As I cross the 50-year boundary, my head is full. Full of ideas, full of things I want to do, full of the grocery list, full of regrets, and…

Full of stuff I wish I could tell my younger self. Stuff that’s based on how I thought, felt, and viewed the world at around 20 years old.

I’d like to find him and say these things, not because I’m unhappy where I am, but because of the waste. Wasted time, wasted emotions, and wasted growth.

Even though the audience is me, I suspect that you will find much of this helpful for yourself, at any age.

Here is the stuff that I’d tell my younger self…my 20-year old self.

Take More Risks

β€œSecurity is mostly a superstition. Life is either a daring adventure or nothing.”

– Helen Keller

Specifically with my own ego.

Several studies have shown that people who are at the end of their lives regret things they didn’t do, not the things they did that went wrong or at which they failed.

These regrets of omission are for the risks they didn’t take towards becoming their “true selves” and “living their dream life.”

Nobody walks up to you and lifts the veil on your authentic self. Nor does anybody walk up to you and hand you your dream life. Only you can figure these out.

And to do so, it’s going to take putting yourself out there and taking risks.

The risk of failing.

The risk of not being good at it.

The risk of losing.

The risk of making the wrong the decision.

The risk of looking like you made the wrong decision.

The risk of looking stupid.

The risk of getting laughed at.

The risk of someone else getting upset at you.

The risk of rejection.

The risk of letting someone know how you really feel.

The risk of what “they’re” going to think.

In hindsight, I can see now how fear ruled over me. Fear of what? All those things listed above. That was an easy list to write. I could keep going.

When my kids drive off, I always tell them in jest, “Drive fast and take chances!” I don’t mean it literally, and they know that. But it’s a just a little out-of-context reminder that they’re going to have to take some risks.

There is no reward without risk, and your ideal and authentic self is worth the risk.

Stop Playing By Their Rules

β€œDon’t β€˜I wonder’ through life. Just make it happen.” 

– Alex Banayan

A great example is illustrated by Alex Banayan in his book, The Third Door.

He tells the story of obtaining interviews with some of the most successful and influential people on the planet. People such as Bill Gates, Warren Buffet, Steven Spielberg, Tim Ferris, Larry King, etc.

The summary: he found that in all situations there are 3 doors through which you can walk (paraphrased from thirddoorbook.com):

  • Front Door: This is the main entrance for the ticket buyers. The people that follow the rules to see the show. It’s where 99 percent of the people wait in line, hoping to get in.
  • Back Door: This is the door for the people that have an “in”. Maybe they know somebody that can let them in, or introduce them to the right person.
  • Third Door: This is the door that the truly successful person creates…out of thin air. It’s created by shear force of will, effort, and creativity. It’s the entrance where you have to jump out of line, run down the alley, bang on the door a hundred times, crack open the window, and sneak through the kitchen.

Most people are front-door people. My 20-year old self was the consummate front door person. Figure out the rules, and play by them. To have success, you simply work within the framework and “get good”.

When front door people don’t succeed, they usually think it’s the back door people that are keeping them from success.

“Of course she got the contract, she know’s so-and-so.”

“Of course he was the one who got in, his family is wealthy.”

“Of course he got the promotion, he always has lunch with the boss.”

“Of course she created a successful business, she’s a stay-at-home mom with all the time in the world.”

But those aren’t back door successes. They are 3rd door successes. It’s the door you create and walk through that wins you the game.

Nobody is keeping you from success, or stealing your success unfairly. You’re just not playing the game according the winning rule book.

A warning: Once the third door approach is embraced, it becomes a super power that can be used for good or evil. Wield the power carefully.

Remember the celebrity college admissions scandal? Those kids didn’t get in to the colleges BECAUSE their parents were wealthy or famous (the back door).

They got in because their parents WANTED IT ENOUGH that they were WILLING TO USE their resources and influence to create the third door. They reframed the rules.

That’s obviously an example of using the third door power for evil, and it’s not what I am condoning. What I am condoning is the creativity and courage it takes to find or create that third door.

Once you find the 3rd door, beware of “they”. They will label you a brown-noser. They will wonder why you’re no longer hanging out with them at the corner of bitch and moan. They will even talk behind your back.

But those are the front door people.

Is it more important to stay in your lane, or to actually make an impact?

The rules are for everyone else.

Get Around the Right People

β€œYou are the average of the five people you spend the most time with.”

– Jim Rohn

Truth from the late Jim Rohn!

Perhaps the biggest influence on my journey, level of success (or failure), feelings, and overall happiness are those with whom I spend my time.

