10 Things You Can Do Today to Start a Lifestyle Business

By Sean Ogle •  Updated: 07/02/23 •  15 min read

In 2008, I had a pretty good idea that my day job wasn’t going to be a long-term solution for me.

However, it wouldn’t be for another 18 months until I’d actually leave my job.

During most of those 18 months, I stayed stagnant and made no progress toward the goals I’d really set for myself – namely, traveling the world and building a business.

It wasn’t because I didn’t want to, but it was mostly because I didn’t know where to start. 

In 2009, things started coming together a little bit more, but it really only took about 5 months from the time that I started taking action to the time I parted ways from my job.

It’s amazing how just a little bit of action can go a very long way.

Your Excuses for Not Starting are Legit

All the time, I hear from people who want to start a lifestyle business for themselves but simply don’t know where to start.

And you know what? I get it!

It can be daunting, especially if you’ve spent the last decade or two sitting in a cubicle building things for other people.

Then you factor in family responsibilities and keeping some semblance of social life, and the thought of actually doing more work in your spare time seems so ridiculous you don’t do anything about it.

And then the cycle starts again.

Sound familiar?

lr desk cover

Here’s some good news, it doesn’t take as much drastic action as you think it does to start building a lifestyle business.

In fact, many of the most beneficial steps to building a business are probably things you either are doing or have been considering doing anyway; you just haven’t realized it.

The goal of today’s post is to give you 10 extremely actionable tasks that you can start doing today that will begin pushing you towards a business of your own and the lifestyle you’ve been wanting for years.

Here’s how to start a lifestyle business:

That may or may not all make sense right now, so let’s jump in and show you exactly how to start building a successful lifestyle business today.

Ready to take some action towards a better life? Sweet, let’s do this.

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#1: Get a domain, hosting, and install WordPress

This is hands down the easiest, most tangible thing you can possibly do today to get closer to a business of your own.

Every blog I’ve ever created has been on WordPress. It’s powerful, easy to use, and even easier to set up.

I don’t care what you start building. It could be a blog, business website, or even a fan page for your favorite Spice Girl (hey, don’t judge, that might be a great niche site). Doesn’t matter.

What matters is that you get hosting a hosting account and install WordPress on your new domain.

You can do this in less than 15 minutes.

Once you feel comfortable with that, all of the other steps become much more attainable because you’re removing one of the biggest technical barriers out there.

I personally recommend you start with Bluehost. It’s less than $50 a year for your first year of hosting and your domain name.

Here’s my review and why I think it’s likely the best fit for you:

Action Step: Go through our How to Start a Blog tutorial. We take you step by step through every single stage of the process of getting a domain, getting hosting, and installing WordPress.

#2: Send emails to 20 people who are living the life you want

Who better to build a relationship with than the people who have already successfully done what you’re striving towards?

I sent an email to Chris Guillebeau on March 6th, 2009, that completely changed my life.

We met for coffee, formed a relationship, and he became an essential part of my transformation from employee to entrepreneur. He became a mentor of sorts.

Chris Guillebeau Email

The actual email I sent to Chris in March 2009…

That being said, there’s a right and a wrong way to approach influencers.

Don’t give them a 10-paragraph essay about your problems and life story. They’re busy; respect their time. Simply send them a quick note introducing yourself, and give a specific example of how something they’ve done or written has influenced you.

This opens up the door for further communication down the road.

Often your natural inclination is going to be to tell them as much info as possible and then offer them everything under the sun in terms of help. Don’t go there.

Slowly build the relationship as an equal, and if there’s an opportunity to meet them in person, go for it.

Action Step: Do this for 20 people, and there’s a very good chance at least a few will develop into personal relationships that will be really valuable as you move forward.

#3: Find someone in the same place as you

Just as important (if not more so) is finding someone who is going through the exact same thing you are.

For me, it was my best friend Ryan.

He’d quit his job and moved to Hawaii, and as I watched him begin to live out his dreams, I sure as hell wasn’t going to be the one who got left behind.

