The HARSH TRUTH About Quitting Your Job and Being Your Own Boss

Watch This Video Before You Quit Your Job. Being Your Own Boss is not as easy as it looks and becoming self-employed or an entrepreneur doesn’t give you all the freedom you were promised.

The Harsh truth is a lot of people who become self-employed don’t set boundaries, burn out, and are not prepared for the new level of financial responsibility and risk as well as stress on their mental health.

Nobody prepares you for the isolation, challenges, and financial stresses of entrepreneurship or self-employment. Most of this is because the far minority of people become Entrepreneurs of Self-Employed, most people are Employees, because of the security exchanged for a lack of independence and higher levels of responsibility.


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How to Start Your Own Business
My Journey To 6 Figures

00:00 Job Security
01:45 What Nobody Tells You
04:45 Planning to Leave Your Job
06:24 Getting Healthcare Coverage
07:11 Don’t Get Sued by Your Job
08:42 Working for Yourself
13:43 Setting Boundaries
14:57 Being Isolated
16:55 The Upside

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Roberto Blake is a Creative Entrepreneur, Keynote Speaker, and YouTube Certified Educator. He is the founder of Awesome Creator Academy and host of the Create Something Awesome Today Podcast.

Roberto Blake helps entrepreneurs and social media influencers, through educational videos on YouTube, motivational content on Instagram and career development advice on LinkedIn, as well as offering 1 on 1 Coaching and a Group Coaching Program.

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Disclaimers: all opinions are my own, sponsors are acknowledged. Not financial advice, for entertainment purposes only.

