Dec. 14, 2021

#6: Be Your Own Boss? Answer This Question First!

The global pandemic has shaken up our daily lives and routines. And now is a time that people are considering not just remote working—but venturing out on their own as a freelancer or by starting their own company.

The global pandemic has shaken up our daily lives and routines. And now is a time that people are considering not just remote working—but venturing out on their own as a freelancer or by starting their own company.

To be your own boss or not to be, that is the question...And this might be a question you are pondering yourself now. 

But how do you know whether to take the plunge or not? 

In this episode, I’m going to share with you two key elements in your personality that just might be the deciding factors of whether or not you will be able to succeed in a bid to become self-employed.

Avoid this knowledge at your own risk—or embrace it and make a decision that will greatly improve your chances of success.

Enjoy the episode (and don’t forget to feed your tigers!).







If you're considering going freelance or starting your own company, you'll likely find this episode of value. Because I'm going to reveal two personality qualities that just might determine whether or not you succeed as an independent worker or business owner. And if you're already freelancing, or running a company and facing challenges sustaining yourself, there's something potentially here for you too, you're going to be able to consider whether you possess these two traits in enough quantity, which just might shed some light on an underlying cause of your business-related problems. Either way, you're going to come away from this episode, knowing the essential innate talents that are almost always part of a person's success when they go the route of being self-employed. 

I'm Steven Rudolph. And this is the Feed Your Tigers podcast in writing to help you align your talents with what you do so you thrive. 

I received a message this week from the listener of Feed Your Tigers, which inspired today's topic. And in the message, this listener asked, How do you know whether to stay with the safety and security of a job or to go freelance or start a company? There's so much I could lose by working for myself. Okay, let's look at this situation. You are not the only person in this circumstance considering this right now. In fact, there are millions of people right now wondering the same thing. Especially after COVID People have been laid off, or furloughed, hours reduced. And now companies want you back. Yeah, it's like, hey, sorry, we had to like cut you back there. But the good stuff wasn't going good for a while. But now things are looking better and come on back and maybe can't give you the benefits or the pay that we have people saying Hold on a second, Charlie, not so fast. 

Kinda like the situation that I'm in right now, you know, kind of being in my pajamas and setting my own hours. And I'm not so sure I'm ready to come back on those terms or even ready to come back at all. There's a term for this, you might have heard, it's called The Great resignation. That's what that he says is happening right now, where people are just flipping the big digital finger to their employers and saying, You know what, it's time for me to take charge of my life and to go solo right now. And you might be in a situation right now of having to choose from that. Whether or not I'm not talking about working from home, that's different. I'm talking about being self-employed, being a freelancer, or starting your own company. So it's, it's really quite different. You know, here, it's on your shoulders. It's not that someone's cutting you the check, and you get to wake up and you go to work from nine to five, and you do your job. And at five o'clock, you shut it all off. And you go in and you enjoy your life until you know, the next morning or till Monday morning or whenever that... 

No, I'm talking about carrying the whole burden on your shoulders and making your daily bread, earning your daily bread earning your living for yourself as an independent worker, or company owner. So let's look at before we get into the details, a quick look at the upside. And the downside of this. So what's the upside of going solo? Well, the first obviously, is flexibility. You get to set your own hours, create your own lifestyle, you work on your own schedule, and people have been finding that so pleasurable if you have kids like I do, I've got a toddler is now 18 months, it's so great just to be able to, you know, go take care of her anytime that she needs a little bit of help, I can put my work on pause and come back and pick up work again. And so having that kind of flexibility is really is just, it's just a great pleasure. The next is independence, being your own boss making your own decisions. There's a lot of pleasure and satisfaction in having that kind of freedom. The next is to have the freedom to choose who you work with.

When you work for a company, you're often told who you have to work with, even if you don't like them, and they're a pain in you know what, so being able to choose your own clients. And lastly to control your workload. So you decide if you want to work more or you want to slow it down or take a week off or two weeks off, or if you want to travel someplace and be a bit of a digital nomad. And so all of that is under your control. That's the upside. 

