Get my 5-day email funnel that generated $400,000 from a single launch

Want an email sales funnel that's already proven to work? Get the entire word-for-word email funnel that generated $400,000 from a single launch and apply it to your own business.

Yes! Send me the funnel now
Start Here: “The Ultimate Guide to Habits”

What if you make the leap…and fail?

34 Comments- Get free updates of new posts here

12 11

How many of us have faced a decision…and we didn’t know how to decide?

I’ll take you back to one that changed my life. In college, I was deciding between taking a job at Google — a well-paid job that would have put me into an “elite” job category — or starting my own company.

How do you decide what to do?

Do you look at the salary you’d make and decide? (Easy to say no, “go for your dreams!” but what if Option 1 pays you an extra $50,000 over Option 2?)

Do you think about what your parents will say?

What other criteria can you use to make a big decision?

One thing we’ve ALL encountered is advice from others. Oh man, everyone loves to give advice. And most of it is bad! Ramit, take the job…you should be lucky Google wants you! Ramit, definitely start your own company…you can always go back to Google!

How do you decide amidst all these conflicting pieces of advice?

What if you make the wrong decision?

Before I tell you what I did, take a moment to ask yourself: What would you do?

How many of us are in this situation right now — faced with a decision and we don’t know how to decide? Maybe it’s about ending a relationship…or leaving a job…or even where to live.

I got a question from IWT reader JB, who asked: “What if I take the leap out of the high-paying, big-firm job and don’t succeed? What if I make a mistake?”

Here’s my response in another edition of ASK RAMIT:

Share your story in the comments below.


12 11

Related Articles

It’s my birthday. 3 things I learned

Today is my birthday. Every time one of my friends has a birthday, I ask them to share some birthday ...

Read More

Best travel credit cards from a man who’s traveled to 193 countries

Are you finally ready to book your dream vacation BUT… you want to make sure you get all the rewards ...

Read More


12 11
  1. Heya Ramit,

    you are right on multiple points here! I just quit a job of nearly 100k€ and joined a couple of friends in their little startup earning no money. And I am 43 years old and before that I was very risk averse. So what you just told us, is exactly what were the reasons for me to quit.

    What made me take the plunge? 1. I always can get back to cubicle country. Always! 2. In twenty years I wont be in the situation regretting not having bailed out of big corporate. So I jumped. And I like it!

    Taking about the voice in your head: the voice screaming “dont do it, stay here, stay safe” is just your little reptilian brain. The fear of sleeping under the bridge having lost your home and stuff is just totally irrational. There is always a return ticket waiting for you.


    • Except that you *can’t* always go back.

      I quit a job where I had literally written my own job description and chosen my own job title; when I decided to quit, the company said they would “welcome me back with open arms”; fast-forward 12 months later, when I asked for even an entry-level job back at my old company, the open arms were not forthcoming.

      I still have no regrets about quitting at the top of my game and I have learned a ton in the interim. In fact, it’s all working out, but I want to point out that the stronger argument here is not “You can always go back to your old company” but “You will likely be able to feed yourself *somehow*, even if it means joining the grey economy.”

  2. I read a great brook recently by the Heath Brother called “Decisive: How to make better choices in life and work.”

    They have a nice formula for making better decisions. It’s called the WRAP formula:

    W – Widen Your Options. Don’t think of things as “this OR this.” This of ways you can do “This AND this.” In this case, could you work at Google and keep working on your company on the side?

    R – Reality test your assumptions. Ramit alluded to this in his response, but if you have this fear that you could never go back to your job, you need to test that assumption. Is is true you couldn’t go back? Could you arrange a leave of absence? Or could you “ooch” your way into your own company, and only leave your job once you hit X revenue?

    A – Attain distance before deciding. You have invisible scripts that put up strong emotional filters for your decision. Ask yourself, what would your best friend do? What would your successor do?

    P – Prepare to be wrong. Lets say your company fails. How can you make sure you can mitigate the impact of that failure? Could you make sure you continue natural networking while you’re working on your company so you can easily find a job? Can you say “I’ll find a job if my company doesn’t hit X Y and Z goals in this time frame?”

    It’s a great book with a great framework for making decisions.


    • “Don’t think of things as “this OR this.” This of ways you can do “This AND this.””

      Just don’t fall into the trap of being paralyzed by having too many choices. The old “I want to do this…and this…and I don’t want to turn my back on this” and then you never do any of it.

