I’ve been helping people build online businesses for well over a decade now.
I’m all about making money online through your words and using that newfound income and freedom to build the lifestyle you want.
That’s what a lifestyle business is all about. It isn’t about working four hours a week or living on a beach. If that is what you want, go for it. But, for me, it’s spending time with my family, getting out on the golf course, and going on some awesome adventures.
My lifestyle businesses have all helped me do that.
That doesn’t mean it was always easy.
I’ve made a lot of mistakes along the way.
There are hundreds of people in Location Rebel Academy who have had huge success building a real lifestyle business.
But most people don’t. Most people make some crucial mistakes early on that set them up for failure over the long term.
I want to see that change.
I’ve made all these mistakes over the last few years in one form or another. What’s important is you recognize what’s happening and change course as quickly as possible.
This can help you move forward and see success in building your freelance writing, copywriting, or niche site business.
Table of Contents
The 5 Biggest Mistakes I’ve Made Personally
These won’t necessarily apply to you, but if I’m going to call other people out for their mistakes, I should at least own up to mine.
Here are the biggest mistakes I’ve personally made over the years:
1) Don’t Try and Recreate Someone Else’s Lifestyle
Now that books like The
The problem with this is that I’ve seen a lot of people try to emulate someone else’s path. They haven’t figured out what their dream is, so they try to live out someone else’s.
There are all kinds of problems with this.
For one, that’s someone else’s passion, not yours.
If you aren’t totally into hang gliding, how can you expect to make it through the long startup process to open up that kind of business in Brazil? Oh, you want to get into copywriting to work for yourself and bring in $100k a year so you can…oh wait, you don’t know what you want to do?
You’ll be even more miserable than you were before.
No one can recreate my business or anyone else’s, for that matter. It’s my unique story and years of blogging/traveling/learning that make Location Rebel and related businesses what it is today.
Before you make a leap, understand what you’re leaping toward and why you’re leaping towards it. You’ll be more successful and happier, and you won’t piss off the dude whose business you’re copying.
Action step: Really think about your why. Why are you focused on creating a lifestyle brand, and how can you use it to reach goals (not just financial) in your life?
The Four Hour Work Week was the original book that inspired millions of people to start living life on their own terms. If you're looking to make a dramatic change in your life, this is a good starting point.
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2) Start with the basics
That’s awesome you want to create a hundred niche sites. Oh, and you’re going to do it all in the next 30 days? With no background in SEO or marketing?! Sweet, I’m sure you’ll make one miiiillliooon dollars off of that.
Right.
How many times have you seen that one work out? Very rarely.
What’s the problem here?
Often people who go this route aren’t starting with the basics. Until you have the skills and confidence to be able to pull something like that off, you’re just going to be wasting your time. So how do you start with the basics?
Here’s the three-step process we teach in Location Rebel Academy:
- Learn Skills
- Find Freelance Clients
- Apply to your own projects
Learning the basic skills, things like WordPress, copywriting, and SEO, will give you a solid base for whatever online or lifestyle venture you get involved with.
Then, by picking one skill and freelancing it, you’re building confidence and a base of income that will help ensure you’ve got some money coming in when you’re moving on to step 3.
Finally, once you’ve gained some confidence, you apply all of your skills to your own projects.
And even once you’ve moved onto all of those ideas…100 niche sites, as great as it sounds, are still probably a bad idea.
Action Step: Pick one or two complementary skills (like email marketing and copywriting) and go all in on learning them over the next month or two to build skills rapidly. Then get marketing and secure a few clients. Try looking at local clients first; it’s a hidden goldmine.
3) You Can Have It All, But Not All at Once
These days I’m a pretty firm believer that you can have anything you want if you want it bad enough. If my life goal was to own a Ferrari, I could make that happen — but I’d most likely be sacrificing a lot in order to achieve that. For reaching goals, I recommend the stair-step method.
This works on a much smaller scale as well.
