Corbett Barr

Lifestyle Business Weekly

At What Age is it Hardest to Radically Change Your Life?

what age is it hardest to radically change your life?

Some people have commented around the web lately that most of the lifestyle design resources out there tend to focus on the younger crowd. I would agree, most lifestyle design bloggers seem to be in the Gen-Y camp. Not all (I happen to be closer to Gen-X than Gen-Y), but most are under 30.

Why is that? Are most of the people pursuing lifestyle design really that young? It could be that the people talking about lifestyle design are younger, but in fact plenty of “older people” are also trying to radically change their lives too.

Or, it could be that pursuing an alternative lifestyle design just gets more difficult as you get older. Life’s pressures and responsibilities mount and radically changing your life becomes harder and harder.

Is that really true? At what age is it hardest to radically change your life?

From Gen-Y to Baby Boomers, let’s talk about each generation and what about each phase of life might help or hinder someone’s ability to radically change course. In addition to age, obviously your marital status, whether you have kids and your financial status are all important too.

I would love to hear your opinion in the comments.

Let’s start with the vocal majority.

Recent Post-College (or College Drop-Out) to Late 20s

Ah, youth. There are so many benefits to starting things young. Especially in lifestyle design. If you want to pursue your passions or live unconventionally, starting in your 20s makes a lot of sense.

When you’re first out of college (or even if you skip college), you’re already used to living on next-to-nothing. This is a great situation to be in, as it gives you the flexibility to take some time to earn a living from whatever you’ve chosen for yourself.

For example, if your goal is to earn a living working online, it’s much easier to support yourself as a 22 year old than it is to support yourself as a 45 year old who’s married and has two kids. The income requirements could vary by 5 to 10 thousand dollars a month.

There’s also something about the optimism of youth that can make things easier for you. When you expect something to be possible, you might spend more effort looking for a solution. Your positive attitude might also help you see opportunities that a jaded person might not.

On the other hand, there is a strong temptation when you’re fresh out of college to take that first seemingly high-salary job. It’s what all your friends are doing, and it seems like the easy way to a comfortable life, which it really can be.

It all depends on what you’re looking for, and at this age maybe you don’t know exactly what you’re looking for in life yet.

Late 20s to 40

Here’s the category I fit into, and I suspect many of you reading do too (but maybe you’ve been a little shy in participating in these conversations in the past). I think the younger generation is growing up with social media and blogs and they are more likely to contribute to online conversations, but I digress.

By the late-20s, most people will have taken a crack at some type of career. That career probably wasn’t chosen for all the right reasons, and you may have even just “fallen” into it. If you’re not in love with your career, at some point you might have second thoughts about your chosen path.

Having experienced a “typical” life path can be a great motivator to do something different. It can help you realize what you really value in life. That’s something that people who start on a more unconventional path right after college will lack.

On the other hand, societal/familial pressures to “not rock the boat” are probably stronger by the time you’re in your 30s. Your friends and family have already established themselves and may respond to your idea to try something different by telling you “not to throw your life away.”

Then, there are financial resources and requirements. In your late-20s and 30s, you may finally be building a modest financial cushion. That padding can allow you to live off of savings for some time while you switch careers or pursue entrepreneurship.

Unfortunately, the standard of living you’ve grown accustomed to has no doubt grown since you first entered the work force, and you now need to make more from whatever new thing you’ve chosen than you would have if you’d started at an earlier age.

You will also have a much greater fear factor to get over. When you’ve spent a decade or so doing something that’s at least comfortable, pursuing something completely unknown will probably scare you and cause stress like you’ve never experienced. Welcome to entrepreneurship. It’s an emotional roller coaster that only gets more difficult as you get older.

40 to Mid-50s

After 40, does pursuing a big life/career change get easier or harder? Let’s remove marriage and children from the equation here (see below for more details) and just focus on age.

Many of the trends that started in your mid-20s and continued up until this phase of your life have probably continued. This can be help or hinder your ability to make a big life change.

For example, your standard of living has probably grown even more, although probably not as rapidly as it did from 25 to 35. It may have even plateaued somewhat. That’s good, because it can mean that any financial cushion you have will last longer if you choose to use it for a mini retirement or sabbatical or to pursue a career change.

What about your mental state in this phase? Not speaking from experience, I can only postulate at what might be going through your mind. In some ways, you might say that someone in their 40s or 50s has more to lose career-wise. You are probably getting closer to a “traditional” retirement, and drastically changing careers at this point could jeopardize that.

At this phase, more than any other, your financial situation probably has the greatest impact on how easy it will be to pursue a new lifestyle design.

If life has been hard and you don’t have much saved, maybe you think “what do I have to lose?” If life has been grand and you’ve saved a lot, maybe you can afford to try something new without impacting your future retirement. It could be that the middle ground is most troublesome.

Special Considerations: Being Married

When you’re married (or heavily involved with a partner), you might have some convincing to do before you run off with your latest business idea, or set out to change the world. Hopefully your spouse will understand, but there’s a strong chance that you didn’t talk about some aspects of your new lifestyle goals before you became serious.

What happens when your spouse doesn’t agree with your idea of a better lifestyle? How can you best achieve what you both want?

Special Considerations: Having Kids

There is no doubt about it, kids can make lifestyle design a little trickier. Each decision you make will carry a little more weight and impact more people (your family). It’s understandable that the majority of people choose to remain in a stable/traditional job when they have children (or at least young children).

What about people who have kids but still want to create an unconventional lifestyle? What about travel, entrepreneurship or following your passions? How difficult are these things to accomplish with kids? Is it more difficult to pull off lifestyle design with children than any other life phase or situation?

For the full scoop, I’ll have to defer to you who have children. I don’t have any and don’t want to speak out of turn.

