Five Reasons You Might Not Want to Be Your Own Boss | DO 6

Joining the ranks of the self-employed, the world of entrepreneurship and going into business for yourself aren’t the bowls of cherries late-night T.V. and the Internet are wanting you to believe they are. “Time freedom” and “money freedom” are the rewards of “being your own boss” done right, yet they come with a price. Commitment, discipline, hard work and perseverance are the only currencies accepted. Are you prepared to pay it?

If you’re pursuing your passion and you’ve given serious consideration to these five reasons why you might not want to be your own boss, you’ve got a shot. If not, think twice before quitting the “day job.”

“The person who knows HOW will always have a job. The person who knows WHY will always be his boss.” -Alanis Morissette

Should I be my own boss?Joining the ranks of the self-employed, the world of entrepreneurship and going into business for yourself aren’t the bowls of cherries late-night T.V. and the Internet are wanting you to believe they are. “Time freedom” and “money freedom” are the rewards of “being your own boss” done right, yet they come with a price. Commitment, discipline, hard work and perseverance are the only currencies accepted. Are you prepared to pay it?

If you’re pursuing your passion and you’ve given serious consideration to these five reasons why you might not want to be your own boss, you’ve got a shot. If not, think twice before quitting the “day job.”

“The person who knows HOW will always have a job. The person who knows WHY will always be his boss.” -Alanis Morissette

Here’s a different perspective from author Seth Godin.

Your Do Over | Discover a Better Life | Get Lasting Results | Inspiration | Motivation | Success (mp3)

Resources mentioned in this episode:

Podcast Transcript:

Five reasons you might want to be your own boss.


Intro: Hi, this is Matt “The Do Over Guy”, and this is Your Do Over: Episode Six.

Narrator: During an era where countless people, businesses, and organizations are feeling the pinch, running out of time, running out of money, losing confidence, feeling as if life is unfair, praying for another chance, and unless something is done- life is going to pass them by. Life is going to pass them by. Fortunately, in the nick of time there is now a place where the ignored underestimated and unknown steps to producing results and making life work are revealed. Save your career. Save your business. Save health. Save your relationships. Save your life. Get from where you are to where you want to be, faster and with greater ease than you ever thought possible.  Say hello to “Your Do Over”.

Welcome to “Your Do Over”, where once a week you will hear, learn, and take action on the ignored, underestimated, and unknown steps to producing results. Now, this is the show where I show people dissatisfied with their current situation, how to start over, discover at better life and get lasting results, easier, faster, smarter. I am broadcasting live from downtown Los Angeles with a really great show and tons of fantastic stuff for you today I am just as fired up as I was the last show, perhaps   even more so, and why is that you may ask? Well, I got sick right after the Thanksgiving holiday and I am feeling really good right now, I am back to my old self, but even more so it’s feeling really good with how well the show is being received, as I was sick this last week and was unable to record any shows, but will I was bumming around the house kind of waiting to get better, it was pretty amazing to watch the downloads of the show rise and rise. I mean that really felt good. So, thanks for all the ears out there and thanks for coming back again and again. I found a new host for my podcast by the way; everything seems to be running a lot smoother.  The artwork for the show is finally appearing on iTunes and if you will remember a couple of episodes ago that was a big thorn in my side and during the hosting transition you might have experienced some double downloads of episodes I am sorry for that, but it is all cleared up and won’t again. So thanks for hanging in there with me and it is only episode six and iTunes has me in their new and noteworthy section, and I am really honored to be there, and each week the show is downloaded more times than the previous week and the momentum just seems like it is going in the right direction.  And, the free MP3 that I just released, well that was a couple of episodes ago, the Three Pillars for creating the Ultimate Do Over, it is a huge hit. I mean if you have not gotten your copy you can still get it a, free do over dot com. I am getting tons of great feedback on that I even noticed a few people tweeting the link on twitter this week. And so, thank you so much for the support. I didn’t even know that was coming, and I am really grateful, so thank you, and I mean that from the bottom of my heart.  I have got an important announcement for you at the end of our show, but let’s get into the main subject. I know at the end of the last episode I promoted this show as the ten big mistakes that self employed rookies make. We are going to get to them believe me, and there are more than ten by the way, but I pulled together the biggest ten, I don’t know, maybe I should have made it twenty, but before I get to the ten mistakes, I think what makes sense is if I point out where you might not want to put yourself in a position to make these mistakes at all. Maybe I can dissuade you from becoming self employed all together, I mean maybe it is not for you, because it is not for everybody, but I know you have thought about it. You’re thinking about quitting that day job and your thinking about going to work for yourself, you are thinking about pursuing you passion and all. And I just want to check in with you, is that a fleeting thought? Is that a fantasy?  Or is it a much more serious intention for you? I get it though, I have been there,  maybe it is that one way two hour commute that is just driving you nuts, or that nagging boss, or to that one nagging boss that doesn’t have a clue as to what he’s