All too often, I see people who want everything in their business when they are starting out. I received an email the other day from someone still in their day job that said something to the effect of:
“Sean, I’m really excited about getting my new business up and running. I’ve got all kinds of stuff in the works, including:
- A blog with 5 posts a week
- A new podcast
- 3 niche sites
- A free pdf product
- A membership site
- A YouTube channel
Oh, and I’m getting ready to travel through Asia when I quit in a few months.”
The guy had all of about 2 blog posts done and hadn’t done any work on his theme.
The classic example of trying to do too much, too quickly.
All of those things are great…but not when you’re starting out.
Focus on maybe two of those things. Figure out what your main goals are, and then work relentlessly on the things that will get you closer to those goals.
You can totally travel through SE Asia, work on a blog, and maybe one other thing, but if you’re going to attempt all of that at once, you’ll half-ass everything and never make any real progress towards the ultimate goal of making that your full-time work.
Action Step: If you are really excited by the idea of multiple niches, sit down and come up with 100 ideas for each of them. Pretty quickly, you’ll start seeing where you can talk a lot about something or it’s just shiny object syndrome.
4) Don’t Be Afraid to Spend Money
This one, I get. I can be a bit of a cheap ass at times, and I totally was early on. But hindsight is 20/20, right? There are certain small investments that can pay off in spades and are necessary.
Best example?
A premium blog theme. I used the free version of my blog theme for two years before finally investing in a good-looking custom site design. But you don’t even have to take it that far.
Buy a premium theme from Theme Forest. They have solid frameworks and make it so easy to customize your site and make it look however you want. That’s all I did for my golf site, Breaking Eighty.
With free themes, nothing is ever easy, and if you do find a good one, you’ll probably find a thousand other blogs that look just like yours.
Afraid to spend for ConvertKit or SEMRush? Get over it. These tools could be the best money you spend on your business.
ConvertKit is the email marketing software I personally use to run my business, and I believe it's the best fit for most people. Use for free up to 1,000 subscribers!
The old adage “You’ve gotta spend money to make money” has a lot of truth in it. Sure, you can bootstrap the hell out of your business and spend very close to zero dollars, but you’re going to make your life a lot more difficult than it needs to be.
And honestly? There are so many tools out there that offer 7 day or 30 day trials. Here’s where being organized makes a difference. If you know what you are doing and how you can use these tools, you can get a ton of information in those trial periods and save yourself.
If you’re bootstrapping, think about that. If you’re just being cheap — spend the money.
Stay in an extra night a week and take the money you saved and invest in yourself and your business — you won’t regret it.
Action Step: Set aside some money every month for skill-building, tools, or education. That way, when it’s time to spend, you’ve got some cash in the pot ready to go.
5) Building a Brand is More Important Than You Think
Often times when I see people skip mistake #2 above (start with the basics), they jump right into building an info product or niche site, and they skip one very, VERY important step: establishing truly establishing a brand.
Right now, we’re in a trust recession. With AI taking over the content landscape, more than ever people are skeptical. They want to find real people they like and can trust.
Don’t put the cart before the horse. Build your brand, build your audience, and build trust.
Doing that is going to set you up long-term to succeed.
It’s worth noting that this way of establishing expertise and authority doesn’t have to be a blog. It could be a podcast, YouTube channel, writing a newsletter, or posting on LinkedIn or X — any place where you share your views on your topic on a consistent basis.
Your brand and the things associated with it are some of your biggest assets. If all you’re doing is creating niche websites, one Google algorithm change can wipe out your business.
Even if everything I have online was deleted and I had to start from scratch, there’s still value in the Location Rebel name, my email list, my reputation, etc. The bottom line is, for me personally, without the brand, there is no business.
Action Step: Pick two places to build your expertise. That may be a blog and X, writing a newsletter and LinkedIn, etc., go all in on those, and then once you’ve built a brand, add in more channels.
6) Take Your Work Seriously
If you’ve recently quit or are traveling around the world, a new blog or business can seem like an awesome little side project. One of my best friends, Ryan, started an awesome blog that was quickly gaining traction and making him some money. But he never took it seriously as a business.
What happened?
He let the site sit for a year, somewhere along the way, it got hacked, and then he didn’t want to pay the hefty fee to get it fixed once he finally noticed what happened.
