Overcoming The Financial Obstacles to Living A Life On Your Terms


“I really want to quit my job, but I just can’t afford it.”

“If it were only me, maybe I would take the risk, but I can’t subject my children to that kind of uncertainty.”

“What would I do about health insurance? I really need the benefits right now.”

“I don’t have enough money in savings yet.”

The world may revolve around love, but I’d be lying if I said that money wasn’t important.

Money is important. Money is how we can objectively trade value for value without resorting to bartering.

Mo’ money may mean mo’ problems, but most of us would rather have more of it than less of it, and I imagine that anyone reading this knows what it’s like to not have enough for what you want to do.

You’ve got bills to pay, mouths to feed, people to medicate, addictions to feed (I’m talking about cheese of course), and countless other little necessities that somehow add up to more than you’re worth. At the end of the month you’re left wondering where the hell it all went. (Ever done your taxes and think about what you have to show for tens of thousands of dollars?)

So when some jackass like me comes around telling you to quit your job and follow your heart, you want to drop everything you’re doing and punch me in the face with the force of all the practicalities weighing down on you.

I know the feeling.

I’m not a financial expert. I can barely figure out how much change I’m supposed to get back when I pay for something, let alone manage a portfolio of finances.

However, I do know what it’s like to be a regular person with little to no money.

I know what it’s like to want for more. I know what it’s like to quit a well-paying job with no prospects, a poorly formulated plan, and not enough in savings.

I also know what it’s like to be alright, regardless of all the forces against me, regardless of the odds. I know what it takes to make it happen.

Intangible Obstacles

Like always, it’s the obstacles in our mind that are the most challenging to overcome. In my experience, these are the only real financial obstacles standing between you and the pursuit of living. Everything else you can figure out easily as long as your head is in the right place.

Adjusting Your Standards

So much of what determines where you place your priorities depends on what you value. Whatever you value will be what’s most important to you, and that’s where you’ll put most of your attention.

What would happen if you made happiness and/or fulfillment your highest value? How would your life change if your priority was always on your mental and emotional well-being? How would your decisions change? What would you start doing? What would you stop doing?

This is fundamental. It’s also really hard to do.

It mostly has to do with creating a habit and sticking to it. Over time, you will start to automatically make decisions based on your new set of priorities.

The best way to describe this mindset change is when someone has a near death experience, or when someone finds out they’re terminally ill, and all of a sudden the things they thought were so important before feel empty and meaningless.

What really changed? Nothing changed. Only their attitude towards life changed and that’s everything.

Why is it that some people are perfectly happy living in a hut on a beach, homeschooling 12 children while others would be miserable in anything less than 400 air-conditioned square feet per person? They have two different standards. You can get whatever you want by raising or lowering yours by changing what you value most in life.

You can get to this place by putting your happiness and well-being before everything. Put it before ambition, before money, before what others will think, even before the desires of your family and friends.

Burn Baby Burn

I’ve said it once and I’ll say it again. If you want to do something then do it. Don’t go half in. Don’t keep one foot in the door just in case. That implies you have doubts about what you’re doing. Even if you don’t think so, your subconscious might feel differently.

Burn the boats. Don’t give yourself an easy way to turn back. I’m not saying to burn bridges or tank your life. Simply give all your attention and belief to what you’re trying to accomplish. If that means making money without a formal job, then don’t quit just to look for other jobs while you’re working. Don’t start a side project without the serious intention to quit eventually and make it happen.

This goes for anything of course. Even if you don’t want to quit and you just want a promotion or you want to marry that beautiful girl you’ve loved since you were 12. Be all in and believe in what you’re doing.

I truly think that ‘believing’ works. Not so much because it has some kind of magical properties we mortals can’t understand, but because if you believe, you’re going to do something about it.

Burn baby, burn.

Get Comfortable With Being Uncomfortable

I never give you anything less than the raw truth. You’re going to worry. Although worrying does zero good. It negatively affects everything in life, but you’re not going to help worrying a bit at first.

In the beginning you’re naturally going to be scared. You’ll question the sanity of your decision. It’s possible that you’ll have some kind of breakdown at some point where the full magnitude of what you did finally hits you.

