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Quit Your Job Without Quitting Your Lifestyle

playful-828594_1920We have all dreamed about winning the lottery or inheriting a large sum of money. However it happens, somehow we find ourselves the beneficiary of a large windfall.

If you woke up tomorrow with $10 million in the bank what would you do?

Quit your job and travel? Quit your job and start a business? Buy a big house, a fancy car, and a vacation home? Would you retire and spend the rest of your waking hours relaxing on the beach drinking margaritas? By the way, the perfect lifestyle for a Financial Slacker. You will notice that most of the responses begin with, “quit your job and…”

Just a pipe dream you are probably thinking. It will never happen.

But why not? Instead of a fantasy, what if there was a realistic way to achieve this dream?

What if you could spend your days doing something you enjoy rather than trudging to a corporate job you dread?

Maybe you could spend your time volunteering. They say that nothing brings satisfaction to your life more than giving back. Or maybe spend more time with your family. You only have one chance to see your kids grow up.

Save, save, save

Most personal finance gurus will tell you the key to achieving this type of financial independence is by saving and making do with less.

But how much fun is that? And in our must-have-it-now lifestyle, that seems like more self-discipline than you care to muster. We are looking for immediate gratification. Or at least gratification that doesn’t take 20, 30, or 40 years to achieve.

I remember a wealthy friend once told me he couldn’t understand why the biggest financial goal that any of his siblings had was to pay off their mortgage. Living a life without lifestyle purchases is like eating salad everyday. It might make you slim, but there’s more to life and you’ll be missing out.

I’m not suggesting you eat all your meals at the French Laundry, but wouldn’t it be nice to try it just once?

And I’m also not saying that you shouldn’t be saving. Spending beyond your means (or even up to your means) will not work. Putting away as much money as possible as early as possible will pay significant dividends (and other investment earnings) down the road. But rather than living a life of deprivation, why not seek out a better approach?

Earn a good income. Spend on what makes you happy. Don’t spend on things that you don’t need or want. Invest the excess wisely.

Over time, the money will add up. And maybe you will get to a point where your financial assets can passively generate enough investment income to pay for your expenses. But until you reach that point, you will need outside income.

Generating income needs to be your primary focus in the beginning.

How we generate that income will require you to change your life. You need to change your state of mind from one in which you earn a regular salary to one in which you generate income without the constraints of a day job.

And the first step is self-reflection.

Figure out what you’re good at and what you enjoy

We all have skills. Maybe you can write. Maybe you can play golf. Maybe you are a good speaker. Whatever your particular skill, it’s important that you get introspective and spend some time figuring it out.

As I personally went through this exercise, I realized that I am a good writer, a better editor, and I’m especially good at pulling together resources needed to get something accomplished. I am also a skilled financial analyst.

As you think about what you are good at and what you enjoy, start also thinking about how you can monetize your interest or skill.

Notice that I used the word interest rather than passion. If you start down the path of trying to find your passion, you may wake up years from now having not made any progress. Trust me. I’ve been there. When you use the label passion, it seems to put too much importance on it. You have added judgement to whatever it is you come up with. And maybe you don’t want your self-worth getting all tied up in this thing that you’re trying to make money doing. So, if you stick with thinking about your interests and skills, you’ll be better off.

Figure out how to package that interest or those skills into something others want (and will pay for). Let’s say you decide your interest is golf. I don’t know how much money is spent on golf equipment, but it has to be huge. (I could figure it out, but I am a Financial Slacker after all so I’ll leave that to you). I have spent thousands of dollars on golf equipment, lessons, greens fees, clothes, and I’m not even that much into buying equipment. I have friends who buy new clubs every year. That said, if you create a golf blog and can build a readership of golf enthusiasts, sellers of golf equipment would love the opportunity (and will pay you for it) to get their products in front of your readers.

As you continue thinking about monetizing your interests and skills, you’ll start getting more and more ideas. I have found that’s one of the great benefits that comes from the change in mindset. You are no longer limited by the constraints of your day job. You will notice problems that need to be solved and start to see those problems as opportunities. You will begin thinking about the resources needed and how you can access those resources. In short, the world will become a changed place, just waiting for you to act.

For me, putting together my interest and skills led me to create this website and related businesses – consulting, providing investment advice, writing.

Starting a business

Once you have decided on your interest or skill, the next step is to get your business launched. Others will talk about researching more and surveying potential customers before you launch. I tend to believe you are better off getting going. A business is an ever-evolving entity. As such, you will never be able to plan for any and all eventualities. Instead, get up and running and manage the issues as they arise.

Whether it’s an online business, selling something you make, or providing a service, having your own business is a key step toward generating financial freedom. It will probably not be a get rich quick endeavor. And it will require a significant amount of work. But unless you start, you will never get there.

Starting a business is not easy. And it can be especially daunting if you have been earning a salary for many years. If that’s the case, do not leave your job without another one lined up. Instead, start the business on the side. Use your weekends and evenings. Watch a little less TV and spend the time on something that will pay for itself down the road. Call it an investment in your future. Be an entrepreneur without quitting your day job.

And although having a steady stream of earnings getting direct deposited into you bank is a good thing, don’t allow yourself to get too comfortable. Don’t allow the security of a paycheck stop you from getting something going.

Starting a business is risky…but so is having a job

Have you ever been laid off? I have. Even if you are prepared, it’s not fun.

I always compare having a day job to a company with one client. A company with a single client would be pretty risky. So why do people think that it’s more risky to start a business where hopefully you will have many clients and therefore many sources of income to having a day job that equates to having only a single source of income?

I believe it’s because we have been conditioned to think that way. This is especially the case with my generation – the X gen. It seems that the Millennium generation is much more adapt at earning income in non-traditional ways, one of the most dominant being freelance work.

Although freelance work doesn’t create as many opportunities to leverage your time into greater and greater earnings as other businesses, freelancing is a great way to get started toward financial freedom.

Whatever business you decide to start, they key is to get it started. The sooner the better. And keep at it. Most successful businesses evolve from an initial idea that doesn’t make any money into something that does. The trial and error process of trying different things during this time is invaluable in helping you learn what works, what doesn’t, and why.

Enjoy the journey.


If you have been down this path, I want to hear about it. Have you started a business? Did it do well or not? Are you thinking about how to get to the next step? Looking for guidance or maybe just want to hear from others about the thought process? Did you quit your job and start a business? Or did you start a business on the side?

Please comment.



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