Having someone for accountability and support is so so important – especially early on.

There will be times when you struggle, you will feel like you’re not making as much progress as you should be, and where you just want to give up on it all and watch more Netflix.

This is totally normal. But it also really helps to have someone who’s going to keep you moving forward.

Action Step: Find a buddy you can connect with who is in the same boat as you, stay in touch, and support each other. Our LRA community is a great place to start.

#4: Do the brainstorming exercise

One of the most common excuses I hear is, “I want to do something, but I don’t have any ideas.”

I promise that you have way more ideas than you think.

I think you can start a website that will make you a couple hundred bucks a month around literally any topic. 

For example, I built a site around my love of golf. More recently, I started a new one all about cocktails and hotels.

Park Hyatt Tokyo

I had to do my best Scarlett Johansson impression when staying at the Park Hyatt in Tokyo recently.

So, what’s the brainstorming exercise?

Make a list of every product, hobby, niche, and interest you have. Really think about how you might be able to build a site around it.

Seriously, spend 20 minutes on this. You should have at least 50 items.

Then begin narrowing down which ones make the most sense.

For more help with this, check out “How to Build a Niche Site that Brings in At Least $500 a Month.”

For most people, it’s not a lack of ideas. It’s a lack of taking action.

Just pick something!

When you’re first starting out, there is no wrong decision. Just going through the process will put you miles ahead of where you would have been otherwise.

Action Step: Read “How to Come Up with an Incredible Business Idea (and Validate It)”. This will help you structure this exercise and come up with some great ideas.

#5: Start freelance writing

If you’ve been a reader here for a while, you know that I’m a firm advocate of a three-step process for building a lifestyle business:

  1. Build Skills – If you don’t know what you’re doing, you won’t be successful. Take the time to educate yourself.
  2. Freelance – Pick one of the primary skills in the post above and build a freelance business around it. This will give you some income and the confidence to know you can make this work.
  3. Take those Skills and Build Your Own Projects – Once you have the basics, you can do whatever you want. Membership sites, e-commerce, info products, affiliate sites – the list goes on.
That being said, there’s one thing that’s easier than most, which you can start making money with right now: freelance writing.

Hundreds of people have leveraged freelance writing inside Location Rebel to successfully transition into their own businesses online. It’s the easiest way to start making money this week.

Here are a few ways to get into writing

It’s not always super sexy, but it’s a fantastic way to make the transition from employee to employer.

You likely still have some freelance writing questions. This should cover nearly all of them:

Action Step: Start a daily writing practice. And if you need inspiration to just start writing, check out this post on the tools that can help you get writing every day.

#6: Register for Freelance Job Boards

Back in the day, I’d tell you to sign up for Upwork. Unfortunately, if you’re just starting out as a writer, Upwork is not the best place to go.

It’s very saturated, and it’s a race to the bottom.

The best way to get freelance clients is actually by:

But that can be a little daunting until you get your feet wet in your business.

So the path of least resistance? Sign up for other freelance job boards.

It may take a while before you get a job through one of them (cold pitching is more effective), but what’s important is that you take action. And this is a great way to do it.

We’ve got a list of over 100 places to get freelance writing jobs.

Also, look in your local area — you may find lots of local small businesses wanting to take on work. Word-of-mouth marketing is another great approach. One of our members found multiple jobs that way.

When looking for work, you have to throw everything against the wall, and the people that do? They’re the ones that see success.

Action Step: Sign up for at least 5 of these websites to start looking for work. And start creating your spreadsheet. You can get 100 names in it in less than a week.

#7: Set attainable goals with how to actions

“Be making $1k/month by January” is not a good goal.

Why not?

Because you have no direct control over it – not only that, the time frame is way too far out.  Something like this can be a good thing to shoot for the long term, but you need much smaller, more attainable milestones throughout the process.

We like to call this the Milestone Mindset, and it’s all about building a system that can help you achieve what you want.

As I mentioned, you’ll have ups and downs, but if you’re continually reaching your goals, you’ll have much more confidence to stick with it.