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entrepreneurship and the idea of being your own boss is something that more people than ever are probably interested in in the wake of the last 18 months we’ve all had with that in mind quitting your day job is a big deal if you want to quit your job i can understand that there might be a lot of justified reasons for doing that but as someone who has quit jobs before and someone who’s been fired before i understood understand the realistic financial anxiety that comes with leaving what you think or experienced was secure stable employment hint the last 18 months have taught us job security is a myth but i also think that self-employment and entrepreneurship can be over glamorized sometimes i don’t really believe that there’s a toxic hustle culture i think that that’s propaganda i think that what is real is toxic productivity largely in to five workplace environments i also think that sometimes rookie entrepreneurs who have not been doing it for more than five or ten years often really evangelize the work that they’re doing at an unhealthy unsustainable pace that people have been doing it for five years understand realistically to be unsustainable and to be unhealthy but guess what if you’ve lived any kind of life that’s not been privileged you know that we don’t always get to do things we like we don’t always get to do things that are healthy and we don’t always get to prioritize our mental health because there is this thing called survival that we have to actually do and that’s just some real talk harsh as it might be in today’s video what i really want to dive into and i don’t want to waste your time i want to talk about the truth and reality about becoming self-employed being your own boss and then the important transition to starting to work with other people outsource and how you can do things to take care of yourself a little bit better during this process because i think that again a lot of well-intentioned people who haven’t been doing this nearly long enough are putting out information that makes people work at an unsustainable and unrealistic pace with unrealistic goals so one of the first things is understanding why we are quitting our job in the first place and not doing it from a purely emotional place if you’re looking at leaving your job you probably have very good very valid reasons but we also need to be thoughtful and realistic especially if it’s a decision that affects more than us if you’re a person that’s single not in a relationship no kids no dependents nobody relying on you you have a lot more freedom you can take a lot more risk and the rewards could be great for you if that’s not your situation then you have to be even more careful about making a massive change that disrupts the lives of the people who do rely on you and that’s something that i don’t think a lot of people really take into consideration when they make this type of content you have to account for the fact that you can’t speak to everybody or please everybody but you can’t acknowledge that people have different circumstances it’s also easier to quit a job and bounce back and get new opportunities when you’re much younger in life i’m 37 years old i left the workforce i think around 27 28 something in that neighborhood and when i did that the reality is that i had a couple of things in my favor while i didn’t have any safety net i didn’t have family members i could rely on financially and um i didn’t have a degree i basically had no privilege but i did have experience and i did understand how to make money and i had very specialized skills i also had the benefit of this i had been planning to leave my job for over a year anyway and so in a fire mirror i quit blaze of glory of course i left and that’s not something i recommend everyone do if you can leave equitably or you can leave in a situation where the opportunity or option to get referrals or go back that’s the most responsible thing you can do but not every situation especially one where you feel maybe you’re being disrespected is going to allow for that so i understand trust me i’ve already been there it’s not my first rodeo back in my day anyway so what is planning to leave your job look like one realizing that you need to budget and have a very firm grasp of your personal finances how much money is going out what survival really looks like what you need that’s very important if you can save any money at all my case i only had about a month of runway then that’s very important but i think it’s also easier if you’re already doing a side hustle and not one that violates your employment contract in any way but if you have a side hustle if you can do something on your weekends or your evenings that’s not burning you out or exhausting or draining if if your situation allows for that because again sometimes it won’t sometimes you will have to grind i’m not going to pretend otherwise i’m not going to sit here and be fake humble or try to relate to you or tell you that you’re going to absolutely have to prioritize your physical and mental health because i have already been there i already know that not every financial situation gives you the luxury of taking good care of yourself i also know that that’s not sustainable and that if you’re going to do it it’s a sprint and you’re going to be exhausted afterwards but you don’t keep sprinting you get what i’m saying it is something where on occasion we have to live through a season of hustle to avoid a lifetime of hardship we have to overcome tremendous unreasonable difficulty hopefully stronger as a result of it to be able to persevere through life because we’re acknowledging that it won’t always be fun and it won’t always be favorable to us and it won’t always be fair i told you this was gonna be harsh i told you i don’t sugar cook things i told you i’m not playing around so what we have to do is look at these things and make a reasonable plan if you’re someone who really needs their healthcare coverage for whatever reason you have to look at what transitioning for that looks like now if you’re doing freelance work on the side it’s possible you can become part of a freelancer’s association you can become part of a freelancer’s association you might be able to become part of a group policy in the same way that you do as an employee so there’s kind of a collectivist thing happening there and that might make it more reasonable and affordable and get you on a good plan and if you are able to um talk to someone and if you talk to like i think it’s called cobra you might be able to kind of seamlessly have no interruption in your benefits as you start to transition if you make a plan for it now you also want to make sure you’re not doing things that violate your current employment contract by the way while you’re doing your freelance work and your side hustle stuff because you don’t want to put yourself in a position to be fired before you’re ready or in a position to be sued or anything like that you want to be respectful and if possible transparent about it as long as you’re not doing something that is directly competitive with the job it should be okay now some of you it won’t be freelance skills like photography or graphic design or anything like that for some of you it will be something more like um doordash or rover or uber or it could even be a side hustle with youtube or something like that if it’s not a skill based freelance hustle with something like photography or design or doing fiverr by the way if you’re looking for some side income maybe you should check out fiverr for freelancing they’re not sponsoring this video i will link to them down below that’s an affiliate link try it out it is the most popular freelancing platform i’ve had positive and negative things to say to them in the past i will be making a dedicated review of what i think of them now because it’s been about five years since i made a video on them things change the world’s a very different place than it was just 18 months ago isn’t it so with that in mind just try to do things as transparently and as thoughtfully as possible uh you you may feel like you’re not getting a good deal sometimes but that’s not an excuse to do things in an unreasonable or unfair way something you also have to account for is if you do become your own boss and let’s say you start to transition in freelance let’s say you it goes very well or you become a full-time freelancer or you start some type of ecommerce business or you start a full-time youtube channel you quit your job and it’s going great and you’re making money best case scenario the real issue and problem will be motivation and discipline you had the accountability of other people to keep you in line when you had your nine-to-five job and there were real consequences for not showing up and doing your work when you become your own boss you get an over estimated or inflated sense of your own freedom and power over your time and therefore you’re not always responsible and giving time to your business and to your clients in the way that you should because now that you are not beholden to punching a clock you really are trying to stretch your legs and flex your muscles and experience more that freedom you were promised and this this idea this overrized glamorized idea of freedom is not initially real in the first maybe two to three years of you being a solo entrepreneur self-employed or building a business or being a full-time content creator it is largely when you’re in the process of building something that’s going to be sustainable and can truly and fully not only replace your previous income but take on the new responsibilities that you will have when you move from being an employee to self-employed now you have another level of self-employment taxes and you become responsible for fica medicaid medicare all that you become responsible for those things there might be local taxes you become responsible for if you live in new york or california that