I have however, met many amazing families who are on extended trips with as many as four kids, ranging in ages from 2 to 17. The thing I love most about those adventurous families is how close they all are to one-another, relative to the “typical” Western family.

Financial status has a lot to do with what people might feel comfortable doing in life with kids. It doesn’t have to be a limiting factor, though. Many of the families we’ve met while traveling are of extremely modest means, but have somehow found ways to make alternative lifestyles possible.

Other Situations

What other situations are worth discussing here? What about lifestyle design after age 55? What about people with disabilities? What about when you have to care for family members?

At what age (or in what situation) do you think it’s hardest to radically change your life? At what age/situation is it easiest? Please share in the comments below!

photo by lyzadanger

Corbett Barr

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  1. I don’t really think age has much to do with it at all — it’s more about your mindset and the kind of support you have. Probably also determination :)

    • That’s the spirit! But seriously, you don’t think age or other situational factors have anything to do with it?

    • I like this take on it. :-)

      I also think that after 55 (or after kids are grown) is a great opportunity for folks to put some spirit into their lives and take a chance or two (calculated chance).

      Stay active and keep the entrepreneurial spirit alive.

  2. Corbett, I think it is hard to change your life radically at any age. I’m 39, and we’ll be leaving for our trip around the world later this year. This is the second radical change in my life, the first being at 29 when I got a divorce and left the small town I was living in to find a brand-new life and career by myself in a city thousands of miles away.

    I can’t say that either one was easier due to age or relationship status. Both have taken a lot of personal commitment and the willingness to trust in my gut even if everyone else was questioning what I was doing.

    You’ll most likely walk away from some money (at least initially), and you’ll make plenty of mistakes along the way and have to realize that is part of the process, not a reason to tuck your tail and run back to your old life.

    It may be easier to walk away from money when you are younger, though it is much easier to follow your gut when you have the self-assurance of life experience. I think it all evens out to make the decision equally hard for everyone (but also equally fulfilling).

    I’d love to hear from more of your 40+ readers who are making radical life changes.

    • Great points, Betsy. Maybe it does all even out in the end. Some people who can’t seem to make major changes in their 20s may never be able to. Others might find it easy at any age. The rest of us (the majority) will only make major changes a handful of times and will probably find it tough no matter the age. Maybe it gets easier if you’ve been through radical changes a couple of times before?

  3. I’ve lost track of how many mid-life crises I’ve experienced, but I turn 40 this week, and have been making big changes to the way I live my life (again).

    I’d like to think it as myself evolving as I learn and as the world changes. Some aspects are my doing, such as not caring as much about collecting piles of shiny things anymore. I’ve had lots of expensive stuff in past lives, but am now down to making things very spartan for myself. My desires have changed dramatically over the years, and I do my best to keep my mind open to different things.

    The world keeps changing as well, with better and simpler technologies that make some areas of the past all but extinct and create new ways of doing things. I like to stay on top of them as I find it exciting, but also allows for more movement, discovery, and growth with each new development that comes along.

    I don’t know what is harder at what age. We all develop in different ways. I certainly wish I knew at 20 what I think I know now. But the world of today didn’t exist back then, and I have enjoyed the ride that has taken me to know what I know now. Even when it was bumpy and I thought it was going to kill me.

    • The interplay between wisdom and technology is a great topic. At what point in life do you have optimal wisdom combined with the ability to assimilate and make use of new technologies? It’s different for everyone, certainly, but an interesting question nonetheless.

  4. I am a CPA by background and training. Hard to imagine someone more anal retentive … more linear thinking. I made my first major life change at 44. Got divorced … moved to a big city … got remarried (she is also a CPA). My wife and I started our own firm, specializing in business valuations. We were very financially successful.

    Today I am 53. We’re selling off most of our assets and investing a ton of savings into a new venture – We just bought a 25 foot RV and are packing up our belongings and our two dogs to travel the US and Canada to become ambassadors for people would would prefer to travel with their pets. Am I scared? Hell yes!! But I was more scared about staying put … working in a field where I had lost my passion.

    I figure we only need to make it to December 21, 2012. If we’re all alive after that – well then I’ll worry about what’s next :)

    • I love the concept for your new venture, Rod. My wife and I like to travel with our dog, but it’s always a little more difficult. If a site could make it easy to find pet friendly accommodations and info, it would be great.

      FYI, here is one of my pet peeves about the sites that exist around “pet friendly” hotels. Most of them tell you that a hotel accepts pets, but NONE of them seem to list how much the extra pet charge will be for that specific hotel. It takes a lot of digging and/or phone calls to get the real scoop that Fido will cost an extra $100 bucks or whatever.

      Anyways, best of luck with your new venture. It’s great to hear about people in their 50s doing something like that. You always think of younger people when talking about startups.

      • Happy to help you with your pet peeve. has detailed pet polices for our hotels and campgrounds (if one isn’t listed, it’ll be there soon). So you’ll know all about # pets allowed, weight restrictions, breed restrictions, and yes – fees.

    • Hey Rod my second husband and I did a similar trip 2 years ago. Packed up our two cats in a 34′ motorhome, rented out our house and hit the road for a 17,000 mile, 6 month journey. Oh quick my $70,000 a year job to do it too.

      • PS we started blogging our adventure, not as well set up as yours – on this site Sort of did it to keep in touch with family and journal our travels and then it just got away from us when we were moving every 4 days and didn’t always have internet. Got home and life took over again. Would love to finish it or continue it one day.

  5. I can say, that as a 32 year old trying to change his life, as well as having a newborn baby, it’s much MUCH harder to do it now, than it would have been in my 20’s. I have so many more responsibilities now, which makes my ability to try and fail at something that much smaller. I find myself being far more conservative than I want to be, with respect to risk.

