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Michael Gardon

  • Writer's pictureMichael Gardon

The Investment In Loss Superpower - The Break Issue 12

Updated: Mar 19

Welcome to The Break! We are all on a mission to break our careers (and that’s a good thing!). Join us to gain the confidence to break out every single week, and pass this along to someone who needs it.

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Today At A Glance

  • A personal note on sharing wins

  • Pivot Concept: Investment In Loss

  • New Job board for our community!

  • Latest Podcast with Tom Brunskill of Forage.

Celebrating a win = loving the process I’ve never been one to celebrate little wins along my path to an ultimate goal. But as I’ve gotten older embracing ‘the process’ along the way has become more important because I realized I spend so much more life trying to get to the goal than I spend during its final achievement.

I’ve had help realizing this from a few mentors and coaches. While so many people preach about “falling in love with the process” what I’ve come away with is that one way to train yourself to love the process is to celebrate along the way.

So in that spirit, I wanted to share that my kids and I (and our side hustle Quotebook) were featured in the latest issue of Wonderdads Magazine.

I know not everyone on this email list is not a parent, but I’m trying to teach my kids how to be entrepreneurial, make memories and now, embrace the process along the way!

Investment In Loss Mindset Arguably more than anything, your mindset determines your growth and your ability to change - at least this is my experience. Have you ever had a moment where you read something and suddenly you see the entire world in a different way?

That’s a mindset shift.

One of those moments that had the biggest impact on me came in 2009. I was a struggling trader. I made more money than I probably would have in any other job at the age of 27, but I was stressed out beyond believe, and who am I kidding - I wasn’t a superstar.

I was determined that I would succeed or I would die sitting in my chair - literally that was my self talk. Very unhealthy. I would wake up in the middle of the night with panic attacks and wasn’t sure if I’d ever wake up again if I went back to sleep. My mindset was, I could never quit and my health didn’t matter.

And then I read one chapter . . . of one book.

That book was The Art of Learning. The chapter was titled Investment in Loss.

My world changed. I quit my job the very next day with no real plan. But I was armed with a new confidence and permission that I could pivot, adapt and change as long as I viewed all of my actions as investments.

What Is Investment In Loss? Investment in loss simply means that we often need to take a step back in order to make a giant leap forward, and that step backward is an investment.

We may take a loss in the near term, but we trust and expect that our investment will produce growth for us.

This concept is key to learning anything. Why?

Because to do anything new or different, we have to give up something. We give up our time on nights and weekends to search for a new job. We give up that same time income when we quit our jobs to find a new path.

And elite athletes invest in loss when they make transitions in their careers to get to the next level. Two famous examples:

  • Tiger Woods to two years, threw away his old swing, worked with a coach to build a new swing that could take him to the next level.

  • Michael Jordan, had to become more of a jump shooter later in his career instead of dunking everything. He three-peated again after this transition.

Up until the moment I discovered Investment in Loss, I always looked at the world linearly, and thought my progress always had to be incremental. I had to stick to a path, and it didn’t matter the pain I took personally.

Here’s a video I did on the subject:

Embracing this concept set me on a path where I did not fear change, I made change a strength. I went on to break my career multiple times and adapt to changes, but anticipating them and “investing” in the skills I needed to get to the next level.


  • Quitting my trading career to get into entrepreneurship

  • Learning how to write to sell

  • Spending $10,000 to design and produce Quotebook before I knew I’d sell any

  • Spending nights nurturing Rejoin Media as a side hustle to get it to full time

  • Leaving a cushy corporate consulting gig for unknown entrepreneurship

At each pivot, I viewed the actions I needed to take as an investment and then worked to mitigate the risks of that investment.

Now I don’t fear change. I think change is my superpower.

The Break Job Board I’ve been trying to figure out a way to bring new opportunities to our community of Breakers. I finally teamed up with Pallet to create a curated job board for our community! These jobs are tech focused, remote first opportunities. I’d love it if you followed. Maybe, just maybe you’ll find your next big opportunity here.

Here are a few featured opportunities:

Also, If you’re looking to support the community and have a job to post, you can do so by clicking the ‘Post a Job’ button.

What’s happening on the pod? I caught up with Tom Brunskill, CEO of Forage who’s company is helping job seekers skill up and get exposure to different jobs before they apply. Check it out below and please like and subscribe to our channel so you don’t miss out on the next episodes!

Listen to this episode w/ Tom Brunskill Thanks for reading The Break! Subscribe for free to receive new posts and support my work. Subscribe now

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. Share

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