I realized I had a problem when I was thinking of taking a 2-week vacation years ago. I started to get really mad just THINKING about how the conversation was going to go with my boss.
This was all in my head:
Ramit: “I’m planning to take a 2-week vacation at the end of June. I’ll make sure all my projects are handed off to the right people.”
Boss: “What? 2 weeks?”
Ramit: “Um, yes”
Boss: (Starts listing reasons I can’t go): “Two weeks is a really long time…” “Aren’t you over your vacation time this year?” “We need you here in June. Maybe later this year.”
Ramit: “WHAT THE FUCK” (throws mug on the floor)
At that point, I realized I was not really a good employee any more.
I know, I know. We don’t all concoct grandiose conversations in our heads. (My favorite fantasy conversation always takes place at Subway — I think because the sandwich makers are always FOB Indian guys — where I see a really mean customer being rude to them, and I dispatch a devastating response. The rude customer shrinks away and the rest of people in line start cheering. I am given a free sandwich.)
Fine, I admit it. This isn’t normal. But how many of us have thought about the drudgery of working in our same jobs for the next 30 years?
Of punching a 9-to-5 (or worse) clock while furtively counting up our glacially accruing vacation days?
And of the relief of taking a few days off a year — only to start dreading the return to work?
Over the last few emails, we’ve been talking about our huge bucket list goals. Now that I run my own business, one of my favorite things is the FLEXIBILITY to set my own schedule.
Here’s a screenshot of me planning a lunch at 3pm on a weekday:
When I was first thinking of starting an online business, I had no idea what it really meant. Now that I’ve been running one for nearly 10 years, I can appreciate the way it lets me live a rich life.
- I can work from my apartment in SF or stay in NYC (usually, once I detect the first hint of sweat on my body, I immediately fly to SF)
- I can take impromptu trips to see college friends around the country
- I never have to worry about buying appetizers or taking a taxi. If I want to do it, I can
Of those 3, that last point is the most interesting to me. When I was a young and stupid idiot, first thinking of being a “successful entrepreneur,” I had delusional ideas that it would be all about walking into a car dealership, pointing at a car, and buying it with cash. God, kill me.
Living a rich life isn’t just about once-in-a-lifetime, black-carpet events.
The truth is, a rich life is lived in the minor decisions you make on a daily basis. If my parents want to come visit me, I can afford to send them tickets and upgrade their seats so they can sleep better. If you want to outsource some of your work to a cleaning person, you can. And If you want to get more fit, you can hire a personal trainer (and schedule your workouts any time of the day).
A recent email from my assistant.
It’s about the FREEDOM to decide what you want to do, without having to worry about clocking in or saving $8 on an appetizer.
Sure, everyone is nodding their heads now. Freedom sounds great! But most of us never get beyond the conversations-in-our heads…because we’re afraid of what might happen if we try something new.
But when I first tried to start something online, I was petrified. Will anyone buy this from me? What if they call me a sellout? How do I even come up with an idea?
I went through each of these things. And guess what — each of my fears was TRUE. People DID call me a sellout. They told me I was stupid, nobody would ever read me, and (delusionally) that my eyebrows were ugly.
Once I learned how to turn my own skills into a successful online business, they faded away. It’s like a burglar casing a house — if they see you lock your door and set the alarm, they’re going to move onto an easier target.
If I had let my fears control me, I would be sitting at a cubicle, scheming about another angry conversation I was going to have for TWO WEEKS of vacation. Ugh.
Guys, we all have these fears — fears of not having an idea, of not being good enough to start something unconventional, fears of selling ourselves. EVERYONE HAS THEM. The difference is, some people let those fears control them like a vise around their necks. And other people say, “You know what? Maybe I’m right. Maybe I’m wrong. Who knows? I’m going to test those fears and try something new. If it doesn’t work, all I’ve lost is a couple months. But if it works…my life will be totally different.”
Let me show you how I deal with my fears (yes, even I have them) about building an online business. I tell you all about it in a new 8-minute video.
Risk taking: Why you need to put yourself out there:
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