SIMPLIFY SERIES: What is a Lifestyle Entrepreneur?

What is a lifestyle entrepreneur?

We’re all familiar with the general entrepreneur. They’re the ones with a knack for business; the kids selling lemonade out on the sidewalk, or mowing lawns for everyone in their neighborhood. They embark in the business world with an idea and a pitch, hoping to land investors or funding. They build their empire quickly, taking big risks thriving at the center of their growing company. They’re the Bill Gates and Steve Jobs of our world. We know them well.

But there’s a new kind of entrepreneur entering the scene, one whose popularity has grown almost seemingly overnight. They are the lifestyle entrepreneur. The lifestyle entrepreneur is one who often exists quietly in the background, slowly waiting for their budding business to grow into an empire. These entrepreneurs aren’t at the center of their business, in fact, it mostly revolves around them. They put their ideal lifestyle first and let the business work around them. They’re the Lewis Howes and the Tim Ferriss of our world. We may not know them well now, but we certainly will.

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What is a Lifestyle Entrepreneur?

The term “Lifestyle Entrepreneur” was coined by Lewis Howes, and though it has various different meanings, the general idea is that the lifestyle entrepreneur is a person who creates a business with the intention of altering their lifestyle, and not for the sole purpose of making profits. They focus more on the rewards provided to those who enjoy and have a passion for what they’re doing in life. Generally their business does well because of their true passion – it can be contagious. People (and customers especially) can’t help but to flock toward those who’ve “figured it out” – the ones making money doing what they truly love.

And though the lifestyle part looks different for each lifestyle entrepreneur, the point is they don’t work in their business and then come home for the day – their business supports their life, it’s a part of it, it’s in everything they do because it’s what they’re passionate about.  

Regardless of the differences among lifestyle entrepreneurs as individuals, they all tend to share some similar traits. Here are some things that set lifestyle entrepreneurs apart from the business crowd.

Lifestyle Entrepreneurs Put Life First

Of course money is important to anyone starting a business or working in the professional field in general, but for some entrepreneurs, money isn’t everything. A lifestyle entrepreneur will often measure success by how much they love their work, not how much they earn.

To a lifestyle entrepreneur the freedom to work in their own way by their own rules, the flexible schedule from any location, and the ability to spend more time with the people important to them are all more important than the money in the bank. Paying the bills and being able to survive are still a must for them. They wouldn’t thrive in their lifestyle if they weren’t making ends meet. The difference is that they aren’t defining themselves by their net worth – they don’t focus so heavily on the numbers, and center their business around the other benefits they receive.   

Lifestyle entrepreneurs

Lifestyle Entrepreneurs Spend Time in Their Business Because They Love It, Not Because They Feel Like They *Have* To

For the lifestyle entrepreneur, business and life become one symbiotically working machine – and that’s a great thing! – because they’ve taken what they love and figured out how to make that pay for their lifestyle, rather than the other way around. It’s an idea that is sometimes called a muse business, one that starts with an interest and then turns into a product or service.

It can be thought of as a sort of means to an end, though oftentimes for a lifestyle entrepreneur there is no hard “end” in sight. They’re doing what they love so what’s the rush? Their business may take some time to build, but for them that’s cake compared with spending the rest of their life working a standard 9 to 5.    

Lifestyle Entrepreneurs Turn Passions and Interests into Products and Services

Given that your standard lifestyle entrepreneur is going to wind up putting in a lot of long hours building up the business that will eventually buy their freedom, it’s critical that they build off of this idea of a muse business and stick with it. Though the particular qualities for a business will vary depending upon the person building it, they should at least adhere to a few standards of success.

First, the business needs to be able to grow without demanding a ton of extra time. If freedom and flexibility are the heart and soul of a lifestyle entrepreneur’s ideals, a ton of extra time being “plugged in” isn’t going to align with that.

Of course, there are going to be times when the lifestyle entrepreneur is going to have to put in a few extra hours here, maybe a weekend there, which is fine, because they’ve built it all around something they enjoy. There isn’t anyone breathing down their neck or keeping them on the clock, so if they don’t like what they’re doing, it can be detrimental to their business.

