18 Steps I Took To Retire At 44…With A Family

(This article was previously posted on Journal)

These are the steps I took to retire at age 44, but every person has a different set of circumstances. Therefore you must customize these steps to your own situation!

That is why the point of these steps is not to feed you every single detail, but rather to provide bullet points to think about.

What do these items mean to you?

How would you go about making them a reality?

The possibilities are endless; the choices are all yours.

For me, the main two things required to retire mega early were to:

Set up a meager but constant passive income stream.

Move someplace nice yet relatively cheap…(and if overseas, get your income in the higher currency).

The main philosophy to keep in mind is: Human beings were NOT designed to spend their whole lives working. So put effort into your early retirement plan, then implement the plan and kick back!

1: Don’t listen to people who say you can’t do it. They’re wrong.

Don’t let people demotivate you from your dream of early retirement. There are far too many folks retired in their 30’s and 40’s to believe it can’t be done. It absolutely can…but until you are committed, the other steps won’t matter. You have to believe the dream is attainable, and ignore the naysayers.

What one man can do, another can do! – David Mamet

2: Don’t listen to yourself if you say you can’t do it. You can!

We tell ourselves what we can’t do when we should be saying the opposite. Some folks want be dancers, and they learn how. Some want to be Senators and they run for office. Some just want to retire…but most postpone it and postpone it…we tell ourselves the time isn’t right, or we cannot afford it.

To retire mega early, you’ve got to want it and to make it happen; it won’t happen by itself.

Ask yourself:

What would I do if I could do anything I want?

Tell yourself:

I CAN do anything I want!

I can do anything I want and nothing can stop me.

3: Find your motivation. Or you won’t have any.

Remind yourself:

Work does not make me ‘who I am.’

A person can do anything they want, just not everything they want.

Without a clear motivation to keep in mind, it will be hard to get through the remaining steps… So why do you want to stop working? Clearly, you are thinking about it; you are reading this article, aren’t you? So what is your answer, hmm?

What’s your motivation? Mine was to relax and enjoy time with my kids while they are young.

4: Find your source of passive income. Or better yet, several.

As mentioned, the point here is not to feed you every morsel but to give you the idea that what I’m suggesting is even possible! It is; I’m doing it.

Research which methods will work best for you to set up your passive income stream. There are several to choose from. If your company offers a pension, take it! What are you waiting for? If you enjoy working online, folks are making a ton of money with affiliate marketing websites, monetizing YouTube videos, etc.

It takes time to set it up, but many folks hire others to do the work for them. You see it all the time on sites like Upwork; clients hire freelancers to build sites then fill them with SEO-laden content, pulling views and hopefully ad-clicks to generate revenue (i.e. passive income!)… The key to making money in online ventures is quantity. You need a lot of content and lots of views.

If you have money to invest in real estate, renting out properties is a means of generating passive income, so long as the rent surpasses the mortgage, property management fees, etc. Therein lies the rub, but it is doable!

5: Live someplace really affordable. Even if it means leaving the country.

Reminder yourself:

At the end of the day, that’s what life is all about. Not working. Living.

From 2015 to 2017, we lived overseas in an area where $2,000 pays for a comfortable life for a family of four. A single person could get by on far, far less! There are many gorgeous, cheap places to live on Earth… All it takes is a plane ticket and someone to help you get set up.

Of course, many folks don’t wish to leave their home country, and I can’t blame them. Just depends on how much you have to live on, and if you can find a place you like which is really affordable. Many folks move to more expensive areas in order to get higher-paying jobs. We moved someplace cheap, in order to have no jobs!

And actually, these days our passive income stream exceeds $4,000 a month, so we are able to sock some away for a rainy day!

6: Forget about getting rich. It’ll only drive you crazy.

Ask yourself:

What are the things you believe wealth will buy you, that will make you happy?

The trick is to find your minimal comfortable lifestyle, then make just enough money to afford it. You may find you are far happier spending your days practicing guitar, talking to relatives or friends, learning a new language, or developing forgotten hobbies.

7: Stop buying stuff you don’t need—IMMEDIATELY!

Nearly all of human history involved living a minimalist lifestyle. What happened? How did we get so brainwashed to consume, consume, consume?!

Working harder just to buy stuff you don’t need is a trap.

Going into debt to buy stuff you don’t need is an insidious trap.

Don’t fall into these traps! If you’re already in, climb out now!

8: Reassess what you want versus what you need. Then do it again.

The less money you spend, the more money you have to spend (or better yet, save!).

When you do buy, only buy things with intrinsic value.

9: Get the best bang for your buck. It all adds up.

Clearly the bigger the price tag of an item, the more vital it is to shop around. Don’t just impulse buy something!

Ask yourself:

What is the point of a $60,000 car if you can’t afford to put gas in the tank?

10: Have a backup plan. Or two.

If you are really crazy enough to jump ship from the workforce (I was), make sure to have a backup. Do you have a little cash in savings? A place to stay if you get in over your head? A means to make a few extra bucks, if needed? Or a good resume, should things go awry and you find yourself in sudden, dire need of full-time employment again?

11: Make a budget… and make sure everyone is on board with it.

Don’t live beyond your means.

Make and keep a spending plan. If you do, you’ll find that you are far better able to keep a handle on things. If you don’t, you’ll find yourself in the hole.

12: Keep an eye on exchange rates, if you move overseas.

Getting paid in dollars but living in a country that uses a currency that trades 2-to-1 or even 3-to-1 is a great way to extend your purchasing power. Just make sure to keep an eye on the exchange rate; those things can fluctuate quite a bit.

13: Pay off your debt. Then keep it paid off.

The point of retiring early means not working. But if you are living off credit cards, then not working isn’t working. Either reign in the spending or get back to work until you can get out of debt.

14: Keep saving. Forever.

If retirement is your goal, you must be savvy on your spending habits, AND your saving habits!

Whatever your reason for saving, just be sure to have a nest egg.

Saving is always a good idea. Not a fun idea, but a good one. Save up; you never know when you’ll need a quick stash of cash for an emergency!

15: Research other ways to generate passive income. The more, the merrier!

So you are generating a nice stream or two or three of passive income. Nice! Great job. But don’t rest on your laurels. If one of those streams were to run dry tomorrow, would you be able to absorb the blow…or would you be running to the soup kitchen?

That’s what I thought.

16: Keep learning! No one knows it all…

Going hand-in-hand with Step 15, I think it’s vital to read traditional books on retirement, investing, business…anything to add a few tools to your growing knowledge base! Why not? You’re retired, so you should have the time to read. Just make sure to try and get the books free from the library if ya can!

17: Stay determined and focused on the end goal, not on the obstacles.


Make sure you are not working!

As I finished this, a song came on the radio, with the lyrics, ‘I don’t need no money, as long as I can feel the beat.’ Stay focused on your dream, of being retired…which means following the above steps!

18: Find the free money.

Whether it is college scholarships, grants, or even things like Department of Labor disability claims if you are rightfully entitled to such benefits, do your homework and find areas where you are entitled to monetary benefits. They aren’t going to find YOU! You have to find THEM!

If you fail to plan, you are planning to fail.

Tired expression, but very true! But even if things start to look worrisome, stay optimistic and take the needed steps to get back on track. You will succeed if you don’t allow yourself to fail!

I hope the ideas are of value to you! Best of luck!

Photo taken in Kusadasi, Turkey. Credit: Matt Cates

Published by Matt Cates

Retired USAF Veteran. Freelance writer. Author of 'Haveck: The First Transhuman.'

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