As a 20-year old, I at least knew with whom I DIDN’T want to spend my time.

I remember the palpable soul sucking I experienced around certain people: moaning about their job, moaning about their wife, moaning about the boss, moaning about their physical problems, moaning that it’s someone else’s fault.

But I wasn’t fully aware that seeking out the RIGHT people, not just avoiding the wrong people, is actually the greatest life hack there is.

Want to raise your game? Get around better players.

Feeling blue? Get around joyous people.

Want to feel love? Get around those that love you.

Want to start a successful business? Get around successful entrepreneurs.

Want to have a deeper and more authentic faith? Get around those that have it and aren’t afraid to question it.

Want to move up in your company? Get around those that have those positions now.

Want to feel, look, and be physically healthy? Get around those that eat and train for performance and health.

It’s these people:

  1. People that have what you want
  2. People that are how you want to be
  3. People that have done or are doing what you want to do
  4. People that make you want to be a better person
  5. People that just plain make you feel great

Make your circle an intentional and exclusive group.

Don’t Follow Your Passion, But Always Bring It With you

“We have to stop telling kids to blindly follow their passion and show them the opportunities that exist. “

– Mike Rowe

* Side Note: In my opinion, our culture egregiously overuses the word “passion”. In fact, I find it now has little meaning. Purposefully, I overuse it 11 times in the following paragraphs. You’re welcome.

What? Don’t follow your dreams?! Blasphemy in the day and age of the “you can be anything” fable we tell our kids.

Actually, this isn’t about following or not following your dreams. This is about how you show up in your life each day.

“Follow your passion” is not lousy advice because no one should. It’s lousy advice because it can easily be used as an excuse to NOT go forth and do!

What if you didn’t have a burning passion since you were 8 years old?

What if you are passionate about many things?

What if your passion changes over time?

What if you stink at the skills related to your passion?

Does that mean you should just sit around and do nothing, or play the victim, or be angry, or blame God?

My 20-year old self didn’t really know what my passion was. I was an engineer, but SHOULD I be a musician? How about an astronaut? Maybe a pastor?

I spent an inordinate amount of time and effort on introspection and prayer, ruminating on “what is my passion?” Although I didn’t frame it or think of it that way.

My frame was external. I asked God for my purpose, and then eventually blamed God for my lack of vision.

“What does God want me to do?”

“Just give me a sign, God, and I’ll do it.”

The lightning bolt never came, or hasn’t yet. In fact, I no longer think that lightning bolts come for most people.

But I did find it, or rather, I continue to find it each day. I find it by simply doing the work, and bringing the passion in what I am doing. I find it by trying new things, saying no to some other things, and using some of the other advice I give myself here:

  • Taking risks
  • Finding my voice
  • Getting out of my comfort zone
  • Getting around the right people

Not every day or week is blissful. I don’t look forward to every task I have to accomplish. There are loads of things I’d rather not do, or make me squirm.

But I also now know that not finding passion in what I do is a fault of my own attitude and missed opportunity. Not because they, or the government, or God, or the Universe owes me something.

Do the work to determine what you like, what you are good at, and what is helpful to your community and this world. It’s at the intersection of those things that you will find your personal sweet spot.

If you do feel a calling…a deep-down-in-your-bones-calling, then pursue it. To be successful at it, you will have to bring your passion. It will take courage, drive, focus, and perseverance. You will have to do the hard stuff.

I guarantee that you won’t ever find a calling by sitting at the bar complaining that the world doesn’t “get you.” Nor by only working when you feel like it.

Here it is, put nice and succinctly by Mike Rowe. Go do something, apply yourself and find your purpose by action.

Do the work, and bring your passions with you. You will be amazed at how your days start looking brighter, and your life starts to take off.

Get Comfortable Being Uncomfortable

β€œDo one thing every day that scares you.”

– Eleanor Roosevelt

Expose yourself to emotional danger.

I thought the path to success was about finding the path of least Resistance. I don’t mean “least work”. I mean Steven Pressfield’s Resistance.

Steven’s masterful book, “The War of Art” births Resistance as a real, 3rd party force whose sole purpose is to keep you in your comfort zone. Unfortunately, when you’re in that comfort zone, you’re not growing.

If it felt scary or I wasn’t comfortable, I believed it wasn’t for me. Little did I know then that those were the very things that I should have been pursuing.

Leadership, creativity, entrepreneurship, public speaking, writing, expression of my voice…All things I SHOULD HAVE been pursuing with vigor, but instead I was running away.

Keep my head down, play by the rules, avoid scary, stay in the framework, never get in trouble, and all will turn out dreamy. I can now see the Resistance at work through that mindset.

