Become a Lifestyle Entrepreneur: Complete Guide and 40+ Resources

April 9, 2023

by Skellie @ AnyWired

If you are — or would like to be — an entrepreneur, yet you’d be happy to earn enough to live the life you want rather than becoming filthy rich, lifestyle entrepreneurship might be a good fit for you.

Lifestyle entrepreneurs will generally base their ventures around time minimalism, or something they love, even if there are more profitable (but more time-consuming, or less interesting) options available.

The goal of a lifestyle entrepreneur is not to amass a huge fortune, but instead, to achieve certain definable goals and, beyond that point, to ensure business does not interfere too much with the enjoyment of those goals.

In this article, I’ll be outlining the primary steps to becoming a lifestyle entrepreneur, followed by 40+ educational and practical resources you can use to get started.

The 3 types of lifestyle entrepreneur

Time minimalists. This method is all about taking much of the time commitments out of owning a business and earning an income. This is usually achieved through elimination, outsourcing, the 80/20 principle, simplicity and automation, or through focusing on ’set it and forget it’ products, like eBooks or drop-shipped products.

Example: Doug Price, who created His PPC advertised site sells audio libraries at several hundred dollars a pop and earns over $10,000 a month with under two-hours of maintenance work each week. The business allows Doug to spend plenty of time pursuing his two primary passions: music and travel.

Nomadic entrepreneurs. While the nomadic lifestyle entrepreneur isn’t necessarily working less than anyone else, the nomad’s number 1 aim is freedom of location: an anywhere work style. Work should enable travel, not confine it to one weekend each year.

Example: Lea and Jonathan Woodward run an online branding and marketing business from a variety of international locations, creating an easy mix of travel and work. The business is optimized to be manageable from anywhere in the world.

Doing it for love. For this kind of lifestyle entrepreneur, business revolves around a passionate hobby: something they’d still be doing, even if it didn’t earn a cent. The goal is not to work as little as possible. For this kind of entrepreneur, work is a passion, and maintaining and operating her/his business is woven into a lifestyle, not separate from it.

Example: eBay user richietman (”Richard”) began selling personally restored violins on eBay after a dire health issue forced him to quit his career as an attorney. What was once a passionate hobby became a (no-less passionate) $100,000 per year business.

Which one are you?

Pick your favorite option from this list:

  1. You work part-time hours and earn a full-time income.
  2. You can work from anywhere in the world.
  3. You make a living with a business that is strongly linked to a passion of yours.

If you’re extra-ambitious, you can aim for hybrid models:

  1. You work part-time hours and earn a full-time income, from anywhere.
  2. You work part-time hours and earn a full-time income, from anywhere, doing something you’d be doing even if you didn’t get paid for it.

Time-minimalist business models

1. Information products (i.e. eBooks, audio CDs, interview transcripts, videos).

  • Work with what you know, or what you can easily learn.
  • Research niche markets and find out what information and answers they’re searching for. The AdWords keyword tool is a great tool you can use to do this.
  • Charging more than $50 for your product will make it easier to cover and exceed costs — unless your product really couldn’t be perceived as worth that much.
  • Create a basic website and landing page for your product, and register a domain name.
  • Work out what your product will include in detail, then set up your website and landing page is if you are actually selling an existing product. Add a test price and a link to a checkout button.
  • Instead of a payment info form, create a page informing would-be buyers that you are working on an updated version of your product to be released in the near future. You can add an email sign-up form to return some of these would-be customers.
  • Add Google Analytics to your website to track the amount of people who decide to ‘buy’ your item.
  • Set up a minimum $100 Google Adwords to test how your product would actually fare if you created it. Track how many people proceed to the checkout and are met with your ‘updated product coming soon’ message. You can count all/most of these visitors as buyers.
  • At the end of your test, work out whether your product would have covered advertising costs, and by how much. If your product is $50 and your PPC campaign garners two ’sales’, you’ve broken even.
  • It’s often recommended that you expend $500 testing your product before you actually invest the time/money required to create it. I suggest doing this in $100 blocks so you can re-evaluate your progress and try new strategies as you go along.
  • Note: if you haven’t run a PPC campaign before, Marketing Experiments has some fantastic tutorials and guides to get you started.
  • Once your information product is created, you need only manage your PPC campaigns from time to time.

