Five Reasons You Might Not Want to Be Your Own Boss | 628

be your own boss

Are you tired of your everyday job and you want to be your own boss? Today, you’ll hear about the 5 uncomfortable aspects of having your own business, as well as the tips on how to offset those difficulties. Bear with us and learn what the freedom of having absolute control over your working time means in practice, how to deal with the stress, and why you should not over-promise.

be your own boss

What You Will Learn About Five Reasons You Might Not Want to Be Your Own Boss:

  • Why you have to think twice before you make a decision to become self-employed
  • When you should start working
  • Why you want to make a routine
  • The stress factor and how to deal with it
  • What is actually going to take a lot of your time
  • Why you should under-promise and over-deliver
  • The main reasons you should have for starting your own business

Whenever you’re ready, here are a few ways we can help:

Work with me One-on-One

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  • Also, check these out:


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Fixing and Flipping vs Buying and Holding – Best Way to Create Wealth


Matt Theriault: Alrighty, back again with another episode of Wayback Wednesday, going way back, back into time, like more than nine years ago. Almost 10 years ago. Actually, more than 10 years ago, where it all started, The Do Over Show. We just started our ninth year on The Epic Real Estate Investing podcast, but I’ve been doing this podcasting for almost a decade. They’re over a decade now.

It started with The Do Over Show, and for now right here on Wayback Wednesdays, we’re bringing back those old episodes. I think this is just going to be a really good fit here on the Epic Real Estate Investing Podcast as getting your mind right around your business, regardless of what business it is, getting the right mindset, it’s key. It’s just so important, and it’s where it all starts for your results, right? Actions just aren’t going to happen unless there is a thought that precedes it, and we want those to be good thoughts so we do good actions, and we create great results.

Anyway, these episodes are more than 10 years old now, and many of the domain names and email addresses and stuff like that that you might hear in these episodes probably aren’t going to work. I haven’t gone through and listened to them all over again to go check, so just an FYI. But I was able to go back and re-purchase one of those old domain names. Imagine that, it was still available, as you’ll hear me reference it on The Do Over Show pretty frequently, and that’s the domain name, where you can download the Three Pillars to Creating the Ultimate Do Over. Something like that.

I won’t explain anymore right here, because I’m pretty sure I cover it thoroughly on these old episodes, but it was just an FYI. I wanted to let you know that that is up and live, so if you’d like to grab that recording, you can at That URL is live once again, alrighty? Now, enjoy the show.

Speaker 1: This is Theriault Media.

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 your 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.

Do over, do over, do over, do over, do over, do over, do over.

Matt: Welcome to Your Do Over, the place 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 a better life, and get lasting results easier, faster, smarter.

I’m broadcasting live from downtown Los Angeles with a really great show, and tons of fantastic stuff for you today. I’m just as fired up as I was the last show, perhaps even more so. And why is that, you ask? Well, I got sick right after the Thanksgiving holiday, and I’m feeling really good right now. I’m back to my old self. But more so, it feels really good how well the show is being received.

As I was sick this last week and I was unable to record any shows, but while 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 of the ears out there, I really appreciate it, 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 of the show is finally appearing on iTunes, and if you’ll remember a couple episodes ago, that was a big thorn in my side. During the hosting transition, you might have experienced some double downloads of episodes. I’m sorry for that, but it’s all cleared up. It won’t happen again. So, thanks for hanging in there with me.

It’s only episode six, and iTunes has me in their New and Noteworthy section, so I’m honored to be there. Each week the show is downloaded more times than the previous week, and momentum just seems like it’s going in the right direction. The free MP3 I just released, the … well, it was a couple episodes ago, the Three Pillars of Creating the Ultimate Do Over. It’s a huge hit. I mean, if you haven’t gotten your copy, you can still get it at

I’m getting tons of great feedback on that. I mean, 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. I’m just really grateful, so thank you. I mean that from the bottom of my heart.

Now, I’ve got an important announcement for you at the end of our show, but let’s get into the main subject. Now, I know at the end of the last episode, I had promoted this show as the 10 big mistakes self-employed rookies make, and we’re going to get to them, believe me. And they’re more than 10, by the way, but I’ve pulled together the biggest 10. I don’t know, maybe I should have made it 20, but before I get to the 10 mistakes, I think it would make sense 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’s not for you, because it’s not for everybody, but I know you’ve thought about it. I mean, you’re thinking about quitting that day job, and you’re thinking about going to work for yourself, you’re thinking about pursuing your passion and all, and I just want to check in with you. Is that a fleeting thought? Is it a fantasy, or is it a much more serious intention for you?

