Over the Thanksgiving holiday I’ve been thankful for many things, especially my jobless state, the ability I have to spend lots of time with my family without having to rush back to work & a future that looks so bright to me.

During the holidays I’ve also heard my fair share of ‘times are tough’ stories and people lamenting their lack of work, underemployment and feelings of fear because of financial pressures. I listen and feel bad, I often try to help by explaining ‘oh you could do this and start your own business’ but too many people nod yes, but in their hearts know they’ll never take the plunge.

So for all of those that think they can’t do it or are scared of the ‘what ifs’ of working for yourself, I decided I’d put together a post and list the 21 reasons you should work for yourself. My hope is to point people to this post in the future when they ho-hum around entrepreneurship in favor of just complaining about the man. I also hope that those of you who are on the path to freedom through producing (not consuming) will be encouraged and invigorated by reviewing the 21 reasons your life is going to rock.

21 Reasons You Should Work for Yourself

  1. You set your own number and don’t stop till you get there. In a traditional job you can guesstimate what you’ll make over 2,5 or 20 years – but you never know for sure. Yes, in an ideal world you could make $50,000 a year as a mid level manager, but you could also get fired or your company could go under. You can work 80 hours a week for 10 years and if you saved every penny and didn’t spend anything you may have 5 million in the bank – but you also may be divorced, have kids that hate you and go to bed with a tallboy every night. If you work for yourself you set your own number, you say “I want to make $5,000 a month to be happy” or you say “$10,000,000 in a lump sum is what i need to do whatever I want, whenever I want, wherever I want… for the rest of my life”. Don’t be a slave to other peoples numbers, set your own and then don’t stop till you get there.
  2. Your schedule works for you, not the other way around. Some people are ridiculously productive working 2 hours a day, others need to put in 20 hours a week, but few people operate at their peak productivity 40 hours a week with no breaks, working for someone else. A vast majority of that time is wasted while you IM about how much you hate your boss or stare at the wall wishing for a quick death by instant coffee. Working for someone else means your schedule isn’t your own. You have to meet deadlines and do things that don’t contribute to your ultimate success and don’t allow you to be the best you can be. Work for yourself and every minute you spend on your business will be one you want to maximize, because you’re not getting anything out of bs-ing for two hours – instead your schedule is more of a wham, bam, thank you mam type of deal – where you work until you don’t need to do anymore and then have the rest of the day to do whatever you like.
  3. You can be yourself. Does dancing naked inspire you? Does lying on the floor, doing breathing exercises help you get into the zone? Could you do either of these forms of self expression & release in a typical work environment? No… and please don’t try! But when you work for yourself you can do as you please, you can go to work in your skivvies and hold a board meeting with your stuffed animals if that helps you think. Working for yourself allows you the beautiful freedom of being yourself and once you do it for a while you’ll know you could never go back to the shackles of working for someone else. Leo from Zen Habits talks about how mind clearing and inspirational walking a few miles a day can be, try asking your boss for permission to leave for a few hours a day to exercise & then come back, put in your two weeks notice & start your own business.
  4. You get more than one paycheck. I make money through social media consulting, coaching, finding people virtual assistants and through affiliates. I love this varied income stream because I make money throughout the month, not just every two weeks and the amount always varies. This helps me live the life I want and also contributes to me feeling very secure. I know that no matter what happens, if my business goes under or tragedy strikes, I can always make money through one of my income streams and I can always build new ones if necessary. I love reading Pat Flynn’s income reports, he explains how he makes 5 figures a month through various revenue streams and proves that paying yourself is what helps you grow rich, not skimping on Starbucks’ lattes and cutting coupons.
  5. You can work anywhere. I work at coffee shops, on trains, planes, subways (both the chain restaurant and the thing that takes you from place to place). I work in bed sometimes, while traveling and occasionally in bars (hey, nothing beats writing with a buzz!). When you work for yourself you aren’t constrained to a physical office and often you can operate your business anywhere on the globe with an internet connection and laptop. My friend Colin travels the world while building an awesome business empire and his constant traveling only makes him more productive and creative, not less. 
  6. You can do what you love. There is a lot of arguing between whether you should start a business around passion or around goals, my friend MJ talks about it at length in his book The Millionaire Fastlane… but I think overall what matters is going towards something you love. If you love the idea of living on Lake Como after you’ve sold your business for $25 million, then go for that. If you absolutely love green living and want to change the world by helping people save the environment, go for that. Do what you love whether it’s money, people or hobbies… if you always go towards what your passionate about you’ll consistently have the energy to succeed when others are failing. 