All of that is normal. Get comfortable with feeling these uncomfortable feelings. Keep pushing through. They will pass.

The Happier You Are, The Less You Need

Something happens when you finally begin to do what you really want to do. I don’t know what it is but, suddenly, you’re able to live nearly the exact same lifestyle you lived before, but for a fraction of the cost. It’s almost magical.

The fact of the matter is that the happier you are, the less you need to buy things that will make you happy. I always had a hard time putting this into words, but David from Raptitude explains it beautifully in his post called “Your Lifestyle Has Already Been Designed.” Here’s a quote that resonates with me.

“We buy stuff to cheer ourselves up, to keep up with the Joneses, to fulfill our childhood vision of what our adulthood would be like, to broadcast our status to the world… While I was abroad I wouldn’t have thought twice about spending the day wandering through a national park or reading my book on the beach for a few hours. Now that kind of stuff feels like it’s out of the question. Doing either one would take most” of one of my precious weekend days!

Even if you feel like you’re already living under your means, I bet if I cut 30% off your income and gave you 30% more time to do what you loved, you would be just fine.

Tangible Obstacles

Now that we’ve gotten the important stuff out of the way, I’ll tell you how I deal with the more tangible obstacles that are on your mind. Let me remind you that this is only how I have dealt with them. They also apply only to people who live in the United States.

Health Insurance Benefits

So much of the population thinks that without an employer, it’s close to impossible to get health coverage. They also believe that going with an employer is always cheaper.

The first assumption is totally wrong, and the second isn’t always true. Group rates for companies take in data about the collective health of employees, and if you are relatively healthy, you could be paying more for your unhealthy coworkers. I’ve also seen rates to be less when you have multiple children. It definitely varies, but I can definitely say you don’t need an employer to give you health coverage.

Getting health insurance is a lot like getting car insurance. Shop for rates, talk to people, compare coverage and then buy. I’ve only been denied once and I’ve done a lot of shopping.

The other side to this issue is the way we treat our bodies.

Health insurance has become such an automatic knee-jerk necessity for us because we’re all chronically ill. We eat processed ‘foods’ and ingest animals pumped full of antibiotics while sitting on the couch for days on end. We’re malnourished.

Treat your body well and you probably won’t need insurance. Pay for your own annual checkup. It’s really not that expensive.

Also, there are free clinics all over the USA you can go to if you really think you need to see a doctor. Doctors are not gods and hospitals aren’t perfect. Use nutrition and exercise to manage your health. Stop depending on doctors to fix what you’ve broken.

Hospital Bills

I never use to take care of my body, therefore I ended up in the hospital a lot. Which means I always had a lot of hospital bills. I used to be self-destructive and avoidant when it came to problems, so I usually ignored them hoping they would go away.

They didn’t.

To this day I don’t answer my phone because I’m sure it’s going to be a debt collector and I just don’t want to deal with it.

That’s not how to handle debt.

The fact is, hospitals are more than willing to work with you. The first thing you need to do is make sure your insurance (if you have any) is paying everything they’re responsible for. I’ve run into situations where an insurance company tried to pull something over on me and I had to threaten them with a lawyer. Three days later the bill was $100 and not $1000.

Then, if you still can’t pay it, talk to the hospital and negotiate a payment plan, or a reduced amount for payment in full. This works for credit cards as well. If you give them the option of some money instead of no money, they’re going to take it.

I’ve negotiated payments as low as $25/mo. Having another monthly bill isn’t ideal, but at least your credit score isn’t affected.

Now, if you still can’t pay it you can either take out a loan (I don’t recommend this), or simply tell them you can’t pay and if they can’t work with you then they can do as they please. You’ll have to figure out how important your credit score is compared to how much money is being asked of you. Your credit score is important in a lot of situations, but having bad credit for a few years beats having a miserable life for 30 years.

Having bad credit means putting down larger deposits, not being able to take out loans, and not being trusted in financial situations in general, but I can guarantee (personal experience here!) that you can get along just fine. You’ll get your deposits back and you’ll have less debt because you can’t take out loans.

