Being a poolside boss involves a lot more than sitting by the pool with your laptop or your iPad. It takes a certain character to become a poolside boss, which is synonymous with being self-employed or working in an environment that is different than a regular office cubicle or nine to five work. Being self-employed, it’s usually a 10 to 10 job.

The Making of Poolside Boss

by Tanya Ganian
Tuesday, May 21, 2019



Being a poolside boss involves a lot more than sitting by the pool with your laptop or your iPad. It takes a certain character to become a poolside boss, which is synonymous with being self-employed or working in an environment that is different than a regular office cubicle or nine to five work. Being self-employed, it’s usually a 10 to 10 job.

Just because you don’t have that nine to five structure that an office environment awards you does not mean that as a self-employed person, you’re actually gonna work less.  In fact, you” ll probably work a lot longer hours. But the lifestyle is totally different and not everybody is made to be a poolside boss. So before we get into what it takes to become a poolside boss, I’m going to share a little bit of my story and my background.

Straight out of university, I did what everybody does – I applied everywhere in my field and my trade and I got a nine to five job. This was the beginning of my career. I had no sense of entitlement. I didn’t believe I deserved to get paid top dollars on my first job. So I had settled for $25,000 a year from a software company as a web developer and graphic designer.

Within two years of the regular nine to five, waking up, same routine, go to work, sit in my cubicle,  produce the work that’s given to me – just my job and learning along the way. It came to a point where I started to feel unfulfilled.

I didn’t know if it was the payor the environment or the long working hours or sitting at the same cubicle, turning on the same computer, doing the same thing every single day. I don’t know what it was.

I applied at other places as a web developer. I got a bunch of interviews and I got offered three or four positions and all four were for around the same salary. I, of course, went for the 30,000 offer, thinking I was making big moves and I was moving forward in my career and this company, I was the sole web developer and so I had the opportunity of hiring other web developers and had a lot more managerial responsibility. So I thought this was the way to go and wouldn’t, you know, I was still unhappy.

I was working really, really, really hard, which you know is a trait you have to have when you’re self-employed and working really, really, really, really, really, really, really, really hard for someone else. It gets to a point where you feel like I’m giving too much of myself and yet I don’t know how else to be. So I didn’t know how to give less. My values prevented me from doing less than my hundred percent.

So I would give my hundred percent I would stay longer, I would do more, I would just grind and grind for someone else and I would watch my bosses and owners just make leaps in their business and make leaps in their self-development. And there’s self-growth involved while I help others make those business leaps. And I was feeling like I’m a step that you’re using to get to where you are and I’m not getting anywhere. It wasn’t a complete waste of time, but at the end of the day, I felt very stifled. I knew it wasn’t for me and I was super unhappy. So I decided to take on projects after hours and slowly those projects, those clients, through word of mouth,  just brought me more clients and more projects until I thought came the day that I could sustain myself outside of a nine to five job and make the same amount of money.

So that’s when I made the final decision to quit. I remember thinking I would rather work 80 hours a week for myself than 40 hours for somebody else. And that’s exactly what happened.

I left and started to work on my business. I opened a web design company. I made it official with a website and a telephone number and I became self-employed and I started taking clients and things were going great through word of mouth until I hit a wall and you know, that’s what happens with word of mouth. Leads started to drop but it never occurred to me to go find a nine to five job. What I did instead was work harder and find other avenues to bring in clients to bring in more sales. It just, the nine to five never occurred to me.

Through the process of being self-employed, I really felt a very strong responsibility to me and to my business to bring those sales up and that’s really the character of a poolside boss. You have to be able to be resourceful and self-reliant. Now there’s a huge trend in America and being self-employed is a rising trend with 27 million Americans living their full-time job to become self-employed.

What is self-employment? Self-employment means that you are responsible for your own work for producing the work, for delivering the work, for finding the clients, and for bringing in the money. That really is what self-employment means and for you to do all of those things, it does take a certain type of personality and self-discipline.

It’s very comforting to know that at the end of the week, there’s a paycheck coming. You don’t have to think about it doesn’t matter what you’re doing. That paycheck will come once a week. As a boss, you’re always very aware of sales and what’s coming in and what’s going out. So one thing that you have to be really, really, really good at is how to market yourself. Whether you’re selling a product or service, your potential clients are going to buy into you and so you have to be able to market yourself to your target market, to your niche. You have to make that connection with your potential clients. Have a brand, a brand that makes sense, a brand that reaches your niche and that is consistent and that garners enough exposure.



That’s what being your own boss means. That means there is nobody there. Double checking that you did the work that you showed up, that you turned stuff in, that you delivered on time, that you’re keeping within budget. There is no one watching over you. You need to be that boss. So self-discipline is probably the most important character trait that you have to have to be self-employed.

Another character trait that you have to have self-motivation. Trust me – Monday morning, nobody wants to work Friday afternoon. Nobody wants to work but you have to understand that just because you don’t want to doesn’t mean you don’t do it and when the motivation isn’t there anymore, that’s when your discipline is going to kick in.

It is so important to be self-disciplined that at the end of the day, whether you can or can’t market yourself consistently, whether you can’t do or can regulate yourself, whether you can or can’t motivate yourself, all of it comes down to discipline. If a link in the chain fails, it’s discipline that’s going to hold that chain together.

Another thing that you need to really be good at for you to be a successful self-employed entrepreneur is time management. If you get sucked into that Instagram vortex or the Facebook vortex and you’ve been scrolling for 35 minutes, where did the time pass by? You are not staying focused.

To be able to be a poolside boss, to be able to be self-employed, you really need to know how to market yourself, how to be self-disciplined, how to manage your time accordingly, and how to motivate yourself. Being self-employed at the end of the day is not for everybody. If you need that sort of nine-to-five structure, if you need to be told what to do, if you need direction and you need a lot of direction, being your own boss is not for you.