Figure It Out Friday: How Do I Take The Leap With No BackUp Plan?

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‘Figure It Out Fridays’ is a new weekly blog series  where you submit your questions and struggles about designing your Uncaged career – and I give you my straight up advice. Because sometimes you just want someone to tell you what to do.


I want to quit my corporate job and bartending job so I can blog, launch my magazine, write books, also open a spiritual healing and life coaching business. I’ve dreams and desires and they are about to bust out! However, I am in complete fear of giving up A) a steady paycheck and knowing precisely how much money I have each week and the security of knowing I can pay my bills B) health insurance.

Everything inside of me is literally screaming, “Just fucking do it, even if you have to live in your car”

Sigh… How did you take the leap? How do you take the leap with literally zero reserves saved up but your soul feels like it’s dying every day you put on your heels and walk into that office.


I responded to a similar version of this question a few weeks ago, so I may be repeating myself, but it’s worth repeating.


My general advice goes as such: Don’t quit your day job… unless you are totally ok with risk, debt, and total uncertainty.


Here’s my story of how I started my business. It will be different than yours, which will be different than anyone else’s, so keep that in mind. At the end of the day, you have to decide what will work for you.

I had been off work for about a year. When I say “off work”, I mean I decided to just take some time off from having a job and enjoy life in Toronto. I rode my bike a lot, napped in the park, did a ton of yoga, went to the Dominican twice, spent a month in BC camping, climbed my butt off and generally just didn’t worry about money. Was I going into debt? Yes, a little. Did I care? Not a bit.

After almost a year of this, the whole time teetering on the edge of business building but not quite there yet, my boyfriend and I decided we were going to go on an epic (I’m over that word) roadtrip and live in a van for 8 months. “Sweet”, I thought. “That will save me rent money!” I also realized that it was now or never to start my business. I wasn’t prepared to wait another 8 months, which meant I had to start NOW so that things would be up and running when I was on the road.

So I got my ass in gear and hired some help for my website, hired a copywriter, hired a coach, got a few clients, and got another job. 

I worked my ass off for someone else for the next 6 months – paying off debt, building a foundation for my business, and saving enough money to pay for upcoming business expenses that I knew I would want to invest in.

Then I sold everything I owned  to pay off the rest of my debt and bank some coin, and moved into a van and ran my business from the road (the logistics of which will come in a later post, I’m sure). My goal was to make $250/month from my new business while I travelled.

Now – I’m not too worried about risk, debt and mega uncertainty. I knew I’d have very few expenses, some savings for backup, and more than that, thanks to many years of living the broke-ass backpacker lifestyle, I knew I could figure it out if I ever totally ran out of money.

But not everyone can live like this/wants to live like this. So you really, really need to decide what will work for you.


If you want me to tell you what to do, my best advice is to not make everything so black or white.


Keep your day job, and in the meantime start your business. If you’re worried about money, then this is the obvious option, but most people seem to think they have to decide between the two. Why can’t you do both?

If it’s really money that’s holding you back (is it? Get super honest with yourself… It might be something else. Fear of failure? Fear of not being good enough? All that shit is usually disguised as money stuff), then decide how much money you need to live off comfortably (whatever that means for you), and then either wait to leave your job til you’re making that amount, or have enough money saved to live off for at least 6 months with no income while you get your business off the ground. Pretty straightforward, right?

Then – and this part is equally important as the money part – figure out ways to make your job great til you leave. Start to appreciate the money you’re making, knowing that it’s funding your dream business. Start a countdown on your calendar at work til you leave. Change your attitude about  your job and learn to love it while you’re still there. Your job is your ticket to freedom right now, so start treating it as such!

Then leave when you’re financially ready to leave.

Orrrr… just quit now and figure it out. Ha


My point is, the end of the day only you know what you’re willing to risk, so get clear on what what is, and then choose something. Cuz staying in limbo fretting over “to leap or not to leap” is guaranteed to get you nowhere.


What do you think? How did you make the leap? Are you a risk-taker, or a cautious planner? Drop your comments below and tell us what your exit strategy is/was!

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Read 7 Comments & Leave Yours

  1. jenner807

    What a super fun article! And so true for someone on the edge. I truly appreciate this advice, it’s truthful, no bullshit and really says it like it is. I LOVE that…… YOU are in charge and you decide how you feel, and what to do////but it’s all in the gray – always.

    Rock on! Your site is amazing and inspiring. It’s a great space. Thanks for sharing :)

  2. jenner807 Thank you!! It’s SO true – everyone is different, and what feels safe for one person might be a totally crazy risk for someone else. At the end of the day though, I say if you’re freaked out, do what you need to do so it feels safer for you… then leap! xo

  3. SheRadiantCoach

    Love your straight-forward advice Becca (as always). As we have discussed (and I wrote about for you), so many people have a negative view of working while starting a business. I personally get physically ill when I get into debt…so when I launched both my businesses I knew I wanted to work  to keep the steady money coming it. You are SOOO right, to each their own and we all must tap into what works for us.

  4. SheRadiantCoach Yes! It’s kind of silly that people think it has to be one or the other. NOTHING is ever that black and white / all or nothing! Thanks for the comment Anna!

  5. barelylucid5

    One thing I’ve seen time and time again is that people who take the risks are often rewarded. I do agree that it has to be a risk you’re at least a little comfortable taking, though. I was really nervous about leaving my last job and going into business for myself full-time, even though my bf had offered to cover the bills…I don’t like being dependent on anyone. I was a communications director at a healthcare foundation and making nearly six figures, but I was miserable. My boss had no concept of work-life balance and was very abusive as well.
    I made pro and con lists, I crunched some numbers, and ultimately decided to stick it out for another four months to give me a very nice cushion to fall back on. I quit last December and it was the best thing I ever did. I’ve been busy ever since, but now I’m working for myself and often I make as much or more a month as I was making at the foundation…totally NOT what I expected! But since I was okay with making a lot less, the money is just a nice bonus.
    I think that having a plan in place, getting rid of debt and building your business on the side while you use your day job to build a nest egg is great advice. It totally worked for me. It’s worth putting off the dream just a little bit longer to make sure you do it well and it has the best chance of succeeding.
    It may be helpful to write a business plan before quitting your job, just to narrow down what you really want to do. The original poster’s goals are great, but that’s a lot for one person to do at the same time. I’d suggest choosing the thing (or two things) she’s most passionate about and see how it could work as a career before taking the leap.

  6. barelylucid5 I’m glad you found a way to do it that works for you… and that’s the key, right? Figuring out what YOU need to make it work, and then doing it your way. Thanks for the comment!

  7. YourGo2Kelley

    Love this post! And I think it is spot on. Everyone and every situation is different and in the end, we all have to decide what is comfortable for us. Or what is right, even if it is temporarily uncomfortable. Personally, I’m not comfortable leaving my day job until I have some money coming in from my business. So, I’m working the day job while building the dream. I have a goal of being on my own by July 1, 2014 and that’s now just over a year, so I better get my shit together. :)