Here are a few examples to get you going:

See where I’m going with this? Each of these are small but, more importantly, in your control. You can answer yes or no to “Did I do x?” — that’s what help makes a great goal.

Set a ton of small goals for each week and month, and you’ll slowly but surely make progress toward the business of your dreams.

Action Step: Take one big goal you have right now, and break it down into milestone baby steps.

#8: Build A Habit

One of my favorite business books is Atomic Habits by James Clear. When you’re working for yourself, building good habits is more important than ever.

Start with one.  That one will make it much easier to form another and another…

For me personally, I rarely eat breakfast. So I decided to start making breakfast every morning. It’s amazing how that one commitment has led to greater productivity and doing things like going to the gym every day.

Another great habit that will help your business is building marketing into your day. If you need to break it down by day of the week:

If you make an hour a day of marketing a habit, you’re going to get so much further with your freelancing career.

You can use a tool like Ask Me Every to help you stay accountable for this one keystone habit.

Action Step: Start small and pick one positive habit you want to build and set yourself a reminder to do it daily.

#9: Improve your copywriting skills

Life is all about selling. Whether you’re convincing someone to go to coffee with you, buy your product, or simply side with you on which bar is best for drinks on a Friday night.

If you can sell and persuade, your life is going to be much easier.

It’s important to note that I don’t mean you should be deceitful or scammy in your persuasion. You should simply recognize it’s a part of life and do everything you can to put yourself in a good position to succeed.

If you’re going to do anything online, copywriting (persuading through written words) is especially important.

Luckily there are some resources out there that will get you moving in the right direction really quickly.

These are the resources that have helped me improve the most:

Action Step: Pick up one of the copywriting books (or any good copywriting book) and give it a read so you can start learning copywriting techniques.

#10: Create something

Anytime I’m feeling unproductive, I look at my desktop, where I have a note that says, “Are You Consuming or Creating?”

Regardless of what you do in your lifestyle business, you’re going to be creating something. So you might as well start now.

Write a blog post, edit a photo, start a website – create something. If you get in the habit to create as much as you consume, you’ll be amazed at how quickly things can progress.

Action Step: Try taking a 30 day challenge. Make it easy to start right now by creating challenge a that will help you take action starting today.

BONUS: Join Location Rebel Academy

You don’t need to spend any money or join any course to have a successful online lifestyle business. Anyone that tells you otherwise is lying – you can find all the information you need out there for free.

That being said, there are tools and resources that make the path much easier – and Location Rebel Academy is one of those resources.

It has detailed blueprints to help you with all ten of the previous steps in this post. It has a community of thousands of people who were exactly where you are right now – and have built successful businesses on their own.

Having that support system coupled with an exact roadmap for what you need to do is everything I wish I had when I was getting started.

You don’t need this program, but I’d love to see you inside if you’re ready to make a commitment to building a life where the only boss is yourself. It certainly will take a lot of the pain and confusion out of learning how to start a lifestyle business!

This post was updated for accuracy in July 2023.

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Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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76 comments on "10 Things You Can Do Today to Start a Lifestyle Business"

  1. Siegfried says:

    I really, REALLY like this article! As someone who is trying to start successful web based business I totally agree to all the excuses 😉
    I think I may steal your idea and write article like this myself 😀
    Best regards!

    1. Sean says:

      Glad you enjoyed it!

  2. Love this actionable list Sean! I would add something that used to hold me back (and still does if I’m not vigilant): START! Don’t wait for the perfect idea, the best time, or to feel like you know what you’re doing. You must start before you’re ready.

    1. Sean says:

      Absolutely, its amazing how if you just start on something, things fall in place pretty quickly.

    2. Terry says:

      You got me on this one Deacon, so I’m just gonna START !

  3. Sean,

    I saw your posting on FB this morning, and thought I’d take a moment to say thanks for your commitment to helping the rest of us find our way.