doing or she’s doing.  The work is uninspiring and the hours are too long, or maybe it is the office politics. Or, in a nutshell you just flat out hate what you do for a living, and you are not alone there are a lot of people in this country that feel the same way you do. You know whatever has you pondering the idea of going to work for yourself, I mean, I think we can agree that what you are doing isn’t anything that you are actually passionate if it was then you wouldn’t be contemplating leaving, so I get it. So, if quitting that day job is the eminent New Year’s resolution for 2011. I just want to cover a few things before you make that leap. I want to make sure you don’t do something that you later regret, I mean being self employed is not for everybody and you’ll need very careful as you will find tons of encouragement out there, you will find it on TV and you will find it all over the internet today on how simple it is to turn your passion into profit. Don’t be fooled, it may be simple but it is not easy. Now don’t get me wrong I love working for myself, I love making my own hours. I love the flexibility, I love working from the comfort of my own home. And I love earning a great income doing what I love, it is awesome!  But I am going to be brutally honest with you today; it hasn’t always been like this. I mean knowing what I know now, I am not sure I would have chosen the road of the self-employed.  I mean there are other ways that I now know about that lead to freedom, financial freedom and time freedom as well. Now there are five things that I wish somebody would have told me before I got started, I mean, before I became self employed.  And there are five reasons why you will probably want to consider, and maybe re consider, before taking that plunge, before making that commitment.  And on the other side of that I am going to give you some tips on how to offset these uncomfortable aspects, or potentially uncomfortable aspects of being your own boss. I am not going to leave you hanging.

Okay, so, number one, one thing that you are going to want to consider is no one is going to tell you when to start work. Now I know this doesn’t sound like much of a drawback and you know if you get to work for yourself you get to keep your own hours, that is one of the cool parts about it, that is one of the things that we pursue, you don’t have to be at your desk at eight a.m., and you don’t even have to get out of bed before noon, if you don’t want, however, it’s easy, really easy to end up wasting really valuable time and when you are working for yourself you are going to become all too aware of how time equals money.  I mean that is going to become painfully clear. And, if you are working with clients that are going to be expecting to contact you by phone. I mean you are going to have to operate by their hours and if you have clients that want swift replies to e-mails, during office hours those are the hours that you are going to have to keep. I mean, you might find out that you are missing out on potential gigs also if you are not keeping regular hours.

So, here is what I recommend. I recommend that you choose working hours based on when you are at your best, now I am a morning person, so I am often at my desk at 7:30 a.m., and you know other self employed people like to work late in the evening, I’ve got a friend that frequently sends me messages, and I wake-up in the morning and I see that he sent me an e-mail at 2:00 am, so I just suppose that is when he is at his best, because I get those messages from him all the time. But you need to be clear about what days are working days and doesn’t necessarily have to be Monday through Friday, but regardless you will want to create a routine, your own routine. You know working for someone else you essentially have a routine imposed on you.  Now that you are working for yourself you are going to have to impose a routine on yourself.  I mean, routines work, and they create consistency.  And when you are working for yourself you are quickly going to discover that consistency can be elusive. So, you are going to want a routine , you want a predictable routine, you want your customers and your clients, you want that customer base to be familiar with your routine, so it’s predictable it creates constancy.