I get it though, I’ve been there. I mean, maybe it’s that one-way, two-hour commute that’s just driving you nuts, or that nagging boss, or particularly that one nagging boss that doesn’t have a clue as to what he’s doing, right? Or she’s doing. The work is uninspiring, the hours are too long. I don’t know, maybe it’s the office politics. Or in a nutshell, you just flat-out hate what you do for a living, and that’s okay, because you’re not alone. There’s a lot of people in this country that feel the same way you do.

You know, just whatever has you pondering the idea of going to work for yourself, I mean, I think we can agree that what you’re doing isn’t anything that you’re actually passionate about. If it was, you probably wouldn’t be contemplating leaving, so I get it. If quitting that day job is the imminent 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, it’s not for everybody, and you’ll need to be very careful, as you’ll find tons of encouragement out there. You’ll find it on TV, and you’ll 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’s 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’s awesome, but I’m going to be brutally honest with you today. It hasn’t always been like this, and knowing what I know now, I mean, I’m not so sure I would have chosen the road of the self-employed. I mean, there are other ways 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. There are five reasons you’ll probably want to consider, and maybe even reconsider, before taking that plunge, before making that commitment. On the other side of that, I’m going to give you some tips on how to offset these five uncomfortable aspects, or potentially uncomfortable aspects, of being your own boss. I’m not going to leave you hanging, okay?

All right, so number one, one thing you’re 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 if you work for yourself, I mean, you get to keep your own hours. I mean, that’s one of the cool parts about it. It’s one of the things that we pursue. You don’t have to be at your desk at 8:00 a.m., and you don’t even have to get out of bed before noon if you don’t want.

However, it’s easy, it’s very easy, to end up wasting really valuable time, and when you’re working for yourself, I mean, you’re going to become all too aware of how time equals money. I mean, that’s going to become painfully clear. If you work with clients that are going to expect to contact you by phone, I mean, you’re going to have to operate by their hours. If you have clients that want swift replies to emails during office hours, I mean, those are the hours you’re going to have to keep. I mean, you might find that you’re losing out on potential gigs also if you’re not keeping regular hours.

So, here’s what I recommend. I recommend that you choose working hours based on when you are at your best. Now, I’m a morning person, so I’m often at my desk at 7:30 a.m. Other self-employed people, they like to work late in the evening. I’ve got a friend that frequently sends me messages. I wake up in the morning, and I see that he’s sent me an email at 2:00 a.m., so I just suppose that’s when he’s at his best, because I get those messages from him all the time.

But you need to be clear about which days are working days. It doesn’t necessarily have to be Monday through Friday, but regardless, you’ll want to create a routine, your own routine. Working for somebody else, you had a routine essentially imposed on you. Now that you’re working for yourself, you’re going to have to impose a routine on yourself.

I mean, routines work. They create consistency, and when you’re working for yourself, you’re quickly going to discover that consistency can be elusive. So, you want a routine, and 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 consistency.

Number two, nobody tells you when to stop working. I mean, that’s the flip side to having a start time is that you don’t have a stop time either. I mean, this can become a real problem, and it is for a lot of self-employed people. It can lead to substandard work, and it can lead to high stress levels, and eventual burnout. I mean, even if you love doing what you’re doing, if you do it 24 hours a day, you’re going to burn out.

However, much you love doing what you do for a living, you need some time to rest and to recharge. What you want to recognize is that when you work for yourself, your job and your hours of work, they can expand beyond all recognition. I mean, they can go into the wee hours of the night, even if they started in the wee hours of the morning. I recommend you give yourself a firm stop time each day, perhaps tied to your family or household schedule.

Make sure you at least have a couple of hours of non-work time before bed. Work can easily go to bed with you, and it can keep you tossing and turning all night. Just as you’re going to create a work routine, you want to work some you time into that routine as well. I mean, it just keeps you sane. It takes discipline, however, to stick with a routine, particularly if there isn’t a boss to see to it that you do stick to it. You’re the boss now. You have to make sure 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’s just going to be this amazing, utopian experience replete with time freedom, and self-expression. I mean, all we do is sit around all day and watch daytime TV in our pajamas, right? No. The reality is that you’re going to be ditching the stresses of an employee for an entirely different, oftentimes even heavier group of stresses.

