What if you make the leap…and fail?

Ramit Sethi

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.


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  1. Volker

    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.


    • Mr. Legend

      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. Dale

    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.


    • Anca

      “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. Caitlin

    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. Anne

    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.

    • BrianF

      @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. Anca

    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. Simon

    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. Tracy

    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. Lisa

    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. greg gardner

    “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”

    • Kim

      Thanks Greg. Boy, did I need to hear that. Especially today.

  10. Betsey


    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.

  11. Kim


    Here goes: I work in a family business.The job I am doing within the company really is a bad fit for me. I have been doing writing, corporate training, and teaching belly dancing on the side. Up until very recently, I have been able to tell myself I can deal with doing what I am doing within the family company as long as I had my side interests to sustain me. But, lately that has not been enough. Add the family dynamic in, and I find myself living with massive amounts of stress.
    I have 3 degrees: Education, Dance & Theater, and nursing.
    I am doing sales operations on a day-to-day basis.

    I prefer analyzing and presenting information in many forms. That’s what gets me jazzed up. That and teaching women the art of belly dancing. There is nothing like the feeling I get when a woman walks into my class, not feeling very good about herself, and standing in the back row,, and then, magically, by the 3rd or 4th class, she is in the front row with a big smile on her face and standing a little straighter. I LOVE that!!! 😀

    I’m sorry if I sound a little whiny, Ramit. You caught me at a weak moment.

  12. Wiebke

    Kids and other expenses- hahah! I know how you mean it 🙂

  13. Zul

    This hits spot on with my current situation. I graduated less than 2 years ago, and entered a company where, by luck, I was put in the driving seat of a project despite being a fresh graduate. It was hell at first with foreigners yelling at me left and right since I had no idea how to do my job. I stuck on and finished that project, making quite a tidy profit for my company. It was a contract employment, but they assured me that if another project sprung up, they’d hired me back (they then tanked, leaving all my hopes gone).

    I went unemployed for a few months, but I got a great resume so I wasn’t worried much. Then a friend I met at work offered a joint venture. I hopped right in and made sure the project got finished in time. Well, life ain’t all roses since I neglected to handle the paperwork, and ended up getting cheated with nothing to show.

    I was desperate, so I sent my resume around and got a low-paying job just so I could stay afloat. My former boss decided to contact me since he wanted to establish a new company with all new partners, and now here I am. I just got fired from the low paying job (some conflict in management of the project), and has spent a month managing this new company. However, we aren’t really going anywhere, making me question my decisions now.

    Should I go on, hoping for a break soon? or should I just go back into the workforce? I know what I want to do now, so I’ll just take that leap. Hey, I’m still young. Not much baggage for me to carry yet.

  14. Mia

    What if I made wrong choice that ruined my life? I quit college (I was under scholarship that time, a shining star, loved by teachers) to start a family which I thought going to make me happy. Boy, I was so stupid as I thought money and career would never make me happy. It turns out it was the worst decision I’ve ever made. I’m divorced, broke, unemployed, lost my freedom and I had to let other people to take my lovely kids because I can’t afford to feed them. I gained weight, lost my motivation, depressed for years and had felt life was not worth living.

    If only I knew how to make wise decision that time!

    • stacey

      MIa, perhaps that was the “right” decision at the time. How were you to know things would work out like this? You wanted that the most at the time. So, instead of thinking that that was the only moment of your life you could choose your destiny, think what decisions you could make now. What “right” decision could you make this week? Plus if you ruined your life, it wouldn’t have been by one decision, I doubt your life is ruined. You said money and career would never make you happy – well money and career alone – that’s means you value your family first. So perhaps you could reframe the way you are seeing your situation? Could your ex help with bills for the kids? Could you retrain? Could you get another scholarship and finish college? Sometimes the “right” think might be dealing with life when things go “wrong”. I am sure you can turn things around. Think about what you can do now, as I am sure the fairy tale you are thinking could have gone wrong – perhaps you would have been fired unfairly, who knows, a tragedy could have eventuated with the other choice too.