is the thing that nobody tells you and will talk about because the internet has conditioned them to believe that no one wants to hear them complain about their money problems and what it does as a result of us not being able to do that is you are misled about what your responsibilities are and how hard harder you have to work and that you can’t just replace your nine-to-five income you are now responsible for taxes at a very high rate you are now also responsible for your own health care cost on top of that and you assume all the risk and legal liability for the business which means you now have to have business insurance and you also have to have a separate business bank account and if you’re really smart that also comes with paying for an accountant and bookkeeper you’re welcome welcome to self-employment welcome to all that freedom no it very much becomes great power comes with great responsibility and you now being responsible for all these things as a self-employed person with no safety net no backups nobody else to make sure you get it all done and often nobody to help you do it is mentally taxing and stressful at a much higher level than you might have experienced in your previous job at least at first and nobody is honest with you about that and tells you about it and like i said it’s because no one wants to hear people making more money than them complain about their problems and that means that when other people try to do it they feel overwhelmed and they feel very anxious and they might feel impostor syndrome and like they’re a failure because they’re not crushing it ironically it’s not other entrepreneurs that are creating that problem it’s people who don’t like anybody talking honestly about money or telling you about their hardships because they are making a certain amount six figures or more compared to other people who may not be making that and i understand that i understand that people are very sensitive to that especially in the wake of the last year and a half that we’ve all had but making it a taboo for people who understand a higher level of personal finance understand a higher level of what new tax responsibilities become for anybody that’s doing a side hustle a lot of people were shocked to find out that they have these new responsibilities when they started trying to make a little bit of extra money for themselves only to find out that they were not making the money they thought because now they were introduced into a new set of taxes that they were never taught in school how to be responsible for when they didn’t realize um the the difference in what uh group policy versus an individual policy what the savings difference was it’s because people are not allowed who make money to speak very honestly about it unless they are they’re pandering and being overly humble and say that everything they did was luck and they can’t talk to you about these very realistic situations as openly as they would like to that’s the thing that’s most disappointing to me in the culture not people telling you to work hard or that hard work and smart work pays off that is not hurting people what’s hurting people is the fact that they are being kept from very specific information that would help them and that’s why as uncomfortable as making this video is for me i’m doing it anyway someone telling me all of this would have made an absolute difference in my life when i first started it would have made all the difference in the world and i would have had healthier boundaries which is another thing when you start working for yourself nobody your friends your family your former co-workers nobody will respect your boundaries everyone will feel that because you are in charge of your time that you should make them a priority and drop whatever you’re doing they will not respect the time that you have to give to your business because you are not being held to a clock by an employer anymore in the way that they’re accustomed to and to some extent i do understand this is just the difference in lifestyle and situations but it is ultimately taking you for granted when people do that and don’t respect your boundaries there are also people who if you do make any of this money and you become successful they may without realizing it take you for granted overstep bounds ask for too many favors and not understand the complexities or stress level of what you’re doing or the added stress or insecurity it puts on you when they keep asking you to do things or guilting you into doing things considering the sacrifices you had to make and the stress that you might be going under you’ll also find yourself somewhat more isolated because now you’re in an outlier situation most people are employees they’re not self-employed or small business owners they’re just not uh you know ninety percent of people are not in your circumstance in that situation which means that you’re not going to be able to relate to people in the same way you’re not going to share their uh problems you’re not going to share their experiences anymore and the thing is you’ll start to have different values this is not your money changing you this is you adapting to survive your new circumstances in your environment which is something else people do not appreciate is every single one of us is a human being we are built from an evolutionary standpoint to survive and then attempt to thrive and we do this based on the circumstances that were put into in the environment around us uh also our own internal choices our values our character all those things add up but it is both it really is and as those things change they influence you and that will also create these gaps these differences between you and people maybe that you grew up with who haven’t changed they stayed static might alienate you from some of your friends and family or people who used to be in your life it’ll also change some of your relationship dynamics if you ever get to a significant income bracket you’ll start to have to be very careful and thoughtful about people around you because unfortunately i have to tell you that sometimes there’ll be people around you not for the right reasons there will be people around you that unfortunately especially if you’re a very kind-hearted person it’s just the truth that people who are empathetic and kind of get taken advantage of that’s how it is unfortunately and it doesn’t change when you get more successful except for there’s a lot more of it and you have to be more guarded even if you don’t want to be it’s just how it’s going to be now to not discourage you and because that was very depressing i do have to give you some realities here you will find that because you have control over your time that you also have a greater sense of empowerment and freedom you do have to manage that with discipline but it’s also great to be the master of your time you also have to start thinking about efficiency not giving something more time that it needs or deserves and not doing busy work the reality is that if you work a nine-to-five job oftentimes you’re not rewarded for becoming more skilled uh becoming faster becoming smarter as a self-employed person and entrepreneur you are rewarded in proportion to how fast you get things done how efficiently and effectively you perform and also the quality of your work improving over time does result in gains you may never be rewarded for that in a traditional work structure but you absolutely are rewarded for it by the market itself when you become self-employed or build a business that is the truth and that is why i’m encouraging more of you to pursue it because you have talent skills abilities creativity that can scale because it’s non-linear labor is linear you’re not going to get as much scale out of that but creativity is non-linear and exponential growth so for a lot of you that’s why if you are creative you’re living in the best time ever the creator economy could change your life forever like it did with me and so it is possible and i’m not trying to just pump you up i’m telling you that you can look at opportunities that you’ve never seen before very differently if you shift your lens in focus and you understand what is happening and what is very different now than your parents time you have a lot more options you have a lot more opportunities if you are within the sound of my voice or you’re watching this video you probably have the means of production to do something very amazing you have the ability to do something with e-commerce or content creation or affiliate marketing or even freelance services on platforms like fiverr and it could actually end up outpacing what you could earn through traditional employment and wages because nobody is setting the cap on how much value you can create and how much money you can make in exchange for that value money is a tool and it’s also a measurement and acknowledgement of value when you become self-employed you can create unlimited value and you can use these platforms to scale that value it’s not unreasonable also that through access to these things that you’ll develop new skills they’re worth a lot more money than just the sweat of your brow and that can be life-changing so there’s the truth the good the bad and the ugly about being self-employed and being your own boss i’d love your feedback and comments on this video what did you think what was your biggest takeaway from this video let me know in the comment section if you enjoyed this video then definitely check out the video on my journey from being broke to making six figures i’ll link that video in the description down below for you also check out my playlist and this is a playlist that can tell you how to start an online business from home i tell you a little bit more about my journey that will also be linked in the description down below as always thank you so much for watching and don’t forget go out there and create something awesome today take care


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