    I first wrote to you a little over a year ago, and I realize how far I’ve come. I was living in Arizona, and jumped at an opportunity to work in Oregon. That didn’t work out after 3 months, but the good thing was that it got me to the coast! I’m now in a little bit of heaven in Siskiyou County, CA, looking out at the Trinity Alps from my bedroom. I have my own location independent business which I have slowly grown over the past couple of years, which is now sustaining us fully. My partner and I do freelance writing and editing from our own little agency.

    I’ve had several false starts with a blog, but I know now exactly what to do! Thanks for the reminder. I’m learning, and I owe it all to you!

    1. Sean says:

      Julian, wow that just made my morning! Thank you for sharing, and so excited to hear about your success!

  4. Hey Sean,

    Another great post. I’ve been implementing many of your suggestions from other posts into my search to make something for myself. Keep inspiring.

  5. This is a great list. I’m literally going to create a graphic for my desktop that reads, “Are you Consuming or Creating”. Totally stealing that

  6. Martin says:

    Man, it was November 7th of 2008. I put the excuses aside. I went to bluehost and signed up for my first domain. My design site, the content was average at best, and I was clueless. Guess what? There’s no better training that on-the-job. I learned and went with the flow.

    Now the people that I looked up to in my field I consider to be friends. I’ve met them on many occasions and have even earned accolades in my niche.

    Step #1 is the most important one. Nothing else matters for now.

    I would add another tip: stop consuming business-advice books for now! I have a close friend who spends hundreds of dollars every month on these books. Yet he hasn’t done anything but build his library.

    I read a new book every few months as a reward. You won’t find the answers you’re looking for anywhere but inside of yourself.

    1. Sean says:

      I totally agree. Once you’ve made a habit of starting and taking action, the books can be useful, but if you’re just trying to stockpile knowledge, but dont have any real world experiences to base it off of – they arent doing you any good.

      Thanks for sharing your story, and congrats on making it work!

  7. monique says:

    Great article! I’ve already set my “work” hours and divided it out into tasks, but you’re right – I need to create a weekly list of goals and add that task to the mix. Thanks for the inspiration!

  8. Dubem Menakata says:

    Wow this post was absolutely immense!! I have been looking to start my blog for a few months now and I actually have all the tools to do it. This post is really inspiring and I am going to set a date of April 6th to get it online with 3 articles. I’m defo going to keep coming back!

  9. William says:

    Great post! I think the most important thing people should take from this is to take action! Get started… you WILL make mistakes. And then learn from them, improve, and just never stop. Also, create something! I firmly believe having as many virtual “properties” as possible will give you more opportunities than anything else. Diversify, but don’t spread yourself too thin. After a while, you will be VERY surprised by how much you can accomplish and how much value you can create. Simply get started and don’t look back!

  10. Simon says:

    Sean, what do you suggest people do for health insurance when they leave their jobs?

    Are you without health insurance right now, but do you think you’ll be fine considering outside-of-USA costs aren’t so bad?

    1. Sean says:


      Right now I live in Portland and pay for my own health insurance. When I first took off to Thailand in 2010, I got travel insurance which was really cheap and covered up to $100k for accidents. For instance, if I broke my leg surfing, it was covered.

      I would never recommend anyone go without health insurance. Its one of my biggest monthly expenses, but you never know whats going to happen. If you’re going abroad and really cant afford it, at least get basic travel insurance. At the time mine was $260 total for 6 months.

      1. Simon says:

        Yeah, it boggles my mind how cheap travel insurance is compared to health insurance in the USA. Hopefully they will fix the issue one day soon.

  11. Ann says:

    It makes me nervous to even start, but as I know, doing what scares me is the only way to grow. This articles reminds me to banish the negative self talk about my ideas not being good enough, me not being smart enough, blah! Blah! Blah! You’ve laid out the framework, I just have to step in and quit worrying about being brilliant! I need to begin, and the brilliance will follow!

  12. Really great post Sean! This ties in well with one of my favorite quotes:
    “Progress has little to do with speed. But much to do with direction.” – unknown author
    As long as we keep moving forward, we will be closer to our goals. Thanks for the inspiring push this morning!

