The Ladder of Freedom
One night, I was walking home from the gym in NYC and had to stop and take a video of this.
I call it HELLSCAPE ON EARTH.
Looking at this building full of people working at 7pm, what do you feel?
I feel TRAPPED. Ever since I was a kid, I never wanted to work in a cubicle with fluorescent lights. I certainly never wanted to have people walking outside in the fresh air, looking at me through the glass in my conference room window like a zoo animal.
I know it’s irrational, but I’ve hated this since I started working at 14 years old.
Now, I don’t mind working hard and I don’t mind putting in lots of hours when times are busy. But I hate the idea of HAVING to go into an office.
“Dear Boss, can I please take a 2-day vacation?
Can I please use the bathroom?” NO!
I remember telling my college friends this. They all looked at me like I was insane. We were all going to go work in cubicles…that’s what you do, right?
Actually, no. You don’t have to.
When I was offered a job at Google, I ran the other direction. I took a massive pay cut, lived in a house with 4 other guys, and chose a different path.
YES — it’s an amazing privilege to even be able to think about what “our path” is. So many people have to work at whatever job they can find to provide for their families. My immigrant parents came here and my dad took what job he could get. But together with my mom, they learned enough to give the next generation — my siblings and me — enough freedom that we could choose what we wanted to do.
I’m very grateful for that opportunity. And now I get to share what I’ve learned with you.
As I’ve met more IWT readers, I’ve asked what your Rich Life is. I’ve learned it’s not simply to make more money (not even $1 million per year).
It’s also to choose the LIFESTYLE you want. For me, it was never having to go into an office with fluorescent lights and people wearing Patagonia vests. What is it for you?
Is your Rich Life…
- Never having to wake up to a blaring alarm clock?
- Being able to travel for 3 weeks at a time — and flying business class?
- Being able to buy something without worrying about the price?
Here’s what I decided for my Rich Life.
I run my business from my home office — no commute, no fluorescent lights. I can wake up, have a leisurely morning, and walk 10 feet to start working.
BTW I splurged on a dual-monitor setup:
I wanted the freedom of traveling now, not 40 years from now. So I built it into my life. Every year, I travel for 6 weeks.
Here’s my office for the day at The Oberoi Vanyavilas in India.
I worked for one hour per week — over a 6-week trip —
and my business kept growing.
Fun fact: When that picture was taken in India, I checked on the daily sales for my business. The sales receipt from the previous day was for $14,591. That’s how much my business brought in in one day, with no office and no conference rooms.
I know this is unusual — but it’s not an accident.
It’s the result of building a business that supports my Rich Life.
What would yours look like? Would you have a home office? Would you travel more? Would you take the afternoons off to spend it with your kids or a workout class?
Your Rich Life is yours. But it means you have to decide, then create it.
This is a totally different way of thinking about lifestyle. Most people take a random job, look around longingly at travel pics on Instagram, dream of “freedom,” then shrug and walk into a brown-carpeted conference room with lukewarm coffee and a conference room speakerphone. That’s my personal hell.
We wonder why we have a hard time getting out of bed and motivating ourselves to get things done. No, taking a 2-day vacation to “recharge” won’t change anything. 5 minutes of meditating won’t change it, either. You have to be courageous enough to confront the system you exist in…and decide to change it.
We all want freedom. We all want the flexibility to be spontaneous. We all want the ability to say YES when someone or something we love comes along.
Are we willing to make the changes to get it?
Once you start, you’ll discover there are lots of different levels of freedom. And you choose where you want to be.
I call this The Ladder of Freedom.
LEVEL 1: Freedom from $3 worries
This is the ability to stop sweating the small stuff.
A reader told me about taking a taxi in NYC and staring at the taxi sign ticking up by $0.50…block after block after block.
“God,” he said. “I could see the price going higher, knowing I was going to have to skip lunch the next day. I was thinking to myself, ‘Should I just get out here? I could probably walk from here. But it’s raining…’”
I remember being in my early 20s and thinking EXACTLY the same thing. I went to a restaurant and saw an appetizer that looked so good…and then turned the page and just got an entree.
For lots of people, that’s just how life goes.
It’s easy to be worried about small expenses when we’re surrounded by so-called “experts” lecturing us about how our $3 lattes will destroy our lives. (Which is why it’s still surprising to most people to find out that you could cut back on $3 lattes all day…and even over 50 years, it wouldn’t add up to much. You can see the math in my post about multimillionaires lecturing you about avocado toast.)
At a certain point — as you get older, as you earn more, and as your time becomes more scarce — we all reconsider the calculus of is it worth it? For example, my mom would have NEVER bought pre-cut vegetables: They were too expensive. Now, I do. An extra $2 means nothing to me, and the 20 minutes saved is valuable.
Put another way: Would you worry about the cost of a $0.25 piece of candy? No, because it would have no effect on your life at all.
Same with $3 expenses.
This first level of freedom is freedom from worrying about $3 expenses. You never have to worry about coffee or appetizers or picking up a round of drinks for your friends — because the money will not affect your life at all.
LEVEL 2: Freedom to ask $30,000 questions
This is the ability to buy the things you love, guilt-free.
At this level, you’re not worrying about $3 questions — you’re actually leaning into $30,000 questions.
You don’t have to cut back on tiny expenses. Because you’re keeping your eye on the Big Wins, tiny $10 or even $100 expenses are irrelevant.
