The Millennial Misstep

Entrepreneurs everywhere are tricking themselves into dissatisfaction, self-loathing, and unnecessary pain because they have adopted the wrong belief system about success and happiness. This mindset causes these aspiring coaches and course creators to spend all their money on business coaches and software and all their time envying more successful competitors.

The millennial misstep is the adoption of this incorrect belief system about success, life, and happiness. But there is another way. A different belief system. Let me explain:

I gazed out over the bay to the mainland. The sun was shining and the sky clear. We had found a small oasis in the middle of the apocalytpic smoke storm caused by local fires. No ash fell like snow in the summer. Breathing the air didn't sear my lungs.

It was far from the ideal moment I had imagined, but this was it. I swooped down onto one knee and proposed to my girlfriend. She said yes.

Of course, I didn't intend it to go this way. Since December, we had planned a trip to Hawai'i where I was going to propose.  Pandemic travel restrictions forced us to cancel that trip.

We booked a nice weekend getaway in the mountains. Two days before that trip, fires started and cut power from the local town. Everyone evacuated. Strike two for summer trips and strike two for proposal plans.

I was ready to propose, but didn't know how, anymore. When we randomly decided to go out to the islands for a day hike, I knew that was my chance. I found the best vantage point, gave a little speech, and it was a beautiful moment.

I want to share this speech with you (at least how I remember it), because it explains the Millennial Misstep that caused me to miss 4 years of opportunity in my life and in my relationship with Kristen. Here goes:



Our biggest problem is that we believe in this ideal state where we make so much money that finances cease to matter and then we sail off into the sunset, get married, have kids, and our life proceeds without any problems.

It has caused us dissatisfaction and unhappiness because we're so fixated on this goal that we haven't achieved. It distracts us from the truth: we are incredibly blessed. We are young, healthy, smart, in love. We have so many things going our way. But our fixation on the struggle has corrupted our beliefs about success.

This has caused us to neglect the present moment, waiting for success to fall in our laps. But that's not how it works. We have to take the opportunities that are presented to us each day. We have to move forward with our lives.

As long as we live, there are going to be problems. Our capacity to solve them is how we level up in life.

I realized that, regardless of this perfect dream of riding off into the sunset, life needs to move forward now. We need to aggressively pursue what we want for our lives. Otherwise we'll never get there. We will continue to live in this fairy tale while real life passes us by.

I've known for a long time what I want. And what I want is for you to marry me...


And, as they say, the rest is history.

Let's break this down. The millennial misstep espouses the following beliefs:

  • Success will come to me if I'm open to it
  • Fixation on the end goal, the destination, rather than the journey.
  • Optionality is more valuable than commitment. Gotta stay on the look out for blue oceans. I will be happy when I can travel the world and live the laptop lifestyle.
  • It's okay to struggle and hustle now because the future will be better when I "make it." My guru says that will happen in a month or two.

These are the beliefs that caused me to wait. I waited to get engaged. I waited to spend time with family. I waited to live my life. I waited to be happy. And what did waiting get me? Loss.

Waiting for opportunities to fall in my lap caused me to miss them. Not only did I miss the first order opportunities, but I missed countless second order opportunities that I'll never know about. I let time escape like sand through my fingers and hated every minute of it. I knew I wasn't reaching my potential, but couldn't break free from the belief system that held me back.

As Patrick O’Shaugnessy says in Growth without Goals, "Most of the things we do and believe result from stories that we tell ourselves."

Stories about fame. Stories about abundance. Traveling the world. Stories that have been engraved into your psyche again and again watching successful entrepreneurs on Instagram and Facebook. This dream that you have for yourself, that after hustling and grinding, you finally reach success. Your business explodes and your worries disappear forever.

And so every moment you're not successful wears on you. Jealousy builds up when you see others achieve their goals. You keep posting, keep writing, keep reaching out to people... but you don't make any progress towards your goals. You don't even know how to set goals. All you want is to finally get traction and start making a consistent income. But nothing seems to work for you.

These stories cause you to wait for success to fall in your lap while you continue to worship gurus and waste all your money following them to the moon and back.

Returning to Growth without Goals, Patrick O’Shaugnessy quotes Scott Adams, the creator of Dilbert, saying:

goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary. That feeling wears on you. In time, it becomes heavy and uncomfortable. It might even drive you out of the game…

This couldn't be more true. After 4 years of this mindset, I hit rock bottom. I couldn't continue believing these stories. I was suffering physical symptoms from the stress and mental symptoms of anxiety and self-loathing. I had to change my beliefs or get out of the game.

Here is the belief system that I adopted to keep going. Notice that it's almost exactly the opposite of the previous set of beliefs.

  • I will aggressively pursue the outcomes that I want
  • Fixation on the daily - the few important activities that matter. Time with Kristen, time to write.
  • Happiness comes from commitment. Optionality is for losers.
  • Now is all there is. I'm not going to waste any energy struggling or hustling. I'm going to build my business in a consistent, sustainable way, enjoy time with family, and be happy. All at the same time.

The difference between these belief systems is your intentionality. When you commit to this second set of beliefs, you focus on what you control: The daily actions that make you happy. And only when you commit to this process for the long-term will you achieve your dreams.

In his book, The Great Mental Models Vol 2, Shane Parrish describes this shift as the difference between velocity and speed: direction. Think of of the classic diagram from Essentialism by Greg McKeown.

Essentialism, by Greg McKeown

When you want to be successful, you run around as fast as possible, do as much direct outreach, write more landing pages and lead magnets, download more software, and try to be busier. You move fast. But you lack focus. You lack intentionality.

When you choose a few daily activities, you have direction. "I am going to do these things every day regardless of how many likes or clients I get because I like doing this." Focus and intentionality become your ally, allowing you to go farther, faster. Direction gives you velocity.

In another passage from Growth without Goals, Patrick O’Shaugnessy argues that "Long term “success” probably just comes from an emphasis on process and mindset in the present. Long term thinking is also made possible by denying its opposite: short-term thinking."

So what are these daily activities/processes that give you direction and result in your long-term success? I'll recommend a few:

  1. Contact your list. Build rapport, share something valuable, and make an offer to take then next step with you.
  2. Grow your list. Reach out to a potential partner and ask to get on their podcast or email their list.  It's scary at first, but this really only takes 15 minutes to do well once you get going.
  3. Take care of yourself. Less booze, social media, TV. More whole foods, mediation, exercise, and sleep.
  4. Laugh. Play.

To know exactly what's on your list, ask yourself, "would you still do it if you never got paid?"

I always used to hate this question. The point is to make money, right? But the truth is that you have to be willing to do it without pay. Some for a long time. Others for a short time. But you have to love doing it nonetheless.

There is no point in doing things that you hate to try to make money. If you don't love it, make a change. Produce content differently, find a way to enjoy your diet, or get out of the game and go do something else that you like.

Aggressively pursue what you love instead of what you think is required of you. Success follows intentionality. The longer you wait, the more likely you are to miss it.

Your next big idea
Every day I send one big idea to your email inbox so you can grow and keep an engaged audience, create more content in less time, and never run out of ideas.
When you subscribe today, I'll show you the free app I use to get daily inspiration for content topics so I never run out of ideas.
Click the button below to subscribe.

Privacy Policy | Terms and Conditions
Copyright 2022
All Rights Reserved