Now the downside, of course, is the inconsistent income. That's one of the first things that you're not getting that steady paycheck. And, you know, you have to be prepared for the times when it's going to be lean and there'll be times hopefully that there's also a good amount of cash flow coming in, but it will be inconsistent. The next is having to drum up the business. So getting out there and finding those clients and bringing them in and following up with them, you have to also ensure that you get paid and, and so on. So you're responsible ultimately, you know, the buck stops with you. And that's, that's a big consideration for many people. On top of that, you've got a lack of benefits. Not that benefits are being handed over to you, you've got to pay out of pocket for them. And the last is taxes. It's not an easy affair when you are working independently. Because there's a lot of paperwork that's involved, there are so many more things that you need to keep track of, you will most likely need a tax professional to work with you. And, and there's a lot, there's a lot that goes in, especially if you're working with a company. So those are some of the downsides. 

Now, here are some of the factors that you would need to consider when deciding to go solo. The first is finances, do you have the necessary finances in the bank to be able to afford to take this step? Do you have enough runway? What happens if you know, you go solo as a freelancer and you're working for three months, four months, by six months, eight months, and you're not able to earn enough? Are you going to have enough runway to be able to make it to the time where you're able to earn for yourself or earn enough to cover your expenses? Or lean times? What happens? Sometimes when something happens, whether it's a COVID-like situation, and suddenly things dry up? Are you going to have the wherewithal to be able to weather that? 

So those are some of the factors to consider when deciding to go solo either as a freelancer or when starting a company. But there's one more angle that people fail to ask themselves. And I consider this to be the most fundamental question, which is, is it in your nature, do you have the innate qualities that are at the core of working independently or not. So many people step over this, they just walk right over it and start looking at those other angles. And they might have those other points checked off. But they don't have the essential talents, the essential Tigers that would enable them to succeed as a self-employed individual. 

The next is responsibilities, you might have children or a spouse or parents that you need to take care of. So are you going to be able to work through that? And what about time and energy? There's a considerable amount of energy that goes into managing yourself into managing your business that you don't necessarily have to expand when you're working for somebody else. So you need to consider that. And the last is do you have the grit, as Angela Duckworth likes to call it the grit to stick it out and to stick with it for a long period of time, do you have that passion and perseverance? 

And so here we go to work successfully as a self-employed individual, either freelancer or company owner, there are two talents or tigers, as I like to call them that are essential for success. The first is an entrepreneurial Tiger. And the second is an administrative Tiger. Now, I'd like to encourage you to really, really consider what I'm going to share. Think deeply on this one because I have seen many people ignore this very basic information to their peril. Even after I explained it to them, or after they've understood it independently, they are so hell-bent on being self-employed, they cannot see the delusion that they don't have the natural qualities to be able to sustain themselves as self-employed individuals. It's kind of like that optical illusion, you know when they show you those two lines, and they say your which line is longer, which line is shorter. And they're actually both the same size and you're looking your eyes saying wow, that one is definitely longer now you know, it's an optical illusion, but your brain just can't see it. It's the same thing. People don't have these basic innate qualities, the strength of the large entrepreneurial tiger and the large administrative Tiger, but yet, they just are so much focused on having their own company and working independently, that they ignore this and their mind creates this optical illusion or tiger delusion or whatever you would like to call it. 

So I am encouraging you, I am requesting you to sincerely consider what I'm going to say, as essential. Now, in this podcast, you'll hear me referring to Tigers all the time. It's called Feed Your Tigers after all, and these tigers deal with 19 of your talents, your innate abilities, your natural tendencies. If you want to explore all of them in detail, go to the show notes and find the link that I've put for the 19 Tigers, which will bring you to a page that is full of details on each Tiger. And it gives you descriptions, examples, and more. But in this episode, on being your own boss, going solo, I talk about the entrepreneurial tiger and the administrative Tiger. And I'm going to look at them in a little bit of detail now. 

