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5 Lessons From Leaving Corporate 25 Years Early.

leave corporate lessons Sep 25, 2023

 The butterflies. The new Men’s Warehouse suit I just bought was freshly pressed and ready to rock.

I was bombarded with new faces after sailing up to the 19th floor. Names that would take me weeks to get.

I was finally showed to my desk. A cube in the ‘bullpen’ with all the other junior bankers who would spend countless hours - including well into the night - in these very desks.

Little did I know - it would be my last ‘first day’ for a new job. This was 17 years ago. And I haven’t had that feeling since.

Here’s five things I’ve learned over that time that have helped me end where I am now -

Living in a different country, running a one-person business, that I can do on MY terms.

Here we go…

1/ You can start a business with no money.
My first move out of the corporate world was running a fitness studio. My partner and I signed a lease. Needed equipment. Renovated the space. Hired a designer. Some of it was our money. Some of it was from investors. All told, we were in for over $100,000.

After we closed the studio (and returned all the money to investors, plus interest), and a brief stint at ‘retirement’ for me - I started coaching. It required nothing more than an internet connection, a social media account, and a few other (free) software programs that I could manage from my phone.

If you want to see what they are, you can read more here.

Don’t let the idea that you need a lot of money hold you back. Figure out the most cost effective way to get moving - and do it. This approach costs you next to nothing to get started. 

2/ Corporate:Tram as Solopreneur:Roller Coaster. 
Emotionally. And pay wise. A corporate job is at an emotional '7' at all times (more or less). Do your job well enough to not get fired and you get the bi-weekly bank account top-up. And the emotional stability that comes with that is a side effect.

You don’t worry about where the next sale is coming from, or how you’re going out to find new clients (depending on your role, obviously). The work is just - there. You do it. You get paid.

Now solopreneurship is a lot different.

A '3' one day as a few sales calls don't go your way. Or you have no growth / low engagement on social media.

A '10' another day when you finish a project you’ve been working on, or someone messages you to work with you.

No steady paycheck. When you eat what you kill - there aren’t that many rest days. You can ‘get ahead’ of the things you need to do, but you’re always on the hunt.

3/ Enjoying your work > Wishing days to zoom by.
There was nothing worse than the idea of office 'face time'. Or having to ‘prove’ your worth by talking more than needed. Interjecting yourself when you could totally stay quiet.

It was never about hating work. It’s about not having to do work that you simply don’t care about.

We don't mind work. We mind work that we don’t enjoy. So when you’re doing things you actually enjoy doing - you’ll gladly do them all day.

When I ‘retired’ for 2+ years after closing our fitness studio, it was fantastic - but I still craved something purposeful to do. An activity or project with achievable milestones. And that feeling of accomplishing something.

Work is good for us. We learn. We earn. We use our brains in ways that keep us fresh. And young.

Why do you think so many people look for other work after retiring?

It’s not ‘work’ that we’re avoiding. It’s work we’re forced to do that we don’t like or care about that is the problem.

And if you don't like it – you'll feel forced. And will never outlast those that like the work. Head here for help finding work you love

4/ Lifestyle arbitrage > Lifestyle inflation.
We’ve seen it a million times - and can tell when it's happening. Bigger house (or a second house!). Newer cars. Nicer clothes. Luxury vacations. The increased salary leads to more spending on everything else.

And slowly creating a situation where the person becomes handcuffed to a higher level of earning to support the ‘addiction’ to nicer things. If often leads to being ‘thing rich’ - but cash poor. Still paycheck-to-paycheck, unable to handle a salary disruption or cash emergency. Higher pay and better appearance - but still an uncomfortable position.

On the other hand - lifestyle arbitrage - earning a salary with geographically independent work, then living in an area where the money goes further. The whole digital nomad movement is based on this very idea.

You may sacrifice some of the comforts and convenience of big city living, like being able to get anything you want at any time of day (i.e. New York City), but you pay dearly for that with higher rent, food costs, entertainment, and transportation.

If you can forgo some of these, your money can go a lot further in other parts of the world, like Southeast Asia, South / Central America.

5/ Travel helps you understand what you need.
A breakup-fueled bout of depression made me give retail therapy a shot to get back on my feet. At first, I felt rejuvenated.

When I walked down the street in my new clothes, and returned home to all the new electronics, furniture, and gadgets in my apartment - I felt great. Initially.

But after a while - these became the norm, and I was out over $12,000 (or FOUR months of not working for someone else - money is time, ya know?).

It wasn’t until I went on a trip to scale Africa’s tallest mountain that I truly understand how much I needed in my day-to-day life. I had the best three weeks of my life - with nothing but food, water, some clothes, nature, and close friends. Why couldn’t I replicate that in my regular life? I gave it a shot when I got home, getting rid of almost everything I owned.

And once I realized that I didn’t need a lot of money if I wasn’t buying a lot of things - I then saw that I didn’t need to give away all my time. I broke the consumerism cycle - and it has been a game changer for my freedom.

So, my actionable tip:

Take a trip. Don't check a bag. Observe what you need. Adjust your mindset - and your spending - accordingly.

That's it for my inaugural issue.

I hope you enjoyed it.

See you again next week.



Whenever you're ready, there are three ways I can help you:

1. Free blueprint full of tactical tips to build your escape plan here. 

2. The 'DIY', build your escape plan option with over 50 interactive lessons – The Corporate Escape Academy.

3. We'll build your escape plan together through 1:1 coaching – book a call with me to apply.