    • Mia

      Thanks Stacey for your reply and helpful suggestions! I really appreciate it! Maybe I was just exaggerate my situation a little bit. Yes, I had ruined my past but it does not it ruined my entire life. I am now working towards my better future but it is just a slow progress because I’m still afraid of making decisions and stuck in ‘if only’ way of thinking.

  15. Ranjan Jena

    To add up a quote relating to your article content;

    Whenever you’re in conflict with someone, there is one factor that can make the difference between damaging your relationship and deepening it. That factor is attitude.

  16. Jordan

    I’ll agree with Ranjan: it sounds simplistic, but a positive attitude can affect a lot. I won’t try to Monday morning quarterback any of the other commenters’ life stories and I feel bad for them, but the way in which you react to the situation will make a huge difference. Viktor Frankl’s situation in his book Man’s Search for Meaning is a perfect example of how something positive can come out of something horrible (the Holocaust). It was Frankl’s internal resolve/perspective/whatever that got him through it and made him successful later.

    Not to end on a morbid note, and certainly less severe than most, I was “downsized” out of the military a few years ago. At the time it was a huge blow, but it actually created a great opportunity for me. I joined an Air National Guard unit, was part time for many years until I essentially proved myself to the leadership and got a full time job. If I lose this job or decide to leave, I could cry or I could ask myself what the last six years taught me and how I can use that in a better career.

  17. Rita

    Hey Ramit,

    High Five, that’s exactly what i encourage and what i did.

    I left a 6 figure income in cubicle county and pursued yearning to leave a legacy (when i die) than leaving a job behind.

    I call it the hand-me-down script- you know, you’re born, get good grades for 13 years at school to get into a good college, get good grades at uni to for the promise of a good job – that promise is pretty empty – hence so many disgruntled employees . i should know – used to train them.

    SO this hand me down script is so hard to detach ourselves from because we social proof suggests that this script is the right and common road to take. It’s safe, it’s secure.

    But once you detach from this hand me down script thats exited since the industrial revolution, it’s a God given gift and you get to create your own level of common, right, security and importantly passion and purpose.

    One of the best and addictive roller coaster rides.

    Thank God.

  18. Sukhneet Singh

    Thanks for the video. Of course I’ve got your email filtered already so I never miss the good stuff.

    I actually put law school on pause to give a startup a go in March. It’s getting scarier now. Still, the deferred enrollment gives me the option to continue where I left off next year.

    The Bezos Regret Framing works wonders. So many attorneys tell me they wish they took the same course. Very encouraging to hear the successful people in your field saying they wish they did what you did. =)

  19. Michael

    Funny you post this.

    Tuesday was my last day at a retail job (sorry, no Google for me) which, while teaching me a lot about what I don’t want to do and allowing me to purchase RBT and Earn1k, has sucked the soul out of me and degraded my social skills and relationships.

    I talked to several friends on RBT about whether I should quit or not. Sealed the deal. I put in my two weeks notice two days later.

    I realized something similar to what you did in college:
    1) There will never be another time in my life I don’t have to worry about rent and food. Now is the time to take risks.
    2) If my attempt to use Earn1k to make enough to replace my retail job doesn’t work out, my work would take me back in a heartbeat. And if I didn’t want to work there, I could use my experience to go somewhere else easily.
    3) I will regret not trying, whether this works out or not, because the real goal is to plant the seeds for self-publishing. My schedule will be built around supporting that long-term goal. If I didn’t try everything to make that happen, I would immensely regret it.

    So it was great to see this and get a little reminder that I did the right thing.

  20. Jeff Bernstein

    I like this line from the video: “It never gets easier than now.”

    A wise man told me, “Try it, it won’t kill you. And if it will kill you, lean into it.”

  21. Ilana B.

    Time to up the nerd quotient.

    What is the answer to Life, the Universe and Everything? Anyone who’s read The Hitchhiker’s Guide to the Galaxy series, knows that it’s 42. Not only that, if 42 doesn’t sound like the answer, then you’re probably asking the wrong question.

    After my 41st birthday, I started thinking about where I am in my life and where I’ll be on my 42nd birthday. Is what I’m doing the answer to Life, the Universe and Everything for me? No. Actually, it isn’t.