Okay, what's an entrepreneurial Tiger? An entrepreneurial Tiger is a natural ability or tendency, it's a natural tendency to create value, or to extract value in a situation. What does that mean? That could be financial value, it could also be social value. And this happens with people or people who've got large entrepreneurial Tigers or natures. They're in a situation and they see different resources, they see ideas, they see people they see buildings and materials, and their brain brings them together in a way and says, Hmm, if I put these things together, I could create - could be a project, it could be a company, it could be a nonprofit, right? And so that's what the mind does, you would know that you have a large entrepreneurial Tiger when you encounter a problem somewhere and your brain automatically starts thinking about business opportunities. Or if you go into a restaurant, you sit down and you look at the menu and you start looking at the prices of the items and you start to think about the look at the number of people in the restaurant. And you start to calculate what you think their revenues per day might be and start thinking about whether or not this company would this restaurant will be viable. And maybe you start thinking, Hmm, they've got hummus here on the menu. I wonder if I were to make a hummus company. And I could get them to buy it from me instead of making their own hummus. And even though the individual has no intention of doing something like that, they automatically just start thinking that way, they look for the value and they start analyzing it. And they start seeing opportunities and potential and so on. That's just an example of what someone with a strong entrepreneurial nature would do. So let's call that an entrepreneurial Tiger. And it's not like black and white, it's not that you have it or you don't, but some people have bigger ones, and some have smaller ones. And again, if it's large, you could rally people around a vision, maybe even since you were young, you were coming up with business ideas, maybe you've even started a number of businesses or you've sold things before, those would all be indicators that you've got a large entrepreneurial Tiger. So this is one of the Tigers or one of the qualities that are essential and essential part of being successful in a solo business or freelance venture.

The next one we'll look at is an administrative Tiger. What do I mean by that, in administrative nature, or tiger is this tendency to organize things, and create processes and get work accomplished? You would know that your administrative Tiger is a big one. If you go on a trip, and when you're planning a trip, you've got the trip planned out weeks or months ahead of time. If you're leaving for the trip next week, your bags are already packed. And all the arrangements are made. Or if you here are some really good examples that I see with people who've got a big administrative Tiger, which I don't, but I see them. What are the things that they do? The minute you tell them some type of task that needs to be done, they automatically start organizing and breaking things down into smaller pieces. They create deadlines automatically. They log things like schedules and so on. They're naturally good at managing time, prioritizing, and you know even and even help to pay other people to get work done. So this is that quality of management, it could be self-management or other management. 

So, we've looked at two kinds of tigers, the entrepreneurial Tiger, and the administrative Tiger. And as I've mentioned, both of these are essential in large sizes, if you want to be successful working independently. Now there are some stipulations. And I'm going to get to those shortly. But let's just consider each of these, in both circumstances, freelancing and starting a company. 

So let's start with freelancing. So you can freelance just about anything, whether that is content writing, design, marketing, coding, sales, training, and so on. There's almost nothing that can't be freelanced, practically speaking. And each type of freelancing requires different abilities and natural tendencies. So for example, if you were doing graphic design, you would need to have large visual and creative tigers. If you're doing IT security, you'd need to have large, logical, and protective tigers, that protective wants to prevent someone from hacking into your system, and so on. So the Tigers that are common to all types of solo work are the entrepreneurial and administrative.

In the with the entrepreneurial, as I've mentioned, before you are your own institution, you have to bring in the revenue and you have to decide where to focus, and how much to charge. Those all come back to this natural entrepreneurial ability. The entrepreneurial nature will be thinking about where are the revenue sources? And how should I set my pricing? And how will I position my product or serve my service against another one, where is my niche? What sort of strategy should I have and going to market. So these are all of the things that a large entrepreneurial Tiger is going to do naturally. 

And with the administrative Tiger when you are working solo, that's the one that's going to be organizing the schedules, tracking deadlines, seeing that work is submitted on time, tracking hours that you've worked, because you will need to submit in most cases, some kind of billing to clients, invoicing customers, following up with the payment, doing those tax and filing requirements, etc. So the entrepreneurial and the administrative. 