With clairvoyant hindsight, I can recognize the growth monuments along my path. Without fail, each time I grew, made progress, or ended up better, it was because I stepped out, or was forced out of my comfort zone.

I can also look back and regret the opportunities missed or not taken because I was too afraid to take that step. Resistance won those battles.

No matter how much you fight to stay in that zone, however, it’s not always your choice. Whether you want to or not, there will be times when you get shoved outside of your comfort zone.

How will you deal it? It’s times like these that will determine your future self. Will you man-up or will you wither?

You’re going to get laid off.

You will have to give the presentation.

Somebody close to you will hurt you.

Your family will have a crisis.

You will be asked to solve the hard problem.

You will have an existential crisis of faith.

These things are coming. You can count on it. With a mindset that recognizes opportunities, not only can you deal with them, but you can grow through them.

The more you live with sweaty palms, weak knees, and the tension of discomfort, the better equipped you will be to handle them.

Expose yourself to some emotional danger.

Perfection is Your Enemy

β€œI am always doing that which I cannot do, in order that I may learn how to do it.”

– Pablo Picasso

Let’s call the spade a spade here. Perfectionism is simply another excuse not to expose yourself to the emotional danger that is necessary to grow.

I’ve not started a thousand things because I held myself to some unrealistic standard of excellence. BEFORE I EVEN STARTED!

“I have nothing to say…I can’t write like Thoreau, or Crichton, or Maxwell, or Pressfield. Therefore, why try.”

I’ve also not finished a thousand things because I’ve held it up to the same phantom standard of perfection.

“Do my eyes look weird in that video? I don’t think my energy is quite right…I’m not publishing it.”

Perfectionism‘s purpose is to provide an excuse “not to”…not to start, not to finish, not to put the work in, not to think about it anymore…and therefore, not to fail or face scrutiny.

But also, not to grow, not to make progress, not to get better, and not to ever have to deal with what happens when you actually do it.

My younger mind loved being a perfectionist, and the malicious rhetoric that went with it, because it was the perfect excuse.

Failing or struggling my way to success was never my path. I assumed that if it was meant to be, that I’d be inherently good at it. Born with it. The excuse of perfectionism allowed me to continue to believe that.

Luckily, almost 30 years of software development has been a great teacher in the battle against perfectionism. I have learned that the key to developing the best software product has been getting something imperfect, incomplete, and even with known faults into the customer’s hands sooner.

The reason is faster feedback. Feedback is your map to improvement. Feedback + iteration is the path to success. If you are concerned that what you have is not good, then ship it sooner, not later. The feedback will tell you.

The danger of not shipping it before you think you are ready is taking the wrong path for far too long.

Do you ever hang out with the Instant Gratification Monkey? That’s how I know that I’m letting perfectionism get the best of me. Procrastination is an easiest outlet for perfectionism.

This is an on-going battle that still happens almost daily. I’ve procrastinated 30 times writing and publishing this article. All because I have this dread of “it’s not good enough.”

Which is actually, “I’m not good enough.”

Which leads me to…

Tell Yourself the Right Story

“You’re good enough, you’re smart enough, and doggone it, people do like you”

– Stuart Smalley

Self-talk gold from Al Franken’s Stuart Smalley. Do yourself a favor.

That guy looking back at my 20-year old self in the mirror was mean and loved the comfort zone. “You’re not good enough…you aren’t smart enough…nobody cares about your perspective…be invisible…you can’t do that, you need more time and money.”

I was telling myself a terrible story each day. Over and over again.

Do you think Steve Jobs inner voice told him he couldn’t get it done?

Do you think Michael Jordan told himself that he didn’t want the ball at the end of the game?

Do you think Tony Robbins let his neglected child voice tell him he couldn’t make an impact on millions of people?

If you hear something a million times, your subconscious will believe it. The only person that can tell you something a million times is you. So make it the right story.

It’s true that not everybody will like you, or think you are pretty, or resonate with your message, or think your idea is good. Your audience is not everybody.

You will have to get better, do the work, and continue to improve.

And you will have to find your voice, and let it out. Your audience is out there. So is mine.

Own who you are, know where you are, and grow each day toward your authentic self. Your audience needs you, and your perspective.

Wherever you go, you take yourself with you. Make sure that person is telling you the right story.

Why So Serious?

“Don’t remember where I was
I realised life was a game
The more seriously I took things
The harder the rules became

I had no idea what it’d cost
My life passed before my eyes
I found out how little I accomplished
All my plans denied

– Dave Mustaine, A Tout Le Monde

Wisdom from the great poet, Dave Mustaine.