    That doesn’t mean not to try, it just means I need a much bigger financial cushion first. Something that can keep my family going if i were to be unable to bring money in.

    • Great perspective, Josh. I can’t imagine how a newborn would affect your thinking and cause protective feelings to take over. Conservative isn’t necessarily a bad thing when it comes to entrepreneurship, though. The idea that entrepreneurs love risk is dangerous. Successful entrepreneurs actually hate risk and do everything they can to eliminate (or get compensated for) it.

  6. As a person in his early 20’s, I agree that things are a little easier. Although I am living in a small apartment and can be found eating pb&j more than 3x a day, I’m very optimistic in my abilities to create the lifestyle I want.

    The one thing that does come my way rather often, however, is the “When are you going to get serious and…” question. My pursuit of lifestyle design is seen as my naive and childish attempt at an unrealistic dream. Granted, I do work as a circus acrobat, but that doesn’t mean I am not serious about this pursuit.

    We all have our challenges when pursuing lifestyle design. Mine just happens to revolve around bad clown jokes.

  7. Great post! I know that a lot of things vary situation to situation but I think you’ve done a great job of trying to describe what many people feel at different periods of their lives. I am mid-20’s and married, and I think that the marriage def plays a role in determining the direction of my decisions. Luckily, we are both fairly adventurous and willing to take risks where we can. Thanks for the perspective :)

  8. After thinking some more about this great question you posed here, I think it has less to do with a person’s age than in the circumstances they happen to find themselves at any given point. As I said, I’m old, but I don’t have a litter of children and 4 ex-wives who I’m paying alimony. I don’t have a mortgage to try to keep up with or other things that need to be maintained financially. I could have just as easily been in any variation of those situations when you asked this question.

    There are always people who will deal with situations differently no matter their age (there are families with 6 kids living in RV’s and having a grand time of it, despite the typical gasp of disbelief from people in society). I’ve probably gotten to be less “stifled” and old man-like as I’ve gotten older. Much like Rod above and his, I did what I was “supposed to do” for a lot of years too. What a waste of time! :-D

    Life is short and there are too many fun things to do to spend it doing stuff you hate.

    • Well put, James. The things you’re “supposed to do” are sometimes a waste of time. It’s hard to understand that until you’ve been through it.

  9. And some of us mid-30s folks are just aging ‘Lifestyle Designers’ (I always just called in ‘conscious living’ before Tim Ferris hit the scene) – not just embarking on our first major change in life. For me, I consider my lifestyle a continuing evolution, not a series of revolutionary changes. I remember actively questioning life’s defaults – such as marriage, career, education and kids from a fairly early age – and making choices for how I wanted to live, not falling into defaults.

    I think age doesn’t have as much to do with the difficulty of embarking on change – as does the choices one has made in life along the way, and how trapped they feel by the life they’ve fallen into.

    I know people in their late 30s-50s just waiting for the kids to move out to embark on their next change. I know folks making changes with the kids in tow. And I know people that feel a bit trapped by a divorce and split custody keeping them from living life for themselves. I know people of all ages trapped by investments in property that they’re now underwater on. And I know people without other commitments who just lack an agile personality to embrace the life they want. I know youngsters who lack the funding, skills, perspective and life experience to even know what to look for in life. And we’ve met people in our travels in their 60s and 70s out exploring life to the fullest now that they’ve evolved through a lifetime of career and family focus.

    Us conscious living folks come in all ages and stages of life.

    We just hear more from the Gen-Y folks on blogs as they tend to be more saavy with those technologies. And quite honestly, a lot of folks as they age are more focused on living life.. and not stopping to share it :) But look at the thousands of blogs of full time RVers (who are mostly traditional retirement age)- you’ll quickly see, they’re pioneers of lifestyle design.
    – Cherie

    • Great points, Cherie. It’s easy to think that “lifestyle design” or conscious living or whatever you want to call it just started recently and that all the youngsters are blazing some new unconventional path. But you’re right, there have been plenty of people living outside of societal norms for all of history. Just look at artists, for example.

    • Jeff H

      Very well said Cherie- exactly what I was thinking.

  10. Zofie

    The best time to radically change your lifestyle may be when fate make the first step to change it for you. E.g. when you lose that precious supposedly “safe” job, and the economy is too crappy to provide a new one just around the corner. Ideally, that is the point when you realize that you sort of hated that job anyway, and/or that you really didn’t need all this stuff that you were buying with the money you were making. You were just sort of a slave to it all because it was there and you were too scared to give it up. That’s just one example… other things can happen that provide a moment of clarity, and you realize that this is just not how you want to spend the rest of your life. Many of them are things that seem devastating at the time, but turn out to be a blessing in retrospect.

    Anyway all this is to say is that fate is a huge factor in deciding to radically change your life, no matter what your age, relationship status or number of kids is. :)

    • I SOOOO agree with your comment, Zofie. That said, I can’t tell you how many of my friends are losing, or have lost, their jobs … jobs they didn’t like or even hated … and are desperately scrambling to find the exact same job in the exact same industry because they are afraid of … something. I was an early reader of Tim Ferriss’ 4HWW, and there is one thing he said that has really stuck with me: when faced with a choice between unhappiness (say, the status quo) or uncertainty (of a life change) most people choose uncertainty.

      • I had to read that last sentence a few times — you mean most people DON’T choose uncertainty, correct (if they did, awesome, we would have a lot more people out there pursuing self-actualization)? Most people choose comfort and safety, even if that means general unhappiness. Because as Ian says below => it’s stressful to have to fend for yourself, without a steady day job and bi-weekly paycheck. Definitely not for everyone, and kudos to those who have the courage to go on despite uncertainty. Don’t give up!