    beautiful Lake Como

  7. You’re the life of the party. Whenever I go out the inevitable ‘what do you do’ question comes up. Most people have to say boring things like “banker”, “real estate” or “open heart surgeon”… but I get to say (with a smug smile on my face) “I’m an entrepreneur!”. This always takes the cake and people will pepper you with questions on how you started, how your business is doing and how they can get out of their job and work for themselves. Also you often get free drinks out of the ordeal as people feed you liquor in return for ‘start your own business’ advice.
  8. You can live an unconventional lifestyle. When you work for yourself you’re not bound by typical constraints and this gives you the freedom to live a funky lifestyle. Maybe you get your best work done at night, or maybe you are the most alive when you’re kite boarding like bad ass business person & world record holder Tammy Camp. So think about what kind of life will make you the most happy & then go for it, be as outrageous as possible – the best business people I know live some of the most extraordinary lives.
  9. You can find inspiration anywhere. Because I work for myself I’m constantly on the look out for inspiration. Having a ‘breakthrough’ day can mean I try a new marketing strategy that will double or triple my income in the next 6 months and inspiration is key to reaching new heights in business. Since I don’t have a boss breathing down my neck I search for inspiration on trains, in parks, at the movies and in books at all hours of the day. Sometimes I dedicate a whole day to seeking inspiration from unusual places and then applying what I’ve learned to my business. Inspiration isn’t found under fluorescent lights or behind computers, its found by being out in the world & opening your mind through experiencing new things.
  10. You can change early and often. When you work for yourself you have a flexibility few possess. You can quickly change paths or switch routes on your way to achieving your dreams without having to cut through red tape or ask permission. Since I started in entrepreneurship at 19 I’ve probably gone through 10 businesses and 1000 ideas before really striking on the one (outsourcing) that I know is my calling. Being able to change early & often as you pursue your dreams will allow you to trounce your competition and keep up with companies who are 100 times bigger than you.
  11. You can yell at your boss. I do it all the time. I’m constantly getting into fisticuffs with my employer but it’s great because at the end we both realize where we went wrong and have put ourselves and the business back on the right track. Many days I’ll look in the mirror and listen to my boss tell me to pull it together, she’s a little mean and sometimes calls me a slob when I go to work in my pj’s – but for the most part her tough love forces me to be productive. Also knowing that me and my boss are spending the rest of our lives together makes me try harder to please her and even if we get into a tiff we always make up and get back to work with a new found vigor.
  12. You can be frugal. Often big businesses let millions slip through the cracks in expenses that are unnecessary and frivolous, but when you are calling the shots you can be sure to pinch pennies where it matters and spend on what’s important (instead of the opposite approach). Being frugal and bootstrapping until it hurts is foreign to most businesses, but it’s a lesson start ups know well. That’s why companies can go from $400 bucks in the bank, working out of a basement, to a billion dollar valuation in a few short years. Start ups who live on beans and rice and only spend money on what’s important thrive while old school business models die.
  13. You can build your dream team. Through outsourcing and hiring freelancers you can build a dream team of savvy experts that will allow your business to expand exponentially. You don’t have the freedom to do this working for someone else and even if you did you wouldn’t have final say in what projects they go after and how to best apply their skills. When you work for yourself you know you’re the main person who benefits from your businesses success, so you’ll be sure to hire a team that’s excellent and manage them well. 
