Why you should document the journey…

You should announce your goals to the world, and then you should document where you are today.

One of the most common questions I get asked by other writers & creators who want to start writing online is, “Cole, what’s the point? Why should I document and share anything about my life or where I am right now? I haven’t achieved anything yet. Who is going to want to pay attention to me?”

The answer is: nobody… yet.

People like Gary Vaynerchuk have been preaching this for decades. In fact, I vividly remember sitting in the office of my first job out of college watching Gary’s first YouTube episode of #AskGaryVee and thinking, “This is what he means. He’s going to look back on these videos and be so happy he documented the journey.”

And that inspired me to do the same.

Back in 2014, I started recording as many random moments on my iPhone as possible. I didn’t know what I was going to do with them yet. I didn’t know whether they would hold any value, or if I would stand by the things I was saying a decade later. All I knew was that, at some point in the future, I would value the fact that I kept a time capsule—and that I documented myself along the way.

Unfortunately, I fell into the same trap everyone does:

• I recorded footage

• I would write blog posts or newsletters, announcing my goals to the world

• I’d get all fired up about “documenting the journey” and all the ups & downs of getting there

• And then I’d overthink, get in my own way, and end up not hitting publish

I was no more immune to these uncertainties than you, or anyone else.

But the other day, I was going through old photos on my phone—a quick trip down memory lane.

And I came across a video I had completely forgotten about. I don’t remember recording it. I don’t remember sharing it with anyone.

But from what I can gather, I must have recorded this sometime between October to December, 2016.

• I had just herniated a disc in my neck weightlifting, was on painkillers, unable to lift, was depressed, and could feel my identity changing.

• I had just quit my 9-5 job working as an entry-level copywriter at an advertising agency downtown Chicago (September, 2016).

• I had just started making “real money,” going from my ~$44,000/year full-time salary to ~$20,000/month (~$250,000/year) ghostwriting like 4-5 hours per day.

• I had just published my first book—a coming-of-age memoir about becoming one of the highest-ranked World of Warcraft players in North America, called Confessions of a Teenage Gamer.

• I was still living in my studio apartment on the north side of Chicago. My income had gone up dramatically, but my lifestyle hadn’t changed yet.

• I had just started dating a girl long-distance who I’d met in LA (but lived in Arizona), who now, 10 years later, is my wife.

• I had just reconnected with one of my best friends from college, who lived in Atlanta, and we started visiting each other more talking about how we wanted to “start a business together.” (He became my co-founder in 2017 and together we built a ghostwriting agency to millions of dollars in revenue.)

• And I was going through a really hard time with my family, trying so hard to believe in myself and pursue my dream of building a life for myself as a full-time writer while dealing with their disapproval and their own uncertainty about what would happen if I “failed.” (When I told my dad I was going to quit my job and go all-in on writing, the first thing he said was, “How are you going to afford health insurance?”)

Basically, I recorded this video at the exact moment every major variable in my life was changing.

My identity was changing.

My relationship status was changing.

My income was changing.

My lifestyle was changing.

My goals were changing.

And I didn’t know how any of these variables were going to play out. Maximum uncertainty.

The only thing I did know was that I would figure it out—by any means necessary.

I was recording it to my future-self, for my present-self.

When I came across this video and watched it the other day, almost a decade later, I felt so emotional. It was like opening a time-capsule and being able to re-experience a previous chapter of life. I felt so proud of 2016-Me. Because I owe who I am today, and all the things I have achieved, to him.

Chicago Cole.

He was the one who woke up early and stayed up late.

He was the one who chose to write every Saturday and Sunday for as many hours as possible.

He was the one who put his goals and aspirations above everything else.

And he was the one who had enough foresight to pick up the camera and say, “This is what I want out of life, and I’m going to go get it. Watch.”

In fact, part of “documenting the journey” means admitting to yourself that you don’t know how it’s going to play out. You don’t know whether or not you’ll “be successful.” You don’t even know if the version of success you think you want is what you’ll actually get. You don’t know. Maybe it’ll turn out even better than you imagined!

The point is, the reason documenting the journey holds so much nostalgia and long-term value isn’t because of the known. It’s because of the unknown.

If there was a 100% chance things went exactly the way you thought they would, there would be no journey. Because there is no risk.

The risk is what makes it interesting.

And the risk is what makes it rewarding.

It’s never too late to begin documenting where you are on your journey, working in the direction of wherever it is you want to go and whatever it is you want to achieve.

And I promise, wherever you are today… 10 years from now, you will wish you had started sooner.

—Cole

PS: Let me know if you enjoyed this little blast-from-the-past. I have tons of old footage I have never shared. But I will, if you find it as interesting and helpful as I do.