I mean, you won’t have the boss breathing down your neck anymore, 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 customers start canceling orders, or they stop showing up for appointments, or suppliers don’t follow through, or the culture shock of a bank balance you’re completely unfamiliar with.

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’re taking the leap into self-employment, be prepared for it to be stressful a lot of times, perhaps even all of 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 you’re putting yourself in the best possible position right from the start. I’m going to talk a little bit more about that as we go on.

Okay, number four. Here’s a biggie. Now, this typically leads to the demise of most want-to-be self-employed rookies. There’s no guaranteed paycheck. In a traditional job, you know exactly what you’re being paid and when. As being self-employed, you’re going to find that cashflow is sporadic. Now, this can be a particular problem if your self-employment involves a large outlay on equipment or on materials of some sort.

I mean, a lot of self-employed people, they either work on a succession of small jobs with a few hundred dollars coming in from each, often not on time, or they have one huge project, which could mean getting paid in large sums every few months. So, if you’re used to getting a paycheck every two weeks, you may end up running into serious financial problems, especially if you have a non or late paying client. I will say no when you get your late paying client or your non-paying client, because they will be there also.

I mean, you’re going to find 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. 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 was really something I wasn’t expecting, so that’s something you’re going to want to think about.

What I would recommend is that you have an emergency fund, or a buffer that covers you for late and irregular payments. I mean, when you get large sums of money, and you’ll get large sums, resist the temptation to just to run out and splurge, or to celebrate. That was a biggie for me. Every time I got a big paycheck, I just felt like it was time to go out and buy a big meal, and take a couple friends with me. Resist that temptation.

Put unexpected bonuses, such as gifts, or tips, 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 little tips right there will help you quite a bit.

All right, number five, a cold hard fact. This is what you realize when you become self-employed. You realize this really, really quickly. You are on your own. Absolutely nobody out there has your back. It’s all up to you. Now, I know in most office jobs there’s 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’re entitled to some sort of period of leave, or maybe you’re entitled to a severance package, and generally, it’s hard to make huge mistakes as an employee. I mean, there’s someone typically double checking anything that’s really vital.

But when you’re self-employed, I mean, everything is your responsibility. I mean, if you forget to bill a client, that’s your problem. If you’re 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 that you rush it all and just do a poor job, if the quality falls, that’s your problem. Now, what you’ll find is 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 your taxes and bookkeeping, or seek out a mentor. I mean, someone with more experience than you at which you can bounce ideas or the tough decisions 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 a potential financial problems, or potential lawsuits, and make sure that you have the 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 they’ll over promise because they’re so desperate to get the job, and then they take the job on, and then they can’t deliver what they promised. That can lead to big problems. If it doesn’t lead to legal problems, it’ll 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 that I’ve had to do over before I got it right, I’ve never really regretted taking on the life of an entrepreneur.

I mean, sure, I’ve wondered what it would have been like had I had taken that left turn at Albuquerque and I absolutely would have gone about it differently, but we’re going to have those types of thoughts regardless of what we choose to do. Now, as much as I’m enjoying my life and career now, however, personal experiences taught me that self-employment, like anything worthwhile, like any worthwhile endeavor, it ain’t easy. But if it’s wrapped up inside your passion, it can be the most rewarding hard work you could do. Once you start doing what you love, you’ll never work another day in your life.

So, here’s 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 10 reasons why you want to be self-employed. Now, if you can’t come up with 10, that would be a hint as to whether or not you’re ready to jump in full-time as a self-employed person.

Many people, they underestimate this exercise. I don’t want you to do that. What they don’t realize is 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 10. Don’t ignore this exercise. Make your list of 10. If you don’t make your list, if you happen to just ignore this exercise because you don’t think it’s important, you’ll want to look within and question whether you have the desire or discipline, if you have what it takes to be your own boss. I mean, that’s just a thought. You know your situation better than I do.

I mentioned at the beginning that I had an important announcement, and what that is, is recently, I’ve immersed myself in the do-over plan. Yes, my own plan, practicing what I preach, and sticking to it than greater integrity than I ever really have. I mean, I’m a normal human being, and sometimes I get off track too. But I really made a commitment over the last few months.

