Five Lessons I Learned the Hard Way

If You're Young, Read This

Yesterday I turned thirty-two.

Far from old, but no longer — at least in my mind — young and naive. A sweet spot. Enough wisdom to know that I still don’t have any.

Honestly, it feels like I've already been three or four different people since I turned 18. Some good, some bad.

I wouldn't go back and change anything. All of it's been necessary for me to become who I am now:

• Husband

• Dad (in October)

• Homeowner

• Career I love

• Friends and a network I care deeply about

I don't have any "32" lessons. But I do have some things about communication and relationships I wish I could've drilled into my head earlier. Things that would've saved me, and those around me, time and trouble. Mental traps I stayed stuck in, opportunities I missed, and people I wish I would've had the clarity of mind to avoid.

So here we go:

1. Don't try and save ANYONE (especially a girl)

I did this with a few girls I dated; putting time and energy into their potential, rather than their daily actions. There are billions of women in the world. Just because she's funny or smart, doesn't mean she's ever going to take her health seriously, be a nurturing companion, or take responsibility for her behavior. Find the MAJOR things you require in a woman and don't try and "fix" someone who may only have 3/5. This means learning about who you are; what moves you, what inspires you, and how you see the world. And it also means getting out there and trying. Your gut will speak to you. If there are major asymmetries, don’t try and force it. Take the lessons and move on. It's not worth it. The same things go for friends as well.

2. Become Friends With People You Admire

Just because you hit it off with someone doesn't mean you should keep them in your life. Find people who are creating things you admire and embodying virtues, skillsets, and actions that you want to implement in your own life. Be friendly, charismatic, and curious, and you'll be able to attract people at the level you want to be at. This means stepping out of your comfort zone and embracing the feeling of “imposter syndrome”, and turning off the noise from friends who think attending conferences, events, and networking with others is “cringe”. Ask people about what drives them in life and they’ll tell you. People love to talk about themselves. If you're the most successful or ambitious person out of your friends, that’s not a good sign.

3. Not All Shitty Jobs Are Created Equal

If you're a young guy or gal, you'll have to work a shitty job while you build out the thing you really want in life. If you have to work a shitty job choose one that:

• Allows for quick vertical movement into a higher-paid position

• Is closely aligned with what your ambitions or interests are

• Can give you quick cash for a few hours of work (waiting/bartending)

• Connects you with the types of ambitious and successful people that you can build relationships with

Instead of sitting in a dead-end job with a resentful attitude, try and become the person who is learning as much as they can about the way that the business runs. If you can, try and be the best. This doesn’t mean selling your soul to something or someone that is temporary. Lead with curiosity. Try and absorb as much as you can because you never know when or where you’ll take that information elsewhere.

4. Fix Your Biggest Flaws First

We all have things about our personalities and tendencies that we admire and dislike. Most of the time we want to lean into the things that we already like about ourselves, and we completely neglect the red flags we give off to others. For example, If you're prone to interrupting or talking over people, fix that sh*t now. When you have something that turns people off to you, you're missing major opportunities. Seek awareness of who you are and spend time working to understand and correct your flaws.

There are three ways to develop this self-awareness:

• Take a view from above: try and imagine yourself from a birds-eye perspective during the day. Imagine hearing yourself talk, and watching your behavior.

• Keep a close and honest circle: Good friends want you to become better people, bad friends don’t care. If you think you said or did something out of line, ask a friend. If they love you, they’ll provide honest feedback.

• Read more: When we read, we are subconsciously absorbing the archetypes and personalities that we find admirable and compelling. Have an example of someone you’d like to emulate in behavior, character, or action.

5. The Only Way to Know, is to Try

If you're in your twenties, you have an obligation to yourself to step out the door.

I was a:

• Touring musician

• Day laborer

• Journalist

• Substitute teacher

• Line cook

• Bartender

• Baker

• Copywriter

The list goes on.

I explored my interests by trying new things constantly. When you're young, you have time and energy with very little responsibility. The worst thing you can do is choose one path. Get out into the world and explore. Let a hunch or a suspicion carry you. Lift your sails and move to uncharted water. The worst thing you will find is more experience and a deeper understanding of who you’re not.

Give yourself time and learn what lights a fire under your ass.