Nobody gives a sh*t about your career transition

And nobody is coming to save you if it doesn't work out

Have you ever wondered what happens when you finally take the leap of faith to pursue your dream career?

• Loud cheering from your friends and family?

• A triumphant welcome from your chosen new space?

• Fanfares from angels?

Three months ago, I walked out on a long-established corporate career to take a bet on myself as an entrepreneur. Here are the top lessons from my experiences so far.

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Going against the grain is hard

Getting to the start line of an entrepreneurial journey is incredibly hard.

It breaks all the rules you’ve been taught. Work hard, stay in line, do well, serve your company, and wait for the reward. Leaving your job behind is a significant risk, especially in the US, where the golden cage has the intimidating double locks of 401K and health insurance.

Breaking out is not what you’re supposed to do.

Your friends and family will wish you the best, but you’ll hear the edge of nerves in their voices. It’s not that they want you to fail - it’s the opposite. Their fears are rooted in care for you.

You'll start to wobble if you don’t have courage in your convictions. I had to fight through two weeks of applying for new corporate jobs I didn’t want. It felt good doing what I was ‘supposed to do.’

When I sat down to update my LinkedIn headline to reflect my new ambitions, it took me two hours—one hundred and twenty minutes of wrestling with the identity I was trying to shed, one that had served me so well and been ‘part of me’ for so long.

I finally put it to rest by declining a warm lead follow-up call from an interested corporate recruiter. It's undoubtedly a sin in this job market, but it was an essential declaration of intent for me.

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The sensible playbook will tell you: “Build something on the side while you continue your job!”

Anyone who’s ever worked in a high-pressure corporate role will know just how difficult that is. Rousing myself at 5 am to build a business alongside a senior corporate job was never going to work for me:

• A ready-made excuse every day to prioritize your main job

• No *real* pressure to take action and build

• Adding to the mental and physical load I was already under would probably have broken me

The reading and self-development I did accomplish on the side in the last two years opened my eyes to the opposite part of the risk.

What if you never try? What if you live your years out in cubicles and offices to find yourself loaded with regret that you never took a bet on yourself?

What if you spent the best of yourself in service of someone else’s profits?

What if you spend your life playing a game you didn’t enjoy for a prize you didn’t want to win?

That seems like the real risk to me.

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Your new space owes you nothing

After letting the mud settle a little after leaving my old job, I began to explore the entrepreneurial space online.

After finding my feet, I participated in some networking sprints, aiming to get in front of as many fellow entrepreneurs as I could. Surely they’d be wowed by my decades of corporate experience and know the perfect opportunity for me?

Absolutely not.

They didn’t give a crap about what my title used to be, the size of my former team, or any of the other things that are so prized within the corporate matrix. Your money is no good here, Sir.

Imagine playing Sonic the Hedgehog for years, collecting all the bonus rings, and then moving to Mario World and trying to get Mario and Luigi to care about your shiny yellow hoops. We only care for the turtle shells, mushrooms, and stars here, buddy!

Here’s what matters:

• Solving a valuable problem for an engaged audience

• Cashflow

• Momentum

All the slide decks in the world can’t create the illusion of those, no matter how nicely formatted your boxes are.

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In terms of progress, it’s like Vegas out there—so many ways to get rich. How could anyone fail to win?? Many people offer the surefire route to success and are willing to share it with you…in return for a handsome price.

Two ways I had to get smart quickly here:

• Find ways to separate the superficial moneymakers from those with true insight to share.

• Realize how easy it is to get caught in the spin cycle of thinking and planning.

My two most significant sources of momentum have been:

• I joined a select few paid communities after careful research. Behind the paywall, these groups are genuinely willing to share insight and support.

• I took action. Forward progress is empowering. Even if it quickly turns into a dead end in the long term, lessons are learned, and the mental muscles required for motion are strengthened.

It’s not easy, but it’s a rewarding struggle. Welcome to the new kind of hard, I guess.

People aren’t watching as much as you think

To break free from corporate's golden cage, I had to free myself from an overactive need for validation.

It was a regular instrument of limiting self-torture while in the cage and would have weighed heavily in the early absence of excited approval from those around me when I leaped.

Paradoxically, it was only when I had moved past that need that I noticed that most of the time, folks are way too consumed with themselves to even notice what you’re doing, never mind having an opinion about it.

The LinkedIn bio that I labored over changing - I’ve since changed it about ten times, and nobody has batted an eyelid.

The ideas I took early action on to discover dead ends - they publicly came and went, and the Earth carried on spinning, untroubled.

The power to shift your identity, realize complete control of your outcomes, and banish your fear of failure out of concern for others is a really enjoyable position to be in.

You get to feel like Neo after his Matrix kung-fu lessons. Watch out, world!

Choosing your priorities is incredibly freeing.

When I embarked on this journey, I had two critical priorities unrelated to work and income: I wanted to reclaim and reset my physical and mental health.

I have traveled, read, worked out, rested, and done as much as possible to relieve myself of pressure to progress with work—a mini monk-mode session.

This effort has yielded significant returns:

• No headaches or illness for three months

• A perfect set of blood panel results

• Resting heart rate back in the 40s.

• Swapped out inner turmoil for inner peace.

• My relationships with my wife and sons are the best they’ve ever been.

I don’t think it’s possible to put a price on any of these things.

However this adventure ends, I already have all the data I need to know it was the right choice to begin it.

I’ll end with a creator post that helped inspire me to keep going this week.