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Michael Gardon

  • Writer's pictureMichael Gardon

What It Really Feels Like to Bet on Yourself - The Break Issue 47

Updated: Mar 13

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Today At A Glance

  • How it really feels to bet on yourself

  • The psychology of why it feels scarier

  • My big announcement on the future

  • How you can participate in our vision

What it feels like to bet big on yourself

TLDR: Scary AF.

I was in a LinkedIn conversation the other day about “going all in” on yourself. The convo was framed as investing in yourself vs investing in the stock market.

What I found interesting is that the author took the market returns as certain, but when it came to estimating returns on himself (ie education, courses, business, etc) he was MUCH less certain - could be 100% or could be 0.

Reality is somewhere in the middle. Market returns will most certainly not be 10% per year in the future. Why does it feel scary to invest in yourself when we’ll hand over thousands of dollars in the market where we have zero control?

It’s because deep down, we all doubt our abilities, and we think others have the answers. This is the great logical error we make when assessing our own abilities.

My bet on the future

Last week I made a really big decision - the biggest decision I have ever made. I bought out my business partner and I now own 100% of ​​ and all of my content, newsletter and podcast, YES!

I did this because I want to be of real value to people facing career decisions. I think I have a unique perspective to offer. I don’t want to look back at 80 and regret not trying to reach my full potential.

My vision was at odds with my business partner's. We also had different levels of involvement.

Right now careercloud is a transactional, advertising based site.

I could have sold with him and pocketed a good chunk of change, then figure out the next chapter.

But then what? What about my team? What about what I'm meant to do?

I want to build a community. One where we support each other and provide real, hands on value.

I want every reader to flourish.

Not just get a new job.

Not just get a 10% raise.

I want you to fucking flourish personally and professionally.

For years I have been hands on creating content and the revenue streams to sustain the business. It’s felt like my baby without full control, so cutting my partner a large check doesn’t feel good. I had to swallow that pride.

Now I can do what I want to provide real value to millions of people trying to find success. So over the next 6 months or so we are going to take some bold actions to work towards that vision.

But I gotta be honest, It’s really scary.

I’m out a good chunk of money.

There's lots of changes in the traffic and advertising landscape that are impacting us negatively.

It’s all on my shoulders with support from my small but nimble team.

I have no idea how we are going to pull it off.

I’m not sure I fully believe in my ability to do it.

All I know is that I’m meant to help people find their purpose and align work to that so they can find the best version of themselves. I’ve been on a life long mission to find my purpose and I believe I’ve found it here.

So I’m putting my money and reputation and all my skills on the line here.

I want you to come along for the ride.

Over the next few months we’ll be doing a lot of experimenting.

If you’ve gotten any value out of these emails or podcasts, I’d love you to engage with us on this journey.

Let us know how we can help. Let us know what’s not working for you.

Let us know what you want more of and how we can provide more value to you on your journey.

I’m investing in myself and my team right here, right now.

I know you feel that fear, when you’ve thought about change, so lets help each other through.

All I need is engagement and communication.

Drop me an email and let me know your thoughts. I’ll read and respond to every last one.

Here’s to investing in ourselves.



P.S. My Advantage Mapping Program is all about betting on yourself and using signal to guide your decisions - giving you tools to evaluate what progress and success looks like so you can have confidence in your path. We aim to deal well with uncertainty and create a systematic, high odds approach to aligning who you are with what you do. I'd love you to check it out ​​Join the waitlist


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The Latest Conversation on THE BREAK Pod

What happens when you start to notice the invisible scripts that tell you the keys to “success” are be good in school, get a good job, work hard and chase status and accomplishment?

Most people continue to push for those things on the default path. But when you start to notice and question these scripts, you can create a wildly different and more fulfilling path for yourself. But you have to acknowledge the uncertainty, and actually decide how you want to live.

My guest today is Paul Millerd. Paul was a studious management consultant on the “Default Path”, but he started to question that path and ended up opting out entirely. Paul gave up a $150,000 salary at the prestigious McKinsey consulting company in NYC, to travel the world and make ends meet through freelancing.

Then he wrote a book about it, self-published and that book has sold over 20,000 copies in the last 12 months!

I devoured his book, The Pathless Path on Audible over the course of a week in the car rides home from dropping my kids off at school or practice.

It is an absolute masterpiece on taking control and living a life on your terms, not anyone else’s. I’m extremely proud that I got to talk to Paul and bring our conversation to you today. I hope you enjoy this episode on taking The Pathless Path with Paul Millerd.

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.

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