So, number two- nobody tells you when to stop working I mean that is the flip side to having a start time is that you don’t have a stop time either, and this can become a real problem and it is for a lot of self employed people. It can lead to substandard work and can lead to high stress levels and eventual burn out, even if you love doing  what you are doing, if you are doing it 24 hours a day , you are going to burn out. So however much you love doing what you are doing for a living, you need some time to rest and recharge. So, what you want to recognize for yourself is that when you work for yourself your job and your hours of work they can expand beyond all recognition they can go into the wee hours of the night even if they started in the wee hours of the morning. So, I recommend that you give yourself a firm stop time each day. Perhaps tied to you family or household schedule.  And make sure that you have at least a couple of non-work time hours before bed.  You know work can easily go to bed with you and it can keep you tossing and turning all night. And just as you want to create a work routine, you are going to want to work some you time into the routine as well. I mean it just keeps you sane.  It takes discipline however to stick with the routine, particularly if there isn’t a boss to see to it, that you do stick to it, you are the boss now you have to make  sure that you stick to it.

Okay, number three- being self employed is not stress free. I mean a lot of people think that going to work for yourself is, you’re going to be working from home, and it is going to be this amazing  utopian experience replete with time freedom and self expression, I mean all we do all day is sit around and watch day time TV in our pajamas, right? No, the reality is that you are going to be ditching the stresses of an employee for an entirely different often even heavier group of stresses. I mean you won’t have the boss breathing down your neck anymore, okay; there will be no more road rage, since your commute has been essentially eliminated.  The office politics those are no longer an issue, given that you are the office and the politics, and you might experience serious anxiety when a customer’s start cancelling orders or they stop showing up for appointments, or suppliers don’t follow through, or the culture shock of a bank balance that you are completely unfamiliar with. And with this new low bank balance I mean it can cause you to take on more work, or more complex work, or work outside the scope of your experience and expertise, and just more work than you can comfortably handle.  If you are taking the leap into self employment, be prepared for it to be stressful at times. No, be prepared for it to be stressful a lot of times,  perhaps even all the time even all the time right at the beginning.  I just want you to get honest with yourself, how much stress, risk, and uncertainty can you handle?  I mean you can determine exactly what you do and don’t do.  So make sure that you are putting yourself into the best possible position right from the start.  I am going to talk a little bit more about that as we go on.

Okay, number four, here is a biggie. No this typically leads to the demise of most want to be self employed rookies; there is no guaranteed pay check. In a traditional job you know exactly what you are being paid and when, and as being self employed you are going to find that cash flow is sporadic  and this can be a particular problem if yourself employment involves a large outlay on equipment or materials of some sort. I mean a lot of self employed people work on a succession of small jobs with a few hundred dollars coming in on each and often not on time, or they have one huge project which could mean getting paid in large sums every few months, so if you are used to getting a pay check every two weeks you may end up running into serious financial problems, especially if you have a non, or late paying client. No, I will say when you get your non paying or late paying client because they will be there also.  I mean you are going to find that pursuing your passion is not always spent pursuing your passion.  I remember when I was in the music business, I just wanted to spend time in the studio, I just wanted to record, I just wanted to produce, I just wanted to market, and distribute my product and so many times I found myself actually chasing paychecks, chasing  clients, chasing  other distributors, and chasing stores. Just trying to get paid. I became a bill collector and that wasn’t really something that I was not expecting   so that is something that you are going to want to think about, and so what I would recommend is that you have an emergency fund or a buffer that covers you for late an irregular payments. I mean when you get large sums of money, and you will get large sums, resist the temptation to run out and splurge or to celebrate, that was a biggie for me. Every time I got a big pay check I felt it was a time to buy a big meal and take a couple of friends with me. Resist that temptation. Put unexpected bonuses such as gifts or tips, and put them into a savings account and for big projects bill in installments during the work and ask new clients to pay 50% up front.  I mean those tips right there will help you quite a bit.

