Corbett Barr

Lifestyle Business Weekly

27 Things That Are Far Better About Working For Yourself than Working for the Man

I’ve had the pleasure of working for both myself and working for “the man” over the years. Small businesses, Fortune 500s, government, you name it, I’ve seen it.

It’s true, working for yourself can be frustrating, scary, difficult and a constant struggle. On the whole though, to me, working for yourself is the ultimate in personal freedom and fulfillment.

For everything about being self-employed that is a struggle, there are tons of other things that are WAY better than working for the man. I’m going to share 27 of them below. These are from my direct experience. Your experience may differ, depending on your situation and how you set up your business.

Here are 27 things that are far better about working for yourself than working for “the man.” And I’d love to hear in the comments what your favorite aspect of working for yourself is.

  1. You have no one to blame but yourself. Yes, this is a good thing. Looking for other people to blame is a waste of time.

  2. You measure your progress in terms that matter like audiences built, products created, and profits earned instead of “corporate world” terms like face time, busywork and being a team player.

  3. You don’t have to worry about getting a new boss who is an asshole. That is, unless you turn into an asshole yourself.

  4. Vacation time is nearly unlimited. I just spent three weeks in the Pacific Northwest visiting with friends and family and sailing up in British Columbia. Sure, I worked a little, but mostly I just relaxed and enjoyed myself. How many corporate jobs let you take three weeks or more off in a row?

  5. You decide when you work and when you don’t.

  6. You choose which projects to work on. You don’t have to pursue things you aren’t interested in because you know that following your passions is a better way to succeed.

  7. Drinking during work isn’t frowned upon. Although if you work for an ad agency in the 1960s, evidently it isn’t there either.

  8. You can live where you want to. This applies to location flexible situations like working online. There’s no reason I couldn’t be writing this from Berlin or Buenos Aires or Bangkok.

  9. Casual Friday is any day, to the extreme. Ever feel like wearing a robe around the office? Maybe that’s just me.

  10. You can actually be yourself. Like, your real self, not your “business” self.

  11. Every ounce of effort you put into your business benefits you directly. Having pay related to output is a key factor in job satisfaction.

  12. There’s no commute required. You could rent an office far from your home I suppose, but you’re not gonna do that, right?

  13. Getting laid off isn’t possible. Running out of business or clients is possible, but at least you won’t be kept in the dark until a security guard comes to escort you out one day.

  14. You don’t have to sit through endless, pointless, actionless meetings. It’s a wonder anyone gets anything done in companies where you spend 4+ hours a day in meetings. Imagine what you can do with all that extra time.

  15. There are no goddamn cubicles. I hope in 20 years we look back on the cubicle and realize how sad an existence it is for people who spend 8+ hours a day in them. It’s downright cruel. Like you’re part of the Matrix or something.

  16. The office coffee is much better. For that matter, all the food is better when you work for yourself. No crappy cafeteria, no watered-down office coffee, no lunches at Subway or whatever because you can’t take more than 10 minutes away from your desk. And if you quit coffee, you can ask your boss to start buying tea.

  17. If you get tired of your office surroundings, you can change your scenery anytime. I love being able to work from a coffee shop, or my wife’s art studio, or my Parent’s house or wherever there’s an Internet connection really. A change in scenery can do wonders for your creativity.

  18. You don’t have to feel guilty about doing personal things. Want to leave early to see your kid’s soccer game? How about taking that cooking class you’ve always wanted to that starts at 5pm? What about working out during the day when the gyms are empty? Your schedule is your own when you work for yourself, and there’s none of that worthless office guilt from your boss to worry about.

  19. Who you work with is up to you. You’re in charge of hiring; you get to select the clients; you get to choose the freelancers and consultants. You can choose people who inspire and motivate you and leave out the jerks or boring people.

  20. If you don’t want to do something, in most cases you don’t have to do it. Well, except for paying taxes, that is.

  21. Your income is limited only by your creativity and willingness to work.

  22. No aspect of working for a big company can touch the deep satisfaction and fulfillment you experience from being completely self-sufficient. Knowing that you are completely and solely responsible for contributing enough value to the world to earn your keep is one of life’s great rewards. It’s something you have to experience to fully understand.