2. Find a product to sell via drop shipping

  • Work with products you know, or can easily learn about.
  • Research niche markets and find out what kinds of products they’re searching for, and who — if anyone — is meeting their needs.
  • Ideally, your products should cost $50+. A smaller volume of sales with a high profit margin is generally easier to manage.
  • Find a wholesaler who will drop ship your product (try: Drop shipping means you forward orders to a wholesaler, and they will handle stock and delivery for you. You pocket the difference between wholesale and retail price, minus drop shipping fees, without ever having to touch or store the items you sell. Neat, huh?
  • Create a Yahoo! store dedicated to your product idea.
  • Test your store with a PPC campaign, as outlined above, before spending more than $500 on it.
  • If tests are successful, the process of running your business should only involve sending off orders and managing PPC campaigns from time to time. I’d suggest outsourcing customer service as soon as possible.

For more ideas, see the Automate section of The 4-Hour Work Week.

Nomadic business models

The above two ‘time-minimalist’ models are also nomadic models, capable of being managed from anywhere. Here are some more ideas for web-based entrepreneurship:

  1. Develop (or hire someone to develop) a useful web application. You can run a beta migrating into a subscription fee, or offer both free and premium accounts.
  2. Create a for-profit blog and outsource content creation to high-quality writers.
  3. Share your expertise through paid content (see Brian Clark’s free Teaching Sells eBook for more information.)
  4. Start a consulting business or firm.
  5. Create a free version of a website-model that is usually paid, then recoup costs through advertising.
  6. Flip websites and blogs.
  7. Trade stocks online.
  8. Hire local salespeople to run a grounded business.
  9. Collaborate with grounded business-partners remotely.

Tools to run a nomadic venture:

A for love, not (just) money business model

Work from your passions, hobbies and interests first — then link these to possible opportunities. A niche focus will help your venture stand out and reduce competition. Consider these options:

  1. Start an online store selling items you are personally interested in. If you love comic books, you might start an online store selling hard to find comic books, or comic books starring specific characters, for example. While it’s certainly possible to start a grounded store, difficulties in targeting small niches and bigger overhead costs make this a riskier option.
  2. Get paid to do something you usually do for free. If you already like building computers, you could create custom-built models and sell them. If you know a lot about a particular topic and like giving advice on it, consider selling premium content or becoming a consultant dealing in that topic. These are just a few examples.
  3. If you love hunting for collectibles but are limited by how much you can afford to buy, start reselling these collectibles to others, allowing for a lot of guilt-free item hunting!
  4. Open a guest-house and rent rooms in a place you have always wanted to live. Mark Hayward is a friend of mine currently living this dream in beautiful Culebra, Puerto Rico.

Being passionate about a product will help you identify bargains, sell items other people interested in your niche actually want, and enjoy the process of selecting stock. You have more to worry about your products being too generic than you have to worry about them being too obscure — by many accounts, catering to small, under-served niche audiences is the way to go.

Tips on doing what you love

  • Put your enjoyment before profit when making business decisions (as long as you have enough income to live off).
  • Growth is not always the best option if stress and complications go with it.
  • Don’t take on staff unless it makes things easier. A lot of entrepreneurs are happy until they decide to start taking on staff, then realize after the fact that they intensely dislike managing workers!
  • Think about ways to minimize or eliminate the least enjoyable or least interesting aspects of your venture, even if it means sacrificing some profits.
  • Work/life balance can be a renewed problem when you love your work. That’s great — but you love your family and friends, too. Resist the temptation to work all the time, as other aspects of your life will wilt in the background.

40+ Practical and Inspirational Resources for the Lifestyle Entrepreneur

Books on lifestyle entrepreneurship

Reasons to start

  • 10 Reasons You Should Never Get a Job — Steve Pavlina

    “It’s funny that when people reach a certain age, such as after graduating college, they assume it’s time to go out and get a job. But like many things the masses do, just because everyone does it doesn’t mean it’s a good idea. In fact, if you’re reasonably intelligent, getting a job is one of the worst things you can do to support yourself. There are far better ways to make a living than selling yourself into indentured servitude.”

How to start

  • 10 Tips For Moving From Programmer to Entrepreneur — Ian Landsman
    “… the best code in the world is meaningless if nobody knows about your product. Code is meaningless if the IRS comes and throws you in jail because you didn’t do your taxes. Code is meaningless if you get sued because you didn’t bother having a software license created by a lawyer.”
  • 36 Startup Tips: From Software Engineering to PR and More! — Alex Iskold
    “A team of 2-3 rockstar engineers can build pretty much any system because they are good at what they do, love building software, focus on the goal, and don’t get in each other’s way. A team of 20 so-so engineers will not get very far. The mythical man-month book debunked the notion of scaling by adding more programmers to the project. The truth is that most successful software today is built by just a handful of good engineers. Less is more applies equally to code and to the number of people working on it.”
  • How to Start a Startup — by Paul Graham
    “You need three things to create a successful startup: to start with good people, to make something customers actually want, and to spend as little money as possible. Most startups that fail do it because they fail at one of these. A startup that does all three will probably succeed.”
  • The Secrets of Creating and Growing an Online Business — Matt Inglot
    “Starting an online business is no doubt a popular entrepreneurial venture these days. Through the internet a product can be created, marketed, sold, paid for, and delivered for fractions of the cost of doing so outside of the virtual world. Often times the physical location of your business doesn’t even matter - as long as you have an internet connection and a $300 computer. Did I mention you can work from home with flexible hours?”