    I’ve been working on my side incomes and recently have been so busy with all the projects that I don’t have time for anything else. So in February, I made the decision to quit my stable job so that I could pursue more interesting projects instead. I go through periods of doubt and worry that I won’t know where my next meal is coming from.

    I sat down and figured out my assets, liabilities and monthly expenses, and thought about where my income streams will come from. I discovered that the worst case scenario is not that bad.

    I set the date for my resignation, August 1, and my last day in the office will be just before my 42nd birthday (September 23). So I can go and figure out what the answer is to Life, the Universe and Everything. Or I can figure out what the right question is.

    Most importantly, I’m overcoming the fear that keeps me in a stable job that doesn’t inspire me and doesn’t have a lot of potential for me. And building up the courage to give myself permission to do what I think might actually be my Dream Job.

    Thanks, Ramit, for the video. It’s exactly what I needed at exactly the right time.

  22. Rose

    Hi Ramit,

    Thank you for sharing this video. Sometimes I just feel like I want to cry because I want to live a better life, but it seems like I’m not doing enough. Or maybe I need to look at my processes and see which part isn’t working, but anyways I’m just rambling. I finally got a prospect thanks to what I’ve learned on Earn1k, but I think I scared them with my price. Anyways, I’ll let you know what happens. Thanks again Ramit.

  23. Jessica

    I took a HUGE gamble. I not only left the corporate world but made sure I couldn’t go back because 1 I’m kinda stubborn and 2 I was MISERABLE. I wanted to switch careers and I wanted to put full effort into the switch and the new career in entertainment. I took a few part time jobs all within this field and after a little over a year I have a full time job in video editing and I LOVE IT. It feels good to walk down the street with a smile on your face.

    • JustMe

      I’ve been researching editing this week as a dream job. Is there a way to contact you to ask a couple questions about your new career?

  24. Sunday

    Hi Ramit,
    The fear of the unknown is always the bane of many that desire to do business. JB’s question reflects the mind of many marketers and you cannot really blame him for asking. However, your response couldn’t be more direct.

    It is good to take risk but risk should be calculated. If risks are calculated well enough before any decision is taken then it becomes readily encouraging to take the necessary leap.

    The above comment was left in, where this post was shared.
    Sunday – contributor

  25. JJ

    I made the leap in 2007 when I was a grad student in Science. I had failed my qualifying exams and decided to switch to Finance. Looking in hindsight, the timing could not have been any worse. I enrolled in a MS in Finance program but could not find any work/internships in 2008-2009 when plenty of experienced professionals out of work for a long time. I regretted the decision but decided to own up to it. I finished my degree and took a year to land an entry level job.

    For a long time, I felt I had made the leap AND already failed.. but discovering this site early this year changed my perspective and gave me hope. If I could make myself into a Top Performer AND convince others in my network that I am one, I will not be negatively affected, in the long run, by the fact that I graduated with a Finance degree in the midst of the worst recession in recent memory.

  26. Yadgyu

    If you fail, no one is going to step in to help you. People will pray for you and tell you to stay positive, but no one is going to provide for you. That is the reality of life. If you fail, it will be all on you. No good wishes or pats on the back will put a dollar in your pocket or food in your belly.

    I would suggest that anyone bored with their day jobs take a stroll through the poor parts of town or the county. I have seen the desperation and sadness in the eyes of those that can only hope to have a boring day job. Shit ain’t pretty. None of those guys are babbling about “barriers” or “psychology” stopping them from quitting a job. They are poor and do not enjoy it.

    Instead of taking a big risk and losing everything, take smaller risks and build up your income. It may take a decade or more to earn a steady income. But what is the rush? It is harder to dig yourself out of a bad situation than it is to slowly climb out of a boring one. The time building a business is going to pass anyway. You might as well work your way towards a slow success than fail fast and hard.

    Failure is not fun.

  27. Krystian

    Thanks for great video Ramit.
    To make a leap and have the ability to go back is a good advice. However, there are times when after you make a decision, it’s hard to go back. For example, I had a great job as software programmer. I made a leap and started my own business about 2 years ago. Now, it’s somewhat hard to go back… – I would say I have chosen the other way of my life and I love it 🙂