Twitter Responses

I asked on Twitter “What’s your favorite benefit of working for yourself?” Here are some of my favorite responses:

  1. Freedom to dictate my day’s schedule and who I interact with. And working till 3am when the creativity is flowing.” – @cstreet10

  2. Flexibility. The ability to work as much or little as I like, when and where I please.” – @kchrist

  3. The flexibility and control over my time and freedom.” – @stanigator

  4. No corporate BS.@cosminsky

  5. Fulfillment.” – @massbehavior

What else do you like (or look forward to) about working for yourself? Please tell us in the comments.

If you liked this post, I would appreciate if you share it with someone who might care or link to it from your own site. Thanks for reading!

photo by gonzalo_ar

Corbett Barr

A weekly curated email of useful links for people interested in lifestyle businesses and independent entrepreneurship.


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  1. I look forward to what I describe as “The Blur”. Where there’s no distinction between Monday thru Friday. There’s no Sunday night anxiety and there’s no TGIF relief. “The Blur” where all days are blendid whether it’s Tuesday or Thursday, you can do your work without anxiety over which day of the week it is.

    • Awesome description, Greg. Although I have to tell you that I find myself still in the weekday / weekend pattern, if only because many of my friends still work a 9 to 5. When we’re in Mexico though, there is very little distinction, and definitely no TGIF / Sunday night dread no matter where I am.

  2. Pam

    Sole control over the temperature of my workspace. Listening to music I enjoy instead of trying to ignore whatever’s blasting over the wall from the cube next door. Not overhearing co-worker’s loud, drama-fueled, profanity-laced personal phone calls. It’s time to kick my exit planning into a higher gear!

  3. Working for yourself also means that you don’t have to deal with bureaucracy to get things done. If you want change then you make it. There’s no need to wait for approval.

  4. On that note, a swell just hit and I’ll be chasing waves down in San Clemente this morning. Good stuff Corbett. You’ll have to come down and catch a few waves here with me one of these days.

  5. Great post Corbett. I’ve been realizing many of these benefits over the last week as I travel the east coast. Although that said, I’ve definitely hit some of the downsides as well. Its kind of tough to prepare for a product launch when hanging out in NYC for the first time. Oh well, no one to blame but myself as you said!

    Bummed I missed you in PDX last week, hope to meet up sometime soon.

    • Hey Sean, I definitely agree about trying to work while traveling. It’s not so easy. Especially when you’re with friends or family who are taking time off. I hope you enjoyed NYC at least. Sorry I missed you in PDX as well. Are you going to blogworld?

  6. Hey Corbett,

    Thanks for the mention. Had 2 previous blog posts responding to reasons 2 and 14.


  7. Erik R

    Gotta say, that NOT commuting is definitely a favorite. I’ve got neighbors who take a 2 hour commute each way (4 total hours) to their jobs, and they have been doing that for over 25 years.

    Imagine that! Lets just imagine that they only worked 180 days during the year. That is 720 hours of commuting. Or exactly one month of their life spent going to and from work.

    Multiply that times 25 years…

    That’s insane!!!

    • Speaking of insane, I once had a 1-2 hour commute each way (depending on traffic). It nearly drove me insane, and it completely drove me to change jobs.

  8. Corbett, this list rocks! Corporate America doesn’t allow for 3 week vacations (I was lucky to get 16!!)

    Working in that deteriorated building all day long–I hope to never return to that. Rock on!

  9. Working from home also means you’re in control of your own life, really. You want to make something happen, make it happen.

  10. Renee

    Sometimes in life, you just need to fall apart, come completely unglued. When you work for yourself, you actually have the luxury to do that! No keeping up the exhausting pretense that everything in life is great. Which paradoxically, allows you to get back to the good parts of life that much faster – because you took the time off to take care of yourself.

    • Haha, great point, Renee. It’s pretty embarrassing when you let the wheels come off at a regular job.

      You know, something else I really enjoy is the ability to take a nap in the afternoon when you feel like it.