By now, he could have had a thriving business and community, but he never took it seriously. Caveat: He loves his life traveling and living in Germany now, but it’s still definitely a missed opportunity.
Sorry bud, but had to call you out on this one.
Moral of the story? If you’re serious about building a business, act like it.
Your blog is more than a blog. It’s a business. And the people who take that seriously see a lot more success.
Build routines around your work. If you’re working on your venture full time, figure out what hours you’re most productive, and sit your ass down in your chair and do the work.
If you’re doing it on the side, do the same thing. Figure out when you can work and actually do it.
If you treat your business like a fun side project, that’s exactly what it’ll be. If you take it seriously, and treat it as your new day job, in time, you’ll be right where you want to be.
Action step: Monitor when you feel most productive and your free hours and dedicate time every day to working on your projects. And make it real focused work where you try to accomplish 1-3 things.
7) Don’t Work in a Vacuum
I’ve said repeatedly over the years that if you want to be successful in doing this, you have to find a supportive community. For as many people as I know living out their perfect lifestyle, the concept still isn’t mainstream.
If you tell many of the people close to you that you want to start a business on your own, they’ll probably give you a myriad of reasons as to why that’s a bad idea.
That’s why it’s more important than ever to have a solid support system while you’re working through things.
This is one of the most common mistakes I see as well. People will hole up in front of their computers and treat the whole thing like they are in a vacuum. They won’t go out and meet other entrepreneurs, and often won’t even try and communicate with like-minded people online.
Not only are you doing your education a disservice, but it won’t be long before your sanity wears thin, and you scrap the whole thing.
This is probably the most important thing I’ll say in this post. If you’re serious about building a successful lifestyle business, find a supportive, like-minded community as soon as possible.
Action Step: Make friends with other freelancers, business owners in your community, people who are in your niche, and so on. These people will be great resources to help you move forward.
Location Rebel Academy is one of the longest running courses and communities for showing you EXACTLY how to build a lifestyle business, that allows you to quit your job, work from anywhere, and spend more time doing the stuff you love.
Have You Made These Mistakes While Creating a Business?
None of us are perfect, and we all make mistakes no matter how hard we try not to.
Consider this post a reminder.
It’s easy to let things get in the way of our dream lifestyles but focus on continually improving your business, and you’ll thank yourself later on when you have full freedom in your life. When you don’t have to miss things like your kid’s first steps because you were at work or when you meet the person of your dreams while traveling through the French Riviera.
That’s why we’re doing all of this anyway, right? To live a life where we can do more of the stuff we like to do, on a daily basis.
If you know you want to build a life like this but aren’t entirely sure how to get started. Check out our free 6 part course. It’ll get you heading down the right path.
This post was updated for accuracy as of September 2024.
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.Join over 40,000 people who have taken our 6 part freelance writing course. Sign up below and let’s do this together.
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Sean,
Killer post with a healthy dose of ‘tough love’ for aspiring Location Rebels. This comes at a very opportune time.
#3 is the most poignant for me, as I’m the consummate ‘Renaissance Man’; the kind of guy who wants to know everything about everything and do it all. While this makes me insatiably curious, when it comes to putting it in action, it’s been a major detriment. In the last week, I’ve forced myself to pick ONLY 3 THINGS I will do as I move forward (Travel around the Middle East/SE Asia, SEO freelance, and build my SEO product).
As much as I like options (especially us Americans and our relentless focus on ‘freedom to choose’), they can often be limiting as hell to actually achieving anything material. While I knew this the whole time, it was torture to limit myself to these 3 high-value activities. But, if my personal history is any guide, then the decisions that make me squirm the most are the ones I’m later so thankful I stuck with.
Keep it up, bro.
Psychologist Barry Schwartz has a killer TED talk on this: http://www.ted.com/talks/barry_schwartz_on_the_paradox_of_choice.html
Dude, good to hear you’ve narrowed down your focus, and for you I think that’s going to be a really good path. Looking forward to seeing everything evolve, and keep it up!
Thanks, bro. I’ll keep you posted on progress.