Alright, number five- a cold hard fact,  this is what you realize when you become self employed and you realize this really, really quickly you are on your own, absolutely nobody has your back it’s all up to you. Now I know in most office jobs there is a limit to how much you can literally screw up. I mean even if you do something so awful that you get fired, I mean typically you are entitled to some sort of period of leave or maybe you are entitled to a severance package, and generally it is hard to make huge mistakes as an employee there is always someone there typically double checking anything that is really vital, but when you are self employed everything is your responsibility. I mean if you forget to bill a client that is your problem, if you are so poorly organized that your clients start leaving you or if you can’t get yourself motivated to complete your work, or if you take on so much on that you rush it all and just do a poor job, the quality falls, that is your problem, and what you’ll find is that it might take a long time for you to build a good reputation at what you do. But, it can take just a few seconds to completely destroy that reputation; I mean you might even get sued by an angry client- it happens. So, what I recommend is you get professional advice where applicable, okay, perhaps when doing you taxes and book keeping, or seek out a mentor, someone with more experience than you, that you can bounce ideas or tough experiences off of, I mean that can be a really big help, depending on where you live you might need to set up a limited liability company so that you can’t be held personally liable for potential financial problems, or potential lawsuits. And make sure that you have your time and energy to do your best work, and be careful about managing client expectations.  Don’t promise what you can’t deliver. I really encourage you to under promise and over deliver. A lot of times new self employed people will go out there and over promise because they are so desperate to get the job, and then they take the job on and they can’t deliver what they promised. That can lead to big problems; if it doesn’t lead to legal problems it will certainly lead to non-repeat business, meaning that client probably won’t use you again.

Now, I know this is somewhat of a pessimistic tone for this show, but it is reality, being self employed ain’t all lollipops and rainbows.  Now, having said that as tough as some of my experiences have been, as many times as I have had to do over before I got it right I have never regretted taking on the life of an entrepreneur.  I mean sure I would have wondered what it would have been like if I took that left turn at Albuquerque, and I absolutely would have gone about it differently.  But we are going to have those types of thoughts regardless of what we choose to do. Now as much as I am enjoying my life and career right now however, personal experience has taught me like anything worthwhile, like any worthwhile Endeavour, it ain’t easy.  But, if it is wrapped up inside your passion it can be the most rewarding hard work that you can do. Once you start doing what you love you will never work another day in your life.  So, here is your homework.  As soon as you possibly can, I mean do it right now, do it right now, when today’s episode is complete,  make a list of at least ten reasons why you want to be self employed, now if you can’t come up with ten that would be a hint as to whether or not you are ready to jump in as a full time as a self employed person, many people they underestimate this  exorcise; I don’t want you to do that  and what they don’t realize is that this exercise is everything,  I mean, if you don’t have a big enough why, or enough reasons as to why you want to be your own boss, I mean the odds of you succeeding are seriously against you.  SO make your list of ten, don’t ignore this exercise, make your list of ten, and if you don’t make your list, and you happen to just ignore this exercise because you don’t think it is important you will want to look within an question whether you have the desire or the discipline, if you have what it takes to be your own boss.  I mean that is just a thought, I mean you have your situation better than I do.

