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The Break Issue 26: 5 Lessons From a Brutal Year



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Today's Issue

In today’s issue, I'm detailing the top 5 lessons I learned this year, from doing my year end review.


It's a brutally honest take on some things I learned the hard way this year.


Let’s dive in.


Looking for a last minute Holiday Gift?


Check out my kids' side hustle, Quotebook . Quotebook is a great gift for a young couple or family with young kids to start building the daily habit of being (and capturing) funny(ness). The kids and I built Quotebook out of our tradition of capturing all the funny things we say in our family, and reliving them whenever we want to laugh.



5 Lessons From My End Of Year Review


The end of a year is a time for reflection for me. It is a time where I dedicate days to looking back and assessing life in general. I’ve done some form of a EOY self assessment every year for the last 2 decades. Every year it evolves, as my priorities change.


In my 20’s the assessment was geared toward goal setting in the new year, and particularly on money.


In 2018, when I broke my corporate career, it was focused on my frustrations, and how to design my way out.


Today, it’s about managing my energy, creativity and setting up systems to facilitate the life I want.


2022 was a very challenging year for me on many fronts. I grappled with work paralysis, watched outside investments shrink my net worth and struggled to continue growing my core business. I worked more and felt like a flailing crazy person. So this year in particular, I’m reflecting a lot on what I’ve learned in the last 12 months, so I can apply what not to do in the future.


Here’s what I learned:


1. Trust myself


It’s hard to believe at 41 I’m still learning this. I made a massive leap forward in 2018 when I decided to Break my career and work for myself.


It’s one of the proudest moments of my life.


But I still need to fully trust myself. In 2022, I got into a number of investing activities that felt bad to me (even when they were going well).


I didn’t do them because of FOMO. It was 80% because everyone else seemed to think they were good ideas, and I didn’t weight my own analysis, logic and judgement enough.


After all, how could all these smart people think the opposite of me? I’m not that smart. They must be right. Well, turns out I was right. This is fucking dangerous and needs to stop.


I need to understand the spots I can trust myself and where I can’t. I learned no one in my peer group does the type of critical thinking that I do.


Advantage Mapping helped me figure this out this year. So, I can apply this advantage in investment decisions by pairing my analysis with another optimistic point of view that has the same rigor and weight appropriately.


That’s how good investment decisions get made.


2. I’ve had it with “smart” people


Being “Smart” is not a proxy for good judgement, but our society has used “smarts” as a lazy way of managing risk. The problem is the world is dynamic and unknowable. Smart people tell you answers the think they know. Wise people ask great questions to frame problems as testable.


Smart people are just as prone to making mistakes, and they end up making them with much bigger stakes attached because our society attaches more opportunity and responsibility to “smart.”


This is why I really don’t like the term expert either.


I’ve been called smart before. I’m not. I can show you my standardized test scores :) I will always challenge someone who calls me smart - I have a negative physical reaction when I hear it. I want to be wise, not smart.


3. Control what I can control, and the easiest way to do that is to bet on myself


Because I can control my actions. I can’t control other people’s actions. Relying on others is necessary, but should be limited. This is an ethos of my company (small and close over big and broad). I’m all for being diversified, but being spread too thin is hard to manage. When I think I need to diversify, I need to evaluate how I can instead make another bet on myself.


4. I want to coach people


I didn’t really realize this until this year. When I did my Advantage Map , I found that an activity that brings me immense energy is when I get to meet one on one with people and helping them think through a challenging situation.


I reflected on this and connected it to the energy I get from coaching my kids in sports.


So in 2023, I’m going to be bringing forth some more ways to help career Breakers execute on their dreams.


5. I have an impact


I only started writing a few months ago on my idea around Advantage Mapping, Options Portfolio and work-life balance.


But I’ve been invited to speak at a conference, asked by total strangers to coach them, got my podcast sponsored, and been encouraged to keep spreading my message by folks like you. So thank you - this is what fuels me to do more, not awards, titles or money.


I always ask my podcast guests what gets them excited about the next 12 months, so here is mine:


I’m excited to build a meaningful community of career breakers here, and I’m excited to chart the stories of our tribe overcoming their uncertainty, to take bold action towards their dreams in 2023.


From my family to yours, I hope you have a wonderful Holiday Break and we’ll catch you on the flip side.

Mike


P.S. I'd love to hear from you.


What’s your biggest takeaway from this issue?


Reply to this email and let me know.


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What’s happening on the pod?


This week I chat with Jennie Blumenthal. We talked about her background, how to know when you’ve reached the point that your job is taking more than it’s giving, and the big lies we’re all told about how to approach our careers.


You made it to the end! Hopefully you learned something about breaking your career today! If so, please share this with someone you care about.


P.S. What did you think of today's email? Click one of the ratings below to send us your feedback. We'd love to know what you think!


⭐️⭐️⭐️⭐️⭐️ This was super helpful! ⭐️⭐️⭐️ Could be better. ⭐️ This one needs work!

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