  13. Mark Powers says:

    Funny you should mention “The Power of Habit.” Almost through with it myself and it stirred up many ideas that are helping me to shift the way(s) I work. Largely [as the book says] changing the “routine” I follow after experiencing particular “cues,” these shifts are something that are necessary for me to get away from my recent methods of approaching things, push forward and accomplish much of what you and I discussed yesterday. Many thanks to you, Sean, for being a regular source of inspiration and so generously lending support and advice!

  14. Miisa Mink says:

    Brilliant Sean. I’ve decided to learn all of this and more. I’m 42 and most of my friends don’t understand where the world is going. They are just falling onto the wrong side of the cliff. I’m a branding professional but I want to combine that with the digital world and see where it takes me. Thank you for sharing and for great tips! One question, do you now about HubSpot? Does it beat WordPress?

    1. Sean says:

      A good friend of mine actually works for Hubspot. As I understand it, they are two pretty different products. Hubspot is more about marketing and analytics whereas WordPress is a CMS.

  15. Hey Sean,

    This is my absolute favorite post I’ve read from you ever! It really got me fired up and swat away the excuse that I have to wait for my house to sell before I can quit and leave… all I need to do is get that train moving so I can jump from the one I’m on a little more safely.

    I’ve been procrastinating on this for a while now and this post was the kick in the ass I needed. Look out for RawBodyTraining.com I’m starting it TODAY.

  16. ApexStrat says:

    Hey Sean,
    Nice post, between this, “How to build your first online asset in 48hrs” and “How to build a niche site that brings in at least $500 a month” I think you’ve covered just about everything you could want to know to get started. Totally agree with your first point, just giving something a go is a great first step. Keeping a diary of what you’ve learnt is a good way to keep your motivation up while you go through this stage, until you start bringing some money in.

    1. Sean says:

      That was the goal 🙂 Create the easiest to follow, most actionable content I can for getting started.

  17. Sean says:

    Great post Sean! I love how action-oriented the list is. No more making excuses because you just provided a action-list.

    In addition to elance, I would add odesk and possibly even fiverr. Sometimes those little jobs can lead to something bigger. Or you can always be a “broker” and fulfill your services using those resources.

  18. Candice says:

    Thank You for this article. It really spoke to me and my situation.
    You are right, excuses exist but its also because of the fear of the unknown and also afraid of being lost and failure.
    But there is no greater time than now to live our life.
    Live & Love Your Life

  19. Ajit Shah says:

    awesome stuff! Sean ..
    really enjoyed reading it and compelled to take action

    and explained really in simple terms..

    thank you very much

  20. Hi Sean,
    Another great post following your post on how to create a niche site. I have a couple of questions I would really love to get your opinion on.

    First off, you helped inspire me to quit the rat race and I will be leaving my job in 2 weeks and moving to Bali where the current plan is to do Freelance PPC work. This is what I currently do as a job in Sydney and am half decent it at. I have a site that is nearly built for that business. Ideally I want to get a number of my own clients paying a decent management fee however doing some work on freelancer and oDesk is also an option but as the rates are typically low that will just be to keep me going.

    I will need to work on marketing that site to get clients as well as spend time doing the actual client work. The “problem” I guess is that there are other thing is that I would like to work on. I have quite a few ideas for niche blogs or rather, there are a lot of topics I would like to write about such as:
    Travel – an adventure travel guide to bali
    Learning to surf/become a better surfer
    Fitness (travel fitness)
    Body weight workouts
    Living Paleo/Quitting Sugar
    Building an online business/Digital nomadism

    So I often think about starting these niche blogs but I wonder if I would just be better covering them all (all the things I am interested) on my own personal blog rather than try and manage multiple sites.

    I’d be interested in hearing your thoughts.
    (Also do you use the same theme across sites, the golf one looks similar to this one.)

