How to overcome your fear of starting an online business

I fell down at a bowling alley.

The best part of this video is that, seconds before I fell, I literally walked over to my friend, said, “Record this,” and handed them my phone, like I was some world-champion bowler. I wanted to get the video of me taking down this spare so I could brag on Instagram.

Unfortunately, things didn’t exactly go the way I wanted:

Play Video about Bowling Alley

I fell down at a bowling alley.

The best part of this video is that, seconds before I fell, I literally walked over to my friend, said, “Record this,” and handed them my phone, like I was some world-champion bowler. I wanted to get the video of me taking down this spare so I could brag on Instagram.

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New to IWT?
  • Watch Ramit Sethi host Netflix’s “How to Get Rich” 
  • Get the NYT-Bestselling book (over 1 million sold) 
  • Check out the podcast (200K plays per episode)

And join over 800,000 readers getting our Insiders newsletter, where we share exclusive content that's not on the blog:

Do you see how stupid this is?

Nobody talks about failure!

ALL of us are living these public lives of perfection, but below the surface, everyone is falling down, just trying to figure it out. All right, true. Maybe not falling down like dumbass Ramit.

But it’s so rare that people will actually talk about the REAL ways they’ve failed. Not fake failures (“I cared too much”), but real failures — the fear, doubt, and insecurity that come with trying something new.

When I started this site, I was incredibly nervous about getting emails from people questioning my credentials. I didn’t even have an answer! Not surprisingly, as soon as my site started building an audience, I got those exact emails: “So, teaching people to be rich? Are YOU even rich??”

Probably the most nerve-wracking moment in my entire business was in December of 2006, when I sold the first product on this site — a $4.95 ebook called Ramit’s Guide to Kicking Ass.

I knew people would be skeptical, so I decided to try to give people way more than they’d expect: I asked a friend to design beautiful custom cartoons for each page. I cut the price to $4.95. I even gave away half of it for free!

Unfortunately, my worst fears came true. The comments and emails exploded: “Oh, I see. I will teach RAMIT to be rich,” they wrote. “What a scam,” others wrote.

Can you imagine how this felt? After years of writing detailed posts, without ever asking for ANYTHING, suddenly a $5 ebook had made them turn on me?

You know what’s crazy? 8 years later, the commenters are just as harsh. Here’s an email I received just a few days ago:

In the past, this would have eaten at me all week. Now, I take one look and cackle. There will ALWAYS be critics

The only difference is this time I didn’t feel that knot in the pit of my stomach. This time, I was confident enough in myself to brush it off and get right back to work. Today, a deep dive into the FEARS around starting an online business, so you’ll know how we can ignore the critics, focus on doing our very best, and be confident enough to laugh at our own failures.

Fear #1: What if I FAIL?

A few years ago, I was walking to lunch with my friend, and she stopped in a Lululemon store. I walked in with her and wandered over to look at some clothes. As I held up a jacket, she called out across the store, “HEY RAMIT. NICE WOMEN’S JACKET!!”

My ears were burning. I was literally so embarrassed, I’ve never walked back into that store 10 years later. How was I supposed to know it was a women’s jacket??

NONE of us wants to be embarrassed. In fact, wealthy people pay tens of thousands of dollars not to be embarrassed every year (can you think of at least 3+ different ways?). What I learned was that failures are almost always bigger in our heads than in reality. So I picked up a women’s jacket — so what?

Now, years later, I can laugh about it. So you launch a product and it doesn’t sell out. So what? This has happened to me MORE than once. (Did you know that?) So you applied to grad school and got rejected. Is your life over? (This also happened to me. Or when I got a D in one of my classes in college…or so many other failures I’ve had. Most people don’t know about these, either.)

Just like my bowling video, nobody likes to share their failures. We all live perfectly successful lives…on the surface. But inside, they eat at us. And over time, we get so burned by failing that we decide to give up the “child’s mind” where we used to try all kinds of new things. Now it’s just easier to not try anything new at all. Learn a new language? No, that’s too hard. Try that new workout? Ugh, what’ll happen if I’m the worst in the class?

It’s so easy to stay in the shadows. It’s COMFORTABLE there. Nobody looks at you, and nobody points at you and laughs. But you also never take a risk to stand out and try something new.

Which would you rather have? A safe life where nobody points at you…and you’re the same as everyone else? Or would you be willing to take a small risk — not a huge one, just a small one — and dip your toe in the waters of trying something new?

“I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”

–Michael Jordan .

Most of us claim we want to take risks. But if you really did, you would naturally fail as part of the process. So — when was the last time you failed? A week ago? A month ago? Longer? In Gmail, I have a “Failures” tag, and if I’m not failing at least 4x/month, I know I’m not trying enough new things.

If the answer is “I can’t really think of an example,” maybe you’re not actually taking enough risks. You know what’s funny? When I launched my blog, and tried more entrepreneurial things, I still remember what people said: “Ha, what a ridiculous website. So when are you going to get a real job?”

Only NOW, after 10+ years of writing every single week, people hear I live in apartments in NYC and SF and they see me email ridiculous stories to a list of hundreds of thousands of people and fly across the country for last-minute ski trips, they say, “Wow. Running your own business. That must be nice.”

I didn’t do all this without failing. I did it because I knew failing was a natural part of growing.

