My Retirement Dream: to Keep Working!

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Retirement planning

The following is a contribution from Kali at Common Sense Millennial. If you’re interested in contributing to Frugal Rules, please see our guidelines and contact us.


My dad will turn 50 next October and he’ll retire from his job the following February. He’ll have worked for the fire department for 30 years. His reward for all the physical and mental stress endured from working accident scenes and house fires will be a full retirement complete with a pension at a very early age. Unsurprisingly, he’s counting down the days until he’s able to start his life of leisure, pursing his hobbies like photography and horseback riding, with no schedule to interrupt him, no alarm clocks to wake him before he’s ready to get up, and no work for which he’s responsible.

Many share this dream of retirement: long, relaxing days without a bit of work in sight. No paperwork to complete, no clients to please, no hustling to find new business. But my dream of retirement is different. I’m not living frugally, saving as much of my income as possible, and investing for my future so that I can quit working early. My retirement plan does include saving heavily and becoming financially independent so that I can walk out of my 9 to 5 office job and quit the rat race for good one day. However, I don’t want to quit working – I want to do work that I love instead of work I have to do for the paycheck.

My Retirement Dream


My dream is to be able to create location-independent work as a freelance writer so that I can travel the world and work from anywhere with an internet connection. I know there are plenty of people my age doing this very thing as I sit and type this post, but here are the two major differences between our situations:

  1. They make enough money to cover living expenses, but not enough to contribute to retirement accounts or other investments.
  2. They’re planning on coming home at some point and picking up new careers when they do.

I haven’t taken off on an around-the-world tour because I want to be financially secure first. I want to have a nest egg that can continue to earn money while I’m away. When I decide I’m done with my travels and want to come home, I don’t want to worry about immediately having to find another source of income. And I really don’t want to encounter a situation where I’ve been working for years, yet I never made enough to put a cent in a savings account.

That’s how working as a freelance writer abroad became my retirement plan. Just as some people are looking for the freedom to conduct days that start with sipping coffee on the front porch in a rocking chair and end with going fishing, I’m looking for the freedom to travel where I want, stay as long as I want, and come and go when I want.

How I’m Going to Make it Happen


So how am I planning on achieving this non-traditional take on retirement? The biggest key to success will be trying to strike a balance between contributing heavily to retirement accounts now and pulling back on contributions later when I’m traveling. By continuing to work for a small income that covers living expenses when I quit my office job, I won’t need to dip into what I’ve saved to survive. But I also might not be able to contribute as much as I can now for that day that I am ready to be done with work and live off what I’ve saved.

Therefore, I’m throwing everything  I can at those retirement accounts – I’m contributing enough to my employer-sponsored retirement to earn the employer match, I’m maxing out my Roth IRA, and I’m taking my budget surpluses that I get by living frugally and investing those amounts in yet another account. I’m also taking steps now to make what’s currently a passion and a hobby into a source of income. I love writing (and I’m pretty darn good at it!), but I’ve never tried to sell my services. If I want to make it into my new career, I need to start working on that now before I take off to see the world.

What’s Your Retirement Dream


If this version of retirement interests you, take this as your cue to break from conventional wisdom. Maybe you don’t want to see the world, and that’s okay. Maybe you want to move down to the beach and drive the tour boats during the summer, or you want move to Colorado and work at a ski resort. Whatever it is, if you’re seeking the freedom to go where you want and do what you love, know it is possible.

You don’t have to choose between believing in the YOLO mentality, spending all your money now and having to work until you’re nearly dead to retire, or saving 90% of your income today in order to retire early at 40 and hope your investments do well to get you through the next 50 years without a job. There’s a third plan, my plan, but the work has to start now. Be less wasteful and get frugal so you can save more today. Find ways to monetize your current hobby so you can earn more and gain the experience you need to turn it into a viable career. Give yourself a few years to build up a good nest egg, then let it quietly grow in the background while you head off to do work that you love.


What is your retirement dream? Will you go for the traditional route, or more outside the box?


About the Author: Kali blogs about common-sense financial advice at Common Sense Millennial. She’s passionate about personal finance and helping millennials learn how live well on less. Currently, she is pursuing the ultimate dream of writing for a living. You can connect with her by tweeting @CSMillennial.


Photo courtesy of: Tax Credits

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I'm the founder of Frugal Rules, a Dad, husband and veteran of the financial services industry. I'm passionate about helping people learn from my mistakes so that they can enjoy the freedom that comes from living frugally. I'm also a freelance writer, and regularly contribute to GoBankingRates, Investopedia, Lending Tree and more.


  • Love this, Kail. Our retirement dream looks similar! Yes, you are indeed pretty darn good at writing!

  • I would like to think that I would move outside the box when it comes to retirement, but at the same time I’m only 25 and I’m not sure where my career or side hustles will lead me. At minimum I would like to have location independent work, similar to your goal, and be able to choose if I want to pursue it as an alternative to traditional retirement.

    • Sounds like a great plan, DC. And you make a great point – you and I are both so young, and there’s no telling where our side hustles will take us! I want to be flexible and ready for just about anything, but I work best when I have a definitive goal on which to focus. I want to be able to make room for changes, too, though I think like you my minimum requirement is to be location-independent.

  • Matt Becker says:

    I like this a lot! And honestly I don’t think I’ve ever heard anyone describe a plan exactly like this. The reason I love this plan so much is that it’s just a reality that saving money now will have a much bigger impact than saving later. By doing things in this order you’re delaying gratification but prolonging the amount of time you’ll be able to have it. Awesome!

  • Sounds like a great plan, Kali! When you write for a living, all you really need is an internet connection, like you said. I would probably travel more while working if I didn’t have kids!

