How to start on your bucket list this year

Ramit Sethi

This was my view from Barbados a week ago.


One of the things I always wanted to do was get a beach house where a bunch of my friends and I could all stay, drink, eat, and swim in the pool or jump in the ocean.

In Barbados, I continued on with my life of never cooking as, every morning, the in-house cook came up to me and asked, “What do you want to eat today?” We decided to take a boat ride, so the boat came up to our back yard (the ocean), we got in, and went snorkeling for a few hours.

I loved it. And it was awesome to know that hard work let me do one of my “bucket list” items years before I ever thought I would.

Even better, I didn’t have to use limited paid time off for the trip, since one of the perks of having my own business is I can travel when I want to. In fact, while I was gone, my business kept running. I didn’t respond to work emails, but my business continued generating tens of thousands of dollars. I knew that when I got back, everything would be in order, running smoothly.

For me, this is one way to live a Rich Life. The things I love about it:

  • FLEXIBILITY: I can travel any time of the year, in the middle of the week, for 3 days, 10 days, or 2-3 weeks — whatever I want
  • MY CHOICE: I used to chafe at having to wake up to an alarm clock for someone else. The funny thing is, when it was my choice, I’d wake up earlier
  • NO COOKING: I will go to the ends of the earth to not cook. Saute? Broil? What’s that?

We all have different ideas of a rich life. Maybe yours is hiking in the Amazon, or living in Europe for 3 months, or starting a blog on fashion, or becoming a photographer.

Here’s something I realized while I was sitting in Barbados:

If I had taken the conventional path, I never would have ended up here with my friends. I would have been an engineer wearing a badly fitting polo shirt working in a tech company!

So what does that mean for us? How do we go from conventional (which is, by definition, “normal”) to living an extraordinary life? How do we turn a bucket list of things we want to do “some day” into reality?

Today, I want to talk about BACKWARDS ENGINEERING your way to living a rich life. Tim Ferriss has an interesting take on this: In 4-Hour Workweek, he talks about figuring out what it would take to live the life you wanted — even if it means taking an extravagant trip to Asia — and breaking it down. So a 3 week vacation means you need $X…which means $Y/month…which means, if you start an online business, it has to generate $Y/month for you to achieve that dream vacation.

All of a sudden, a dream becomes much more manageable.

Let’s go deeper. I want to analyze an email I got from an IWT reader. See if you can notice the invisible script he’s employing:

Hi Ramit,

…I have a lot of interests and my thoughts are perhaps starting a blog will help me narrow these down to something I can focus on, with an eye to become an expert at.

Do you think starting a generic blog where I rambled about a range of topics be a terrible idea, or a great way to let it grow organically and become a true representation of what I want to do most?



Do you notice what he’s doing? He’s waiting for permission from me.

In fact, here’s what I replied:

“I appreciate your asking me, but you do not need to ask permission from a random internet guy to start a blog. If you want to start one, do it. A great life philosophy is if you wonder, “Should I do X?” ask yourself: Why not?”


How many of us wait for permission in weird ways?

  • “I’m really busy now…I’ll do it later”
  • “I’ll do this when I get a boyfriend/girlfriend”
  • “That would be really fun, but I need to have (3 more weeks of vacation saved up, my ‘ducks in a row,’ to plan it all out first)”
  • “My friends/parents will think it’s weird”

Sometimes I want to shake people in their 20s and 30s upside down and threaten them with a dunda (that’s a roller pin — the same one my mom made rotis with — that she used to chase us around the house with). Do you realize how much better we have it than our parents? And yet we sit around, complaining online.

The truth is, our generation doesn’t have to wait for permission. Years ago, we’d have to work 30 years and pray that we’d somehow, maybe, possibly be OK — that our pension would hold up and we’d be able to retire at 65 or 70.

YES! It’s important to plan ahead, automate our finances, and find a great Dream Job.

But we ALSO have new opportunities available that our parents did not. Do you realize you’re reading a free email that I send every 2-3 days to over 250,000 people? Do you know I’m writing this from my couch in NYC in the middle of the day? And you’re reading this, plus god knows how many other blogs, all with instant free access? When else could this have been possible? Do you understand why I want to hit you in the face right now?

We live in a different world than our parents did. You and I can cut through the 30 years of waiting and use the internet to reach millions of people — and sidestep the entire “waiting for retirement” plan.

Earlier this year, I did a survey of my readers. I asked: “Are you interested in starting an online business?”

onlinebizDo you want to start an online business?

96% of readers said yes, I WANT to start an online business.

We know that an online business is one way to live a Rich Life — one of the most powerful I’ve employed. A successful online business lets you take a 10-day vacation anywhere in the world, or pay for your kids’ tuition, or allows you flexibility to live anywhere.

The truth is, you already have the skills to do it. We can stop waiting for the mythical day that the stars align and get started now.


Do you know your actual earning potential?

Get started with the Earning Potential quiz. Get a custom report based on your unique strengths, and discover how to start making extra money — in as little as an hour.

Start The Quiz

Takes 3 min