What it means to BREAK your work

As Seen In

logo of wsj
logo of wsj
logo of business-insider
logo of business-insider
logo of cnn
logo of cnn
logo of fatherly
logo of fatherly
logo of nbc
logo of nbc

Table Of Contents

What is breaking your career?

In the last couple weeks since re-branding the newsletter (hopefully for the better) I’ve been asked what inspired the name and what it means.

I’ve been stuck several times in my “career” - not knowing the path I should be on. My hunch from talking to many of you, is that this is a common feeling. I’ve also been able to “break” my career several times to pivot or reimagine it.

Whether I did that through ignorance, brilliance or sheer luck remains to be seen, but the fact that I’ve done it multiple times suggests the answer lies somewhere in the middle.

Today’s Break is brought to you by . . . Quotebook

As part of The Break Ethos, I’m a fan of using entrepreneurship and side hustles to fuel creativity and build confidence and skills that give us optionality in the future. I built Quotebook as a side hustle with my kids as a way to teach them about building.

Quotebook is an easy family journal activity where all you have to do is listen to each other and record the memorable or hilarious things that people say. My wife and I have been recording our hilariousness since 2006. Now, I give Quotebooks to everyone I know who is getting married, expecting children or becoming Grandparents.

It’s a super simple way to stay connected to the moments that matter, and they make great gifts that are sure to be remembered for years to come.

Use the code THEBREAK and get 15% off at checkout.

Check out Quotebook

What it means to “Break” your career

Breaking your career sounds scary. We don’t want to break things, we like things how they are. People usually don’t elect to change their circumstances because it’s easier to keep going than do the work to imagine something new for yourself and fight for it. Your career essentially is a big nasty habit that needs breaking.

Join The Break Community

To break your career means that you choose to follow a path that reimagines, rediscovers and reapplies your unique talents and skills in pursuit of a work-life that you whole heartedly want.

Sometimes this will involve completely breaking your career and starting something new. Sometimes this might mean breaking into a new field or into a new company. I’m not here to preach one path. I’m only here to preach doing the work required to make a good choice about what you really want.

The PIIPE formula

To do anything different - grow, change, move - you have to leave an old version of yourself and step into something unknown. You need to shatter the beliefs, habits and inertia that is keeping you where you are, and to find work-life that matters for you. While it sounds easy to just go after what we want, it’s often not. We are comprised of thousands of little habits and beliefs, mostly unconscious, that we’ve picked up like a lint roller picking up cat hair on a fuzzy sweater.

If I’ve done anything well in my “career” it has been reinventing myself. I’ve been a financial futures trader, quit, almost became a management consultant for Deloitte (phew), run failed startups, run successful startups, had a stint as a Fortune 500 Innovation Consultant, and finally built my current company which I’m extremely proud of.

What I’ve learned through this continual process is what I’ve built into my PIIPE formula.


You have to give yourself permission to do something different. This isn’t commitment. Committing requires will. Permission is about surrender. You’re saying to your inner critic and all of your built up beliefs about yourself, that it’s ok for you to try something new. You’re stepping away from short term optimization and towards possibility. When you do this, you give yourself permission to not be perfect, to fail, because there is no perfect plan for the unknown. Give yourself permission to set a new Intention.


Intention is about prioritizing your long term path over everything else. It requires you to feel where you want to go, instead of think your way there. When I built my first freelancing company I had the intention to work with startups and create options for upside growth. When I built Rejoin Media, my intention was to create an amazing work-life for me and the small team I work with. Intention is the direction, not the tactics. The tactics follow your intention. But Intention means that you set the course.


To envision a new path you must take the self imposed cap off of your imagination. As I wrote a couple weeks ago in “How to Get Unstuck,” one of the ways we stay stuck is to not have enough options, and options take imagination. I went over some tactics in that same article, including journaling and Brain Hurricanes, but the 2 most important parts of unlocking your imagination are 1) staying true to your intention and 2) not judging your ideas. Save that for later.


The most typical arc people go through when doing something new is to get super excited and motivated, do a whole bunch of intense work, and then burn out or realize it’s a lot more work than they thought. Doing anything new takes patience. Patience is consistency, and consistency trumps intensity over the long haul. Be patient with yourself, but always true to your intention.

Empathy - for yourself

Empathy is simply understanding or being aware of yourself, your likes, dislikes, tendencies and habits. Empathy is the basis of real change. It is also key to identifying your circle of competence, which I wrote about in “How To Invest In Yourself”. For some this is easy, for me this is more of a challenge, but you can’t make a change unless you know yourself, so get after it today!

What’s Happening on the Pod?

In this episode, I chat with Dave Fano (@davidfano). Dave is a serial entrepreneur, former WeWork executive, and ex-architect who has made it his mission to help people navigate their careers with confidence. His latest venture, Teal, helps people optimize their job search by providing the level of tooling and infrastructure that companies have but for the individual professional. In just over a year, Teal has grown to a community of over 40,000 users committed to advancing their careers.

Listen to this episode w/ Dave Fano

Thanks for reading The Break! Subscribe for free to receive new posts and support my work.