    1. ApexStrat says:

      Hi Kevin, I’ll wait for Sean to give the expert advice, but I would concentrate on one of these ideas and make it as good as it can be. It’s hard enough getting one site off the ground, trying to do multiple at one time will be a nightmare. Pick one, give it 100%, stick with it and you can pick up the other ideas at a later date. There is nothing wrong with doing a few off topic posts from time to time either.

    2. Sean says:

      Kevin, first off, congrats on heading out on your own! You’re going to love living in Bali 🙂

      If you look back through the history of L180, you can tell that I write about a LOT of different stuff. For a long time, I treated it as a personal blog and wrote about whatever I wanted.

      Was that the best way to do it? From a business perspective, probably not. Had I focused more on the “build a business you can run from anywhere” and really provided nothing but actionable posts about that – I probably would grow the site much faster. BUT, I’ve really enjoyed being able to write about whatever I want 🙂

      I can still do that to a point, but for instance I really felt that golf and photography was for a very different audience – which is why I started the separate sites. I then just refer to them in posts where they are relevant.

      If you want a personal blog to write about whatever you want, then by all means, create it. But if you want to treat your blog as more of a business I’d pick one, focus on it, and build it up before expanding too much.

      Just my two cents, hope that helps!

  21. Tomas says:

    One of the best posts I’ve read from You Sean. Just made me move from the morning!

  22. Sean,
    Thank you for sharing your great ideas on life and business. I think we all agree that life is definitely too short. No one wants to live an unhappy and unproductive life. The information you are posting on your blog is invaluable. You are truly an inspiration and you are changing lives!

    Best Wishes!

  23. Great post Sean. I like the good actionable advice for a lot of people.
    Adding to the resources: for some more kick ass copywriting info check out John McIntyre’s blog at http://www.dropdeadcopy.com/blog/

  24. Chas says:

    This is one of my favorite posts of yours as of late. I have obtained a new domain, but, I haven’t done anything with it, as of yet, because what it is to be is continuing to evolve in my mind. In addition to eLance and Odesk which was also mentioned, there is demandstudios.com for freelancers. I have recently ran across a video about finding your mission and a step by step process through a journal that I found to be helpful and inspirational. I hope you don’t mind me sharing it on your blog. Of course it’s up to your discretion. Thank you for all the great tips you have given. Here is the link to the video.~

  25. Matt Kane says:

    Sean – great post. love the way you willingly share all this info. w/ specific action plans to get started and links to further information. Have been enjoying your stuff for years and this is a great piece summarizing some of that.


  26. Patrick says:

    Hi Sean. I just discovered your blog today via a link to this post. This is great advice. Less than two months ago I took that first step in obtaining hosting, a domain, setting up WordPress and starting a blog. I am not entirely sure where I am heading yet, but I have been consuming a lot of information (maybe too much – see my most recent post), and am plugging away. I can certainly say that I am very excited for the prospects that a lifestyle business offers. Thanks again.

  27. Jose says:

    hi Sean, oh man you are giving me the push that I need to start my own business and your articles are so helpful. Now I obtaining my hosting and I made some domains for other business and my church to get some confidence, I just need to start thinking in my own niche aand go for it, but you really are helping my a lot. Thanks

  28. Alex Sheehan says:

    I love the part about eLance. Websites like oDesk, etc. are so often criticized because it is often a search for the lowest bid. However, I feel that eLance has the most reputable clients (and contractors for that matter). Using that to start off my freelance writing definitely gave me the confidence and push I needed. Another bonus is that you get to build a portfolio out of the work you’ve done ,and get paid for it. Also, it’s a good way to develop skills and make mistakes that aren’t too detrimental to your career.

  29. Turner says:

    Great post. I definitely try to constantly be asking myself am I consuming or creating. It is so easy to procrastinate, but taking action, even if you flop is by far the best thing to do. In action kills you.

  30. Great actionable steps – thanks for sharing!

    I’m especially fond of tip #7, as it resonates with something that my mom always told me – “Worry about things in the order they’ll affect you.” Maybe you don’t need to worry about how you’ll quit your job or earn thousands of dollars while working remotely right now. If you don’t even have a blog set up yet, the only thing you need to worry about is installing WordPress. After that, you can figure out what to worry about next, but only after you’ve taken this first step 🙂

  31. Leigh says:

    Awesome article! This is probably my favourite post so far. My biggest sticking point being an aspiring entrepreneur was not knowing where to start. This is a great and simple guide to help you get started!