  14. You can live where you please. Very much like working where you want, when you are an entrepreneur you can usually live where you want as well. Often it’s cheaper to start a business in Chile or Thailand (especially online) and if you’re getting paid in USD or Euros your quality of living will skyrocket as well.
  15. You don’t have to suffer fools. One of my biggest gripes when I worked for other people (serving, tending bar and at night clubs – **shudder**) was suffering fools. I have never worked at a place where I thought ‘this is efficient’, instead I had to deal with idiots who had been stuck in their ways for 15 years and refused to listen to potentially business saving advice. Some of us have good business minds and it is intolerable to put up with people who don’t, especially those who are in positions above you. You’ll just waste your breath, your time and infuriate yourself trying to explain a better way. Even if they did listen, you’re good sense will help line their pockets not yours – so if this sounds familiar, do yourself a favor and stop making other people rich.
  16. You can do whatever the flip you please. It’s true, when you are your own boss you can really do whatever you want. I mean if you do whatever too much and don’t work enough you’ll go broke and end up sleeping on couches – but if you balance total freedom with dogged hard work you’ll lead quite an enjoyable life. I often leave work in the middle of the day and go see a movie, take a walk or people watch – it helps me become more productive when I get back and it’s a great stress release to walk out of the ‘office’ whenever ya please.
  17. You can be healthy & hot. Working in an office 8 hours a day is NOT good for you! Nasty lighting, ugly desks and hideous chairs don’t help your lumbar and they don’t help your psyche! When you work for yourself you can exercise more and spend more time feeling and looking good. This in turn makes your business better because it gives you, the owner, more self confidence and pizazz! I’m taking up running, yoga and dance shortly & it’s all possible because of my flexible schedule and awesome work routine. Being healthy and hot may not seem like it goes hand in hand with a good business, but try it for a few weeks and see if you don’t notice an important in both your personal and work life!
  18. You can strive for your dreams. Have you always wanted to own a private jet, or spend 10 years helping kids in Africa lead better lives? With a traditional job you won’t be retired until 65 and then only .01% will have the funds to chase their dreams and make an impact on the world. Don’t wait till you’re ‘retired’ to strive for your dreams, instead make an impact today and begin projects that will leave a legacy while you work for yourself.
  19. You can be there for your family. I don’t personally have a family yet (Well I mean I have my family, but not a family I married/gave birth to/adopted), but I know that if I did I’d want to have a lot of flexibility when it came to spending time with them. If you work for yourself you can arrange your work day to flatter your family time, not to trump it. Too many times people miss their kids growing up, neglect their significant others and lose out on one of the best parts of life because of incessant work – don’t be ‘that guy/gal’ instead create a lifestyle that allows you to focus on what’s important.
  20. It’s easier than you think. You can start a business for under $100 in this day and age, just grab a URL, brainstorm a business idea & throw up a website. You can test your assumptions and only go with what seems like it has a bright future, while you still work for the man and keep ‘safe’. Or you can be like me and take a plunge, forcing yourself to succeed by giving yourself no options if you fail. Starting a business that’ll change your life may seem daunting, but in reality it’s not as hard as working 40 years for someone else.
  21. You’ll be forced to be creative. When you work for yourself you can’t just ‘coast’ on the highway of life, which I think is an excellent thing. Instead you have to constantly stay on top of things, making sure your business and life doesn’t go off the rails. This adds to excitement and fulfillment in ones life as you have a solid purpose and often get great satisfaction from the work you do. Don’t allow yourself to be part of the mainstream anymore, instead start working for yourself and get scrappy, get creative and build something you’ll be proud of in years to come.