I mentioned at the beginning that I had an important announcement and what that is that recently I have immersed myself in the do over plan, yes, like my own plan,  practicing what I preach, and sticking to it with greater integrity than I ever really have , I mean I am a normal human being and  sometimes I get off track to,  but I really made a commitment over the last few months,  and along with a few fantastic results within the pursuits of my goals, this higher level of integrity has revealed some compelling new  insights and more on those in a minute.  But, look at what is going on in my world right now, due to a heightened level of integrity around my do over plan. After almost four months of stagnation in my real-estate investing  I am experiencing some significant breakthroughs and generating massive momentum in my business,  I mean I am closing three deals this month, probably four,  and I probably have not done that in six months,  the demand for my short sale investing mentor ship it’s higher than it has ever been, I am almost at maximum capacity, and investment capital for my bigger real-estate deals , I mean it is beginning to emerge from the most unlikely places, through my educational efforts, I mean it appears that people are finally getting tired of losing money in their stock portfolio’s and they want their 15 to 20 percent returns back.  And the “Your Do Over” podcast at iTunes, the one that you are listening to right now, I mean it is attracting more subscribers like I can’t even explain. I mean without any promotion what-so-ever.  So what does this all mean to you?  Well, I planned on releasing a do over workbook and an on-line study course, and a one on one coaching program next summer, but these new accomplishments and insights, they have gotten me so excited about my own results that I don’t want to wait, I want to share them with you.  I am going to implement this plan sooner, rather than later. Now, before I reveal to the public how I was able to kick my life up a notch. I want to take a select number of people through the program to see if I can use these new insights to create even faster break through and results for them.  I have some new strategies and ideas that I would like to try that I believe will produce some great results regardless of what you want to accomplish.  So, I am looking for just five people that want to be part of this case study with me. I will be using your dreams and goals as examples in the future and I will be using the entire experience to refine the do over workbook the on-line study course and my one on one coaching. Now the reason that I am choosing just five people to coach, is because I have five different strategies that I want to try, so if you are already experiencing some success I can help you get to the next level, if you are experiencing a low point and need to start over from scratch, I can help you also, I will be focusing on where you are right now, and getting you to where you want to be. Now of course I can’t guarantee any types of results, but I can promise that you will get my very best from the beginning to the end of this program.  I can confidently say however this will work as long as you do. Now, because I am giving away my key strategies and committing a large amount of time an energy to help you achieve your goals I want to be compensated that is natural,  but having said that you are actually helping me refine and create what I find to be a revolutionary  program,  and coaching it is not my full time income anyway, so I am going to keep this fee very,  very reasonable,  for one on one coaching for me for the next sixty days,  I have decided on the onetime fee of  597 dollars,  after the sixty day experiment is complete  you have helped me sharpen and improve this revolutionary program I am going to launch my one on one coaching programs somewhere between the range of  1,297 dollars per month, now my goal is to help you get from where you are right now to where you want to be in the next sixty days.  It will depend on what your ambitions are but even if I get you 50% of the way there, 597 dollars will be steel, none the less, the price feels right and the main goal is for you to succeed. So, I want to make it accessible to anyone that is serious about perusing  and achieving their goals,  so in this program you are going to receive two thirty minute coaching calls per week, for sixty days,  but I plan on spending a lot more time than that with you, because after all the intent of this program after all is to produce great results,  you are going to be able to have unlimited e-mail access to me, I am going to give you a copy of Do Over, that is the foundation of the program,  so I am going to give you a copy of the paperback and the audio book and an eBook so that you can consume the information whichever way is most comfortable for you. I am going to give you a copy of the Do Over Workbook, once it is complete, that is going to be yours for free. I am going to give you a lifetime membership to my on-line study program of materials,  and I am going to give you lifetime free access to my live plan do over workshops, so how I select the first five people very easy, first come first serve, I am simply going to turn of the Pay Pal shopping cart right after I have received the fifth order, so if you want to be part of this goal busting experience go to the , the do over guy forward slash coaching.  I am really looking forward to working with you and hit the ground running in 2011. That’s it for this episode, and by the way I won’t be doing any pitching on this podcast, that is not what it is for, occasionally I will announce a new product or service and I mean less than five percent of the time,  but that is it, this podcast is for you, and it is free to you, and it will always be free, I am in business however and from time to time I will share with you what I am up to and if you want to participate you will be able to. So, coming up next week what I promised last episode, if I haven’t scared you away from becoming self employed, you will want to be here to receive the top ten mistakes self employed rookies make, and you have got your homework assignment and I know you are going to do it right, yes, this is not your learn over, it is your do over. Now if you like what you heard today and, or, if you want to hear something more of, please visit iTunes at your convenience and leave your comments much appreciated, leave your comments,  and suggestions,  alright, I am Matt “The Do Over Guy” and I will see you next time on “Your Do Over”.

Narrator: Thank you for tuning into Your Do Over, where the ignored, underestimated, and unknown steps to producing results and making life work are revealed, and remember: “Knowledge is potential power.” Take action on what you learned today. This is not Your Learn Over, its Your Do Over. To review the resources references reviewed in today’s show and to receive a complete show transcript visit Stay connected to Matt “The Do Over Guy” Theriault on twitter at the Do Over Guy, and on Facebook at