        • Ooooops – sorry. Most people choose unhappiness. It’s like people think the uncertain future outcome could only be worse than than the current unhappiness … no allowance that the uncertain future outcome could be better.

    • Yes, Zofie, sometimes fate can be a great kick in the ass. I forgot to mention that as part of my analysis of people in their early-20s. That generation is dealing with a serious lack of jobs for college graduates (and witnessing their older friends and parents struggle to keep supposedly “safe” jobs). No doubt that is causing more people to seek entrepreneurship as a path from a young age.

  11. Any lifestyle change – any major life decision – comes with stress.

    I recently shifted from a career I hated (the kind where you say “I work at [insert workplace]”, rather than describing yourself as “I’m a [insert title]”) to one that will fall far better in line with my wants, needs and talents. It’s a win on all sides, but I’m still stressed out.

    Any of this kind of work is taxing, not only because of a gain/loss in the situation, but because of how people operate. While I agree that age can add considerations, how difficult any major change is relies heavily on the ability of the individual to cope. Some people are very good under pressure, handling adversity with grace, but can’t fathom acting from a position of power or privilege. Others are better at negotiating success, but can’t handle what most people would call stress at all.

    No matter the age, we’re all better working under conditions we can navigate best.

  12. Great subject, Corbett. I’m currently 44 and living nomadically with our 3 daughters, ages 9, 14, and 16. Most of the people I am meeting (maybe because of my kids and own lifestage) who are also living nomadically are in their late 30’s or older. Many have kids. However, I don’t think that age is the issue as much as life approach. (although you point out some very real trends in each age group). I have met some 20 year olds and even teens for that matter who have much more conventional mindsets than some 80 year olds. Some people think outside the box while others are very comfortable to furnish their box and keep the lid closed. As a coach, most of my clients are older than I am. They are in coaching to chang their lives and are making bold steps to do so. As you point out, many are struggling with the responsibilities towards aging parents but besides that, they’re in a great position to make transitions.

    • It’s true, Carmen. Most of the people we meet who travel extensively every year are in their 30s or older. And they all definitely share a common mindset about what’s important in life (and ability to cope with change and uncertainty).

  13. I’m 46 and every few years find myself in the blessed position of being able to embark on some cool adventure. This is happening now as my hours have been cut dramatically at my job. I have struggled with the “should I go” or not issue. I happily have no family to support, have saved my money and am so excited to get out into the world again. I see no reason not to go except that society says I should stay and look for another job (of which there are few in my field in my area). The only thing holding me back is needing to find a renter for my condo… let me know if you’re wanting to spend a year in Boulder, CO starting in April!
    I have places to go and things to do… but knowing the audience here, so do you :)

    • That sounds exciting, Robyn. I love that idea of starting new adventures every few years. Traditional jobs and lifestyle design aren’t “oil and water” by any means. Taking time off between gigs is a great way to live adventurously without the stress of entrepreneurship.

  14. A great question – I’m 38, my husband is 41 & we have a 21 month old little boy & we desperately want a change.
    It’s not that we don’t have a lovely life right now – we certainly do. My husband is an IT consultant & earns great money, but we’ve gotten ourselves into a reasonable amount of consumer debt & looking back now, it’s come from our desire to live an exciting life here at home, when in reality what we really want is to travel & experience life away from home.

    We had a little taste back in 2007 before we had our little boy & now we want to get travelling again, but the obstacles seem insurmountable :(
    For example:
    – What do we do with all of our “stuff” – I can thin some of it out (sell or give away)
    – Do we give up our rented house?
    – We still have financial obligations (debt repayments, mortgage on an investment property), how do we fund those while away without my husbands’ job

    I know there are straightforward answers for these questions, I guess the biggest hurdle is the financial one.
    I’ve only just come across this blog today, & noticed there are some articles that may answer my questions, so on to some reading :)

    • Great questions, Helena. You’ll probably find some answers on the blog, although I know I haven’t tackled all of the topics you presented. Financial obstacles are often the biggest barriers to changing your life. Sometimes getting over those obstacles requires ample time and determination. I know you may not want to wait long before embarking on something new, but to fund your adventure, you’ll either need a financial cushion or some sort of income you can collect while traveling. In either case it will take research, planning and a little time.

  15. Kez

    God I so want to make a change – I have technical abilities, I’m intelligent, I’ve read numerous books, but I can’t find a product to sell or and I’m bogged down trying to find a profitable niche to serve.

    Australian manufacturers won’t sell to online businesses, we don’t have the money to import and we’re so burdened by debt from a past investment that we haven’t been able to save enough for a house of our own.

    We’re middle aged and want to make a change, but between the inability to find suppliers is bogging us down and stopping us from freeing ourselves.

    We are researching niches and keywords but keep running into blind corners with too much competition and not enough profitability.

    Our animals would preclude us from travelling for months at a time, but I’d like to take mini-breaks for a month or so.

    I’m re-reading the 4-hour work week but all I feel is that my dreams are further away than ever.

    • Hi Kez. I completely understand where you’re coming from. There are weeks when I feel like my goals and dreams are completely out of reach. Sometimes what you need is a fresh perspective so you can look for solutions in different ways.

      Why such a focus on selling physical products? Have you considered affiliate marketing (where you market other people’s products and get compensated when you refer a sale)? What about freelancing? You mentioned you have technical abilities.

      It came across to me like you were looking for a single perfect solution that would let you be location independent. Sometimes looking for one big solution instead of taking baby steps with some imperfect solutions can lead to analysis paralysis. Action is the only thing that will move you closer to your goal. Some action might be wasted, but you can’t achieve anything if you don’t move forward.

  16. Nice post Corbett. I kind of agree with the very first post – it really depends on one’s mindset.

    I think in every age group there will be struggles. Creating a lifestyle design business or being a successful self-employed person isn’t easy. 20’s people also have the challenge of graduating after college, then deciding between going this route or throwing away 4 years of college down the drain as well as around $60 – $100k, while family is pressuring them find a job or career.