Stuff is gonna go sideways.

Embrace it, or at least look for the lesson. Always find the humor.

Remember the best stories of road trips from your youth? Why do you remember them? Because of the things that DIDN’T GO ACCORDING TO PLAN.

You remember the flat tire, and then the flat spare tire, which caused your family to have to stay in the hotel on the highway. There was a pool, you went out to eat dinner, and you had cookies for breakfast. That was the best 12 hours of the entire vacation.

You remember getting to the beach and forgetting to have packed your bathing suit. Your mom bought you 2 new bathing suits.

You remember camping when it was so hot that the “resort” opened up the water park to everyone for free. You went on the water slide 27 times and your dad taught you how to scare your little brother under water.

David Epstein, in his book “Range“, tells numerous stories about successful people who purposefully meandered. People who took opportunities. People who never took the “golden master plan” so seriously that they were blind to life itself.

Not every day, week, or year unfolds exactly as you have it planned. Becoming too focused on a particular outcome creates this weird, paradoxical situation: The harder you try, the harder it becomes.

Often the best and biggest opportunities come about when you are thrown a curveball. With a growth mindset, you can recognize the opportunities. With a fixed mindset, each left or right turn makes you angrier.

Give yourself a break. Laugh about the missteps and misadventures. And always keep your eyes open for opportunities.

Embrace the Grey

“I spent a lot of years trying to outrun or outsmart vulnerability by making things certain and definite, black and white, good and bad. My inability to lean into the discomfort of vulnerability limited the fullness of those important experiences that are wrought with uncertainty: Love, belonging, trust, joy, and creativity to name a few.”

– Brene Brown

I once saw the world as black and white, in or out, right and wrong. There was an objectively correct answer to every question, every problem, every situation.

Or possibly, I wanted to see the world as black and white. I wanted there to be a right and wrong side to every issue.

I wanted that because it was the perfect way to hide and protect myself. I was hiding amongst the “smart people.”

The smart people were on the right side, and the dumb people were on the wrong side. I saw myself as one of the smart people. Paraphrasing Seth Godin, “People like me are the smart people, we think like this, and we are on the right side.”

My job was simply to figure out which side was right, so I could be one of the smart people.

Therefore, I spent a pile of mental and emotional time and effort fitting everything into this paradigm. It was both exhausting and soul-sucking.

It also kept my mind sealed up in a can, my emotional being stagnate, and my perspective squarely in the middle of the mainstream of my little community. Whomever they were.

Luckily, I discovered this particular can opener: ALL sides (usually) have smart people!

Theism vs Atheism: smart people on both sides.

Liberal vs Conservative: smart people on both sides.

Nature vs Nurture: smart people on both sides.

Vegan vs Paleo: smart people on both sides.

Chocolate vs vanilla: smart people on both sides.

If there are such smart people on completely different sides, then maybe there isn’t an objective right and wrong. Maybe it’s way more nuanced. Maybe it’s grey.

When you embrace the grey, you embrace the conversation. You embrace the exchange of ideas, the respect of other’s view points, and the realization of where you may be in error. In turn, you find your perspective.

The grey is where the art is.

It’s where an individual can find his/her interface to the whole.

It’s where change takes place.

It’s where love can germinate, and then grow deeper.

The grey is where you find your authentic perspective.

Open your eyes to the grey.

In Summary: Choose Yourself

James Altucher has it right in his book “Choose Yourself.” This is the best summary of the stuff that my current self would tell my younger self.

Choosing yourself is about taking action. Taking the action to build and find your authentic self. Your career, and your life, will be what you make of it. So don’t wait around to get started. Do these things…

Create something. Use that thing to build another source of income, or joy, or challenge.

Grow your network with people you want to love, and admire, and are where you want to be.

Grow yourself by investing in your skills, physical health, relationships, and your emotional and mental well-being.

Don’t walk into work afraid you may get laid off. Walk into work knowing that if you get laid off, you’re going to be fine.

Continuously expand your frontiers. Say “yes” to adventure, take the risk. Embrace the uncertainty.

Don’t wait around for the right answer. Go find it.

Fail faster, find the lessons, and keep moving forward. Do the hard stuff. Get stronger and get great at being rejected.

Don’t take yourself so darn seriously.

Find the joy in each day and bring your passion. When your partner smiles, be filled with gratitude. When your child is happy, be proud. When your child is sad, be thankful you are there to pick them up.

You may be 20 today, but snap your fingers, and now you’re 50.

Don’t wait around.

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