In fact, you can splurge on the things you love:
- Not just getting flowers once a year for your anniversary — getting a fresh bouquet delivered every week
- Traveling for 3 weeks every year — and sorting your flight by “direct flights only,” not by “cost”
- Treating your friends to dinner, saying, “I’ll get this”
I talked about moving beyond $3 questions for CNBC
If you could spend $5,000/year on something you love, what would it be? Get really specific. Don’t just say “travel.” Say: “I’d fly to Mexico for 10 days with my girlfriend, fly business class (points), stay at this resort I’ve been keeping my eyes on, and take a tequila tour.”
Now think bigger: What if you could spend $50,000/year on something you love? What would you do? Most of us have never thought about this because we’re mired in the $3 weeds. But at this level, you can think bigger.
Here’s what I did:
How about you?
If you had freedom from $30,000 questions, what would you spend more on? What’s the thing you LOVE spending on? Eating out? Travel? Fitness?
LEVEL 3: Freedom from location
This is the ability to work and live wherever you want.
At this level, you have the ability to travel anywhere. You could work from Starbucks or a home office. Or Japan.
And you’re not locked into any location, no matter how cool it is. You can work from Spain for a month, then try someplace else.
You’re not limited to two weeks of vacation a year, either.
Here’s how I use this level of freedom:
Annual CEO trip: Every January, I take a trip with a small group of CEOs. We get a house with a chef and a view, then spend 4 days planning out our year, talking about what worked/what didn’t, and share advice with each other. (If this isn’t your thing, you could do it with a group of friends.)
Annual CEO trip, where we ask for advice,
share our lessons from last year, and plan out this year
6-week extended vacation: At the end of every year, my wife and I take a 6-week trip. The trip gives us time to connect with each other, reflect on the year, and most of all, eat the world’s best food!!! I’ll post food pics on my IG account later.
India, Kenya, Italy, Japan…and more trips coming up. Each year, I work with my team to set up more systems that allow me to be off the grid. Last year, I only checked in for 1 hour a week. The rest was pure vacation.
Don’t be limited by my choice. What would yours be? Some would love a beach trip…others would move to Colorado for ski season…and others would take their kids to Europe for the summer. Dream big!
If you had freedom from location, where would you go?
LEVEL 4: Freedom from time limits
This is the ability to do what you want, when you want to do it.
No endless string of meetings that you didn’t schedule. No alarm clocks. No having to remember “that one thing” to buy from the store.
At this level, you can use money to buy back your time.
Note that if you still love something, you can still do it! For example, I love reading emails from my readers, so I continue to read every single one (though I can’t respond to every one). I also love ironing my clothes. But I hate having to sort through travel options, so I’ve outsourced that.
Here are 30 examples of things my assistant handles and that I no longer have to spend time on thanks to my assistant and the systems we’ve built:
Altogether, this saves me 20 hours every week.
If you had freedom from time, what would your mornings look like?
LEVEL 5: Freedom from expectations
This is the ability to completely craft your own Rich Life.
Maybe you want to buy a house — or not.
Maybe you want to have kids — or not.
Maybe you want to travel around the country in a trailer!
I love this!!
It’s not my Rich Life — I live in a city — but it’s Steve and his wife’s Rich Life.
This is true “freedom from expectations.”
Guys, if I had followed society’s expectations, I would be wearing an ill-fitting XL t-shirt working at Cisco Systems. That’s my idea of hell on earth.
Freedom from expectations means you’ve mastered the $3 level, the $30,000 level, the freedom from location, AND the freedom from time limits.
This level is the culmination of the others — the top of the ladder of freedom — because you’ve truly earned the right to be free from expectations.
Now you can choose the life you want.
Here’s how this worked in my life: When we were planning our wedding, my fiance (now-wife) Cass and I were out to dinner with some friends. We were talking about wedding planning and our friends asked us what we were thinking for a honeymoon.
I told them we were probably going to go on a safari for 7 or 8 days. It was classic American thinking: we’re probably going to go for 7 to 10 days, have a nice time, come back, go to work. We were excited!
Our friends were excited too. One of them said, “That sounds amazing. You know, when we went on our honeymoon, we took three months off and it was amazing.”
Cass and I looked at each other. What?
Then the next couple (also older than us) told us that they took a year off and traveled the world when they got married.
Cass and I walked out of that dinner looking at each other, saying “What the hell just happe—”
We thought they were normal people. But who the hell takes that much time off?
Then we asked another question:
What if we decided to take a different path than the usual 7-day honeymoon?
What if we decided to stay at some of the world’s most amazing places…and also visit locals and eat street food?
And what if we brought our parents with us for part of it — to create memories we’d truly never forget?
In retrospect, I feel a little dumb because my entire business is advising people how to think bigger, but when it came to our honeymoon, I “bought into” the usual 7-day trip like everyone else.
But I’m so glad we had that dinner. And I’m so glad we asked that magical question, “What if?”
We realized we could do this, too. We have the flexibility. We have the finances. We just needed the courage — and the mindset of freedom from expectations — to say YES.
On a horseback safari in Kenya, surrounded by giraffes. Our relationship rule:
If we’re ever on the fence about doing something —
a dinner party, an event — we just say YES.
We ended up taking a 6-week honeymoon to Italy, Kenya, India, and Thailand — and having the time of our lives.
One of the big mistakes that people just starting out make is assuming they have to accomplish all of these rungs at the same time. Wrong! You can start methodically and slowly. These can take a lifetime to truly master, and each step up is a win.
Now I want to hear from you:
I shared some of the changes I’ve made moving up the Ladder of Freedom.
Where are you on the Ladder of Freedom?
Where would you like to go?
Be specific — is it visiting a certain place? Is it never doing your own laundry again? Is it spending 2 hours volunteering every Wednesday evening?
Send me an email (I read every one).
…but you don’t have to take the same path as everyone else. How would it look if you designed a Rich Life on your own terms? Take our quiz and find out: