I'm Creating An "All Weather Life"



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.


Today’s Break is brought to you by . . . Top Stack Resume

TopStack Resume writers create custom, ATS-friendly resumes that will wow hiring managers and recruiters. They can also craft engaging cover letters and LinkedIn™ profile content. And, if you need some extra support during your job search, you can work with one of the company’s career consultants for guidance.

Their unique pay-after option allows you to get started with TopStack risk-free.

Both the Professional and the Premium packages come with a 60-day interview guarantee. Get Started With TopStack


I’m Creating An All Weather Life The Break is all about breaking our careers to find a work-life that we love.

So why am I obsessed with change? Isn’t change risky? Unfortunately, the world is risky.

Right now we’re experiencing the highest inflation in 40 years which is impacting our wallets, our companies’ profit margins and our jobs.

Technology changes fast rendering entire industries obsolete. The stock market is in the tank. But we can still succeed - and that’s not coming from a natural optimist.

How? By adapting and methodically setting up our lives to weather the storm.

Freedom and resilience I think about being free from worry. Having the knowledge and confidence to adapt and figure it out. Having a plan B, C, D. In three words:

Freedom is resilience.

So how do we become resilient? We build the proper foundation, redundancies and diversify.

The All Weather Portfolio Legendary investor and hedge fund manager, Ray Dalio sought out to build one portfolio that would perform well in all economic conditions. This well diversified portfolio would likely underperform in bull markets, but overperform in bear markets.

I love Ray’s approach and thoughtfulness. My recent podcast guest, Dave Kline worked for the man, which is pretty cool! One day, I’ll interview Ray.

The search for this type of portfolio came out of a single insight that I think is particularly relevant to all of our psyches even though we aren’t billionaire hedge fund managers: Ray knew that he can’t predict the future, no one can. So, he needed a way to expect surprises - both positive and negative.

But constructing the portfolio is a challenge because he needed to become an expert in many different asset classes, and figure out how much of each to hold in the portfolio. Stocks, bonds, cash, commodities and gold.

The All Weather Lifestyle The all weather lifestyle is my holy grail, and it is a systematic playbook I am working on from a life design standpoint to reduce risk, increase options and smoothly float over rough patches that will inevitably pop up.

Here are the basic pillars:

  1. Skills that you can be reliably paid for and transcend a specific niche (a job)

  2. Cash - for cushion and investment

  3. Ownership in a growing asset (business, audience, stocks, etc)

  4. Multiple income streams (if one goes down)

  5. A transition plan (how will you move and adapt in between?)

Working on all 5 pillars is paramount, but they can be sequenced. Here are examples from my own journey.

  1. Skills. The most transferable skills are soft skills. Judgement, communication, empathy, performance under pressure. I built these skills early working on investments and trading. This allowed me to move into different industries.

  2. Cash. Cash can be used for cushion or for investment. It has “option value” in that I can use it for many different things. I built the discipline to save from a young age and always have more cash than the experts suggest. For this reason cash is a huge part of my “barbell investing strategy” and why I’ve been able to use cash for investment when other people could not.

  3. Ownership. In 2018 I decided to own my own business. My websites, audience and cash flows are all growing. Most importantly, I control this business.

  4. Multiple income streams. I earn money from advertising, select coaching, content services, my side hustle Quotebook and passive investments. I been through multiple cycles where one of my income streams has gone down to 0.

  5. A transition plan. My transition plan has always been freelancing my core skills. I’ve used freelancing in three separate transition periods to get from job to job, or job to business ownership. Freelancing is the best path to transition that I have found.

There will be more to come on the All Weather Lifestyle as I solidify my thinking on this important topic. All for now, and let me know what you think!

What’s happening on the pod? Mike Podesto saw the bad side of recruiting and conceived of a better way to help job seekers. So he broke his career, then he freelanced and bootstrapped his way to making his vision happen with Find My Profession. Check out his inspiring story.


Listen to this episode w/ Mike Podesto 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