So what's essential to determine whether or not you'll be able to succeed in going solo is that the size of the Tigers should be large enough. In freelancing, I would say that both would need to be medium-large in size, which means the entrepreneurial would need to be rather big, doesn't have to be massively big, the administrator would also need to be rather large. And why I say it doesn't need to be that huge is because you're basically looking after yourself. And so I'll say that it needs to be big enough that you can bring in a steady flow of income. And on the administrative side, you're not managing other people, you're managing yourself. So again, I would say it doesn't have to be really big. We're going to talk about these again, in just a moment when we speak about from the court from the company perspective.

So the question is, how do I know whether or not these tigers are that size? Well, one is that you can look at the criteria in the 19 tiger section in the show notes and read through and just kind of go by a gut reaction. Another way is through the MNTEST that we've created, and you could work with one of our certified MN practitioners, and there are details in the show notes about how you can do that. 

So let's just imagine that they are large enough, I would say if everything else checks off the other points that I've mentioned before, the other factors to consider, you would have the confidence to be able to go forward with it. So what happens if one or both of these tigers is not big enough? Let's have a look. 

What if the entrepreneurial is too small? What it means is that you're not going to be able to do the needful to bring in the business. You're going to find having to go out and drum up customers and do social media marketing and advertising and so on is going to be irritating. You're going to have to analyze the market and see where your niche is and think about packages and product offerings. This might really begin to irritate you. And so that's something that you need to consider and the other side is in what do I do if the administrative is too small because I might start missing deadlines or fail to track my hours properly. Maybe even forget to send my invoice. So these are the kind of problems that arise when the Tigers are not big enough. So now, if both of them are not big enough, I would say, that's really the time that you need to consider whether you should be doing freelance at all. I'm going to get into that in a minute. But what do you do in a situation where your entrepreneurial Tiger is plenty big. But the administrative is not big enough? Well, what happens here is that the entrepreneurial is going to compensate for your lack of administration. In other words, you might bring in so many great opportunities, you'll bring in enough money to support yourself, but you're not going to be as efficient as possible, you're going to lose, it's kind of like bringing a lot of fish into the net, and a lot of them slipping through. So you're going to need to be careful, and you're gonna need to be, you'll need to be prepared to put in a lot of extra work in organizing. 

Therefore, you'll need to set up a system to have somebody with, let's just say a big administrative Tiger help you. And you'll need to rely a lot on technologies, calendars, and schedules. And I would say, consider hiring a virtual assistant. So that would be able to assist you in, in being able to keep track of all these things. And it might sound expensive, but these days, it's not that you would have to have a virtual assistant or what's called a VA, full time, somebody can assist you in a part-time manner. And it can, it can be really affordable. So that's something that I would suggest you think about, there's the other side of the coin, what do you do if the administrative is big enough, but the entrepreneurial is small. So what happens is that you're not going to be bringing in enough through your entrepreneurial efforts, you're going to suffer from generating enough resources to support you. That means in this case, it's like, you catch really few fish, but you're going to be very efficient in keeping the ones that you have, but it still might make it very tight for what do I do? How do I how do I manage?

How do I manage in a case like this? So what you would need to do is that you would need to find support in bolstering your entrepreneurial Tiger. And that could be having a coach or taking some courses that might be able to help you learn techniques in entrepreneurship. The other side might be using freelancing websites, and support materials or courses, there are some great sites out there to help you do that. There are also freelance agencies. And what I mean by that is that there are companies that don't employ you, but they kind of corral freelancers together. And when work comes in, they give the work out to those freelancers, and they keep a percentage of that. So it could be a fantastic way to manage or to compensate for that smaller entrepreneurial Tiger. 

Another would be to get a partner, partner up with somebody who's just got a massive entrepreneurial Tiger, but maybe doesn't have the Tigers that you have otherwise. So in other words, one catches the fish, and the other cooks them up. So those are the different combinations of big and small tigers, the entrepreneurial and the administrative. 

And as I said before, if both are not big, I would really suggest you not go to the freelance route because you're going to struggle on both ends. And you might never get to your work, the work that you do where your other big Tigers have the greatest chance of success. And I've seen so many people fail in this regard. They nearly killed themselves. Once they've accepted, though, they revert to being employed and they find so much peace, they don't have to think about where their money is coming from, where their paycheck is coming from, and they can focus on their work. 

