The Road of Trials: Transform During Hard Times

I've unexpectedly had to take my own advice...

I’ve had a difficult couple years.

It started around when I found out my first child was coming—3 years ago next month.

It’s ending (I think) with the arrival of my second child— whom we’re expecting next week.

Recently I decided to re-listen to, and republish to an old episode of mine, The Road of Trials, and take my own advice.

The Road of Trials is a period of the Hero’s Journey that generally sucks. Moment to moment it seems like little progress is being made. (Hence, in the movies it’s often sped up as a montage.)

But it’s also a period that forces you to take a hard look at your life. When you engage with it properly, it makes you recognize your true abilities and wisdom.

I recorded this episode in 2021, looking back at previous “Road of Trials” moments in my life. I didn’t expect I’d go through another one shortly after…

What my recent years have been like (life update)

If you’ve been following me for some time, you may have noticed I changed a lot in how and what I share online. And that’s basically mirrored what’s been happening in my life.

3+ years ago, I felt I had reached some sort of peak. My business was doing its best ever. I had “found my groove” in how I expressed my ideas online.

But I was getting bored. I felt I couldn’t fully relate to the problems of the guys I was coaching— it had been a while since I felt troubled about life, relationships, or purpose. (viz: Be careful what you wish for.)

I became more interested in side projects, such as my History of Man podcast. I made an adaptogen tea brand, kind of on a whim.

But when we found out we were pregnant, I decided I needed to change some things. Both to be a better provider, but also a better role model. I went through a kind of identity crisis— I felt like who I “was” fit my bachelor-self, and not at all my soon-to-be-father self.

I went into a kind of dark place. I deleted my Youtube and Instagram. (Partly due to a manic moral stand against addictive screen media— but only partly.)

After a six month hiatus, I began making audio-only episodes. In many ways this was great. I felt very authentic in the types of content I was sharing, such as my series on general semantics.

But the truth was, I was also hiding.

I didn’t know how I “fit” in the world, so I avoided it. I made myself almost unfindable on the Internet. Instead, I only spoke to the couple thousand listeners who were already following me back from when I felt more bold.

From there I/my family made a bunch of manic moves. We moved to Mexico. I hired a YouTube coach and followed his formula. It was a decent formula, but it really wasn’t me. We also hated Mexico. Many times last year I wondered how my life went from so fulfilling to so disconnected in such a short period.

In the last few months, I realized I’ve been in a Road of Trials. I’ve been grinding away, feeling nothing is happening.

But that’s not actually true.

This period has forced me to reconnect with my strengths and passions. It’s reminded me of “what got me to the dance”— both in terms of outer success, but more importantly inner fulfillment.

Some cool things are about to happen that I can’t quite share yet. In the meantime, I’m enjoying this “Eastertime” (resurrection), while awaiting my second child.

The next couple weeks I’m going to re-share some of my favorite episodes from recent years. And I’ll be back in May with a totally new look.