Watch me go into details about how I handled more examples of failure:

Fear #2: What if I’m not an expert?

How many of us feel like imposters?

What if I don’t have the right credential? What if she has more experience than me? I didn’t go to the right college.

Imposter Syndrome is real, and it is crippling. So many of us waste our time chasing mythical credentials, waiting for the right day when we suddenly have a certificate from some random organization giving us permission to go out in the world and do what we’re here to do. And then what? Suddenly we find…uh oh, that degree didn’t matter as much as we thought. Now what are we supposed to do?

Don’t get me wrong. I’m a huge fan of education — not only did I study under some of the world’s best professors at Stanford, I continue to invest in my own education every day. But this idea that we all need more “experience” or “credentials” for EVERYTHING is just plain wrong. Take this email I got from a reader, Tom S., recently:

Notice how ANGRY he is. He’s outraged that I would DARE try to help anyone without the right credentials. This is an outdated way of thinking. Let me be blunt:

  • I’m not a CFP, but because of my online business, I’ve helped more people with their money than most CFPs ever will
  • I’m not a “certified career counselor,” but I’ve helped more people find Dream Jobs, and negotiate their salaries than almost any of them will (like these Dream Job success stories)


WE DON’T HAVE TO WAIT FOR A GATEKEEPER TO RECOGNIZE US ANY MORE! This old idea of laboring for 30 years, waiting for some fancy Manhattan TV producer or agent to call us, and then “we’ll be successful” is archaic and wrong.

The most amazing thing is with a few simple tools — a website, an email list, and a little know-how about how to build an online business — you can sidestep them ENTIRELY and go straight to the people who want to hear from you!

There’s a TV network I know. They treat all of their guests horribly. They reschedule you over and over and act like they’re doing you a favor if they allow you the grace of appearing on their show.

Last time they called, I realized I’d rather write an amazing post for you than spend 4 hours preparing, traveling, and recording for a 1.5-minute segment. I told them, “I really appreciate the invitation, but I’m going to pass. Thank you again.” They were flabbergasted.

When you sidestep the gatekeepers and go direct, you have OPTIONS. If you want to start an online business and spend 5 hours/week to make a couple thousand bucks a month, great! If you want to go ALL IN and aim for 6 figures/year — or even $1,000,000+/year — I can show you how.

I don’t want to play in a world where I have to kiss these gatekeepers’ asses.

Instead, I want to play on an equal playing field. Measure me on the results I get for my students in launching an online business. If I get real results, I win. If I don’t, then I lose — and SO BE IT. I’ll take the risk on me, but I’m not going to wait 30 years for some aging producer to give me a phone call. I’ll make my own luck. Suck it, Tom.

Fear #3: “I need to figure it out first”

Like your elderly uncle who drinks too much on Superbowl Sunday and constantly talks about how he’s going to write a book once “he figures it out,” we ALL have a drinking probl–wait. No, I messed that up.

We all use “figure it out” as an excuse to TALK about what we want…but do nothing about it!

96% of IWT readers want to start an online business. How long have we been reading endless blog post after blog post, dreaming about generating automatic income?

How many Facebook photos of a friend sitting on a beach — on a Wednesday! — have we seen?

And yet, when we get the opportunity to actually start one, we do the most curious thing of all: come up with reasons it won’t work for us.

I’ve seen this time and time again when I launch a course. I’ll have readers following along with every exercise, commenting on every post, writing how excited they are to get started.

And when the course finally opens, suddenly we start second-guessing ourselves. “Will this work for me? I’m an international left-handed one-legged narcoleptic…what about THAT? Does your material address people like THAT??”

This is called Special Snowflake Syndrome, and these people will never join. They ask question after question until they find something I say no to — and then they can walk away, satisfied that “of COURSE this wouldn’t work for me.” What an interesting way to live life. To wait to “figure it out” until some day, things magically align 100% perfectly. When you have enough time, the perfect business idea, all your other priorities totally handled.


Your life will never be perfect. Successful people take steps before they’re totally ready. They know that there will NEVER be a perfect time where you have nothing else on your plate. So they make time, and year after year, they invest in themselves.

No wonder when you look at a top performer, you say, “Wow, I could never do that.” Because most people never made the daily decisions he’s been making for years and years!

The great news is you’ve already been doing more than most people ever do: You read about how to improve yourself. Maybe you’ve tried a few strategies from IWT or other sites. When the chance is in front of you, will you take it?

The strategy I use to “figure it out”:

I write down ALL my invisible scripts BEFORE I have to make a decision:

  • I’m uncomfortable doing ___
  • I don’t have enough time
  • I don’t have enough money
  • Will this work for me?
  • What if I fail? Then I’ll KNOW I could never do this…

And for 15 minutes, I just sit down and say, What if I were perfect? How would I answer these questions? How would I make the time? Do I really not have the money, or do I just use that as an excuse / could I make changes in my spending?

If you honestly decide an opportunity is not right for you, great! At least you did it consciously. And if it is…you’re off to the races.

Written by

Host of Netflix's "How to Get Rich", NYT Bestselling Author & host of the hit I Will Teach You To Be Rich Podcast. For over 20 years, Ramit has been sharing proven strategies to help people like you take control of their money and live a Rich Life.