Just weigh your options against what’s important to you and then decide. Don’t reduce yourself to a life of misery because you feel like you have no choice.

Credit Cards

My extreme financial irresponsibility has given me an extraordinary amount of experience with all kinds of debt in general; credit cards and loans are no exception.

Credit cards are awesome if you can pay them off before interest sets in. If you can’t, credit cards are the worse thing ever. If you do happen to get into credit card debt, you can negotiate a lower monthly payment in exchange for not stiffing them. Unfortunately, unlike hospital bills, which are a fixed amount, credit card bills just get bigger and bigger the longer it takes you to pay it off. When it comes to focusing on where to put your money, I’d put it on the credit cards right after shelter, food, and water.

The only exception is if you’ve decided to declare bankruptcy. That’s literally the worse thing that can happen to you. What would happen if you declared bankruptcy? They’d take away everything you have and you basically start from scratch with a few exemptions. Well, comparing that to my misery in my previous job, that’s not too bad. In fact, I would have rather done that than lose my ovary  (see the Life Lover’s Guide for more details). 

Student Loans

Student loans are tricky because they never go away, even if you do file bankrupcy. I have over $100K in student loans. That’s a lot. Only a small percentage of people have that much and I’m sad to say that, again, I am among the unique few.

Payments are usually around $1,000/mo, but because of my financial hardship, they let me defer most of them. They will also work with you based on your income and they’ll help you get the lowest monthly payment possible for you.

How much do you really need in savings?

When I parted ways with my employer, I had a little more than three months of living expenses saved up. When that ran out Lucas and I would have to start making some difficult decisions.

Talk about a hard deadline. This was one of them. But that means I never slacked off. I got shit done. I learned, I connected, I absorbed and I made sure that when that three month mark came around we would not be forced to go back into jobs we hate or sell the house.

I know others who saved up 6 months or a years worth before taking the leap. Still others held their job the entire time they grew their side business so there would be no gap in income. Unfortunately, that doesn’t light enough fire under my ass. I had to do it with less.

I don’t know how much money you need. That really depends on you and I don’t think anyone can tell you the exact dollar amount you’ll need. If you do burn the boats it doesn’t matter how much time you give yourself. You’ll make it if you’re that determined not to go back to where you came from.

That’s what humans do. When pressed against a wall we adapt and we survive so we can live a better life. The higher the stakes, the more likely we are to grow. So don’t be afraid if you don’t yet see the way to the other side – you won’t be able to prevent yourself from making it.


I don’t have direct experience with this, but I do know what’s possible. Rachel and Greg Denning are a great example of what’s possible. I’ll be publishing a podcast shortly of an interview I did with them about how they and their five children live all over the world.

The Bottom Line

I don’t know about every financial obstacle in the world. I also don’t know about every single financial consequence, so don’t take this as official advice about finances. Take it more as guidelines and how to merge your mindset change with the practicalities of living.

Bottom Line: It’s possible to live a life on your terms despite financial difficulties if you decide that living any other way is intolerable for you.

Either make the decision to live your life, or live and die the way you are.

photo credit: Images_of_Money via photopin cc

{ 23 comments… add one }
  • Patrycja June 25, 2013, 5:22 pm

    Liz, I love reading your posts and newsletters. I live on the other part of the globe but we’re so damn alike. I also quit my full time job in an international corporation. I do struggle right now with certain decisions but after having read the above I’m feeling released. It made me think. I am not the only one who struggle. I just need to pull myself together and it will all be ok. Just as it has always been. I am strong and I will survive, no matter what. I must admit today I was feeling down… Thanks to your post I realized a couple of things. The paragraph about attitude towards life particularly hit me. It’s nothing I haven’t known although I tend to forget how lucky I am in life and I should be more grateful for what I have. Even if it’s not that much. Still, I am lucky… Thanks for this reminder. Again, love your posts. Keep rocking, girl. You are inspiration to others. Hugs from Poland.