There’s also something really freeing AND motivating for about burning most of my boats (aka other things I could make money doing, but not ultimately fulfilling or as profitable) and going ‘balls out’ on 1 or 2.
This may be one of the hardest things I’ve done…I’m still kicking and screaming but I know it’s right 🙂
Has anyone recreated Ferriss’s income “autopilot”?
Portable income allows for location independence, but most of the guys talking about lifestyle design
– make physical products that need to be updated and refined, along with all the hassles of making, distributing, shipping, and customer service
– info products that need to be updated and refined, the “product launch treadmill”
– software – which requires ongoing support
– sell some kind of service which either requires them to 1) hunt for clients and do the service themselves, or 2) hunt for clients and then delegate/manage employees to do the service
The Ferriss model was herbal supplements marketed via magazine ads and sold online by 2 affiliates that handled the distribution, shipping, and customer service. According to him, he built this up and did all of the leg work initially, but little by little analyzed his business and automated what he was donig. From there, he was then free to basically live a life of leisure. It was almost like having trust fund income or maybe rental income where you had on staff managers, sales, and repair persons.
It’s ironic considering the last thing he is doing is “living a life of leisure” I’d imagine he works harder than just about anyone out there.
So glad you said #5! Branding is huge now for SEO rankings, and something Google wants to see is a lot of great content in a lot of places.
Here’s the news (it’s another Penguin update, actually): http://blog.hubspot.com/aftermath-penguin-20-branding-now-major-ranking-factor
Allison, thank you for sharing this link! I had a feeling 2.0 had hit, but hadn’t read anything on it yet. Very timely indeed, and it backs up the increase in my own search rankings for this site over the last little while.
I made plenty of these mistakes when I was starting out. I wish I had read this post before I sold it all and moved to Costa Rica!
Great info, as always, Sean. Thanks.
haha totally get that, but even with posts like this, sometimes you just have to make the mistakes and experience the results for yourself.
Like with Siddhartha (by Herman Hesse).
He searched for enlightenment, found the Buddha, and said, “You reached enlightenment by getting there yourself, not by listening to a teacher. Later.”
Hey Sean,
Always enjoy your “stuff” but this article is really from the top shelf.
Thanks for sharing your entrepreneurial learning’s.
Thanks Terrick, that’s good for me to hear.
Sean,
Thank you so much for all of your valuable advice. I think the one tip that I loved most was about getting caught in the vacuum. It is so easy to sit at your house in front of a computer all day, but seriously stifles creativity and networking opportunities. I have only been blogging for few months now, and I have met SO many new people both online and off. Thanks for the great words!
Glad to hear you’ve been being social. It’s SO important, and something many internet entrepreneurs can forget.
This post was right on time. When left unchecked, I tend to find myself drifting towards become a “jack of all trades, master of none”. I constantly need to filter out the distracting projects that I shouldn’t take. Thanks for the reminder
Thats a fine line I walk as well. Over time I found however, that being a jack of many trades, and master of ONE is a good place to be. I’m great at helping people build location independent businesses. I’m pretty good at a bunch of other stuff, but because I’m a master (for lack of a better term) of that one thing, it gives me the ability to expand more over time.
#6 is too important … taking the work seriously. I remember doing web/graphic design as a fun hobby, and not knowing how to take it to the next level.
But I’ll definitely say that I was totally the #3 guy … just wanted to do everything. I’m glad I’m simply focusing on my client projects & surf … with adding just one other project. I left a list of others simply “on-hold” til I complete a project at time … that way not overwhelming myself.
I’m also glad to see you focusing on that, it’s been awesome to see you evolve over the last year, and LOVED your recap in the Location Rebel forum last week. Awesome stuff man, keep it going.
Allison…thanks for that link. I had a sneaking suspicion that was the case, as Google a la Matt Cutts has been hinting at that for the better part of 3-4 years, since Universal Search got underway.
This is a very helpful resource to have, seeing as I have to have a ‘Come to Jesus’ talk with a client about this exact thing soon.