  11. These are a lot of the reasons why I work for myself. You do need to be disciplined though and have the right mindset to keep these benefits from becoming detriments.

    For example “You don’t have to feel guilty about doing personal things.” — since I can always be working on something, I occasionally feel guilty for taking time for myself, even if I have put in crazy long hours. Or the “If you don’t want to do something, in most cases you don’t have to do it” –which is true, but I still have to earn a living which means at least for now I do have to work on some projects that I would prefer not to.

    Still, the benefits of working for yourself outweigh any of the negatives.

    • Hey Forrest, great point. I’m not denying there are many downsides to working for yourself, and the need for self-discipline is huge. Thanks for the comment.

  12. When I was graduating college I went to several ad agencies to see what kind of place I wanted to work at. I was disgusted by what I saw. They were basically taking my entire life and any sort of enjoyment I had away from me. So I started my own business straight out of college without any experience whatsoever. I’ve never had a job in my adult life and have been in business for over 8 years. I’m incredibly proud of that.

    I love the freedom. I can structure my days however I want depending on what I want to do that day or in that time period. I love that I can take advantage of opportunities and not be limited by vacation days. In January ’11 I’ll be taking off for indefinite travel… stoked.

    • Wow, congrats on that Jenny. I always admire people who made self employment work out right after college. That’s not an easy feat.

      Good luck on the upcoming life of travel. Let us know where it takes you (and what it’s like for you working on the road).

  13. Doing what you love.

    There’s the innate satisfaction that comes from building something that’s an extension of yourself, it’s what sustains your interest indefinitely.

  14. A great post again! Thanks Corbett! :)

  15. I’ve just started a new business, am super excited, and because this is so timely to me I had to comment. Here’s to firing my boss! (He’s a good guy, but he’ll understand I just can’t afford to keep him on the time-payroll)

  16. Mathias

    I take this personally ;-)

  17. As someone who has hobbies that frequently require 3-day weekends or sudden days off, working for someone else is an exercise in frustration. After years of calling in “sick” all the time I just gave up and decided that working for myself was really the only way. Both my parents were self employed throughout my entire childhood, so the concept of having my time dictated by someone else is completely foreign to me.

  18. great post! and point #3 is really true! LOL!!

    I am still working my way to work for myself… ;-)

  19. I also love the flexibility of thinking that comes over time. It started out of necessity being in business for yourself, but then you find it working in all areas of your life. For my husband and I, it no longer seems strange to alternate living between a house we co-own with a family member, live and travel in our 5th wheel trailer, make prolonged stays at timeshares, and are kicking around doing some overseas housesitting. Every aspect of life opens up for a new interpretation after a while.

    Plus, you get to play at times just off of the peak times for the rest of the world and get to enjoy places so much more b/c there so much less crowded – you then just get your work done at odd times too.

    I’ve always said, I won’t go back to working for someone else unless it’s the very last option I have for putting food on the table. Made the decision to never look back over 15 years ago and we’re still managing to eat – and doing it better than we were 15 years ago!!

    • Awesome examples, Renee. Thanks so much for sharing. And your point about being able to enjoy places off of peak times is worth repeating.

  20. Hey Corbett,
    Great post and it really reinforces the reasons why I want to leave the rat race and earn an income doing something I can be passionate about.

    I have to support a young family and a mortgage so there’s often a feeling that I need to stay in the 9-5 to make ends meet. Posts like these show that it’s possible to do something you love and earn enough to get by.

    Great stuff, Tim

    • I am on the same situation. I have to take care of my family. But I’ve been trying to break the barrier that separates me in the 9-5 box from freedom.

      Like Srinivas Rao, I want to catch those waves. But I can only dream now.

    • It’s definitely harder with a family and mortgage, although I live in one of the most expensive cities in the world and things have worked out just fine.

  21. You can sell your time, but never buy it back. Making time the only value in the world you can not create/duplicate/earn.
    Something so precious, who do you want to sell it to, your boss or yourself?

    People owe it to themselves to stop being a number in a cubicle.

  22. I look forward to not having to justify my every action, decision or whereabouts. I will be more successful on my own terms, meet wonderful people, continue traveling the world and thrive by the sweat of my own brow.