    I could also understand the difficulties of older people who have more responsibilities like taking care of their spouse and children. But I think it does comes down to a person’s mindset and attitude. I know a lot of people who have lots of free time on their hands and waste a lot of this time or do a lot worse than people who are mentally focused and have busy schedules.

    • It’s true, Hulbert. It is much easier to waste a lot of free time than one might think. I’ve found that many people can get nearly as much done on a self-employment project while they are fully employed and working nights/weekends as someone can get accomplished without the burden of a day job. It all comes down to focus and motivation.

  17. Miika

    Hi Corbett! As a person in my twenties I fall to the category where I can choose I lifestyle I want to live rather easily. I don’t even have to talk about a lifestyle change, since after my graduation three months ago, I haven’t even been looking for a traditional job (I’m debt-free, since higher education in Finland is free). My life’s a blank page at the moment, and it feels great to be able to start filling it as I please. I’m really glad to have found you fellow lifestyle designers, and Corbett, your blog was one of the first I found about the topic!

    To your question, I’d imagine a lifestyle choice is possible regardless of your age. The biggest difference would be that the person in his 40s has already been exposed to the conditioning of the society much longer time, and the ‘expectations’ and ‘responsibilities’ of the society and other people feel much more real. They are, to some extent, but I really think everyone’s entitled to lead the life they want. I think that in most cases your family and relatives don’t support your lifestyle choice, it’s because they don’t understand it and are worried you may end up in trouble (financial etc.). What comes to money, I think if you want an unconventional lifestyle, you should be ready to cut down your costs dramatically before the business starts rolling. It’s mostly a matter of choice. Unless you’re in huge debt, I wouldn’t know about that.

    As to the spouse and kids, I can’t really have an opinion based on my own experiences. Though, I found the documentary about the life of Dorian “Doc” Paskowitz highly inspiring. I guess anything’s possible, if you decide it is. See the trailer

    Sorry for the long post, this was the first time a commented and I feel like there’s a lot to say, haha.

  18. Interesting. I’m 47. I jumped from city to small town and corporate to start-up in my 20s. Now I’ve re-designed my lifestyle w/o going anywhere. Quit the high-paying job to stay home with the kids. Hubby was the king of lifestyle design before I met him… as a yacht-captain afloat nearly 365 days a year and redesigned his lifestyle to a home base for a change. We’ll probably push off again some day… Florida Keys has significant pull to us. BUT… there’s a but in every age, stage and design… we have children with special needs. Perhaps a tad more than “typical” children depending on what their special needs are, children with disabilities add to the complexity (services, therapists, life-support — though I’m lucky not to have to worry about that for my kids) and then, like aging parents, where and how able your children are to settle into their own lifestyle design does affect where and how able or willing or radically I might be to design my own lifestyle going forward.

    I think Cheri said it EXACTLY right as well as a few others. It’s about attitude and having an agile personality. Those of us currently living what you see as ‘the societal norm’ kind of life may in fact have designed our lives to this style for a change, until our agility stagnates and we choose another redesign. Living an anchored-down, non-nomadic lifestyle might be as much a design if you choose it mindfully. I roamed. Now I’m settled. I’ll roam again. I don’t have wanderlust. I designed it thus!

  19. Interesting topic Corbett. It’s certainly harder to do something like this as you get older for all the reasons you cited. When you have kids, you really have an obligation to look out for their best interest so “stability” matters more. And to your point, life gets expensive as you get older. I do have friends that have three kids and are successful attorney’s that make over $200K a year. They shut down their practice for a year or two at a time and travel the world, homeschooling their kids on the high seas. When the get back they just focus on making money for the next trip. Very much a 4 Hour WW type of approach but modified for their situation. I think this approach works assuming you have the skill set to turn on/off a solo practioner business model (attorney, graphic design, outsourced coder, etc…).

    • And assuming you can revive your business when you get back. I think that’s a big fear people have, that if they shut down their business for a little while, they won’t be able to get it running again. Depends on the situation and person, I suppose.

  20. Another great question Corbett.

    Age matters but not as much as each individuals own risk aversion. There are people unwilling to make major changes and do something out of the ordinary at any age. There are others that aren’t afraid to change countries, start businesses, go back to school, etc. well in into older ages.

    I was 27 when I first came to Japan. I left with one week of planning, no job and very little money. Traveling while single is much easier and much cheaper than when you become accustomed to a richer lifestyle.

    Now that I am 40, leaving Japan was a more difficult decision. I had a business and still have a house, car and many possessions. I am married so I have to take my wife’s opinion into account. We also are no longer willing to stay in hostels and eat instant meals so we demand a little more luxury. We can still live cheap, just not as cheap as our twenties.

    We wanted to travel for several years but it took a long time to extricate ourselves from our obligations. It finally took the public commitment of my ‘one year plan’ to force us to act no matter what. It was a lot more work to break connections now that we have more built up.

    It definitely is much more difficult as your the quality of your lifestyle increases. I think age is not so much the deciding factor as is how much you have to lose. A rich 25 year old probably won’t be willing to give up a great salary, house and luxuries anymore than a 45 year old would. We just have less to lose in twenties so that it less of a risk.

    • And at some point, it may not be “harder” to change your life, but you may be less interested in doing so. Developing relationships and belonging to a community are great things that you only have so many opportunities to do in life. I can see why it was hard for you to pull away from Japan after being there for 13 years.

    • You speak of being “rich” but define that by money? I would say that for many people being rich or having a rich life is more about the doing than the having. I can honestly say the things that have given me the most pleasure and memories over my 45 years are events, people, and things I’ve experienced. Some of which take money for sure – but to me being rich isn’t all about money. Just a side note.