How to be good at it

  • 100 Ways to be a Better Entrepreneur —

    “A common mistake for many entrepreneurs is that they “just don’t have time” to work on the things that will make them better at what they do. They get caught up in the daily operations of their business and can’t see past that. You may have heard the old saw that some things are urgent and some are important, but few things are both. Many business owners spend their time on the urgent things because their lack of planning and long-term perspective continually creates additional urgent things. Self-education is a good example of something that is extremely important but not at all urgent.”

  • Free! Why $0.00 Is the Future of Business — Chris Anderson
    Give away the cell phone, sell the monthly plan; make the videogame console cheap and sell expensive games; install fancy coffeemakers in offices at no charge so you can sell managers expensive coffee sachets.”
  • Random Thoughts on Being an Entrepreneur — Hugh Macleod
    “People remember the quality long after they’ve forgotten the price. Unless you try to rip them off.”
  • The Top 10 Lies of Entrepreneurs — Guy Kawasaki

    “An entrepreneur’s projections are never conservative. If they were, they would be $0.”

  • The Zen of Business Plans — Guy Kawasaki
    “While creation of the business plan should be a group effort involving all the principal players in the company, the actual writing of the business plan–literally sitting down at a computer and pounding out the document–should be a solo effort.”
  • How to Make a Million Dollars — Marshall Brain
    “Last week I was invited to speak to a group of 200 students at Duke University. The organizers gave me pretty much free rein in picking my topic, so I decided to talk about this.”
  • Internet Pioneers on What Not to Do — Jeffrey Gangemi

    “Potential pitfalls along the way to building a successful online business are many, whether you’re taking your brick-and-mortar operation onto the Web or making your existing online outfit smarter.”

  • Top 20 Entrepreneurial Quotes — Yasmine
    “Some people dream of great accomplishments, while others stay awake and do them - Anonymous”

Entrepreneurial reading

  • The 100 Daily Must-Reads for Entrepreneurs — Bootstrapper

    “These days, it seems that almost everyone has a blog, so it’s often hard to separate what’s really worth reading from what isn’t. Luckily, we’ve done the work for you and narrowed it down to 100 highly informative sites.”

  • Springwise
    “New business ideas for entrepreneurial minds.”
  • Startup Spark
    “Sparking startups with advice, inspiration and a bit of craziness…”
    “Online magazine for business and small business.”
  • Startup Nation
    “Source for small business advice, help starting a business, and an entrepreneurial forum.”
  • Just for Small Business
    “Starting and growing a small business requires the mastery of multiple disciplines. Make sure you’re not missing out on trends and advice on finances, operations, and marketing, among other things.”
    “Small business resources and small business information for the entrepreneur.”
    “Killer resources for entrepreneurs.”

Doing what you love

  • How to Find What You Love to Do — Brian Kim

    “People think you have to travel around the world, experience new things, etc to find what you love to do. No. You just have to sit down and decide. The answer is already within you. You just have to dig it up and avoid procrastinating. Your brain has absorbed all sorts of information and experiences and it has the answer ready to be unraveled.”

  • Making a Profit Out of Passion: Lifestyle Entrepreneurship — George Rodriguez
    “According to the market research company Warrillow and Co., as many as 90 percent of the roughly 20 million American small business owners appear to be motivated by lifestyle more than money.”

Nomadic entrepreneurship

  • Is Location Independent Life Cheaper Than Living in Just One Place? — Lea Woodward
    “There are some things in life that are just accepted; the notion that a life of permanent travel is expensive and only for movie stars and famous people is one of them. In this post, I might just blow that myth right out of the water.”
  • Round-the-world Trip Planner — Airtreks
    “This TripPlanner™ enables you to plan multi-destination “mini-retirements” with ease by adding an unlimited number of cities and countries, flying in any direction you choose.”

Free classes and courses on entrepreneurship

  • 7 Universities and Websites Offering Free Business Entrepreneurship Classes Online
    “Approximately 10 million entrepreneurs think about starting a business in the U.S. every year. Only 3 million of them actually do it. Be one of the 3 million with these free online business entrepreneurship courses.”
  • 99 Free Online Classes on Business and Entrepreneurship
    “Are you looking to take business and entrepreneurship classes but are worried about the money and time availability? The courses below are all free and can be taken at your own leisure.”