    • Liz June 26, 2013, 11:52 am

      I love that feeling of release. It’s so freeing isn’t it? You will survive and more. It’s ok to be down every once in a while. I resent people who tell me to be happy every moment of every day, but knowing it will pass helps with the intensity of the pain.

      Hugs from America! (I’d love to know how to pronounce your name. )

      • Patrycja June 26, 2013, 2:51 pm

        Yeah, I feel better today, thanks 🙂 I figured that I am the one to tell everybody that “when one door closes, another window opens” so why the heck am I feeling down?? It will be much better soon and I know it, I just need to focus ans start acting.

        How to pronounce my name? 😀 Wow, let me try… it would be something like

        • Patrycja June 27, 2013, 10:23 am


          • Liz June 27, 2013, 7:45 pm

            Hahaha that doesn’t help at all! Is it ‘Pah-tree-ts-yah’?

          • Patrycja June 28, 2013, 6:47 pm

            Indeed! 🙂

  • fran June 25, 2013, 6:44 pm

    Liz this is a great post! And very timely for me too. I live in the UK so don’t have the health insurance scenario (at least not yet). I went bankrupt in 2010 after a business failed whilst trying to leave my job. It was an extremely difficult time before I made the decision and although I lost all my life savings these had actually gone into building the business anyway. But I can understand how people commit suicide whilst being in this apparently no hope situation. However, I did not loose my house as it was in negative equity and with fantastic help from the UK Insolvency Service I bought it for £1.00 because of this. In fact the most helpful people at this time were those who were dealing with the bankruptcy including an agent I used (not expensive) and the courts. I had to borrow the fees though but paid them back within 3 months. My employer also gave me my permanent
    contract back ( some jobs won’t employ anyone who’s bankrupt) and all my co-workers carried on as normal.
    It has effected me though and I don’t think I’ll ever get over it; I can’t get credit or loans or move from the house and will have to sell it eventually to pay back the mortgage. I get very frustrated because I think if I still had the savings I would be able to retire etc etc.

    But as you say, you can manage on 30% less of less or whatever the figure is. And my children have learnt how to manage their finances brilliantly.. I have had to borrow small amounts from them from their student loans! And get a phone contract via one of them!

    But I still want to leave my job but scared to do so; scared of making another mistake; scared in case I can’t help them financially if they need me to. I desperately want to set up my blog and buy a small house in France. But I’m scared and also scarred now.

    But again I’ve been off work with depression for 2 months now because I know it’s not the right thing for me to be doing. So yes, my decision has to be made to live my life on my terms, or live and die the way I am now.

    I think the decision is almost there! On my terms.

    Love youxxxxxxxxxx

    • Liz June 26, 2013, 11:56 am

      Oh man, love you back so much more.
      I don’t know what bankrupcy is like in the UK, and I haven’t experienced it here, but I’m sure it’s an awful experience. I didn’t mean to minimize it, I just meant to compare two extremes.

      Try not to think that you’ll never get over it. There’s really nothing to get over is there? It happened, and where you are now is where you are and that’s that. I’m actually about to publish a post on regret pretty soon that might help with the ‘if…then…’ statements.

      What helps me is really telling myself that what I have right now is it, and that ‘if’ doesn’t exist and will never exist as I imagine it. So I can either choose to be angry and frustrated about some imaginary scenario I’ve created in my mind, or I can choose to be in the present and live while I have the chance.

      Just writing that made me feel more calm :). Thanks for the help. <3

  • Kate Kindle June 25, 2013, 9:50 pm

    Whew!!!!!!!! Yes, many of us have to do what we want to. Tell me, Liz, are you a certified Life Coach?

    • Liz June 26, 2013, 11:58 am

      Hey Kate! Nope, I’m not! Are you?

      • Kate Kindle June 26, 2013, 8:07 pm

        No, I’m not either. What they do, is identify the problem, and if medicine is not the answer, they come up with practical solutions. Fast!

  • cj June 25, 2013, 10:00 pm

    Liz!!! A valuable post for those wanting something better than mediocre. Tammy and I quit our teaching jobs 2005/2006 and have never looked back. As you suggest, we take very good care of ourselves, so health insurance is not a big deal. Once we became aware of our finances, we hacked off our student loans, a home loan, and got every bill down as low as they can go. So, yes, there were financial struggles, but they were well worth the trouble. We have adjusted to the ebb and flow of funds.