  21. Rainy

    Great question, and great feedback. Nomadic living was my dream, but while prepping to make it a dream come true, life changed. At 43 I am still a very flexible person, and could live with very little and be happy, it’s not about living without anything for me. The changes are not always what happens to us, rather what happens to the people in our lives.

    Seven years ago I packed up, sold everything quit a very lucrative job and moved from Boston to Oregon. I loved it, and when I got bored, I made a plan to head to Mexico next. I was sidetracked by a sick mom who is a widow. Sometimes you have to make choices based on other people. It is very easy for others to say “just do it”. I was not comfortable with letting strangers take care of my mom, and a nursing home is not what I considered a solution. It would be great if she was able to travel and enjoy a nomadic lifestyle with me, but it’s not to be. I also have a 52 year old brother who had a stoke this year and needs care as well. These are things that happen with age to everyone. Yes, we make choices. I chose to stay and care for my family as I know they would for me. I am sad sometimes that I had tochange some dreams, but I would have it no other way. Life is still amazing, and travel is something that can be done without relocating.

    I do wish I had done more when I was younger, but regrets are pretty pointless. The future holds more plans and dreams, and we cannot control how life will change, just embrace it.

    In a rambling way, what I would like to share is this; for the man,y many who constantly say things like ” you must not want it enough if your not living it” Please stop. We are not aware of every persons situation, and we are not here to judge, or to make others feel less than for not making every dream a reality.

    Peace, love and happy travels to all.

    • I agree with your comments and decisions, Rainy. I think it also speaks to the idea that if people in one’s life are healthy and the opportunity presents itself one should go. It may not always be like that. I’m glad you had a few years of living the nomadic life.
      All these comments are reinforcing to me that now is the time to make a shift, if at least temporarily.

  22. This reminds me of that quote – not sure who it’s attributable to:

    “When you are in your 20s, you are very concerned about what people think about you. When you are in your 30s, you don’t really care that much about what people think about you. And when you get into your 40s, you discover the real truth: Nobody was even thinking about you at all.”

    I did our first big move (apart from moving away from home to go to school) from Canada down to Texas with a jeep, a cat, a 2 month old baby and a 12 y.o. when I was 35. To my friends that thought I was nuts, I said “We’re not trees, we don’t have physical roots that dictate where we have to live.”

    After a few years, we moved back home so that my oldest could finish up high school in a better school system – and because he hates change and nagged me constantly to come back home. He’s a Taurus if that means anything. :-)

    I find on the early retirement forum – there are many people doing neat things like RVing, moving to new locations, traveling around the world… Most of them are 40+ and waited until after their kids were grown and out of the house. I’m not going to wait that long since my youngest is only 9 (and adventurous) and despite not having a burning desire to home-school, I’m willing to do it since that’s what it will take.

    Like another poster has commented, as I have an RV, I go on RV forums a lot too and many of them are full-timing or part-timing in the winter months or traveling from job to job in their RV’s. Most are in their 50’s – 60’s, but some are up into their 80’s as well.

    I have a friend who’s 43 whose son is also 9 y.o. who plans on selling her home and going south for the winters in an RV and coming home to work in the summer months. For her, it took seeing me making plans to do so to ignite the fire in her to do the same and realize that financially she would come out about the same given the costs of a mortgage etc. vs. traveling in a motorhome. So I think that for many, it just requires exposure to a new world of options. Particularly to see friends that they personally know doing that kind of thing.

    One thing that age and experience does provide you with is the wake-up call that you’re not getting any younger, as well as the confidence in yourself that no matter what happens, you can probably handle it and that it won’t be that big of a deal 10 years from now.

  23. At 41, it is all about managing expectations. The largest expectation I am currently managing is my own. My teenage daughter starts University a year this spring. One of the things I don’t want her to be saddled with is a student loan. That is my expectation that I am grappling with.

    Just over a year ago now I landed after an 8 month walk-about while working my offline job online. So, I know it can be done, and I know what I like an don’t like about living with no fixed address. But that is another rant for another day. When I traveled before I was less cautious about hiccups in my cash flow (I don’t want to call it job security) than I am now. For the next 5 years, I just can’t take the same risks I would have taken a year ago or 5 years from now. That being said I am still working toward my ‘location independent lifestyle’, but I need to factor in paying for a Universality education while doing it… or about 100K after taxes over the next 4-5 years above what it takes to keep me happy. I have saved a bit for this, so I can pay for a year or so of it right now. But I need to make the rest before the bills come due or tap into my other investments which I don’t want to do (especially before the stock market recovers in about 10 years).

    That is what my own blog is all about – a 40ty year old context to location independence… working an offline job online and pursing online opportunities with a more deliberate flare (like having an actual business plan).

    • Great story, Paul. I like your pragmatic approach to dealing with the situation, deliberately. Let us know how things progress.

  24. Great post with lots of thought. I don’t think it is ever easy to radically change your life — at any age. There are so many stigmas associated with taking that huge step, so many unknowns, and with the economy the way it is today (at least in the US), making that first step into unchartered territory is absolutley terrifying.

    That being said, as someone who just turned 30 and is completely overhauling my life, I think I am ready for it. I have had a career, lived in comfort and am ready to trade all of that in for a chance to give my dreams the chance they deserve.

    I know it won’t be easy — I am traveling Europe and North Africa March through late September and draining my savings account to do so.

    When I return home, I will have no job, no money, no privacy since I will be moving in with my parents while I look for a job or a way to translate my experiences into the career I want. I can only hope that when I get back I will have the drive to write about it, PR myself and continue my life as a traveler and writer.