  • The Warrior says:

    My retirement dream is to be doing what I want when I want. I want to be running a few businesses and have the freedom to go about my own schedule. That’s The Warrior Family Plan at least. Not for everyone but definitely for us.

    Back to hustlin’….

    The Warrior

  • In a weird sort of way I already feel kind of like what I would be doing in retirement. I work for myself and see that I’ll still be doing that even past the normal retirement age. It’s great to build up a skill (like you’re doing with writing) to be able to use that in “retirement.” There are so many jobs that when you leave, you leave. LIke my dad and him being a dentist. There really is no freelance dentistry, so he went the traditional route of retirement. The beauty is that there are many things now you can do anywhere with the internet. Good luck with your goals!

    • Thanks Tonya 🙂 I think it’s awesome you’re already working for yourself. I feel like when you’re able to do that, things feel a lot less like work in the negative sense of the word – or at least, a lot less like work than dragging you butt to someone else’s office all day, every day!

  • Stefanie says:

    I’m not sure what retirement dream is just yet. I’m not opposed to continuing to build my business and write, but I don’t want to feel stressed about money. I want financial freedom.

  • Michelle says:

    I love reading about digital nomads! We’d be interested in it too, but I think we also want to have a side business on top of writing. I love working so I can never see myself stopping either.

    • I would love to be one of those folks you’re reading about one day! One of my dreams is to start up a travel blog – my husband is big time into photography, so I keep telling him together we’d make an awesome blogging team! That’s awesome that you’re already thinking about a side business on top of writing.. I keep trying to come up with business ideas, but I’m very bad at it. And I’m glad you understand about the love of work, when it’s work you love 🙂

  • E.M. says:

    Our plans are very similar =). I would love to travel the world, and not have to worry about starting over with a job upon returning. Plus, what if you love a place you visited so much, you want to move there? Being a freelancer gives you so much flexibility, it really is great. You just have to want it enough to make it possible!

  • Someone once told me that “if you love what you do it’s not really work”. I like to think that one day my passions will be able to support my family’s income needs and lifestyle. I would like to slowly build a residential real estate portfolio that I could rely on for income in my golden years. If I’m lucky, we (my family and I) might even be able to benefit from that passive income sooner than my 62nd birthday (I still have 30 years to go).

    Now-a-days working during retirement has become the rule rather than the exception. However, I do believe that if we have a financial plan and stay frugal (stick to our budgets), we might not have to settle for less than an awesome retirement. Thanks for sharing Kali!

    • I like your plan to build a real estate portfolio – that is something I am interested in as a passive income stream, but I’m not sold quite yet. Just not sure I could be a good landlord! I think you’re right, working during what should be people’s retirement years is becoming more and more the norm and I certainly don’t want to put myself in a position where I HAVE to work beyond the point I want to. Like you said, by saving now and being frugal I hope to avoid that trap!

  • Well step one would definitely be to pay off the student loans! We will be so used to living the super frugal lifestyle that putting money away will be easy, right!?

    Once our kids are grown, we would like to travel and do service abroad without having to worry about how we will pay for it.

    • Definitely crucial to pay off any and all debts first. I am really, really fortunate that I did not have to take out student loans, and I feel like it’s definitely made our financial journey a little easier. I hope you guys are able to travel and work abroad! I may be a bit biased, but I certainly think that’s a very worthy goal for anyone to have 😉

  • I can’t ever see myself stopping work.
    I enjoy it, the buzz of doing deals, meeting interesting people.
    Reaching financial independence though is something I’m no where near achieving yet.
    Financial independence is the point where the cloak of stress is finally lifted.
    Bring it on

    • Couldn’t agree more – I love doing work that I’m passionate about, and being in a position where I’m working for myself. One important thing I’ve learned about myself is that I feel depressed when I don’t feel I’m being useful, so I can’t imagine fully retiring anytime soon! Financial independence is still something I’d like to achieve, though, for the exact reason you pointed out – FI will lift a whole lot of stress and pressure off us. It would be a nice piece of security to have.

  • Yeah, I don’t ever want to retire-retire. That sounds boring! But I also want the financial freedom to do whatever I want…but not just when I am older. Doing whatever you love means you don’t have to “retire.”

  • Micro says:

    I think it really boils down to your definition of what work is. Is getting paid for doing something considered working? If it is yes, then really, most people will never quit working when they are retired. After living your whole life staying busy everyday, you can’t just flip a switch and not do anything. Eventually you get bored and want to do something to keep yourself occupied. If you get paid for it, awesome, if now, you have the savings that you should be fine. I plan on doing hobby work when I retire and it may or may not produce income. Either way, I’ll still consider it being retired.

  • While I don’t think I’ll be able to make enough money writing I like the idea of still working part time to supplement my income costs in the future. your plan sounds great!

  • I really don’t plan on retiring ever. I know I would get bored and want to work on some side business ideas. Plus I’m a realtor and I enjoy my job, so there’s no telling how long I’ll continue to work in this industry. I’d be fine with doing it on a part time basis as well as some side projects. For me, the retirement plan is when I have $1M saved up earning interest for me. And then I’ll still work, but probably not as hard and use my free time to travel and learn new skills for fun!

  • Great post. It shows the responsibility and mindset of a thirty something and not the carefree life of a twenty something. Build up you capital and start streaming some income and then go play.

  • kathryn says:

    My husband and I retired 3 years ago, at ages 46 & 50. During the time when our 4 children were small, we concentrated on paying off our home. When the kids were teenagers, we took out all the equity, and started buying rental properties. After six years, we owned 40 rentals. We did a trial run for one, of living off our rental income, and banking our employed income. Then we took the plunge and never looked back. By this time the kids were all finished high school. We turned the family home into a rental, and bought a 5-unit apt house. We all took an apt, and share in the expenses.
    Life is great. They lead their lives, and we travel a lot.

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