“There are almost 7 billion people on this planet. Someday, I hope, there will be almost 7 billion companies.”
Ambitious people with “success” on the brain usually vacillate between (polar opposite) options:
Choosing either extreme is a dangerous option for most people.
Luckily, there’s a third option — one where you can generate stability and prosperity.
Ready? Here we go.
Logically, you know this. Following “herd” wisdom means you end up in Mediocre-Ville.
Crowd 1: Climb the ladder
Millennials like me were the last generation to grow up fully indoctrinated in Industrial Era thinking. We poured our hearts into picking the “right” default path. Only recently are we realizing that it’s an old-world career strategy.
10+ years in a prestigious career like consulting, investment banking, or software can feel like a rocket ship at first. But eventually, your work situation just feels lonely and life-sucking. The ladder loses its luster.
There’s also the “all your eggs in one basket” issue. If you’re going all in on one path (or employer), you’re leaving countless personal opportunities on the table. Not a wise move in our digital era: the age of permissionless leverage.
Lastly, when you look down the ladder, droves of hungry young workers are climbing upward, aiming to displace your position. That’s terrifying.
Crowd 2: Escape the 9-5
Then there’s the other end of the spectrum: “escape your 9-5!”
Maybe you dream of freelance design, coaching, consulting, or building a mini SaaS.
The upsides of profit-keeping and autonomy get all the glamor, but let’s highlight the serious risks:
Most people should NOT leave their 9-5. (Only crazy people like me who spent years psycho-analyzing themselves and running countless experiments.)
A healthy 9-5 situation provides stability and growth opportunities that you should learn to leverage (but on your terms).
On average, humans aren’t wired for this type of risk-taking. We’re built for community, not leaving the tribe.
All-out entrepreneurship is fraught with danger. The great majority of people should not become full-time entrepreneurs.
So, on the one hand, ladder climbing is a dying fad. And on the other, escaping the 9-5 is too risky for the majority.
What to do? What to do?
Do not climb the ladder. Do not leave your 9-5. Instead, plant your flag in a healthy middle ground.
Use your 9-5 as a tool while being an entrepreneur.
This enables stability + prosperity.
In working with my coaching clients, I call this strategy Optimize-Flourish.
Part 1 (Optimize): Maximize returns at your 9-5 for the least effort. Essentially, play the corporate game while conserving as much time, energy, and discretionary income as possible.
Part 2 (Flourish): Continually conduct entrepreneurial experiments via side hustles to build new abilities and capacity within you. More irons in the fire: skills, opportunities, relationships, serendipity. Building entrepreneurial muscle creates long-term life options for you and your family.
See how this works? I’m sure you’re thinking, “that’s sensible.” Then why aren’t people implementing the Optimize-Flourish strategy?
In nearly every instance, these are imagined roadblocks. Limiting beliefs.
Practically speaking, you are the only thing in your way.
Here’s what I know you want:
Simply said, we want to flourish.
It’s about moving toward your highest potential. You’re wired for that.
That’s why you need to become an entrepreneur — to blaze your own path.
When you’re spending one-third of your life on another person’s mission (in a 9-5), you’re inherently NOT doing your own thing. Instead, you’re doing someone else’s thing. And you can be damn sure you’ll regret that on your deathbed.
3 principles for implementing Optimize-Flourish:
1. Analyze Upside vs. Downside
2. Gradually implement Optimize-Flourish
3. Commit to your new Future Self
Simple, right? But also, incredibly hard…just like everything else in life that’s truly worth it.
I can’t stress this enough: experimenting with entrepreneurship is the most incredible life upgrade you can undertake.
It’s a forcing function for 10X-ing your personal growth. Corporate can’t do that, and you can’t “will” your way there.
As my friend Dennis Geelan told me in a recent podcast interview:
“I grew more in 3 years as an entrepreneur than during my 20 years in corporate.”
Is it your turn?
PS - when ready, here’s how we can help you:
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