Second, the foundation of a muse business is that it’s automated for the most part; the lifestyle entrepreneur is a professional at delegating tasks, and constructing things in such a way that they are easily repeatable. They are well organized and don’t make major changes all the time, which means that they aren’t spending extra time monitoring tasks or redoing those that weren’t done right. They have time to focus on the big picture, so they can grow over time, in a way that works for their business.

It’s about striking a balance between knowing what only they can do, and knowing what can easily be outsourced to virtual professionals.

Lifestyle entrepreneur

Lifestyle Entrepreneurs Embrace the Value of Outsourcing Early On – and Reap the Benefits Later

Which brings us to the last characteristic: lifestyle entrepreneurs know the value of outsourcing. In fact, small businesses often center their success around outsourcing the tasks that used to have to be completed by an in-house team.

Technological advances have made it easier than ever for businesses to outsource all kinds of professionals, from receptionists and assistants, to entire sales, marketing, and accounting departments. If a function repeats at regular intervals, it’s likely something that can be systematized, automated, and handled by an entirely virtual team.

We’ve written plenty of articles about why businesses should take advantage of virtual assistants and tips for succeeding with virtual help, but at the heart and center of it is this idea that the virtual assistants take these everyday, repeatable tasks – the social media posts, phone calls, copy editing tasks, etc. – and complete them as if they were a part of the actual in-house team. There are cost saving benefits on top of time saving benefits and increased efficiency – all details that are familiar to the lifestyle entrepreneur who’s comfortable handing off a thing or two.

The business style of a lifestyle entrepreneur isn’t for everyone, but it’s a growing trend that’s here to stay. It’s likely that technology will continue to empower these kinds of people to get out there and craft the life they’re excited to live. May they continue to bring us innovation and inspiration (and maybe a little envy for their laptop lifestyle!).

How To Actually Take a Vacation as a Small Business Owner or Entrepreneur

Small business entrepreneur vacation blog

If you’ve read our article on Why Business Owners Should Be Comfortable Taking a Vacation, you understand just how beneficial a vacation can be for your productivity, creativity, and overall well being. The thought of going on vacation is an exciting one for most people, but when you’re a small business owner or entrepreneur the idea of time off can be somewhat daunting.

Instead of booking flights and planning the details of your excursion, you’re busy thinking about the projects that may get missed or the emergencies that might arise. But vacations are an important part of any working person’s life, regardless if they own a business, and they’re possible if you have a good strategy with a bit of planning.

It can be scary to think about leaving your business behind for a few days or weeks at a time, but we’ve got some advice on how to actually take a vacation and ensure that your business is still thriving when you return.   

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Delegate and Keep Your Staff Prepared

One of the best ways to get your business to a place that it’s well-prepared for your absence is to delegate your tasks – especially the ones you don’t need to be doing anymore anyway. Having a trusted person or group of employees who can handle the bulk of your work while you’re out can ease your mind, and will show you that you can also rely on those people to cover tasks on a normal daily basis too, allowing you to focus on the business and expand your opportunities.      

Having someone that you trust in place to watch the business is only half the battle though. You still have to make sure they’re well prepared to handle the regular tasks in addition to any surprises that may come their way.

Have meetings with your staff well in advance to discuss the types of things they’ll be covering while you’re gone, and run through what-if scenarios to prepare for the unexpected. Train the most important key player as if you were hiring a replacement for yourself, because, in essence, you are (for the short-term anyway). You can leave detailed instructions or checklists for them to access in case they’re still unsure of something while you’re away, and if you’re still not comfortable, set aside a window of time when they can call you each day, just to check in if nothing else.

You may find it useful to do a test run before you actually leave, to make sure everything runs smoothly, or you can take a shorter vacation the first time around and gauge future trip lengths based on how it goes.

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Set Boundaries Ahead of Time and Make Them Clear      

If it makes you more comfortable to check-in here and there on vacation that’s fine, but set your expectations ahead of time and stick to them. Let your staff and fellow vacationers know so they can make plans around them.

Realistically speaking, if you planned ahead and prepare your staff for your absence there won’t be a need for daily check-ins anyway – and it will be better for everyone if you don’t plug-in quite so often. But a block of time here or there probably won’t hurt anything, especially if people know to expect it ahead of time. If your staff has questions, they can wait until you’re available to answer them, and likewise, your family or friends will understand that you’re taking the time so it won’t disrupt any plans.   