I hope this has convinced you that it’s time to start working for yourself, recession or no recession. There has never been a better time to start a business since most people are scared and clinging onto safety harder than ever. This gives you the perfect opportunity to soar to new heights as the majority of cry babies complain about their life but refuse to do anything to change it.

Did I miss anything? Do you have a few reasons of your own why people should work for themselves? If so please let me know below and shout out if you’ve already kicked ‘the man’ to the curb and are pursuing your dreams by working for yourself.

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  • Specialkay78

    Love it! Another great one, Marin.

  • http://www.bradleygauthier.com Bradley Gauthier

    Number 8 is my personal favorite! Great list!

  • http://twitter.com/gwil Garrett Wilson

    Loveeee ittt! All very true!

  • Mike Crosby

    Hi Maren–Enjoyed the post.

    I'm fortunate to be self-employed. It's been well over 20 years, and I've never regretted it. I went and actually got a real job a few years ago, it lasted 2 weeks.

    I'm just not meant to work for anyone. This week I worked 8 hours and made what used to take me 3 months working for the man. And this I plan to do till I die.

  • http://rawfoodswitch.com Nathalie Lussier

    I'm finding #17 to be especially true since I started doing hot yoga… it's like everything shifts and gets easier. :)

    Love your list!

  • http://twitter.com/brettalanseo Brett Alan

    Great article. I find it interesting how many people will work 40, 50, maybe even 60+ hours a week for their employer in hope of a 2K raise at the end of year and maybe a slight title change after a couple years. Yet, they are unwilling to put in 10 hours a week to start a business that could be providing much more than the amount of your raise over the course of a year. Sounds cliche, but it's just one of those mindset things.

  • http://pluginid.com Brett

    Yes. Yes. Yes.

    This whole post encapsulates why I feel like I'm a born entrepreneur and am willing to fight through the grind for the freedom that I desire so much.

    My dream: never work a job that I hate. I want to make that a reality.

  • http://www.tammycamp.com Tammy Camp

    Hey Maren,

    Oh the unconventional lifestyle indeed! Well, no backing out of it now for me because I'm unhireable at this point ;)

    Tx

  • http://twitter.com/PursuinSerenity Pursuing Serenity

    Great list! I started my first site last week. It's so exciting!

  • http://www.upgradereality.com Diggy

    Hey Maren,
    I hope you had a nice Thanksgiving! I agree with all your points about working for yourself, but it takes courage and persistence to be your own boss and build your own business.

    I've recently quit everything I'm doing and giving myself until the end of next year to make my online business a success with at least $5000 a month steady income.

    When I achieve that, then I have the freedom to live where and how I please, which will be a huge weight off my shoulders.

    I can tell you that it's really scary and uncertain, yet at the same time it's the most awesome adventure that you can go on.

    Enjoy the festive season and keep rocking!
    Diggy

  • http://twitter.com/Yakezie The Yakezie

    Good list Maren! The freedom is probably the most important aspect of working for yourself. No rules, just our own.

    However, I have to say after filling out my 2011 benefits package online, that having that security for health care sure does feel good.

  • http://www.megabizflakes.com samuel

    Awesome post Kate! I agree with your points. Thanks a lot for sharing. Have fun.

  • http://harvestwages.com harvestwages

    Nice post Kate,

    i recently wrote a post about the “don't quit poem”. yet some of my audience were troubled.

    The 'don't quit poem' actually encourages us not to quit so soon, or give up.

    With this post, you encourage the self employed and some how tell the employed to 'QUIT' – 'you won't make it', ' this is not where you belong'.

    I'm also troubled, Can i know when not to quit my occupation?. How to identify what to stick to; is it when I feel happy about doing the job?

    Some people are still happy with their 9to5 jobs and don't even have 'quit' as an option, even though they complain about their boss and their underemployment state.

    i just think some are even afraid to make it in life – they are afraid to succeed. They won't apply the 'law of action' after reading this post, yet the smart would step for it.

    I only grow happier since i started paying myself.

  • http://pulse.yahoo.com/_3IKLMLXHL25GHZSI2E2UTR5RM4 Margaret

    What a nice pep talk. However, I started my own business @ six months ago, and it's essentially gone nowhere. Yep, time to retool, but unless something takes soon, it's back to working for the Idiot Man, trying to keep my mouth shut and my ideas brought to heel, in the near future. : (

  • http://www.singlemomfreelancewriting.com/ Jennifer

    This is a post everyone who is whining about not being able to get ahead needs to read. I feel sorry for my friends that keep waiting for their life to get better. Doing the same thing day after day when it comes to work is not going to do it. There are just some people who have yet to realize this important truth.

  • http://www.Escapingthe9to5.com/ Maren Kate

    It's true Jennifer, today was an especially hard day for me work/health (food poisoning from duck!) but still it was 150% better than working for someone else, I got to sleep in, take my time on my work & I still love every minute of it.

