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4 Things I Would Do If I Could Go Back Ten Years

If you could go back ten years in your life, what would you change?

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You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.”

Some of you reading this recognize this quote from the late Steve Jobs. Jobs had this big vision for his work and was a master at getting people to look at the big picture of his work.

Jobs was very good at selling his vision, from customers to employers to his fellow executives.

And part of his genius was his ability to get you to trust everything would work out.

As I was writing this week’s newsletter, I thought of this quote about trusting that the dots would connect for us in the future.

And I came up with a reflection on the last ten years of my life.

The last ten years of my life have been quite a ride.

From buying a one-way ticket to New York City with only $1500 in my bank account to my time in Denver, I have beautiful memories that will stay with me.

I also have made some impactful mistakes that will stay with me.

Mistakes like selling bitcoin when it was $1800 and offloading Facebook shares at $30 a share.

Mistakes like holding grudges against my loved ones at the expense of my own life and health

One big mistake was letting my ego get in the way of having meaningful relationships.

If I could go back ten years in my life, here are the four things I would do.

Go all in on writing with an unwavering commitment

Ten years later, writers are critical to all areas of business. From emails to landing pages to social media posts, the art of the written word is more valuable than ever. And you can make good money doing it.

Writing would be my singular focus if I were to do it over the last ten years—articles, blogs, newsletters, you name it. I would have found a way to make it happen.

I would have posted on social media my writing much more consistently.

I would have focused on an email newsletter.

I wouldn't have waited ten years to write my second book. I'd be on my 4th one by now.

I would be all in.

But this isn’t about writing nor a career I am reflect genuinely ten years ago.

It’s about being committed and unwavering in that commitment.

It’s about going all in on something you are passionate about.

Don't give up on something you love to do. Be committed to it.

Not because of the money. Not because of anything else.

Do it because you love it.

Cut the self-sabotage

I took myself out a lot, especially in my work career. I never threw my hat in the ring for promotions. I thought it was because I would lose my friends if I moved up the corporate ladder.

I had a chance to go to Columbia for a Master's Degree only to not apply.

Not because of financial support or professional career path.

It wasn't that at all.

It was because I felt unworthy to give myself a chance to be great.

The way I saw myself kept me from having a chance to go after what I desired.

Self-sabotage is something of an epidemic in our society., We ask for things, get them, and then do everything we can to light a fire to it.

We’re afraid that will somehow mess it up so we try to get rid of it as fast as we can.

Going back ten years, I probably wouldn't have thrown my hat in the ring for promotions knowing where I am now.

But it would be for different reasons, not because I didn't think I was worthy.

Forgive My Dad

Many of you who read my newsletter know the story of my cross-country road trip with my dad and how that trip healed our relationship. While that trip was the trip of a lifetime, I wished it would have happened much sooner. The aftermath of resentment against him took me out.

I kept myself from making money for fear I would end up like him having money.

I kept myself out of working for myself, fearing I would be all about work and nothing else.

These were two of my many perceptions about him.

When we took that road trip, I realized that my unhappiness and depression at times in my life were not because of him. It was because I was unwilling to accept him for who he was. I was not allowing myself to create freedom in my life because freedom comes from letting go.

Had I forgiven him much earlier in my life under the notion that everything I have in my life now would have come to me sooner, I would have done it in a heartbeat.

Make reading as critical as breathing

I used to think reading was for nerds when I was just out of the military. I was too obsessed with my pride and ego, less about putting myself in a student mindset.

Reading is the ultimate path to wealth, abundance, and knowledge.

Whether it’s ten pages a day or a book a week, reading every day puts you in a position of success much faster.

I learned this lesson from a former boss who happened to be prior military. He told me that reading must be as critical as breathing if I ever wanted to get ahead of the pack in life.

And if I wanted to create a rocket ship-like trajectory in my career and life, read biographies.

Biographies are some of the densest and most profound books out there. Reading the right one will teach you more than a 4-year degree.

Now, I’m not knocking college, nor do I believe college isn’t valid. There is something to reading a book about Ulysses S Grant that taught me an incredible amount about strategy and leadership.

Lessons from that book have helped me advise my clients on their content production and marketing.