If you decide to have scheduled check-ins though, make sure it’s clear that this is the only time you’ll be doing work stuff while away. If you’ve set up boundaries that people know you won’t be working outside of, your work won’t disrupt your vacation nearly as much. If that means you have to turn off your phone or mute notifications outside of these times that’s fine, but you’ll get more out of your vacation if you can unplug often, and your fellow vacationers will thank you.

Let Customers and Clients Know You’ll Be Away

This is especially important if you’re the one that does most of the legwork when it comes to interacting with customers or clients, but it’s a nice courtesy even if you’re somewhat removed. Let them know exactly when you’ll be gone and who best to reach out to if a question or issue arises so that there aren’t any surprises.    

If you have multiple people taking over for you while you’re away, let these employees know ahead of time who will be able to answer which particular types of questions, and then make a list of those people to send to your client so they aren’t getting bounced around if they call.

Preparing your employees and your clients ahead of time increases trust for both parties and sets you up for success, so it’s a win-win situation.  

how to take vacation small business owner entrepreneur blog

Be Okay with Almost Perfect

The reality of the matter is, regardless of how much you prepare, things still might not exactly go as you planned. If you go into your vacation knowing this, not only will you be able to relax better while you’re away, but when you get back you’ll be able to use the issue as a learning experience, rather than a reason to panic.

If you trained your staff well before leaving and set them up for success, the mistakes they do make – if any – are likely going to be minor. With all of the resources you empowered them with before leaving (and with a periodical check-in if it’s needed), they’ll realistically be able to handle anything that comes their way.

If you handle the mistake with a cool head upon returning, your staff will feel more confident when you decide to leave again in the future and will know how to avoid the same mistakes again.

Schedule That Vacation

It can be easy to fall into the trap of thinking that your business will fall apart without you there 24/7, but in reality if you and your staff are prepared, you’ve set up the right expectations, and you have fail-safes like check-ins in place, things are probably going to run just as smoothly as they would if you were there.

It may take a few times of you taking a vacation before the process is perfect, but each time you can fine-tune it until you feel comfortable stepping out whenever it’s needed. Empower your staff, set the necessary boundaries, make preparations, and trust the process if you’re ready to get out there and go on your next adventure.

Why Business Owners Should Be Comfortable Taking a Vacation

Business owner entrepreneur vacation blog

Come back in two weeks for our follow up piece about how to get your business to the point where you actually can take a vacation.


As a recent Forbes article by Victor Lipman pointed out, America is becoming the “No Vacation Nation.” So much so, in fact, that 47% of Americans didn’t take all of their vacation time last year. And while the reasons for not taking the time off varied slightly (“too many projects or deadlines,” “decrease the chance for advancement,” and even being pressured not to take one by their manager), the bottom line is, American workers simply aren’t taking time off – but they should be.

The effects of not taking time to recharge can be felt by anyone in the workforce but can be especially hard on entrepreneurs and business owners who tend to put their all in the company they worked hard to build. Taking a vacation is about more than just travel, though. Studies show that our productivity dips after logging long hours for an extended period of time (CNBC), so burning the midnight oil might actually be doing more harm than good in the long run.

There are a countless number of benefits to unplugging and taking a little “me” time every once in a while. Here are a few good reasons why business owners and entrepreneurs should be comfortable taking a vacation.  

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Recharging Is Good for Your Brain and Your Body

Working non-stop all the time can really take a toll. In fact, a study at the University College London found that people who worked more than 55 hours per week had a 13% greater risk of heart attack and were 33% more likely to suffer a stroke when compared to those who worked 35-40 hours per week (Harvard Health Publishing). So being overworked is about more than more than just a little-added stress.   

Being stuck on “go” for so long can leave you mentally drained as well, which leaves you vulnerable to making mistakes, and zaps your creative energy. Sure, you’re making it through the day-to-day stuff just fine, but are you still finding it easy to come up with exciting new directions for your business? If not, a small break from the grind might just be the thing that gets those juices flowing again so that you can get back to innovating.

And if you’re looking for a reason outside of a good mental charge, studies have shown that spending some time outdoors can improve memory, help ward off depression, and lower blood pressure to name a few. Business Insider recently listed off 12 science-backed reasons to spend more time in nature and, I don’t know about you, but I don’t think I need much more convincing.