Now let's take a look at the other aspect, starting a company or if you're running a company, running it successfully. So getting into this is rather involved. And I'm a little bit cautious about going into the details. But I would be remiss if I didn't mention it at all. So I'm going to do so in brief. And I'm not going to get into types of companies, whether it's a restaurant or a spa, or a florist or software outsourcing. But there are so many factors when it comes to opening a company. There's so much nuance in there that's built on different fundamentals of entrepreneurship. But the core of the success of that foundation can always be traced back to these two natures, these two tigers, the entrepreneurial and the administrative. So many of the points the same points that I've mentioned about freelancing holds true also for running the company, but in this case, They actually need to be stronger. Freelancing is at the self-employment level, the individual level, but companies are created to grow, especially to and grow to accommodate or to employ others. So the complexities, the demands are far greater, you need to think about funding at the beginning, freelancing, you don't necessarily need to think about funding, you have to cover your runway. Usually, when you're making a company, there are going to be costs related to research and development, you're going to have to get contracts, lawyers, understanding customers' needs, negotiating, technologies, and so on. And so I'll say this, if you have both a high entrepreneurial or strong entrepreneurial tiger and a strong administrative Tiger, you've got the foundations, it doesn't stop there. And again, I said before, there's a lot more nuanced than this. But I just want to cover the basics today. If both of them are strong, I would say you're in a really good position to move forward or to validate that you've got the essential qualities to make a company succeed. However, however, there are these situations where both might not be large. 

So what do you do when, let's just say one is large, and the other is not necessarily large, let's take a look and see both cases how it works. If you've got a large entrepreneurial Tiger, but you've got a small administrative Tiger, there's one thing that you can do, which is, as I've mentioned before, you could get a virtual assistant. And in some cases, like, in my case, have somebody work with you full time as an assistant. And that was that's been necessary for me over the years, I have always had somebody in all of my entrepreneurial ventures, working with me in admin, my entrepreneurial is a big one, and my administrative is a small one. And so there is that person, whether it's been in technology projects, or otherwise, someone has been there to keep me on track. In fact, in a way, it's like, I've hired my own boss. And I've had to lower my ego to accept the fact that I'm just naturally going to forget things, I'm not going to remember to do certain tasks or to keep up with things. But that's not a problem, as long as somebody else is there to catch the fish from falling through the net. Because if I didn't do this, what would happen is, I'd be catching lots of fish, and they would all be falling through a hole in the net. And so that's why this is this is an essential gap, a hole to plug. What about the opposite side, that you are high in administrative nature, but or you have a large administrative Tiger, but you've got a small entrepreneurial one. And here, I would say, be careful, because it's going to be hard for you to generate that business. And therefore what I would suggest is getting a partner or somebody who's strong in this area. Mentors can work and courses can work, but if you're building a company, and you are the owner, you are the originator of that you're not working with a large entrepreneurial Tiger, it's going to limit you. And therefore I would really suggest getting somebody to work with you who is who's got that just a massive entrepreneurial Tiger there. So that's the way that I see it. And I think about people who really want to have their own company, they want to work independently. And I so much understand that. 

And one of the reasons for doing that is by working for yourself, at least with a company, you've got the ability to own equity. And there's a great opportunity in that for you to create or to generate wealth over the long term. With freelancing, you do get to have your own lifestyle, and you can do the kinds of things you want, as I was saying before, work your own hours and choose your clients when you've got a company. But at the same time, even though you do have those privileges, you will only earn typically, as much as you work. In other words, when you are working, you're clocking hours and you're being paid for that. So the only way to really generate wealth is to live well below your means and to save as much money as you can. But when it comes to a company, you've got the ability to have equity in it, which means that as the company grows, there's there will be a time where you could either sell your interest in the company or you would be able to take bonuses, etc or draws on the company. 