Great post Sean! I appreciate your insight and encouragement to do something different and stick with it! Hope to see you soon ~ Jess
Hi Sean,
I’ve been wondering whether there’s been a fall out in lifestyle design since the whole movement occurred when so many people were getting fired and could not find work back in 2008-2009. It’s great to see people actually DO SOMETHING about their situation like starting a blog and a business.
Have you seen a lot of people fail at the lifestyle blog movement? I actually haven’t observed anybody shut down and get a day job. It seems like there are more lifestylers now than ever before with plenty of people making 5 figure a month incomes now.
I’m I just not being observant enough?
Thanks!
Sam
Yeah I’ve seen a LOT of blogs come and go. For instance, when I started I had a small mastermind of new bloggers, and I think I’m the only one left..
Where did they end up going? Back to work?
Working on #7 right now. It’s been tough for me to find like minded people here locally to get together with. I can find folks online, but it’s not the same to me. So, what I’m considering is seeing if I can start a think tank around here and invite/entice microbusiness owners to get together on some regular basis to brainstorm. I motivated and know where I want to go with my business but I’m also not conceited enough to think that I can’t learn from other similiar thinkers. Great post!
Exactly what I needed to read this morning. I’m getting way ahead of myself with future project ideas to complement my my main site, when my main site isn’t even live yet. Time to concentrate on making this a success before doing anything else!
Cheers,
Kris
Exactly!
I’m not a lifestyle entrepreneur, but I did become location independent last year and a lot of this rang very true. Especially the “do everything at once” part. Have to. Stop. With that. Justin’s comment about “jack of all trades, master of none” is a good way to put it.
This post was really great. I rarely comment or interact but I follow most of what you do online. I started out a couple years ago finding and following a ton of lifestyle/travel/business/etc blogs, but yours is one of the very few I still make time to read because your content is consistent, well-laid out and helpful. Thanks for all the free guidance you provide. 🙂
One question I did have for you is: why you don’t use more of your own pictures for your blog posts? Because I’ve seen your photography stuff and tutorials, and the pictures on the blog here are great, but nothing compared to some of your other photos. I was wondering if there is a reason for that or if it just happened that way.
Valerie, Thanks for the kind words! I almost always try to use my own photos when I can. The hard thing is unless I’m doing a travel post it can be hard to find photos for certain topics. For instance, I dont have many photos that go with “mistakes”. Sometimes I say screw it and post up a good travel photo anyway, but I try to keep it consistent. I’d like to go out and shoot more stuff specifically to use in blog posts – so thanks for the comment, it’s good to get feedback like that.
Sean,
In your newsletter you asked what type of things your readers would like to see you write about. This article is the type of subject that I like seeing you write about. Regarding point #1, he is a great article from Forbes that tackles that very subject.~
http://www.forbes.com/sites/michaelskok/2013/05/21/as-a-budding-entrepreneur-where-do-you-start/?goback=%2Egde_2877_member_243339987
Just out of curiosity, why did you ditch the Pinterest button? Also, I was wondering if you’ve ever posted anything on Typepad, and what is your take on that site? Thanks.
I think Typepad is good for the right type of person/blog. I know a lot of craft bloggers use it, but has never been anything I’ve given much thought. Pinterest button is still there, but just not showing up correctly, might be a plugin issue. That said, I don’t get a ton of traffic from Pinterest, so that was more of an experiment anyway.
Really enjoying your posts lately Sean, you’re getting better and better at breaking down the step by step actions required to move closer to your goal and where to go for resources.
Keep up the good work.
Thanks Ben, the goal has been to make the majority of the stuff on the site as actionable as possible.
Sean,
Great points! I’ve read your blog for a while and while I’ve always enjoyed your content; your most recent content has really grabbed my attention.
It’s easy to read Tim’s blog or even Location 180 and get caught up in the “Dream” , sometimes we forget that it is somewhat of a science and I really appreciate you pulling back the curtain for us on several occasions.
Looking forward to more great posts in the future, and hopefully taking the above advice will give our fledgling site the blueprint it needs to succeed.