    I know I would never let the fear of what may be, the fear of changing my life, paralyze me into NOT doing something I so passionately desire. I think it’s even better to radically change your life as you get older — you are wiser and hopefully are better able to identify priorities.

  25. it’s never too late to change your life!

  26. Jellena

    I’m 18 and I already know (or I think I know) what I want to do in my life and I’m fighting to achieve that..It’s never too early or too late to fulfill your dreams and just have to have a clear image in your head of what you want to do..and everything else comes along…

    • Jellena,

      kudos to you for knowing (or thinking you know) what to do with your life at 18. I hope you continue to do so and achieve all your dreams. However, and I hope this isn’t out of line but, as someone who thought I knew exactly what I wanted at 18, just to find out years later it wasn’t really what I wanted at all, and now I’m 32 and piecing together what I already have with what I still want (and those two don’t always mesh)… I guess all I’m getting at is, as you pursue your goals, keep an open mind and an open heart. Sometimes those two things can save you a lot of grief later on.

  27. As someone in their early 40s, married, and with kids, making any kind of radical change is tough- but it isn’t impossible!

    If I had my way, we would be traveling throughout Europe, enjoying the income brought in from many passive income streams. But with the marriage and kids variables, this, unfortunately, is not feasible. However, this doesn’t mean we can’t vacation there (which we are planning on doing this year) nor does it mean it won’t be partially funded by passive income streams (I have a couple of eBooks in the works along with a couple of other passive income stream ideas).

    I think the key is mindset. While you may not be able to completely overhaul your life (and subsequently, the lives of those in your immediate family), you can make some changes within those boundaries which can take your life in a new and more fulfilling direction.

    Wesley Craig Green

  28. My biggest epiphany/game-changing moment thus far was when I was 22 and realized I really did NOT like the path I was going down. It wasn’t exactly easy but very rewarding. I’m only 25 now but I expect that there will be more of these radical changes in the my future.

    I DO think it’s easier to make radical changes when your young- it’s actually the basis of my whole website. Less responsabilities and obligations make it much easier to act in your own self interest. Nonetheless the ability to figure out what you need and how to change your life to make it happen is an important skill at any age.

  29. Truly it is NOT about age, it’s about “can do” attitude & knowing that “if there is a will, there is a way”. There is never a “perfect” time to make a radical change & always excuses and reasons why not to do it.

    Motivated people who focus on “how” they can do it, will find a way at ANY age or circumstance! Even a man born without arms & legs and a family with 8 kids have done it.

    We’ve been on our open ended, non-stop world tour as a family since 2006 which started with us in our 50’s & our child was 5. Prep was hard work, but doing it has been easy, MUCH easier than we imagined & a very rewarding, free life.

    We live large & travel the world on just 23 dollars a day per person (most of it so far in “expensive” Europe). As Tim Ferriss said about us ” Living richly does not require riches.” (We’re case studies in his 4HWW book). I’ve had a lifetime of “radical changes” at many ages & thrived on all of them & I think adaptability and persistence are keys.

    Some personalities thrive on change & living “out side the box” and some hate it…no matter what the age. Humans tend to like routines, ruts & status quo, so strong motivation (from inside or outside or both) tends to play a part in radical change. Love and Freedom are my primary motivators.

    We see more people going for radical change now, primarily because the economic shifts ( & technical innovations) are forcing more to think differently.

    But this is not a totally new phenomenon. I took 6 months off in my early 20’s road tripping around the U.S. I had an adventurist father so grew up traveling and moving very often and thrived on that lifestyle ( as did my 3 siblings).

    My beloved Canadian great grandfather was also a world explorer so I guess it runs in the genes and I’m sure he wasn’t the only one in his generation. The Terhorts have been pioneers as “permanent travelers” since the 1980’s.

    Perhaps at any time, but certainly in our coming world being adept at “radical change” will be an asset at any age & a very important skill to teach our children as global citizens of the 21st century.

    I have mobility challenges, a special needs child, 2 relatives who got stage 4 cancer after we left, & have dealt with a paralyzed right arm for the last 7 months due to a bike wreck on the Danube etc. Lifestyle Design, world traveling life & radically changing your life does not mean that one’s life will no longer have any challenges. It’s about solving the problems in new ways that serve all.

  30. I think it’s more of the mindset and the environment around. The longer and further a person has been in the default lifestyle will make it harder for them to make a change because they’ve been comfortable with the system. A friend with a higher position in the company mentioned to me that due to her ranking, it’s harder to drop all her current responsibilities and make changes compared to people with lower positions. Something similar is the situation where, you still get phone calls from the office even when you are officially on leave/vacation. I guess it really boils down to the decision to take action already and not waiting for the ‘until something/someone…’ comes along .

  31. I think that change of any kind is quite stressful, even if you CHOOSE to make it…The MOST stressful kind though, is when you do not make the choice yourself…i.e. not only do you lose that “safe job”, but you suddenly find it difficult to obtain work in that “safe” career…I could scream every time I hear or read about how the “safe” professionals in Healthcare are.. …It is SATURATED with new GRADS that are being hired so that hospitals do not have to pay as much as one would pay me (30 years experience…)…Also, institutions are not hiring full-time, but only PRN…So much of me wants to change my career, but I am (gulp..cough…clears her throat…) 57…(Of course you’d never guess….)
    First of all, I am ready to never work again, and travel the world…As this is impossible, as we speak, I am getting a bit of work here and there, but it is so tempting to want to throw it all in and make a complete change in career, though that would take forever (at least a good 4 years), and how old would I be then? (Not willing to count at this time…will think about it tomorrow…)…When does it all end? Does one ever actually get to utilize the word, “Retirement?”…Honestly, in the end, I just don’t see being able to live on so much less, so as I usually tell people, I will probably die on the job!!!