  3. Ramit, this video could not have come at a better time. My situation is a little different, because the job I left a month ago was a crappy one that still didn’t pay enough for me to be financially comfortable. Still, it was secure and a paycheck I could count on. I had my own entertainment business on the side, and their were enough big wins over there for me to know that if I devoted all of my time to the business, I might get incredible results.

    After thinking about it for way too long, I left the job to focus completely on my business, and sure enough, just this week started being plagued by self-doubt. Watching this video reminded me of why I made the choice I did. I too had reminded myself that I could always go back and get that same job back or another crappy one – and that’s still true. Don’t think that will be happening though – I’m hardwired to succeed (due to my incredible stubbornness if nothing else!)

  4. Right, but what if you are NOT a top performer? I am pretty sure that if I leave my corporate job, I will never find anything similar at a similar wage. If I take the risk and fail, maybe I would have to accept any corporate job that I will not like either, for far less money.

    • @Anne, you may want to consider asking your current employer what their definition of a top performer is. Take that definition to heart, dominate so that you become the definition of a top performer. Problem solved.

  5. You can handle failure. You’ll only end up friendless and living under a bridge if you let yourself. (Oh, and people telling you to stay where it’s safe are either projecting their own fear that they can’t handle failure, or they think they can’t handle it if something terrible happens to you.)

    The best learning in life comes from mistakes. If you don’t think so, you might not have taken any risks ever.

  6. Over time I have learnt one thing. I take the less travelled paths and it has always made the difference. Has the entreprenuerial journey been easy, definitely not. Tonnes of mistakes along the road! But the lesson has been time and again, rise up, dust myself, learn from my mistakes and try again!

    When making such a decision I consider how happy I might bein my new undertaking or job and the worse that can happen. If I like the odds, I soldier on ahead!

  7. See I think your wrong in the fact that if you leave you can come back. I finished college with a dual major (math & computers) in my early 20s. Got married had a kid and down sized my job to work for my dad for several years while my son was little. Then my dad had enough and I entered the workforce again. Couldn’t find a darn thing, and I tried hard. Settled for a great part time job and stayed there till the job was let go after about 5 years. By that time I had a daughter too, so took a year off to raise the kids. My marriage tanked and I needed a good job so I went all out, sent out thousands of resumes, went to the local CC to brush up on my computer skills learned 3 more languages there and self taught myself another. And for a thousand plus resumes sent I had 1 interview. And that fell threw. Now at 40 I have a 17 year old son an 8 year old daughter, I scramble to make ends meet on my own. I chose to put my kids first in the beginning, but kept my skills set up and when I was really pushing for a full time job went to school to fine tune things all to no avail. Now I do question my choices, and in the long run I probably did make the wrong choice because I couldn’t go back to a job where I could be productive and have everything. Instead I have a wonderful and close relationship with my kids, so I didn’t loose everything but more $$ to have fun would definitely be appreciated.

  8. I am 50 and I am less risk adverse than when my children lived at home. My husband and I worked in fairly good jobs that allowed us to raise 3 boys comfortably. As soon as my youngest left home, we invested everything we have, except our retirement accounts, in a rental property close to our home. we also rented out our large 4 bedroom, 2 bath home and moved into one of the 1 bedroom, 1 bath units to maximize profits so we can pay the property off completely before retirement. I would not have done this when the boys were little and we could end up homeless. I, too, said what could happen? If something goes wrong and we lose the rental property, we can always go back to work and move back into our home which is now mortgage free. If this goes well, we have a larger reliable retirement income and more freedom to do as we want later.

  9. “People who don’t take risks usually make two big mistakes a year. People who do take risks usually make two big mistakes a year”

  10. Ramit,

    As always, your advice is thoughtful and helpful.

    Before starting Dream Job a few weeks ago, I would not have thought about leaving my company of 11 years, but now I can open my mind to the possibilities. Yes, there is a huge risk to leaving a job where I have such a long history, but it is very freeing to think that I could find a better match to my knowledge, skills and interests than I have now.

    Any decision to leave has to be weighed against how it would effect other aspects of my life, other people in my life and the risk I take if I have made a mistake. But I also have to weigh the risk of not taking the new opportunity (new people to meet, new knowledge, skills, happiness, etc.). Risk lies on both sides of the decision.

    Thank you for the perspective on risk and your story, Ramit.