    The more terrifying prospect is growing old and regretting never having tried.

    • Kwesi June 26, 2013, 8:58 am

      I love this post liz! I realized i am not far off from your guide lines. creating a lifestyle is such a beautiful thing that i could not live life without this pleasure of dreaming and making it happen. Health and well being is the corner stone of my life and that drives me to go for the simple things such as , good music, growing your own veggies if you have the space , quiet walks and enjoying fitness workouts and preparing healthy dishes and inviting friends to eat. I like money because i need stuff but don’t love it. I don’t spend somebody’s money which is the credit card, i spend what i have and if i should go broke, which i don’t mind sometimes , i call my friend and they love to give but then again i don’t remember the last time i asked. We all have life as we breath but creating a lifestyle you dream of is living by your terms. Most of all getting people in shape is my passion and gives me living.
      I love you.

      • Liz June 26, 2013, 12:04 pm

        I love you too Kwesi! I’m glad to see you more on the blog in addition to my inbox!
        I’ve always wanted to grow my own veggies, but every time I try, they die. I don’t know what I’m doing wrong. Surly it’s not as hard as I’m making it out to be. Seed, dirt, water, sunlight, and out comes a tomato right? Not for me!
        People do love to help don’t they?
        The most common passion people have is to help others in some way. And we think the world is only full of evil. I wholeheartedly disagree. You’re proof!

    • Liz June 26, 2013, 12:06 pm

      Yea CJ! I can totally relate to the ebb and flow of funds. Payday is no day and everyday and who knows what will happen? But you adapt and a new normal sets in and soon you sort of forget what it was like to live any other way.

      • cj June 26, 2013, 1:11 pm

        You know, Liz. You are so right about that. I’d like to think I can recall the details of how it used to be, but I am too busy really and I cannot remember how teaching really was anyhow. A remarkable and valuable human trait, huh?

  • Kevin Cole June 26, 2013, 9:14 am

    Damn Liz this was thorough. You tackled this from both angles. Having the proper mindset and having the financial shit in order is definitely vital.

    I’ve always said that money does not equal happiness but it does equal survival. If we’re smart with our money and embrace simple living things get a whole lot easier. I’m one of the lucky few who saw all the debt and financial troubles of others at a pretty early age so I’ve been able to avoid it all. But regardless financial obstacles will always rear their ugly head.

    It’s just a matter of being content with less money so that you can do what makes you most happy. I’d say that’s a pretty solid trade 🙂

    • Liz June 26, 2013, 12:04 pm

      I’ll take that trade any day Kevin.

  • Tammy R June 26, 2013, 10:38 pm

    Liz, this is so well written and so honest. Thank you.

    It really can be done, and what you say is true. CJ and I make less than we did when we taught full time, but we cannot place a dollar amount on the happiness we now have from getting to spend every day, all day, together. We both have health insurance. We are contributing more to our retirement funds. We own a small townhouse. And we do it with less money because our priorities are not in buying things but having experiences. I love your message here!!!

  • Sue | Motivational Coach July 1, 2013, 8:13 am

    Thanks for sharing this to us. I agree with you, credit card debts are like monsters. They can scare you wherever you go. I think the only way to free yourself from financial crisis is to always live below your means. It will require you a lot of self discipline. But the benefits is lifetime.

  • Lyle @ The Joy of Simple September 1, 2013, 8:01 pm

    “Don’t keep one foot in the door just in case.” – You and I are definitely on the same page!! Back up plans allow you to fail, while jumping off the cliff with no parachute, gives you no choice but to make stuff happen.

    While I took the leap twenty years ago, I do appreciate this post and the message you are attempting to impart on those who may need a slight push 🙂

    Thanks for a wonderfully inspired post and take care. I am now off to read more 🙂


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  • Declare Bankruptcy November 25, 2013, 8:26 pm

    Yes this is true. All of the information listed above is very useful to others who want’s to know how to save their small amount of money.


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