  32. I’ve thought about lifestyle design a lot recently, and I have a wife and two teenage children, so it’s not going to be easy. But in my opinion, ideally, you need three things, support, determination and confidence. I suspect those couples with children living the nomad life both agree with each other, so there is support. What about when you’re partner thinks you are mad! This is where you need lots of confidence. When you don’t have support you need lots of determination. I know I don’t have the support of my partner and I’ll be changing my life whether she agrees or not. Selfish? Maybe. But what’s the point of dying with your song still inside you? But what’s clear to me is I will need stacks of confidence and determination.

  33. Denise

    When I was 22 I had a really clear sense of what kind of life I wanted to lead. Then I spent the next…oh, well too many years desperately trying to live my version of the American dream as sold to me by corporate America all the while trying to please my parents and impress my friends. So, after various corporate careers and years spent feathering the nest I see what a mess I’ve made.

    I finally sat my rear down and started asking myself the really hard questions and realized that my 22 year old self was onto something. I’m ready to rip the band-aid off and just go for it but I have two amazing teens and a pretty awesome husband that I live with and WANT to consider.

    I think that spouses and children and mortgages and years of accumulating crap that I didn’t need in the first place can definitely slow us down in making significant life changes. I also believe that regardless of our circumstances it can be done.

    I’m in the over 40 set and see this as really my last chance to have the amazing life of adventure I dreamed of at 22. So without rocking the boat too much, I have my yard sales and haul the rest of the junk of to Goodwill. I’ve slashed our budget, am paying off debt, and saving when I can. I read and research and write as I try to figure out an authentic way to generate the income I will need. I’m questioning, REALLY questioning and trying to be very mindful about everything I say and do and buy and about how I spend my time. I share my ideas, my hopes, and dreams with my family to generate their enthusiasm and support.

    All this being said, I had an excuse at every age. In my 20s, my excuse was that I needed to establish my career and allow my husband to establish his and finish school. In my 30s, my excuse was that it was all about the kids. Everything was for them. In my 40s, there’s just no time for any more excuses.

    Corbett, I love your site and really appreciate your sharing your experiences. It’s helping me sharpen my focus and giving me so many ideas. The community you’ve cultivated is inspiring as well and I learn so much from the comment they make.


  34. Dennis

    It isn’t easier after 60. I remember seeing a documentary about how they catch monkeys. They chain a coconut to the ground with a hole in it and put some rice in it. At first they use a big hole. Later they switch to a small one. The monkey grabs the rice but will not let go. They then net the monkey.

    As you get older, it is hard to let go: your house, your retirement savings, your job. It is not easy to get another job at that age and start over. You are trapped.

    The point is: plant your apple trees when you are young. You will never get to harvest the apples if you wait late into life.

    I hope the youth follows thier dreams while they can. The best time to plant an apple tree is 20 years ago. The second best time is now.

  35. David

    Ifind it very scary in my mid 40’s to change. I have 3 degrees, 3 kids all with me, lost my wife and home. Have a new partner, but took voluntary redundancy to go study and get paid full time. But no job afterwards. Its scary, the big thing is where would I have to work to earn a living, would I move the children, how would that work,… phew lots of challenges let alone working out how to redo full time study after 15 years.

  36. I was reading everyone’s comments but I had to skip down to the end as I realized it’s now 2am! I agree with a lot of the comments already made like it’s about mindset not age, and it also depends on life circumstances at the time.

    I’ve always been entrepreneurial most of my life. I went to college for 2 years to become a photographer and always knew I’d start my own studio which I did with my now ex-husband when we were about 21. Fast forward to me at age 34 we got a divorce and one of us had to leave the business – so forced life change. I chose to leave and took on a job as a rep for a company in the photo industry. I had burned out as a studio owner working 80+ hours a week for less than 25k a year! I was ready for something else so I took the job which was more of a subcontract anyway.

    It got me out in the world through the job and overseas which I’d never done before – got the travel bug big time! I did that for 9 years and in 2009 was getting remarried vowed to quit the job making 70k, rented out our house and hit the road with our cats in an RV for 6 months.

    I’m now 45, have a partner that has the same mindset (this is huge!) and family that is supportive because I’ve always done done my own way. I think that’s probably the biggest thing – it’s not off the wall for me, they accept it LOL. But when we do things like travel 4-5 times a year or did our big RV trip people came out of the woodwork about how they wished they could do something like that. I tell them they can, but they aren’t wiling to do with we do – live simpler, drive old cars, and not focus on $$$ and stuff. That’s my experience – now I’m learning to blog and make money online instead of a location dependant business and I love it.

  37. Sherri Hutchings

    Hi Corbett,

    Great subject! I wish I had seen it when you first posted it. This is something I am personally struggling with at the moment. I am a whopping 57 years old, probably considered ancient to be thinking about writing a blog.

    However, chronological age doesnt always have a lot to do with it. My husband and I decided to move to Germany when we were 45 years old, three kids in tow, only six months after building our “dream” house. Of course, I was the cheerleader for this adventure, which lasted eleven years. I am now writing this from England, due to yet another job change my husband made last year.


    I will say, however, that the hardest part IS the technology. There is so much stuff out there to read, learn, digest and implement. IT IS DAUNTING. This is where it takes more than a pep talk. How much of a challenge can I withstand? This is a question that anyone, at any age, must ask themselves.

    As for me….if I can do Germany I can do anything. :)

  38. Brian

    I’m currently in the process of changing my lifestyle slowly but surely. I’m 29 and married with two awesome children that are 4 and 2. The most difficult part is taking the leap of faith, not knowing how it could effect your family. The expense of children is not cheap and I would worry that I wouldn’t be able to put food on the table. As others have said, I would have to have a pretty large cushion to take the leap and quit my job (that I hate). Great article, thanks for all the free information!

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