Manufacturers and drop-shipping

Time-minimalist and solo entrepreneurship

  • Automate Your Income by Simplifying Your Life — Leo Babauta
    “Instead of working hard to earn money every day and every month, work hard to set up your income stream, and then do minimal work from then on out to maintain that stream.”
  • Go it Alone! The Secret to Building a Successful Business on Your Own — Bruce Judson
    “In a first-of-its-kind initiative, HarperCollins Publishers has made the full content of Go It Alone! available free for readers at this Web site. You can access the life-changing ideas in this book, at no cost.”
  • Five Ways to Create Passive Income With Little or No Money — Brian Lee
    “When I learned about the concept of passive income, I immediately became excited about it. I read every book I could get my hands on about wealth, personal finance, real estate, and entrepreneurship. Most of these books were heavy on concepts, but light on specifics. With this in mind, I went to seminars and started mingling with people who were already doing it to find out how they started. Here are five suggestions from what I’ve learned.”
  • Solo Entrepreneurs: Big Bucks From Tiny Computing Startups — Alice LaPlante
    “One-person companies are earning upwards of $1 million in revenues annually. How do they do it? With high-speed Internet connectivity, mobile apps, automation, and a little help from their customers.”
  • Passive Income — Brian Lee
    “The problem with this traditional view is that time is traded for money, thereby limiting the amount of money a person can make by the amount of time he/she has.”
  • Selling Royalty Free Files to Make Money — Collis Ta’eed
    “Selling stock files is something most commonly associated with photography, however these days it’s possible to sell flash, illustrations, audio, video, fonts, websites and 3d. Thanks to microstock sites, it has also become incredibly accessible as well.”
  • More Passive Income Strategies — Brian Lee
    “You’ve compartmentalized the money and assigned it a different strategy than your normal income. Since you make enough to cover your expenses with your normal job, you allow your passive income to create a life of its own.”

Business practicalities

  • Free Sample Business Plans
    “Get inspired with our gallery of 500+ business plans.”
  • Top 25 Apps to Grow Your Business —

    “In this guide we cover the 25 best web 2.0 applications for entrepreneurs who are looking for simple, cheap, and effective solutions to solving some of the tasks facing their small business or startup.”

The lifestyle part

(This bit is really up to you. And that’s the fun part.)

  • Ideal Lifestyle Costing — Timothy Ferriss
    “It’s less than you think.”
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8 Responses to “Become a Lifestyle Entrepreneur: Complete Guide and 40+ Resources”

  1. Links: Fatigue and lifestyle entrepreneurship « Anna’s journal on April 10th, 2008 6:26 am

    [...] Become a Lifestyle Entrepreneur at Categories [...]

  2. Karl Edwards on April 10th, 2008 9:05 am

    What a wonderful resource. Thank you.
    Living one’s vision and passion on the one hand is often in serious tension with the viable financial models that can sustain mortgage payments and the kids’ college tuition.
    Finding ways to align these goals is trickier than many of the self-help authors will admit.

    Karl Edwards’s last blog post..Question of the Week

  3. Sundress Girl on April 10th, 2008 2:53 pm

    Awesome list of resources! Thanks!!

    Sundress Girl’s last blog post..How To Find Sexy Sundresses for 2008

  4. Etavitom on April 11th, 2008 2:37 pm

    Thank you very much for this profound post!!

  5. Steve on April 12th, 2008 10:45 am

    Wow, thanks for all those links. This will be me busy for a while :)

  6. Cam on April 14th, 2008 10:41 pm

    What a great list of resources, and very interesting.

    I’d definitely say I’m a time minimalist.

    While I love what I do in my businesses, one of the main benefits is freedom to do stuff other than work all the time!

    Which one are you?

    Cam’s last blog post..Procrastination - Snap Out Of It

  7. Barbara Ling on May 5th, 2008 5:57 am

    What a great list of resources!! I know what I’ll be doing today - excellent reads. I’ll have to bookmark this post for the future.



    Barbara Ling’s last blog post..How kids can make money on the Internet online - The beginning of the experiment

  8. John Calvin on June 24th, 2008 11:51 am

    Great information and a great list of resources. I need to bookmark this since I won’t have time today to go through all the links. The best lifestyle advice I ever got? Do What You Love and the Money Will Follow. It’s all about having the qyality of life you want, not necessarily the things.

    John Calvin’s last blog post..Who is AJ Morgan? The Riddle Grows Deeper

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