  • http://www.Escapingthe9to5.com/ Maren Kate

    Hey Margaret – that stinks! I've had so many start ups fail before hitting my stride. If you'd like to shoot me an email & let me know where you're at maybe i can help ya get back on the right track – feel free: marenkate@gmail.com

  • http://www.Escapingthe9to5.com/ Maren Kate

    If you are happy with your job, really truly happy, then I guess I'd say don't quit. But if you aren't – which seems to be 90% of the employed – then start a business on the side and quit when you can, or get really gutsy and quit before your ready. This will force you to get up and going.

  • http://www.Escapingthe9to5.com/ Maren Kate

    thanks samuel :)

  • http://www.Escapingthe9to5.com/ Maren Kate

    Oh gosh, you're telling me, I just paid $1200 for a 50 minute doctors visit and actually cried as I wrote the check – I don't know why but I just felt so angry over the whole thing.

    So sad… one day I'll have insurance again :) until then I'm just drinking lots of green tea and taking lots of vitamin C!

  • http://www.Escapingthe9to5.com/ Maren Kate

    You're going to do so well! That's a great goal ($5000) because when you are location independent bringing in 5 grand a month is more like 10 and you can really do anything you want! I can't wait to watch you succeed and surpass that goal!

  • http://www.Escapingthe9to5.com/ Maren Kate

    What's the site?

  • http://www.Escapingthe9to5.com/ Maren Kate

    You and me both! It's scary, fun & exciting knowing that you really don't have the option of working for someone else… keeps me on my toes in a big way.

  • http://www.Escapingthe9to5.com/ Maren Kate

    That's a great dream :) My dream is similar: do whatever i want, whenever i want, wherever i want. This really helps me stay focused when the entrepreneurial waters get tough!

  • http://www.Escapingthe9to5.com/ Maren Kate

    I know I've never gotten it, I always feel like it's so much better to make yourself rich – not someone else, alas, different strokes for different folks! But I can barely work 40 hours for myself, much less someone else!

  • http://www.Escapingthe9to5.com/ Maren Kate

    I'm starting to run in the morning & it really makes a difference to my daily productivity – I feel better about myself and not like such a pile when I spend 5 hours in front of the computer after!

  • http://www.Escapingthe9to5.com/ Maren Kate

    Awesome Mike! That is how it should be – working 40 hours = 3 months worth of pay is so the way to do it!

  • http://twitter.com/HomeBizTaxCoach Derrick Carpenter

    And of course there's my personal favorite Business Tax Deductions (which get even better if you're a home-based business ;-) )

  • http://twitter.com/Yakezie The Yakezie

    Wow, $1,200 bucks for a 50 min doctors visit? I hope s/he helped you out with whatever you were seeing him or her for!

    You're incredibly fit and sound like you eat very healthy, so I'm sure you'll be fine! Hope you had a great Thanksgiving weekend and hope to grab a drink with you in SF the next time you stop by!

    Ciao, Sam

  • http://twitter.com/micburns mic burns

    Love this post Maren – It has been the perfect accompaniment to a morning coffee.

    So many points you raised make complete sense to me, but more importantly add reassurance that I've done the right thing (recently quit my “real” job last month after 6 years of.. distraction!).

    I think most people know they should be in control of their own destiny, but need a kick in the a**e to get them on their way – for this reason I've fwd this post to a couple of friends over twitter and facebook as ammunition for common sense!

    Take care!

  • http://www.nicholastozier.com/words Nicholas Tozier

    In the tags: “work for yourself, you can.”

    :D

  • http://castlesintheair.org Nina Yau

    Love your list, Maren! Your tip on looking healthy and hot, so true with many of our digital entrepreneur peers! I currently kick serious ass doing martial arts and can't say a lot of people who struggle on their way to training can say they're doing it just for kicks and giggles. What they really want is to put their boss in front of the training pads and punch his lights out, but alas, they'll just have to suffer punching the stupid pads instead. :)

  • Carolina

    Hi, I find your idea very interesting. The only issue you don't talk about, is retirement and healthcare. I mean, how will you support yourself when you're too old to work? or you don´t want to work anymore because you're 65 and tired.
    And what happens if you get ill and can´t work for several weeks or months? (in my country all that circumstances are covered by the employer).

