And an Alternative Approach to Paying for Life

Image for post
Image for post
Time to Quit

I haven’t worked for an employer in four years, and I’ve never worked full-time for more than a few months. But between the ages of 17 (bussing tables), and 50 (painting houses), I had 47 jobs, so I do have some serious job-quitting experience.

In fact, I enjoy quitting jobs so much that I’m tempted to get another one just so I can quit. Giving that notice, and leaving on that final day, are such delicious pleasures.

My shortest job was working as a highway flagger. Contrary to my naive idea that I would lean on a sign waiting for cars on a quiet flower-lined road, my first day was spent directing traffic through heavy construction at the busiest intersection in town.

My employer decided I didn’t need a radio to communicate with coworkers at the other ends of three curving and converging lines of cars and trucks, so I had no idea when the last vehicle they let through had passed, and therefore no idea when it was safe to allow the next line of traffic to move. There were many near-accidents, and many drivers yelling at me.

I generously (stupidly?) agreed to finish that one eight-hour shift before quitting.

The job I held the longest was as a part-time blackjack dealer. During those eight years I paid off my first home and developed the habits and skills needed to avoid ever again holding a job for more than a few months.

Why Quit?

The question seems disingenuous, since most people don’t truly love their jobs, and even if they enjoy some of the work, they would enjoy it even more working according to their own rules and standards.

I know there are multi-million-dollar lottery winners who say they’ll keep their janitorial or office jobs, but I assume that’s due to an incredible lack of imagination — a deficiency that’s probably corrected once they have some experience spending their windfall.

And maybe you’re the rare person who truly loves your job, but c’mon… would you really report to work even if you didn’t need the money? I doubt it.

So, rather than asking why someone would quit so many jobs, a more relevant question is why should you keep your job?

Alas, there are good answers to that, starting with the need to eat and pay bills and continuing with goals like owning a nice pair of socks or going to Disneyland.

So it’s a money thing. You need to pay for “life.” But, contrary to popular delusion, you don’t have to cling to a particular job, or even be employed all of the time. Instead you can develop your own unique answer to the question…

How Do You Quit Your Job?

You could work your butt off and retire early. Using a good job as away to (eventually) quit all jobs is an approach with some merit, especially if the job you have pays well.

But it just takes too long for my tastes. I can’t imagine working 30 or more hours weekly for fifteen long years (that’s how long it takes, right?) to save enough for early retirement.

Starting a business is another option. That can get you out of your job by the end of this year… and into a bankruptcy court by the end of next year.

Actually, low-risk businesses have provided a huge part of my lifetime income. And my freelance writing currently provides a nice chunk of change, by my lowly standards anyhow.

But working hard for a future “easy life” is exhausting, habit forming, and it takes a lot of time. I have a hidden waterfall to find (tomorrow), a road trip to take (last week), and my wife and I are trying to rescue six stray cats that come for breakfast every morning.

In other words, neither a full-time job nor a regular business can give me the freedom and free time I want.

If, like myself, you consider time the most valuable currency, and you want more control over how you spend it, you might find something useful in my approach to paying for life. Naturally, some of the following may not be relevant to your situation and goals (we are each unique), but here’s the formula that works for me…

  1. Reduce life overhead.
  2. Diversify sources of income.
  3. Keep adding new sources of income.
  4. Use jobs as temporary tools.
  5. Keep finding new frugal strategies.
  6. Always have money in the bank.
  7. Get creative.
  8. Prepare to quit, and then do it.

Let’s look at these one at a time…

1. Reduce Your Life Overhead

“Life overhead” is the total cost of necessary bills, the ones you can’t easily reduce or stop paying next month. It includes rent or mortgage payments, utility bills, property taxes, car payments, and payments on credit cards or any other debt.

When our income was high my wife and I spent freely on trips and going out to eat regularly. But we also had a small, low-maintenance house on which we paid off the mortgage loan in less than three years, so our life overhead was very low.

Our income dropped in half one day (it happens), so we cut back on vacations and meals out, and easily paid the bills. When the remaining half dropped in half again over the next few years, we were still fine, because we had no debt, and no large expenses.

A big house, along with a car payment and credit card debt, means you need a large income just to survive. If you keep the housing affordable, drive a used car, and avoid debt, you can party hearty (if that’s your thing) using your excess income, and then slow down or stop the party as needed.

Keeping your life overhead low is crucial to comfortably quitting jobs when you feel like it, so consider downsizing your house or apartment, paying cash for whatever car you can afford, and avoiding all debt.

It also helps to not have kids.

By the way, studies show that having children doesn’t make you happier Yeah, sure, go ahead and tell your child-desiring partner about the research. Good luck!

Having kids won’t make it impossible to quit jobs at will, but it does complicate matters. Marriage can too, unless you choose someone as open-minded and adaptable as my wonderful wife.