Unclog Your Thinking Path to Find a New Perspective

Sometimes the best way to gain new insight on a problem or project you’re working on is to disengage and find a new perspective once you’ve had some time away. Not to mention the fact that being away from your business will force you to see it in a new way. A new outlook can show you how the business can operate without you there since by leaving you will have of course left it in some capable hands.

Often you’ll hear that a business owner actually missed working while they were away – and that’s great! That means that you’ll come back into work eager and ready to produce at your full potential. Without the break, you may have been so stuck in the motions you were really not thinking about why you were doing them in the first place. You know what they say, distance makes the heart grow fonder.

You’ll come back with excitement and some new ways of looking at things, and hopefully with a deeper appreciation for the people you’ve chosen to share your journey with. Looking at things from the outside can often help you truly see them, so take a step back every once in a while, and see what kind of perspective you can gain.

Find New Inspiration

You can’t have a new perspective without a wealth of new ideas. Just the mental and physical break alone is likely to open up your channels for inspiration, but add in the change of scenery and routine and you’re likely to find some killer insight that may have previously been blocked out by stagnation.

Staying in the same setting for too long can have a surprisingly negative impact on thinking. In fact, pretty high up on Inc.’s list of 25 ways for entrepreneurs to find inspiration is to find new surroundings. It’s been shown to boost creativity and increase productivity, and not stepping away every once in a while can have an adverse effect. You fall easily into a routine, your blinders go up, and you sort of just go through the motions.

Out on vacation, you may meet someone whose conversation sparks a great new idea, you may see a new way of doing things that you may never have thought of before, or maybe you’ll simply come back to work and be able to see things through a new lens. All of these outcomes would be great, but you won’t have any such opportunities behind your desk every day of the year.


If your business is at a point where you feel like it couldn’t possibly run without you, consider reevaluating a bit to find out what it needs to get there (and check out our next blog post for some tips on how to do just that!). You won’t be able to sustain at 100% the entire time your business is running, so why not start figuring out how to get it to a place where it could stand on its own to legs for a while without you?

The evidence for the benefits of vacation is quite convincing, and at the end of the day, stepping away from the job every now and then will pay off in the long run. So book that cruise, plan that week-long hiking trip in the mountains, or even take a long, relaxing weekend with the family. Close your laptop, turn your phone on silent, and go find out what a little time off has to offer for you.    

5 Ways to Start Working On Your Business, Not In It

working on your business not it in blog

Maybe this scenario sounds familiar: a client has a question about your product or wants to change some minor details in their account, so you hop on the phone and offer them some support. You spend a few hours each day sending outreach emails, connecting with potential clients on LinkedIn, or even making cold calls in order to grow your client base; or maybe you’re pouring over financial documents and budgets, or putting some final edits on web content and blog posts until everything looks just right.

You push yourself to the limit and because of that your business is thriving, but you notice that you haven’t seen much growth in a while. You’re happy with where you are at, but you know that your business could reach greater potential if you could just push a little further, maybe put in a few more hours to start seeing the payoffs.

But there are only so many hours you can put in before all of your brain power and energy are spent on the day-to-day things, and you can’t even think about growth, let alone concepts like diversification, innovation, or any of the things that brought you here in the first place.

If any of these situations sound like you, don’t fear! You aren’t suffering from a lack of motivation and you certainly haven’t lost that fire that brought you here in the first place, you’re simply working in your business rather than on your business.

Here are five ways to turn the tables back around to start working on your business once again.

Put Aside Time for Dreaming

Working on the day-to-day stuff is fine, especially early on in your business when time and budgets are limited. But if you’re finding it hard to put aside the time needed to plan and strategize the big picture, then make that time.

Add a block of time to your calendar each day – it can be an hour, 30 minutes, whatever you can spare – and make sure you don’t do anything else during that time – ever. Treat this block of time as if it was a meeting with your most important client or a phone call with a potential investor. Anything you aren’t likely to push aside for other tasks.

If you aren’t growing or innovating your business, there may not be as many of those big client meetings or investment opportunities as there would be with a clear growth plan in place. A small investment in time now can pay off big later.

