do it for more than money.

Do it for your family, your children, your village.

Do it for the best version of yourself.

Doing it for the best version of myself is when I’m actively learning, sharing my learnings with others, bringing different groups of people together, building consensus and creating bridges of understanding and enlightenment.

These things are my raison d’être — my reason for being.

These are values that no matter my net worth at any given moment — I feel myself committed and obligated towards.

It is indescribably liberating the first day you wake up and realize that making more money has no effect on your overarching life mission.

Always Have a?Mission

The 10th and final lesson I learned in my 20s and 30s is to always live a mission-oriented life.

I have seen this destroy so many people, literally engulf them in spiritual flames, and cause them to fall deeply into despair.

I have also seen the opposite — when you have learned this lesson, you literally have a pair of wings, a jetpack all fuelled up ready to take you to the moon.

It doesn’t make you impervious to peril or danger, but its the key to what fuels so many entrepreneurs and allows them to wake up the next day and the next day and the next day.

As some wise person said to me years ago, having a sense of mission allows entrepreneurs to almost giddily leap from failure to failure, until one day success is found.

Always have a?mission

I have religiously kept a vision board and a general roadmap of major and minor goals and dreams and objectives for my life.

I have had great successes. I have founded and exited several businesses in my career.

I have also had countless failures, huge missteps that make me chuckle to myself in my private moments, shaking my head at how things could have gone so comedically wrong.

But through and through — there is always a mission I’m working towards.

There is always a blueprint, a list of goals and objectives and actionables.

I have found that during periods when I’m journaling less or not committing to writing these lists out, when I’m not putting pen to paper and outlining a one-year or 18-month or even 5 year plan — my mental health begins to feel like it’s fraying.

Your missions can change or be amended — your values and the things you hold important will change over the course of your 20s and 30s.

At some point you may even have the experience of looking at your vision board and questioning whether these are things you really want — or whether they are merely things that society has programmed you over time to think that you want.

But don’t be fooled into giving up the practice. Your life will improve exponentially for it.

If you fail to plan — you plan to fail.

So cliche, right?

I’m not perfect. I have hundreds of projects and products and workflows and thoughts and ideas that I have not been able to follow through onor put a nice big check next to on a big shiny To Do List.

But invariably, I have learned there is an expansive power that comes with writing things down — something about intentionality and the energy involved in that intentionality has really shown me over the years to be more true than not.

What are some of the life lessons you learned in your 20s and 30s?

What are some of the life lessons you are learning right now, at whatever age you happen to be? I really want to hear from you and would love to hear your thoughts.

*******

I’m going to be writing a lot more pieces like this in the coming months, and I have made a resolution to amplify the quantity and quality of my content by doubling down on the platforms I love the most, where I spend most of my time — LinkedIn, Medium, Twitter and YouTube. You can also look out for video essays, stories and conversations coming down the pipeline as I learn and discuss key lessons and insights from sales professionals, marketers, founders, investors and entrepreneurs.