All the best,
Andrew
Really great post here – I love your writing style. I must admit that I am one of those people unwilling to spend money and invest in my business. It’s a scary thought to throw this money into things with only a sense of hope that it will pay off in the long run. I also love the point about the importance of building a brand. I’ve just recently teamed up with a branding coach with a sort of exchange of services arrangement, and I’ve already seen incredible results. It’s funny because you never really think of yourself as an actual brand that people identify with, and I’m learning a lot in this process. Thanks for the tips here.
Hey Sean, thank you for the helpful post as always.
All 7 mistakes go back to the first one of not knowing what you want. It’s an issue of the desperate need to run away from something without knowing what they want to run towards.
I think these beginner mistakes are applicable not only to location independence but to everything we want but don’t have right now. Especially fitness.
For example, most people who want to lose weight and look like someone they look up to (a model, a celebrity or something) would commit the same mistakes.
They want to copy the exact diet and training, do advanced versions without getting basics right first, committing to too many changes all at once, blindly try to find the right way on their own when the best “shortcut” is to just pick someone you trust and follow everything they say (e.g. hiring a personal trainer), etc.
I started getting exposure to all these awesome things people like you do on the internet when I wanted to make physical changes. When I found how possible it was to change my own body, I started believing that I could make changes to my life too. And I’ve found that the same lessons I learned from successfully changing my body apply to the next thing I want to do, which is start a business and live life on my own terms. This is the reason why I advocate starting with health and fitness first. Besides, everything’s easier when you’re stronger.
I’ve already committed many of these mistakes. But thankfully, I found you and Location Rebel and while I’m only just starting out, I’m glad that because of it I won’t have to continue spinning my wheels anymore… it’s the best “shortcut” I know. Thank you.
Hi Sean, this is a great post! It’s so true that we let things get in the way of our dream lifestyles – but remaining focused and working to continually improve our business (in small steps, if need be) is a must! Your 7 mistakes are really useful, particularly ‘You Can Have It All, But Not All at Once’. Thank you!
Love it. There is so much ‘just do it’ advice, so it’s refreshing to read something a tad more realistic and acheivable. I went travelling to figure out what I wanted to do, but it was only really coming home that gave me the context to figure out what I wanted to do and the contacts so I can work to make it happen.
Some great insights here, Sean. Thanks for putting it together. I haven’t made the transition yet from hobby to business, but it is something I would like to see about down the road. This year is just for fun and travel though! 🙂 But I can relate to the learning the basics step… I’ve learned so much about blogging, social media, seo, etc in such a short time. I figure now is the chance to lay the groundwork and later I can see what dirction to go, even working for someone else but having the location independence afforded by the internet would be awesome.
I really liked this post! I’m a complete cheapskate as well but I’m learning I need to spend more in order to reap the rewards – my next expense is working with a proper coach – I’ve been putting it off for too long but now I’ve committed I’m really excited!
I absolutely love this! Great post, loads of really good info to take away. Favorited and will be coming back to read again more than once I’m sure.
Hey there,
I too am just beginning in the world of SEO and have been reading the beginners guide, etc. Before stumbling across this world I actually quit my job in Indiana and moved to Hollywood to pursue acting. However I am an avid writer and naturally the idea of a blog would be awesome. So of course I am going to begin one and I think down the line when I learn these techniques to help turn it into a business, it will also enable me to focus on my true passion which is acting.
Also, one question? Why is the big place of travel Asia for everyone in SEO. Just curious…?
Great post. when you don’t work each day on the fundamentals, you start and can’t finish your building. It will collapse. Thanks for sharing this list ! Love and blessings. Johan Persyn
Hey, thanks for the post. I’m trying to make the shift from business owner with office/team members to lifestyle entrepreneur and its tough. I seem to end up back at overworked and over stretched every few months. Although I work in social media marketing I can’t seem to apply the tools I understand to create an effective automated online business. I’m definitely making some of the above mistakes but I have realised my real issue is around a) mindset I.e I have to work very hard to be successful b) in contrast to one of your points but relevant to another. Spending way too much money on too many tools/products all at the same time that are beyond my needs. CRM/Autoresponder/course sites etc/information products. I’ve decided to strip it back and start with one thing at a time And build the new business slowly. Thanks, Sarah