  • http://lovedeedums.blogspot.com/ LoveDeedums

    Your post is a great Rx to those Sunday night doldrums. I'm posting this gem in my cubicle so I can stay motivated every time I accept another time-waster meeting request.

  • http://www.bripblap.com Steve

    Great list – as someone who's about 50% of the way to entrepreneurship after a half-career in corporate America I can say that all of those points are very appealing, and the reason they appeal gets clearer and clearer the longer I stay away from a job and do more and more consulting and similar entrepreneurial activities.

  • http://www.Escapingthe9to5.com/ Maren Kate

    Oh true, didn't think of that one!

  • http://www.Escapingthe9to5.com/ Maren Kate

    Thanks for sharing it! Glad you liked it :) i hope it helps others start working for themselves

  • http://www.Escapingthe9to5.com/ Maren Kate

    haha, thought i may as well try for the allusive “you can” keyword – it starts so many great searches! Example: “You can be a ninja” “You can do it” “You can't do it” :)

  • http://www.Escapingthe9to5.com/ Maren Kate

    Gosh that reminds me, I really want to get really good at martial arts – it'll take some time but I want to know I can kick butt like Jackie Chan if the moment happens!

  • http://www.Escapingthe9to5.com/ Maren Kate

    That's why you create your own number, like mine is high enough that when I cash out with that number (i.e. sell my business) I will be paying myself via super passive income (mutual funds, bonds, etc.) for the rest of my life. You can make sure you're always taken care of if you really kick butt in business now.

  • http://www.Escapingthe9to5.com/ Maren Kate

    P.S. There are also a lot of good independent health care options for people who work for themselves that are pretty affordable, just do some research on Google and you'll find myriads.

  • http://www.Escapingthe9to5.com/ Maren Kate

    Awesome! Stupid meetings, they pain me like nothing else :) let me know when you make your escape and we'll clink virtual glasses over it!

  • http://www.Escapingthe9to5.com/ Maren Kate

    That's awesome, so you are half of the way there! It's great to do it step by step because you get to keep some security while building your own thing on the side.

  • http://www.livecollarfree.com/ James Schipper

    Good list, Maren! The best part is the list just seems to keep growing :-)

  • http://www.alemja.net Alexandra Jackson

    This is something everyone should read, to make them realize they have options, even if it just becomes a side thing on top of your other business ventures.
    The thing I noticed with online businesses, blogs in particular is that while they make time to to learn at first and you will run into walls. However once you get past the hard part they slowly begin to build themselves. I don't quite consider myself over the hill yet but I'm getting there, and it's creates a great feeling when things start clicking.

  • http://twitter.com/TheSoulReporter Nikki Di Virgilio

    Love this. Thank you. Encouraging and supportive. I just quit my job, took the plunge. It's exhilarating. I appreciate your words, and will seek this kind of support more often. There are enough nay-sayers.

  • http://www.facebook.com/profile.php?id=1624233653 Cynthia Cano

    Brilliant! Thank you for this post. I've been looking at how to set myself up as an entrepreneur and you've given me some confidence now to move forward. *HUGZ* xx

  • http://www.investparttime.com Brett

    Hey Maren,
    Thanks for putting up this list! These are some great and motivating points. I am still working part time, but am working hard at putting together a business on the side so I can eventually make the move. It's only a matter of time!

    Brett

  • Justin Guzman

    My lizard brain just wont let me take the “plunge” quite yet. Well… neither will my wife heh. I am ever slowly moving towards a business online. What I find is that you can become quite lazy if you still have a full time job, because there is a fallback option. I see that those who take the plunge and have no other option but too succeed, more often than not, come out on top. Those that dip their toes into the pool have a hard time generating the energy needed to rise to the top. Sorry just thinking out loud in the comments here.

  • http://www.LittlePinkDesigns.com Micah

    Great Post Maren! My wife and I started our first business a few months ago online http://www.LittlePinkDesigns.com. It is still early on but we are very excited.