  32. Another great article Sean! I just landed my first SEO writing gig and am already thinking of ways I can leverage this skill into more income.

  33. Rae says:

    Wow! There’s almost no more room for comments! Good on you! Me and 65 of my best friends got laid off recently, but a lot of us are writers and photographers so you can imagine that we are mostly looking at it as a blessing, a breaking of the golden handcuffs and all. I’ve been sharing your posts with them and at least one person is building herself a niche site because of a post of yours I sent to her. I’ll send this one on for inspiration, too. Also, I showed that post to my husband and he asked me what a “sea nogle” was. Just thought I’d share the laugh. 🙂 Thanks, buddy! Your blog gives me a lot of hope, and I need that right now because I can’t fail (i.e. end up back in an office).

  34. Dustin Rees says:

    Great post, I really enjoyed it! Just stumbled upon your site yesterday and I haven’t closed it out yet. I am in the beginning stages of living the dream and this is exactly the encouragement and direction that I need! Keep up the good work!

  35. David says:

    Nice article… However sometimes I think that “lifestyle business”, “building business while travelling” and similar stuff is some kind of scam 🙂 Really… When I’m at home, working full time on my business, it flourishes – I got many new (and better) projects, I find new business ideas and get approached by different people with their ideas and new opportunities etc. But in terms of lifestyle it absolutely sucks 🙂

    Now thinking about my three weeks in Vietnam in March: my business was on hold on modus and started to stagnate, customers got angry, they couldn’t reach me by phone; I didn’t met any single person to discuss any business opportunity or at least have any serious talk – just young guys in their twenty something, having gap year and try to get drunk and pick up chicks as often as possible. Even though it was fun, I got disturbed all the time by escalated projects and angry customers. Working couple of hours a day wasn’t even nearly enough to maintain the business.

    Bottom line: I think it is quite dangerous illusion, you are guys pushing at your blogs. Either you just take gap year, have as much fun as possible and maybe make some logos or text writing for buying next cocktail bucket, or you work your a.. off and set up a real business. What for me, there won’t be any big travels before I earn my first million :); afterwards I’ll take several months free to bike through South America 😉


    1. Sean says:

      David – I don’t mean to hijack Sean’s excellent post but I can certainly understand client communication and being there in person to grow your business. I myself have a service based business with real clients all in the U.S.. However, I currently live in Cozumel with my wife and 3 daughters. And my business has actually grown since we’ve been here! In fact, I just got 4 more clients last week – all on the phone!

      So, it depends on how your business is set up. You can use Skype, Google Voice, and other tools to make sure you’re still able to communicate. You can also hire or outsource your sales and/or customer service/production. It’s ALL how you set up your business and most businesses (even service based like mine) can be set up to allow you freedom – even on a bike in South America.

      Bottom line, I’m living proof that you don’t have to be a 20-something single guy. You can be a family guy and still live the dream.

      Thanks again Sean for a great post!!

      1. Curtis says:

        I would love to know more about how you are making your service based business work as location independent. I am also a family man and have a freelance carpentry business. At this point I rely fully on the traditional mindset of having to stay in one town and build the relationships.
        Your time appreciated,

    2. Jon Hanson says:

      But if you have a business big enough to make you a million dollars can you imagine the kinds of headaches that will happen if you take several months off if you can’t take a few weeks off now and you’re just scaling it up?

      Your post is a great thing to remember, a business built on personal interaction and a constant hand-on approach is awful if you want to travel, that’s why Sean and others focus their advice on the kinds of businesses that avoid the situation you’re describing.