In any case, arrange for your survival needs to be covered with as little income as possible. And then…

2. Diversify Your Sources of Income

When a job is your entire income it’s tough to quit. You might save enough to quit for a while before finding new employment, but to extend that wonderful period between jobs it helps to have other streams of income coming in.

In one recent year my wife and I made money 25 different ways (last year only a dozen or so), with no one source accounting for more than 25% of the total. Our life overhead consumed just 65% of that total, we could have lost our largest source of income and still paid the bills and banked some savings.

So of course I quit the part-time job I had at the time (security guard for a gated community).

Start developing other sources of income. Suppose you rent out rooms in your home (that’s how I paid off my first mortgage in a few short years), do some freelance gigs online (writing, website design, paid surveys, whatever), and sell some crafts you make.

Let’s say those extra incomes sources total 40% of your paycheck. It’s not enough to replace your employment income, but on the other hand, if you were already covering the bills via your job, you can save 100% of that additional money, right?

In less than three years you’ll have enough saved to take a year off from employment. Or you can develop those other sources until they do replace your job income, which brings us to the next step…

3. Keep Finding New Ways to Make Money

If you keep adding sources of income, at some point you may not ever need a job again. Or at least you’ll be replacing any income sources that decline or are lost.

You have to find what works for you, but here are some possibilities for small and large streams of income.

Start a Business — I prefer low-capital, low-overhead businesses, like the internet publishing company my wife and I started for a few hundred dollars. That brought in a six-figure income for a while, and when it failed we didn’t lose any assets.

Collect Bank Bonuses — I make about $2,000 annually from bank account opening bonuses. I figure it works out to at least $50 per hour for my time, much better than my minimum-wage employment value.

Collect Credit Card Account Opening Bonuses — These, and cash-back from credit cards, are worth close to $2,000 annually as well.

Be a Human Guinea Pig — You can make thousands of dollars for a few weeks if you want to take unproven and probably dangerous drugs. I’ll pass, although I did accept $30 once to try a new aspirin for a week.

Invest in Rental Real Estate — My wife and I haven’t entirely enjoyed our experiences as landlords, but we always made money from our rentals.

Invest in Real Estate Online — New platforms like Fundrise let you invest in real estate with someone else doing all the work. I’m investing on three of these at the moment, making between 7% and 12% annually.

Invest in Your Home — A home is normally a liability (all expenses, no income), but it can be an investment if you buy and live in a fixer upper and sell it for a profit after renovations and a two-year wait (that’s how you avoid taxes on the profit). We’ve done this several times.

Be a Loan Shark — Okay, take it easy on friends and family, but why not charge a healthy interest rate if they can’t do better at the bank? I’ve only lost money on two out of dozens of personal loans, but be careful, and get it in writing.

Try Anything — What else can you try? Anything and everything that doesn’t risk too much. I’ve made money writing Kindle books (it’s free to try), selling things at flea markets, junk picking, working as a mock juror, doing online gigs, and doing a dozen other things.

If nothing else works, you can always…

4. Use Jobs as Tools

I’m not really anti-job (hey, I’ve had more than 40 of them). I see them as great temporary tools for various purposes.

My first job, bussing tables at 17 years-old, had an intended purpose; to fund a two-month hitchhiking trip to Mexico. In my late 40s I worked as general labor for a house flipper just to learn how to invest in fixer-uppers, and used those lessons to make money several times.

Jobs can be used to train yourself for starting a business, as a place to recruit your MLM downline, as a way to learn new skills, and, of course, as a way to pay the bills. In the “prepare to quit” section below I’ll have more to say on how to use your current job.

You might want to diversify employment too. Having two part-time jobs instead of one full-time job means you can quit one without losing so much income.

By the way, here are the jobs I’ve had (used) over the years (only two were full-time, and only for a few months):

  • Restaurant Busboy
  • Dishwasher
  • Food Prep Worker
  • Cook
  • Live-In Babysitter
  • Fast Food Worker
  • Fast Food Restaurant Shift Manager
  • Fast Food Restaurant Assistant Manager
  • Pizza Delivery Driver
  • Pizza Restaurant Assistant Manager
  • Auto Repossession Agent (Repo Man)
  • Chauffeur
  • Resort Event Worker
  • Direct Mail Product Packager
  • Construction Worker
  • Restaurant Equipment Installer
  • Convention Greeter
  • Product Demonstrator
  • House Cleaner
  • Car Parts Assembler
  • Newspaper Deliverer
  • Phone Book Deliverer
  • Process Server
  • Mover
  • Drywall Installer
  • Truck Unloader
  • Bill Collector
  • Blackjack Dealer
  • Roulette Dealer
  • Poker Dealer
  • Real Estate Agent
  • Real Estate Investment Researcher
  • Highway Construction Flagger
  • Carpet Cleaner
  • Pet Sitter
  • Thrift Store Worker
  • Post Office Mail Sorter
  • Newspaper Ad Inserter
  • Special Needs Caretaker
  • Pizza Delivery Driver
  • Sign Holder
  • Construction Worker
  • Tram Driver
  • Security Guard
  • Handyman
  • House Painter

I’m considering stocking shelves at the dollar store later this year, to help cover all the expenses related to my neck cancer (it happens, and it’s gone now). But I know I’ll be bored after a couple months, at which point I’ll enjoy quitting.

