May 28, 2024

The Big Test Before You Leap

In 2019, my now-wife/then-love-interest Demetra and I were engaging in multi-hour Skype dates and inching ever-closer to the point of saying “Hey, we should meet up in person and see if our chemistry translates to the real world.”

Our rapport was phenomenal. The synchronicities were everywhere. It was such a magical period of unfolding in our lives.

And then the test came…

I was at a friend’s birthday party, with about 45 people in attendance, when a cosmic joke of a person was placed in front of me.

She was young, beautiful, and an absolute mess.

Her large breasts were propped up as high as they could go. Her black eyeliner was heavily applied in a way that simultaneously communicated, “I’m looking to get fucked tonight” and “I don’t know what I’m doing.”

She was the exaggerated epitome of exactly what I had been going for (in order to stay emotionally safe and guarded) for the previous decade. Not only that, but she couldn’t have been hitting on me any harder. She was beyond available. She wanted me and only me, and she basically cornered me at this party and wanted all of my attention.

Even while in the middle of speaking with her, I could see and laugh at the absurdity of it all. It couldn’t have been a more overt test by life.

My mind rattled on… “Hey, so you’ve got this promising, real thing over here with Demetra… but wouldn’t it just be easier to go have sex with this wildly attractive and completely willing woman? Why would you deprive yourself of one last hurrah? Who would even know? You wouldn’t have to tell anyone. You could just sneak out of here and have one more victory lap. It’ll be great. It would almost be rude not to.”

While the temptation was real (it felt like a computer simulation had 3D-printed this woman to be maximally tempting to my ego – it was so ridiculous), I could see the test for what it was. I politely told this woman that I was leaving, and after shutting down her second and third round of trying to convince me to stay, I left the party.

And here’s the thing. Could I have gotten away with it? On the physical level, yes, probably. But I would have known. I would have known that when faced with an opportunity to take a pattern behind the barn and shoot it, I failed. Even if I had “gotten away with it,” my integrity would have known. And there’s nothing that could have come from that interaction that would have made it worth it. Engaging with it in any way would have been a huge loss.

And in reality, I saw the test for what it was and moved forward even more powerfully. Retiring my sexually compulsive ways, and committing to following a relationship with Demetra that I knew had the potential to serve my growth for the rest of my life.

Three days after this encounter, Demetra and I decided that she should book her flight to come and see me, and the rest is history.

You see…

When we’re on the precipice of a significant leap, life will test us.

And it often tests you at your weakest point right before you really commit to yourself and what is best for you.

I have seen this time and time again in working with my clients over the years.

The man who craves the freedom of self-employment who, on the precipice of really choosing himself, is offered his first significant raise at his corporate job after years of neglect.

The woman who says she wants to give up the string of one-night stands and superficial situationships who is offered just one last emotionally unavailable fuckboy.

Here’s another way that this showed up for me:

Double Down On The Known, Or Take The Theft As A Sign

In 2011, I was living in San Francisco, California.

At this point in my career, I had been a full-time dating coach for three years, and I was starting to hit a ceiling of growth with the organization that I was a part of.

I started to take photography and video clients on the side to supplement my income (splitting my focus between relationship coaching and media clients) when something unique happened.

I was having lunch (BLT with fries, extra ketchup) with one of my co-workers, in the middle of the day in a safer SF neighbourhood, when, unbeknownst to us, the window of our rental car was smashed out and our bags were stolen.

Packed into my bag were all of my most valuable possessions. My souped up MacBook Pro, my less-than-a-week-old brand new iPad, my nearly brand new DSLR camera, my multi-thousand dollar set of camera lenses, and a whole lot more. It was a $10,000+ loss.

In my co-worker’s bag, there was over $2,000 worth of recreational drugs and drug paraphernalia.

(To this day, I still get a little kick of joy when I think of how amazing of a day the thief must have had when they eventually opened our stolen bags. No matter which bag they opened first, it was a total jackpot.)

Anyways, we eventually wrapped up our lunch, went back to the now-smashed up rental car, noticed that our bags were missing, and it took me about 40 seconds to feel at peace with it. Why? Again, because I saw the message for what it was.

“Alright, I’m not supposed to be doing photo and video work anymore. I am meant to double down on relationship coaching. Understood. I will take action on this immediately.”

I could have chosen the opposite direction. I could have interpreted it as, “Oh man! This sucks! But clearly I am just being asked to double down and work even harder to regain the lost momentum I had in this old, familiar thing that I’ve been doing forever.”

But nope. It simply was what it was. Life clearing a path by shaking the roots of the old thing. Asking me to move on and step up. To commit to the thing that I knew was most connected with my heart. So I did.

Ultimately, when these tests come from life, I see it as an opportunity to use it as fuel to finally hit escape velocity, or a sticky mess that we can roll around in and stay stuck for another season. The choice is always up to us. Most people continue to make the decision that keeps them stuck. They, in essence, live the same six-month period over and over again for decades, and call it life.

But the escape route is always available to us when we are willing to see it for what it is, and take it.

How Do You Know If It’s A Test Or Something To Follow?

After reading these stories, you may find yourself wondering, “But how do I know in what way to interpret the events of my life? How do I know if something is a test or just a new thing to follow?”

Deep down, when we get our minds out of the way, I believe we always know.

But to put words to it…

If the thing that is being offered to us feels deeply familiar… if it feels like more of the same… if it feels like a well-trodden path in your life… or if you get an immediate hit of ego-satisfaction from engaging with it, then it’s probably the test.

Conversely, if it feels scary… if it feels majorly confronting and minorly compelling… if it requires you to deploy courage and leap into the unknown… or if it feels deep down just true in your bones despite your mind’s resistance to it, then that’s probably the path that you need to take.

And so to you, dear reader…

Are there any areas of your life that you’re truly ready to step into?

Have you been receiving any tests as you plan your escape?

Have some of those tests been more challenging (or tempting) than others?

If so, it’s a good thing to notice, and simply be aware of.

I hope that this message finds you courageous, willing, and ready to move confidently into a new chapter.

Dedicated to your success,




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