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Our friends at Retire Early Lifestyle share their thoughts on generating income from side hustles while still being retired and traveling the world. Is it work or is it passion, and is there a difference between work and hobbies you love equally if you get paid for one and not the other?

While taking a break from the sun and surf, relaxing in my hotel room in a tiny beach town on Mexico’s rugged Pacific Coast, my cell phone rang.

‘Howdy, Beautiful!’ my friend of four decades shouted from snow country, thousands of miles away. “Been watchin’ your website for years and I read all your stories. Love ‘em. But I thought you were retired!

How many times over the twenty-plus years since we left the conventional workforce have we heard that challenge? Our responses have ranged from surprised silence to justification of our volunteer work, to just laughing out loud.

Income from side hustles: what’s the line between work and passion?

We run a popular website, photograph our travels, and share our lifestyle adventures with people like you. Some think that by doing this, we have somehow become unfit to call ourselves “retired.”

Today I would like to pose this question to you: “Once you leave the mainstream labor-for-paycheck world and become financially independent, aren’t you free to choose what you do with your time? When is something considered work, and when are you pursuing a passion?

Is it work or is it passion - when are you really retired - retire early lifestyle - frayed passport - income from side hustles

Receiving income from side hustles and passive monetary generation

Most people with whom we have this conversation have one particular definition of retirement: You are not retired if you are receiving money for work performed. Receiving income from side hustles means you are still working.

Well I guess that rules out all of the Wal*Mart Greeters… but seriously, we’d like to counter this simplistic point of view.

If you are a landlord with several rentals that bring in monthly retirement income, can you ever be considered retired? Do you not have to oversee the properties, be responsible for making repairs, pay for maintenance and upkeep and search for qualified tenants? At the very least you must concern yourself with your manager.

What if you are like a friend of ours who discovered he had a latent talent for making sculptures, and now sells his bronze statues all over the Eastern Seaboard at Toney art shows? He receives funds from his commissioned work, but he couldn’t be happier following his passion. What does he care if someone doesn’t think he is retired?

Other friends whom we know well sold their accounting firm and moved to a working ranch – a dream-come-true for them. Instead of pushing paper and tax forms, they now raise horses, scoop poop, grow grapes to make award-winning wine, and cultivate boutique vegetables which they sell at local farmers markets. Is is work or is it passion? No question about it being work. However, they are undoubtedly following a passion and their lives are enriched because of it.

A friend of ours is a domestic goddess with unmistakable artistic flare, and her husband is an adventurous handyman. They purchase old Victorian homes, renovate them room-by-room, and then sell them at profit. Sure they receive income from their labors, but this income isn’t what sustains their portfolio. And why not utilize your talents and implement your dreams at this time of life that should be yours? Is it work or is it passion – and should it matter?

If you have left your Monday-through-Friday job but own a diverse portfolio which you must manage, or if you are trading stocks or receiving dividends, does this monetary compensation for your lifestyle disqualify you out of the official definition of being retired? What if you find the world of finance riveting? Are you supposed to stay away because someone somewhere will think you are disingenuous or not “really” retired?

“If you are working, you are not retired”

Some people believe that if you do any sort of activity that would be considered in any fashion to be work, or if it takes any effort whatsoever, you have become unsuitable to wear the “I’m retired” label.

Yet we know all sorts of single, retired women who raise dogs to sell, train rescue dogs for animal shelters, or have a modest dog-walking “business” that they run in their neighborhoods. How many older retired men have we met over the years and in numerous communities who will fix your plumbing for a pittance, solve an electrical problem, or put down some flooring in your home? What if you want to write music, direct a play, or act in one? All of this takes effort, focus, and work.

What if you wanted to build a boat, restore old classic cars and sell them, or play in a jazz band for the clubs in your town? Are you back to the working grind – or engaging your passion?

On the other side of these examples we know people who refuse offers of compensation for entertaining guests on cruises or on tours because “then they would no longer be retired.” If you have left the working world, are you not ever “allowed” to be productive?

income from side hustles - Is it work or is it passion - when are you really retired - retire early lifestyle - frayed passport

Volunteering or mentoring

One may or may not receive compensation for donating time and expertise. Teaching English as a second language could get you out of the house and add dimension to your day, or it could defray the cost of airline tickets to a foreign country. If you allow this skill to enhance your travel budget have you transgressed against The Rules of Retirement?

I taught Thai massage in Mexico for free and created a note card business for the local women in my neighborhood. Billy coached a women’s basketball team to the finals, imported an electronic scoreboard for the city gym, and built tennis courts in this same Mexican town. Was this work? Definitely. We both put in more hours than we want to know, but the return was making friends and having personal satisfaction for helping others.

Had we continued in our careers, none of this could have been accomplished. One of the benefits of being financially independent is that you can pursue your dreams – whatever they might be. Having a passion to infuse your days just adds so much zest to life.

Who decides when a hobby becomes a job? Or when following your passion becomes something more than you bargained for? You do.

We believe the aim of leaving the traditional workforce is to activate the freedom to choose how to live your life no matter what stage you find yourself in – rather than letting someone else dictate your future ambitions or put a label on you. Once you’ve reached financial independence, you can easily move into rewarding activities or the next challenge of your choice. Getting income from side hustles that you love means you have that freedom.

How you contribute to others in your retirement, and how you spend your time and your money is up to you and only you. Have confidence in yourself, and know the value of your talents and endeavors. It is from here that you will make all the difference in your world and in the world around you.

If you find yourself in a position of wanting to retire without giving up entirely on being active, there are more options for you now than ever before in history. You may want to seek out opportunities for heartfelt jobs, artistic pursuits, and spiritual quests, become RV hosts in a campground, take a volunteer vacation, or seek job adventures abroad.

Websites now abound with information on how to help adults in the second half of life set a course, connect with peers, and find pathways to significant service.

After working and saving money your entire life for retirement, and having the courage to decide to unhook from conventional routine, the last thing you need is peer pressure at sixty years of age.

Leave that rocking chair on the porch for someone else. This is your time to create the life you’ve dreamed of.

Brave Boomers simply won’t go quietly into the good night.

Nor should they.

About the Author

Billy and Akaisha Kaderli are recognized retirement experts and internationally published authors on topics of finance, medical tourism and world travel. With the wealth of information they share on their award winning website, they have been helping people achieve their own retirement dreams since 1991. They wrote the popular books, The Adventurer’s Guide to Early Retirement and Your Retirement Dream IS Possible available on their website bookstore or on

Featured image via Unsplash.

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