Life Advice From Today for Me 12 Years Ago

Dear Craig,

I would say, “I hope this letter finds you well,” but I already know how it finds you.

I know better than anyone else on the planet ever could. 


Because I’m you, only 12 years in the future; we’re currently 50, with 51 approaching faster than we want in a few months. 

Why am I writing you now?

We’ve experienced a lot, and we’ve learned a lot. But I’m not about to tell you what’s about to happen; that’s not how this works. 

Through those experiences, we’ve learned and we’ve grown. 

We also have the gift of hindsight, which, as it turns out, is 20-20.

So, I’m writing to share 5 key lessons you need to embrace now. Knowing you, you’ll read them, be inspired, act on them for a few days, and then return to the status quo. 

And that’s okay; I’ve planted five seeds, and I hope you nurture them and allow them to grow. 

1. Fear

Behind your luxurious lifestyle, hidden behind a paper-thin veil, is great fear. 

We both know it. 

You’re afraid of pursuing your dreams, of becoming who, deep down, you know you really are, and of asking life and anyone in your life for what you need. 

You’re afraid to assert your authenticity, and you hide in plain sight. 

And those fears are fucking terrifying, but not one of them is real. The fear you live in is nothing more than your imagination running wild. 

You’re afraid of what MAY happen. 

What MAY happen is in the future; if you could read the future, you would have played winning lottery numbers by now.

You’re also afraid you won’t survive any of your fears coming true. Guess what? That’s also in the future, and you cannot know who you’ll be and how you’ll respond if your fears come true. 

You believe who you are today is who you’ll be in the future. Quick question: Are you the same person you were 3 months ago, 1 year ago, or 10 years ago?

Of course not; the same applies here. 

Try this for the next month:

Write down your fears. You’ll be amazed to watch some of them vanish on their own just by taking what’s inside and placing it outside.

For the ones that haven’t vanished, face them—one by one. 

Start with the easiest, then work up to the most challenging.

Your life will transform.

2. Alcohol

I get it; alcohol is an inextricably interwoven component of your identity. Hell, you’ve been drinking since the 6th grade and can outdrink people twice your size. 

It’s who you are and what you do. You live for it, and in rare instances when too many days go without a drink you begin to shake. And who can blame you?

It’s your escape; you get to become someone else the moment that 1st sip hits your lips, if only for a little bit. 

It’s beautiful, it’s fantastic, and since your career sucks and is meaningless, it’s something you deserve. 

You earned that escape, and you earned that high. You’ve got to make life better, and the bottle has always been your savior.

Alcohol is your path to the freedom you desire.

But it’s not. Not even fucking close. 

Your relationship with alcohol is a prison cell of your own design. 

I’m not telling you to stop drinking; I know you wouldn’t listen.

I’m only asking you to understand your relationship with alcohol and what you say you want out of life.

Do they align?

We both know the answer.

3. Chasing


You went from being a personal trainer to entering the corporate world at the absolute bottom of the company (remember you had to build your own desk). 

You’re consistently one of the top three salespeople in the country.

You’ve got the plaques, accolades, and President Club trips to Hawaii. 

And you have the lifestyle to match: a couple of BMWs, over 30k in watches in your backpack as you hiked in Hawaii, and that was only part of your collection. 

You’ve got VIP status at two of the best restaurants in Greenwich and live in a gated community in Connecticut. 

You also have a success-sized hole in the middle of your life because your career doesn’t fulfill you.

You also have a gaping void in your life because you believe you need all the stuff and the VIP status to be someone people will like and respect.

You don’t feel worthy or enough, and you’re terrified (see fear above) of who you would be without everything you think makes you who you need to be.  

Enough will never be enough because you don’t believe you’re enough.

So you chase all these things outside yourself to feel whole. 

You’re running an infinite race. 

Until you know you’re worthy enough and accept yourself as is, you will never cross the finish line. 

Because the way you’re living right now? 

The finish line doesn’t exist.

4. Running Away

This is similar to number three, chasing. 

If you think about it, when we move towards something (chasing), we’re always moving away from something. 

Every step forward is one step away from where you began. 

Chasing your lifestyle carries you away from what you’ve been running from since about 7. 

Because around the age of 7 you began to realize it wasn’t safe to be who you were, so you chased solutions to become who you needed to be. So you would feel worthy, enough, and accepted. 

You’re running away from who you’ve always been and who you, deep down, desperately want to be. 

You’re abandoning your creative self. 

The part of you that wants to write a screenplay, invent something, become an entrepreneur. 

You’re running away from being seen, heard, and understood for who you genuinely are. 

Let me ask you:

You’ve been chasing and running away for most of your life, and where has it led you?

Feeling scared, stuck, frustrated, lost, and seeking escapes at the bottom of a bottle and in the magnetic strip of your platinum card. 

And those fleeting moments of escape and relief create an even greater need for escape when you return to reality. 

You’re on a treadmill trying to run away from yourself.

Try stepping off, if only for a week, and see what happens. Pick up a pen and paper and start journaling. Yes, you’ll feel silly in the beginning, and yes, you’ll struggle with what to say.

But in time you’ll come to learn who you are. 

5. Breadcrumbs

Sure, you make hundreds of thousands of dollars a year. You have all the stuff I wrote about above.

You’ve got, by most standard definitions, “it all.”

But do you?

You feel empty, you’re stressed all the time, you feel like an impostor, you know you’re leaving the best parts of you behind a veil of fear.   

Life is more than professional and materialistic success, and you know this is true because of the emptiness you feel. 

When your life lacks joy, purpose, meaning, and fulfillment, it doesn’t matter how much money you have or how many shiny status symbols you own.

You’re settling for breadcrumbs; deep down, you know this.

You’ll be settling until you face your fears and learn how to fill the void you feel from within.

You’ll continue to exist, but you won’t be living. 

Breathe life into your creativity now, not later.

Start writing the screenplay, bring an invention to life, start your own business, scratch your own itch. 

You’ll learn that your luxurious lifestyle isn’t the path; it’s actually one of your biggest obstacles. 

Carve out one hour a day to do the things that light you up; you won’t regret it. 

So those are the 5 lessons, and you’ll never see them. 

There are two critical reasons for this.

For starters, the future hasn’t solved time travel. I can’t mail this or email it back in time. It’s physically impossible.

Secondly, and this is the most important one. 

Even if I could send this back in time, I wouldn’t.

 Everything about to occur in your life brings you to where you are today, and I wouldn’t sacrifice that for all the money or prestige in the world.

You need to experience what you’re about to experience to become who you become. I’d be doing you the most tremendous disservice and injustice if I took that away from you. 

So brace yourself, and know this:

Everything is temporary. You’ll not only survive but also thrive. 

📣 If you’re ready to stand in your power, and unleash your potential the Midlife Mastery Program is for you. Schedule your free call here.