Don't climb the ladder. Don't leave your 9-5. Do this instead.
“There are almost 7 billion people on this planet. Someday, I hope, there will be almost 7 billion companies.”
—Naval Ravikant
Ambitious people with “success” on the brain usually vacillate between (polar opposite) options:
- Climb the ladder (“crush it” within corporate)
- Escape the 9-5
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.
The crowd is always wrong
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:
- You’re accountable for running a fully-functioning business (“no one taught me this!”)
- With no steady paycheck, your variable income can be mental torture (especially when you’re supporting a family)
- Figuring out health insurance (at least for us lucky Americans)
- The long-term failure rate is 65% (I know, subjective)
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?
Optimize-Flourish
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?
Fear.
Fear of:
- “Reinventing myself”
- “Getting in trouble at work”
- “Failing in something scary”
In nearly every instance, these are imagined roadblocks. Limiting beliefs.
Practically speaking, you are the only thing in your way.
Make it real
Here’s what I know you want:
- You want to do work that lights you up
- You want stability and high upside potential
- You want to minimize time spent on distractions
- You want to soak in the moments with loved ones
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
- Take a careful look at your current trajectory: are you satisfied with where things are headed?
- Reflect on how “work” is changing: will your career strategy remain relevant?
- Consider the upside of Optimize-Flourish: what life options does it create?
- Consider the downside of Optimize-Flourish: what are you risking by trying it?
2. Gradually implement Optimize-Flourish
- Optimize by setting 9-5 rules of engagement, mastering bookends of your day, and implementing habits that support your lifestyle design
- Flourish by validating you’re ready for entrepreneurship, kickstarting your side hustle, and continually leveling up your inner circle
- (There’s much more that goes into this strategy, such as side hustle buildout, so we’ll save that for another day)
3. Commit to your new Future Self
- At the core, Optimize-Flourish is an identity change — a commitment to being an improved version of you
- You have to wholly accept that you are an entrepreneur (whoa, exciting!) who happens to also work a corporate job
- With the right long-term commitment and habits, you can have it all: a “stable” 9-5, the “life options” of an entrepreneur, and inner peace along the way
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?
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