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When should you make the jump to work for yourself?

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12 9

Too many weirdos think that to start a business, they have to quit their job, raise millions in venture capital, and start the next Google.

Uh, that sounds pretty risky to me.

Is there another way? Can you start something slowly? What if you want to quit your job and start your own thing, but you have bills and you don’t want to take on a huge risk?

What do you do?

I made the leap to running my own business, and then I taught a bunch of my students how to do it, too. So I wanted to share my answer to today’s “Ask Ramit” question, which comes from Jacquie in Atlanta:

“Financially, is it wiser to work for yourself (freelance/contractor) or to work for a company (who offers healthcare benefits, 401K, etc.)? I am at a crossroad, and the thought of leaving my company both thrills and terrifies me”

Here’s my framework of thinking about when to stay…when to quit…and the best way to do it. All in a short video for you:

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12 9

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12 9
  1. Ramit, I’ve always known that our minds live dual lives. There’s this thing we actually want to do and then there’s this whole segment of “why I can’t do it just yet” segment simultanously alive withing us.

    So, anytime we think about what we want to do, and everytime we discover a situation of doubt, we could say that there’s crossing happening between the effort we’ve to make to achieve something and the rewards we ‘might’ achieve that we’re not really sure of right now.

    If we could come in terms with rewards we can earn after the effort we make, we might just be able to take better decisions as to whether something should be pursued or not…

  2. I agree with you 100% Ramit. It’s not always about dropping everything you’re doing right this second and dive in with both feet. Right now I am a full-time college student, but that doesn’t hinder my efforts at all. I’ve started up tons of things on the side and now I’m starting to get comfortable with the freelance work.

    It’s definitely working smarter, not harder.

  3. Thank you, Ramit. This is great advice! I am still on the teeter of working a FT career job but and working on my horse related web- business that is slowly building up to be something special (just made 1st page ranking on 2 target keywords!). I have one other thing to add to what you shared. I have discovered because of what I have taken the time to learn about web marketing and building a website, etc, there is a HUGE need for that from my existing clients in my current career job as well. So I am now able to develop a second passive income serving the clients I am already serving anyway and have an established trusted relationship with. In other words, as you are making the transition from your career job to your dream independent business, look for opportunities to serve your career market clients even better and gain experience and a passive income all at the same time! Even though I am planning to leave my career job, I have a new vigor and enthusiasm in speaking with my clients because I have the opportunity to offer them a solution to their problems, build my web marketing and site-building skills and provide an avenue to continue our relationship in the future all while setting up the framework for a future passive income. Win Win!

  4. I have already managed to put away 12 months of living expenses, but I’m still too scared to make that leap. Perhaps I now need to turn my attention to racking up those paying clients to get that extra sense of security, before I do anything drastic.

  5. I tell people if you want to work for yourself DO IT.

    Don’t ask for permission or wait until the time is right.

    It takes SO FREAKING long to figure out a system that works where you actually have a business.

    If you wait then you will NEVER make it.

    Start today.

    Start on the side but don’t wait.

  6. You just set me free! 🙂
    I’ve been pondering over the same question for a while now.. Always knew the answer.. nice to be re-enforced by you. Awesome advice Ramit.


  7. Tatenori Hamasaka Link to this comment

    For someone who is ambitious but has family obligations (like myself), I would also add that it`s important to be very patient and do the due diligence (saving, research, etc), while not losing your initial drive. I used To Get frustrated easily when I Wasn`t making as much as money I Wanted, but once I Have set realistic goals, a working system, and got feedback from clients frequently, they helped me To keep on going With my dual job/freelance lifestyle.

  8. What if what I make in my full time job doesn’t even leave room $$ for saving enough for those 12 months? Like, not even close.

    • Then you probably need to negotiate your salary or get a better job. I strongly recommend doing this before you start a company. I cover all of this in exhaustive detail– including exactly how — on my site, newsletter, and courses.

    • Thomas Redstone Link to this comment

      Adding to what Ramit said, you would normally be building your savings from the money you earn using your business, the fact that it can do that for you will only reinforce that your business *is* viable! And can support you living on it alone.
      But, getting a raise is always a great help too!

  9. I think the only time you would really have to drop everything and go all the way is whether or not your side business conflicts with the company that you are currently employed with if you are going with that route. Example, working for a shipping company where you think you can create and operate a better one yourself where you are essentially competing directly with your place of employment.

  10. Dear Ramit,

    I started a small company offering commercial loans, while working. There are many programs offering loans to businesses with credit not so perfect, as required by banks. I’d like an affordable marketing program attracting these businesses. Any suggestions?

    Kind regards,


    P.S. Some of the programs are not mentioned on the web-site.