Time Machine Advice to My Younger Self

The chat that transpired took me on a brief trip down memory lane. That conversation stuck with me, as all good ones do.

I decided to create this post as a running tab of the thoughts that come up as a result of this question. I’ll update it over time.

If I had a time machine, here’s the advice I’d give to my younger self:

Don’t seek security, seek randomness.

In Mr. Davies’ 12th grade English class, we were given a simple homework task. The assignment was to write an original aphorism.

This was my submission:

“To conform for security is to confirm your insecurity.”

The question is, if I knew this intuitively back then, why was it so hard for me to actually live out?

To my high school self, sporting a punk rock t-shirt was the ultimate statement of anti-conformity. But there were still many parts of my life where I was following scripts, living my life trying to fit the mold instead of creating my own.

And as I’m still learning, this goes beyond just what career you choose or direction you take. You’re happier when you’re living at your edge. To me this means chasing intrinsic goals, seeking out what scares me, and not settling for a life based around the expectations of others.

As Terence McKenna said, “If you don’t have a plan, you become part of somebody else’s plan.”

Choose your own adventure.

Growing up, I was a huge fan of the Choose Your Own Adventure books.

In case you’ve never heard of them, these are books written in the second person so that you as the reader are in the driver’s seat. You become active in the story, making choices for the character that affect the outcome.

You’re presented options much like this:

You come to a fork in the road. If you decide to turn right, go to page 9. If you decide to turn left, go to page 14.

I’d tell the past version of myself that real life is a lot like this. At the end of every page, there’s a chance to choose your next direction. Only there aren’t two options, there are thousands. You just might not be able to see them yet.

There are options everywhere if you know where to look.

There are countless options in terms of ways to live our lives.

Deep down we all know this, but it’s easy to be blind to the alternatives—especially when all those around us are approaching life in similar ways. Certain ways of thinking become the norm and the status quo takes over.

Even though we may have a wide variety of interests, society and our school systems pressure us from a young age to specialize and to follow a certain path.

But for those of us with multiple passions that love to learn, explore and try new things, locking ourselves into one set direction can feel suffocating. 

Here’s what I wish I knew back then:

• You can create the exact career you want through entrepreneurship
• You can have the type of relationship you want
• You can live the lifestyle you want in the location of your choosing

If you only take the options you’re presented, you risk sacrificing your own desires to live out the dreams others have for you.

Often times, the first step is finding others who live the lifestyle that you’d like to have and figuring out what steps they took to get there.

I’d tell past version of me to follow along in one of their footsteps until that path no longer called my name.

What you want will change.

In hindsight, past me’s goals were only distant approximations of what present me knows he wants now. But there’s no way I could have known any differently then.

Our childhood selves inherit a lot of what we want through social conditioning or early childhood experiences. We figure out what we want through a process of trial and error. Each step helps move us closer to discovering what our real goals are. 

It stands to reason that I’m still on that same path now, and future me is looking back shaking his head at present me. But that’s all part of the process.

There was a business project that I worked on for a number of years that I suddenly had lost interest in. It had started to feel empty and devoid of meaning. I knew what I really wanted to do but the logical part of myself wouldn’t let me give up on what I’d worked so hard for.

It took me a year to accept that it was time to move on.

That project had fulfilled its purpose: it had taught me what I needed to know to be able to realize what it was I actually wanted to be doing. If I was honest with myself, I would have admitted it earlier.

Change is a good thing, and your instincts will tell you when it’s time to change. Listen to them.

In doing so, you’re moving closer toward building the life you really want.

I’m curious, what advice would you give to your former self?

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Each one of these books gave me a new insight, altered my psychology or helped me see something in a slightly new light:

• Outliers by Malcom Gladwell
• The Subtle Art of Not Giving a F*ck by Mark Manson
• Man’s Search for Meaning by Viktor E. Frankl
• The 4-Hour Workweek by Tim Ferriss
• The Way of the Superior Man by David Deida
• The Truth by Neil Strauss
• Antifragile by Nassim Taleb
• Waking Up by Sam Harris