    Felicia, Photographer, Writer

    • Great point, Felicia, I used to hate that constant need for justification. Although my wife has done a good job of taking on that role now that I work from home ;)

    • I share that sentiment. I work in retail right now and I hate having to justify time off, why I came in late, etc. One of these days I’m going to answer “why are you late?!” with “Because it’s a pretty day and I wanted to take a walk. Deal with it.” I already do shirk work for such things, but I hate that I have to make up ridiculous excuses when I do go in.

  23. Ouch on item # 15. Not only cubicle but any 3 or 4-sided box. It’s so lonely in hear.

  24. Boy you said it best..this list hits home a lot..but people have to understands working for yourself can be stressful at the beginning cause you control your pay check..but once you get over that starts to shine..

    “TrafficColeman “Signing Off”

  25. I’m surprised you limited yourself to 27. :-)

  26. These tips are really practical i have to say and i never thought of some of the points you mentioned here. This post has got me really thinking very deep.

  27. Great post- as most of these ideas are true. When I worked for myself last year for seven months it was the best time of my life. However, I didn’t really know what my true passion was and ran out of time and money.

    So now I’m back in the corporate meat grinder, planning my next escape.

    One thing I would add is less stress. When ever I enter the building and glance at the sea of cubicles, filled with over-worked, blank staring employees, it’s extremely hard to keep up with the upbeat, passionate, funny personality I have.

    Corporate environments suck the life force out of you, your easier to manage that way!


  28. I am not in a cubi­cle but a classroom but I am leaving next July then after a family holiday in August, September I start working for myself. Part time at first and working for someone else (don’t know who yet but there’s someone who wants to hire m) part time and then I aim to eventually work for myself full time. Really REALLY looking forward to it. I DO get 13 weeks paid holiday a year off as a teacher which funds my travels but I REALLY don’t enjoy my job and want a change from teaching. So much to look forward to mid 2011! Bring it on!

    For me I think the best things will include:
    (1) Setting my own schedule (to a point, anyway) I mean scheduling work around life not scheduling my life around work.
    (2) I get more choice about what I do work-wise, when I do it, where I do it and for who.
    (3) Working directly with clients. No middle man (or women, in my case) and no
    trying to meet at least three very different sets of expectations and requirements at the same time.
    (4) No government agencies or whoever the hell they are coming in to check on me (us) and threatening to tell other government agencies if we don’t met their unclear and changing criteria!
    (5) More time for friends, hobbies, hubby etc. (see (1) )
    (6) I can pee whenever I damn well want to without having to ask or tell someone and asking them to cover for me and even justifying WHY I need to pee!
    (7) No nasty colleagues. (Most are nice though) If my client is a pain well I will soon be working with another one
    (8) I get to decide what I want to learn on and develop career-wise.
    (9) I can make decisions quickly rather than having to ask five plus people if I am allowed to, no matter HOW good the resource/program is.
    (10) I can take breaks when I want (Yes I will have to be more self-disciplined too but that’s OK!)
    (11) I can walk in the park more!
    (12) I can make a lot less and probably will for a while but I also have MUCH greater earning potential that as an employee.
    (13) I can spend some of my self-employed time helping hubby build HIS growing business which I also really enjoy
    (14) More time to build and
    learn and hone and use the skills and knowledge that i really enjoy
    (15) (In my case) Working with adults for a change, working one on one mostly (nice change from a classroom and I will be able to meet one person’s need at a time rather than have child X fall over, child Y needs their laces done, child Z is hitting child A and child B is crying all at the same freaking time and wanting me to deal with it.
    (16) I don’t have to multi task unless I want to.
    No more doing assessment paper work and talking to kids at the same time, just to try to get it all done so I can actually have a LIFE
    (17) I can see something through to completion if I choose to e.g. make a website rather than I get to work on something then having to switch to something else and so on or i can chunk things as I wish.
    (18) No more boss to frown at me if I wear jeans.
    (19) No more waste of time irrelevant moany meetings
    (20) In a nutshell – FREEDOM, baby!

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