  36. Brooks says:

    Dude, completely actionable items. 3 of them are being done by me at the moment.
    I’m actually planning a trip to Guatemala this summer for language school but plan to do real estate deals from there via my laptop.
    Sites like yours actually help give me real steps to make that happen.
    So thanks for what you’re doing man.
    I’ve taken inspiration from you to begin a second blog project as well.

  37. Jeremy says:

    That’s gold, Sean !

    My best friend wants to quit her corporate job but has no idea of where to begin.

    I just sent her your post, and nothing else.

    Thank you !
    Jeremy, happy LR member

  38. Cat says:

    #10. Creating > Consuming. So simple, so obvious, but a game-changing thought that has been stuck in my head since I read this blog post. Thanks for sharing!

  39. Marshall says:

    Hey Sean! I’ve been following your blog for a while now and I love your writing.

    Since reading this article I’ve been trying to find SEO jobs, however I haven’t had much luck. Do you have any advice on finding these?

    Thanks and hope you continue to be a boss.

  40. Zara A. says:

    Dear Sean,

    I want to say thank you – not (only) for this post, or the previous one, or the so many before – I want to say thank you for doing what you are doing – really Living Life – thank you for showing so much courage – it gives me (and I’m sure so many other people too) hope and it makes us feel normal (not absurd, crazy, detached-from-reality) for wanting the sameyou i

    You inspire me, as you inspire so many others. So i’m taking a pointer from this post (#7) and posting a comment on a blog (my first ever) whilst figuring out the SEO formula.

    Best wishes,
    Zara A.

  41. Kit Nixon says:


    This post is exactly what I needed to hear today.
    Coming home from my manual labour job, I struggle with finding an actionable step towards my goals. Often, the task is too daunting and I opt for some comfort food and a sitcom.

    I’ve already started on a couple of these things, and let me tell you the momentum is empowering.

    Thanks for doing what you do,

  42. Sean – I agree that there is no better way to immerse yourself in something than having to come up with 350 words on it for an SEO company or for your own blog on a weekly or daily basis. It will show you if you are actually passionate about that field.

  43. Tash says:

    So.. Where in the world can I met you for a coffee?
    Your choice, I’ll be there.

  44. LoneOlivia says:

    This is awesome – finally found something that really helps with telling the actual steps needed to get my business started! Also really happy to see that a lot of other people are in the same boat as me! In Denmark Lifestyle Design is still very unheard of and even though I study Innovation & Entrepreneurship at CphBusiness, no one knows what it is.. 🙂

  45. Chris says:


    I know this is an older post, but damn hit the spot today. I’ve already signed up for a website, which i did through blue host. Thank you by the way for that suggestion early on, I actually had to kick myself in the ass to even post my first entry. It was always man its not good enough.. until I realized that just post the damn thing and build on that.

  46. Mike Sherry says:

    Just catching up on some old posts here, and googling around about travel insurance, health insurance, etc.

    What do you currently have for U.S. insurance now that you’re back living in the States (somewhat) full-time? Would you mind sharing what the monthly premium is and what it covers? That’d be helpful for myself and probably many others who will be making the leap to self employment and location independence in the near future.

    Any recommendations?

    As always, thanks for the great writing and info!

    Cheers, Sean


  47. Freda Lee says:

    Probably years late, lol, but AWESOMEEE blog post, thanks, you’ve given great tips here that I can utilise for my own blog. As we speak I am currently on elance.com.


  48. Michael Knox says:

    This is 100% correct. Working from anywhere is the only way to go!

  49. Mr Adam says:

    Great post, Sean!

    This is exactly where I am at the moment – trying to work out the what & how of my blog & location independent business. And trying to get motivated and dedicated enough (ie. stop getting sidetracked online and TV)

    Since reading this article earlier today, I’ve set some short term goals and written a new blog post. Hopefully I can keep it up!

  50. Ivan Petrovic says:

    Hey Sean,

    I love your post and agree totally with you.
    I think a big problem is that most of the people are affraid of the people around them. I feel the same. All the time I´m thinking about what will my girlfriend, my parents or my friends say. Especially when you put your name on a website. Will they laugh at me or worse?

    What do you think?


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