5. Keep Finding New Frugal Strategies

Finding new ways to cut costs isn’t about sacrificing or being a scrooge. When you discover how to pay less for things you get more for your money and/or you get to work less.

For example, my wife and I developed a taste for nice hotels when our income was higher, so we recently stayed at a Hyatt resort in Sedona, Arizona. But we can’t afford the usual rate of $430 per night, so we stayed for free, using the annual award night from my Hyatt credit card.

Okay, it wasn’t quite free, because I pay a $75 annual fee — but we can afford that. Several other hotel stays this year have been entirely free using credit card points.

We’re always looking for the best happy hour deals at pubs around town, going to free concerts and museums, and stocking up on toilet paper during sales. Pay half as much for things and you get to do twice as much or, possibly, quit another job.

6. Always Have Money in the Bank

You aren’t going to feel comfortable quitting a job if you don’t have some money saved. And if one of your income sources falls or fails entirely, that saved money will carry you until you get a job (temporarily, of course).

Savings also open up other income possibilities. For example, I’ve earned bonuses for opening about ten bank accounts this year, but that was only possible because we could afford to tie up thousands of dollars for months at a time (a typical requirement of the deals).

Not sure you can save anything? If you think about all the money you’ll make in your life, and the fact that many others will make far less and still pay their bills, you know there is a way to save some portion of your income as an emergency/opportunity fund.

7. Get Creative

There are so many things I won’t cover here, partly because there isn’t time and mostly because I know only a fraction of the strategies people use for jobless living. But here are some possibilities…

Take Turns Working — My wife’s job paid the bills while I started my first website. I had a job while she worked on her poetry. You can alternate mini-retirements with your significant other if your expenses are low.

Live in a Bus — My wife and I met three guys living on almost nothing (no jobs necessary) in a converted school bus. We met them while we were living (briefly) in our van at a $3-per-night campground.

Live and Work as a Campground Host — Some campgrounds provide a free site with full RV hookups for their hosts. It’s not a full-time job, and not too taxing.

Join the Peace CorpsBenefits include living expenses, health care, and a check for $8,000 when you finish your two-year adventure.

Find Your Own Way — Get creative and find new ways to avoid jobs. Join the circus (or start one), be a deckhand on a sailboat, or make walking sticks and sell them as you travel.

8. Prepare to Quit

The suggestions above cover general preparations for a jobless lifestyle (or at least one with more frequent breaks in employment). But if you currently have a job that you would like to quit, here are some specific things you should do first, to prepare for that rewarding day.

Build Your Savings — Money in the bank will make everything go more smoothly. You can save faster if you follow the next suggestion…

Reduce Your Discretionary Spending — Maybe you’ve reduced your life overhead, but prior to quitting you should develop more frugal habits in all areas of life. If you can’t do so now, you may not be ready for the drop in income. If your new lifestyle produces even more income than your job did, you can always loosen up on the spending.

Increase Your Income From Other Sources — You won’t have to cut back on expenses as much if you increase your income from other sources. Move your money to higher-interest accounts or invest it for a better yield. Start a few new side gigs. Rent out a bedroom.

Arrange for Health Care Coverage — See how long you can keep the health insurance policy provided through your employer (and save the money to pay for it). Check out marketplace plans and be sure you don’t have a gap between the loss of previous policy and the enrollment period for your new one (time quitting accordingly).

Make a Plan B and C — Have a backup plan or two, in case things don’t go as expected. For example, you might ask former employers if they’ll be hiring in the the near future, or check with parents or a brother to see if the basement bedroom is available, just in case.

Maximize the Value of Your Job — Prior to quitting, squeeze as much value out of your job as possible. Get the phone numbers of co-workers who might help you in the future (possible business partners, roommates, job references). Work overtime to pile up more savings. Use employer-provided health insurance benefits for discretionary care before you lose coverage.

And of course, quit on good terms, both for a possible return and/or a good reference (believe it or not, many of my previous employers told me I was welcome to come back).

Then quit. It’s nice out here in the jobless world.

Written by

Steve Gillman lives in Tucson, Arizona and has successfully avoided full-time employment for decades by making money in various ways (writing is his favorite).

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store