So there's a there's an actual chance to create wealth and doing that And there's so much value in being able to do that. But the challenge is, again, what I said about that illusion or the delusion is that people want that for themselves, they want to have that kind of financial freedom, if not now, even after a period of time when it pays off. But they're new, they're stepping over that. And they're deluding themselves, not looking at what's right under their nose, that they don't have a large entrepreneurial Tiger. And I like to say that, you know, you can own 100% of nothing, or maybe you could own 10% of something that's really large. And if you do that, it would be worth far more. Therefore, what I recommend, in the case of having a large, administrative, but not a large entrepreneurial, is having a partner with a sizable, or partners, with a sizable entrepreneurial Tiger. And again, if both are low, I'm going to say watch out, because it's a recipe for disaster.

I've seen people who have who are unemployed, who have a dream, and they're low in both entrepreneurial and administrative, and they're still trying to make it, they're still forming the company, they're making their website, all that stuff is the easy stuff. They're spending money on these sorts of things, getting a lawyer, you know, when you have to start the company and your articles of incorporation, blah, blah, blah, and it's so much fun, and it's so sexy, but when, when it comes down to it, and you've got to establish things and to grow the company, and to expand it, and to make it last and survive for not months, but years, even when times are lean, if you are weak in those areas, and you're unemployed, and you're trying to do something just to cover your expenses to survive, and you've got a spouse that you have to, and maybe you're divorced, and you've got a child that you also have to support, I know people who are in this exact position, but they've got this dream that they're gonna have their company and it's gonna pay off and it's gonna be a unicorn. 

So it's, it all sounds great when it's, you know, when you talk about it, or when you fantasize about it. But that's not what really brings people to, that brings people to the dreams that they want to realize. So I would say there's nothing wrong with working for somebody else when you can have your Tigers completely engaged if it's your linguistic and creative, and you're being employed as a content writer for somebody, and you get to do that, let's say even you're working remotely, you get to set your hours. And yes, although you have some sacrifices that you're going to have to make. And listen, everybody's got sacrifices that they're going to have to make, a freelancer has to make sacrifices, a company owner has to make a lot of sacrifices. So you're going to have to make sacrifices. But the key is here if you're making sacrifices around areas where, where you do not have big tigers, it's going to sap you of all your energy, and you will not be able to even have enough energy to do your net, the work that you should be doing, according to your big tigers, you're not going to have enough energy even to do that to earn your basic. So that's why I say bring these points together and understand what the right ratio is. And if they are big, both big go for it, yes, become a freelancer or start your own company. Of course, with caveats, we would need to go into this in more detail. Or if one of them is smaller than the other, find the way to get a complimentary puzzle piece, somebody else who could help fill that role either bringing in the entrepreneurial Tiger or bringing in the administrative Tiger. And that will balance things out to allow you to work independently allow you to work in that self-employed manner. But in a way that's not going to strip you of your energy, of your love and pleasure for the work that you want to do. 

So let's sum it up for today. The opportunity to be your own boss has never been better, either as a freelancer or in running your own company. But you need to make a decision about whether or not to take that route and to leave some of those comforts of employment for the life of working for yourself. There might be many factors that go into determining whether or not you can succeed in a self-employed situation. But one factor that is often over overlooked is whether or not you have a natural talent the Tigers required for successfully working independently. And we looked at the entrepreneurial tiger, the one that governs your tendency to create value or rally resources and people together as well as the administrative tiger, the one that gets things done. If you're high in both, there's a good chance you'll find success in the life you're envisioning in self-employment. However, if either Tiger is not a big one, you should consider getting some support from either a coach courses and technology or from other people. And if both are not big, well, you just might have to rethink self-employment and enjoy the structure of a company and the pleasure that an employer brings to allow your dominant tigers to do their thing. Doing so will most likely bring you greater success and happiness. And lastly, if you're already freelancing, or running your own company, and things are not working out the way you'd like, you might want to take a look into your entrepreneurial and administrative tigers to see if you might be falling under this tiger illusion or delusion as I said before, and see if they could be one of the reasons that are holding you back.

That brings us to the end of our episode, be sure to check out the show notes which contain references to the contents of today's program. And if you haven't done so yet, I encourage you to subscribe to the Feed Your Tigers podcast on Spotify, Apple, or Google podcasts so you don't miss any of the future episodes. That's all for today. This is Steven Rudolph and until the next episode, I'd like to remind you to Feed Your Tigers before they eat you.