Systematize What You Can to Make it Repeatable

Efficiency and repeatability are the grease that gets those squeaky business wheels really rolling. If you’ve got tasks that get done at a regular interval and with an almost identical process each time, consider documenting the process to create a system. Once the system is in place, someone (ideally not you) should be able to follow the steps and carry out the project with little difficulty and a small margin of error. The more of these systems you can put into place, the more efficient your business will be, and the more smoothly things will run over time.

Now more than ever, some of these day-to-day tasks can even be automated, so consider looking into the processes that don’t need a human touch every step of the way, and find a software to fit the need. Social media automation is a great example of how this can work. You or someone on your team can write a batch of social media posts at the beginning of the week and set them up in a system like Hootsuite to post them automatically throughout the week on your chosen schedule. It’s quicker than writing a new one each day, and lets you keep your mind focused on other things for the remaining days.

Outsource the Smaller Tasks

Building off of the idea of systemization and automation, if you have tasks in your business that are simple and repeatable, but don’t quite merit hiring a full-time employee, consider outsourcing the tasks to a team of virtual assistants. We’ve written about the benefits of utilizing virtual assistant services before, but the basic idea is outsourcing saves you the money and hassle of hiring in-house employees for small tasks where full-time attention isn’t required.

There are virtual assistant companies that offer the basics – answering calls, scheduling appointments, etc. – and full-service companies that can even help fill roles like sales and marketing in addition to the basics. It’s something we at The Admin Center call “teamsourcing” because in a sense they become an extension of your team. So take the time to do some research and find the one that’s right for you.

After the initial set up the process is really like automation. For the tasks that are simple but still require human involvement, outsourcing is kind of the best of both worlds. Some companies will even manage the automations you already have in place, too, so you can really start taking things off of your plate to spend time on the things that need your attention most.  

Hire Properly, Train Well, and Treat Your Employees With the Golden Rule

It’s great to get those small, day-to-day tasks out of house and in the hands of an experienced team of virtual assistants, but sometimes in-house employees are inevitable and making sure they are a good fit can save you endless time and money down the line.

Finding the right people from the start is going to set you up for success now, but training them thoroughly and treating them well are going to set you up for success forever. Give people all of the tools they’ll need to do well on the job, show them your expectations early on, and then empower them with the confidence they’ll need to meet them. Encourage growth and learning along the way, and you may just find that your employees are inspiring you on the business, too.

If you feel like you’re finding the right people and offering adequate training but still don’t have great retention, consider doing some self-reflection; the more you lose people, the more you’re pulled back in, so do your best to not lose sight of this. Are you paying fairly and to industry standards? Is your work environment pleasant? Do people feel heard and appreciated?  

If you treat your employees with the respect you’d want to be treated, they’re going to return the favor. Not only will they do their job well, but they’re more likely to go above and beyond, really maximizing their capabilities to ensure that you achieve the change you want to see in your business.

Trust That Someone Else Can Do What You Can

No matter how much time you put aside, regardless of the solid systems you have in place or the superstar teams you’ve hired, if you can’t let go of the little stuff, you’re never going to make it out. It can be very tempting to feel like you’re the only person who could possibly perform some of the tasks it takes to run your business. You did them in the beginning and now your business is a success, so of course at times you’ll feel like you’re the only one who knows how to do them just right. When it comes to the small stuff that keeps your business running though, a little bit of trust will set you free.

In reality, that team of outsourced experts is going to have no trouble at all churning out those simple, automated tasks that you sent to them (you know, the ones you set up efficient systems for; the same ones they do for countless other businesses successfully), it’s literally what their business is set up to do. Their model thrives on doing great work just like yours does, and they’re bound to manage your business needs above their own even, often putting their clients first, so it’s safe to say you’re in good hands.

And what about those employees that you hired, tirelessly trained, and work so hard to nurture? If you trusted them then, you can trust them now. At the end of the day, your success is equal to theirs, so they’re going to make sure they’re doing what they can to make it happen.

If you find yourself working in your business and start losing hope about all of those things that fit into the “working on your business” category, consider taking a step back to assess that things really are set up the way they should be. Chances are you’ll find some processes that can be automated, some tasks that can be outsourced, and some quality people that can take some of the load so that you aren’t the only one bearing it.

Your business will always require a bit of you in it – that’s why it’s your business in the first place – but take advantage of all of the possibilities out there and starting working on your business, rather than just in it.