Along with some really 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 what’s going on in my world right now because of this heightened level of integrity around my do-over plan. After almost four months of stagnation in my real estate investing, I’m experiencing some significant breakthroughs in generating massive momentum in my business. I mean, I’m closing three deals this month, probably four. I haven’t done that in probably six months.

The demand for my short sale investing mentorship, it’s higher than it has ever been. I’m almost at maximum capacity. Investment capital for my bigger real estate deals, I mean, it seems to be emerging from the most unlikely places through my educational efforts. I mean, it appears people are finally getting tired of losing money in their stock portfolios, and they want their 15 to 20% returns back.

In the Your Do Over podcast at iTunes, the one you’re listening to right now, I mean, it’s attracting more subscribers like I can’t even explain. I mean, without any promotion whatsoever. So, what does this all mean to you? Well, I had planned to release a Do Over Workbook, an online study course, and a one-on-one coaching program next summer, but these new accomplishments and insights, I mean, they’ve got me so excited about my own results, I don’t want to wait. I want to share them with you.

I’m 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 breakthroughs 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.

I’m looking for just five people that want to be a part of this case study with me, and I’ll be using your goals and dreams as examples in the future, and I’ll be using the entire experience to refine the Do Over Workbook, the online study course, and my one-on-one coaching. Now, the reason I’m choosing just five people to coach is because I have five different strategies of which I want to try. If you’re already experiencing some success, I can help you get to the next level.

If you’re currently experiencing a low point and need to start over from scratch, I can help you also. I’ll 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’m giving away my key strategies and committing a large amount of time and energy to help you achieve your goals, I want to be compensated. That’s natural. But having said that, you’re actually helping me refine and create what I believe to be a revolutionary program, and coaching, it’s not my full-time income anyway, so I’m going to keep this fee very, very reasonable. For one-on-one coaching with me for the next 60 days, I’ve decided on a one-time fee of $597.

Now, after this 60-day experiment is complete and you’ve helped me sharpen and improve this revolutionary program, I’m going to launch my one-on-one coaching program somewhere in the range of $1,297 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 60 days. It will depend on what your ambitions are, but even if I get you 50% of the way there, $597 will be a steal.

Nonetheless, the price feels right, and the main goal is for you to succeed, so I want to make it accessible to anyone that’s really serious about pursuing and achieving their goals. In this program, you’re going to receive two 30-minute coaching calls per week for 60 days, but I plan on spending a lot more time than that with you, because after all, the intent of this program is to produce great results. You’re going to have unlimited email access to me. I’m going to give you a copy of Do Over. That’s the foundation of the program.

So, I’m going to give you a copy of the paperback, and the audiobook, and the eBook so you can consume the information whichever way is most comfortable for you. I’m going to give you a copy of the Do Over Workbook once it’s complete. That’s going to be yours for free. I’m going to give you a lifetime membership to my online study program and materials, and I’m going to give you lifetime free access to my live Do Over Plan Workshops.

How I select the first five people, very easy. First come, first serve. I’m simply going to turn off the PayPal shopping cart right after I’ve received the fifth order. If you want to be part of this goal-busting experience, go to I’m really looking forward to working with you and help you 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. It’s not what it’s for. Occasionally I’ll announce a new product or service, and I mean less than 5% of the time, but that’s it. This podcast is for you, and it’s free to you. It will always be free. I am in business, however, and from time to time, I’ll share with you what I’m up to, and if you want to participate you’ll be able, and if not, that’s 100% okay with me.

So, coming up next week, what I promised last episode, if I haven’t scared you away from becoming self-employed, you’ll want to be here to get the top 10 mistakes self-employed rookies make. And you’ve got your homework assignment, and I know you’re going to do it, right? Yes. This is not your learn over, it’s your do over.

Now, if you like what you heard today, and/or if there is something you would like to hear more of, please visit iTunes at your convenience and leave your comments. Much appreciated. Leave your comments and suggestions. All right, I am Matt “The Do Over Guy,” and I will see you next time on Your Do Over.

Speaker 1: 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.

Take action on what you learned today. This is not your learn over, it’s your do over.

Do over, do over, do over, do over.

To view the resources referenced in today’s show and to retrieve a complete show transcript, visit Stay connected with Matt “The Do Over Guy” Theriault on Twitter @thedooverguy and on Facebook at