So You Want to Be Your Own Boss? What You Need to Know Before You Start

August 24, 2015

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If you read my previous article on how to deal with getting fired, you would know that I lost a very high paying and high-level job during my younger years. At the time I actually had a side business, but was not interested in being self-employed; I actually enjoyed being the boss in some else’s organization. Circumstances forced me to consider self-employment earlier than expected, and as a result becoming my own boss became a necessity in order to continue growing. Before I break down what being your own boss is like, perhaps I can share with you what being a great boss is like.


During my tenure in corporate America, I spent a total of 10 years in various leadership positions. During that time I not only considered myself to be an excellent boss but a remarkable one at that; and while you might think that is quite arrogant for me to say – I can tell you that it all came down to my track record which consisted of three incredible stats:


I Had the Highest “Termination Rate” of Any Other Manager.


This is something that stayed with me almost my entire career; I wasn’t mean, I was fair – and not just fair to those I coached but fair to my entire team. I gave people a chance to be part of something great, and I measured success through effort, not sales or revenue. This effort is always in the person’s control; the sales or results are not, which is why my focus was on effort. As long as they kept trying, I kept helping them. If they were lazy, gave up or simply made excuses, I would terminate them faster than the speed of light. I’ll never forget I actually terminated one employee 20 minutes after he finished his orientation and formal training, simply because he chose to defy instructions on his first day. Keeping a bad employee is a burden to good employees, so no bad apples would stay on my watch.


I Had the Highest “Promotion Rate” of Any Manager.


Regardless of what level of management I was, I would always invest valuable time coaching, motivating and pushing the limitations of what people were capable of.   I created a perfect environment that fostered learning and promoted independent thinking as well as creativity, even if at times it was against the very same principle of the conservative company I worked for. The idea was to invest in people, not to necessarily make them into geniuses, but instead to allow them to learn how to work at 100% capacity. Working for me seemed difficult looking at it from the outside in, but once they were a valuable member of the team, the individuals that worked and put in the required effort eventually realized that they were wanted by just about everyone internally, and even by competitors. I always favored my employee’s growth even if that meant letting them go only to become my competition.


I Kept My Word.


This was what I believed completely separated me from any one of my peers. If I said I would do something, I would do it no matter the circumstances surrounding me. I made many promises to promote people if they were able to crush certain goals, excelled in performance, and brought in new ways to keep growing. The reality was that in my 10 years, there was only 1 promise I couldn’t keep; and unfortunately, it was due to my termination. I never left someone behind even when our CEO didn’t agree with my decisions. I put everyone from my teams on career paths and if they delivered for me. I promised them growth – which I gave each and every one of them – but the same word could be applied to my own actions and having to answer to my own boss whom would ask me for projections, which I never failed to meet. I never knew how I would do it, but I believed in the teams I had created and aligned our goals to these projections. Once we succeeded, we always did so as a team.


Doing those things for a decade and having become very good at them with a solid track record enabled me to call myself a great boss, even if some employees hated me at times. It was only during their time succeeding that they realized the struggle and hardship were what got them there, not during their time of comfort or liking of me.


In 2006, I completely transitioned from being the boss to being my own boss and with no employees on payroll, no HR department, and no structure to manage – it was almost comical to call myself a boss. But, what was I the boss of? How could you possibly be your own boss? It was ironic that the boss who strived upon other people’s success and worked best-leading others to success was now on his own at home and had no one to report to. I guess for me being a boss was always about having a responsibility towards those you lead, not those you answer to. At the end of the day, the ultimate question in leadership is really to be able to favorably answer the question: why should anyone follow you?


I guess during this transition, it was difficult for me to answer that question as I no longer was the confident and amazing person I once was, and no one was around me to follow me; which made it even more difficult to take myself seriously. A few months after being unemployed and desperately trying to make my business Secret Consulting work, I realized that in order to be my own boss I needed to indeed get rid of the idea that I am a boss and instead focus on the idea that I am in control of my own actions, which could lead to becoming a boss once more.


When you become self-employed, three things really start setting in over time but not immediately; these are things you realize early on but don’t really hit you until a few months later:



  1. You Try to Make up Your Salary, but Shouldn’t

This is the biggest mistake you can make and one of the biggest self-imposed limitations you create when you go from working for others to working for yourself. You set your goals and your target income on making up what you were making before or the basic minimum to survive. Both of which are terrible ways to connect your income with your businesses potential. In other words, just because you need 50,000 a year to survive, it should not limit or make 50,000 a year the income goal. You will quickly realize that working for yourself, you can easily make the income you were making but between operating expenses, marketing, travel, gas etc.… it will not be easy figuring out a good salary during your first year. Do not limit your growth to simply cover or outdo the wage you were earning.



  1. You Believe That You Control Your Schedule, but You Don’t.

While you may wake up every day saying how you no longer have to go to work at X time or stay till Y time, you will quickly realize that being self employed means you are working 24 hours a day. You will seriously wish you could turn the phone off and take a nap at 6PM or wake up at 11AM, but unfortunately you will be at the mercy of clients and knowing that the next paycheck will not be on direct deposit and will be a result of your own hard work, which will remind you of why you are on call 24 hours a day, even when your phone is off.



  1. You Tend to Think You Answer to No One – but You Do.

You may not have someone telling you what to do, how to do it or even when to do it, but your clients will dictate a staggering portion of those very same things you hated before. While you may become selective in due time and choose how to attract the right clients or only work with the right people, the earlier stages will make you a slave to anyone willing to pay your company for your services.


So ultimately the three things that we tend to think are the bad parts of having to work for someone are actually not that bad when compared to the mental stress you endure working for yourself. When I finally set myself apart and started becoming profitable in my two businesses (which took me a year or so), I started re-analyzing if working for others was indeed better as I was still not clearing my original salary (bear in mind that it was high), and I was working probably about 90% of the time I was awake (also bear in mind I didn’t sleep much).


Only one thing came to mind when it came back to rethinking this whole self employment thing; the biggest difference between working for yourself vs. working for others isn’t something cliché like ‘you decide you own future’ and all that bullshit, but rather that the time you trade may still be for money like before, but when you’re working for yourself your past work becomes residual in nature. This means that as hard as it may be to gain 1-2 clients, the residual effect of having those two clients holds quite a huge amount of weight on your future, and here is why:



  • Happy clients come back, they send referrals and they talk about you.

Unlike when you work for others, when you deliver great work in your own business, every piece of that comes back to you residually, meaning that doing great work actually pays.



  • Your old clients have value.

When you work for others, the time you trade for money disappears and therefore leaves you with nothing once exchanged. When you build a business, your past clients are past revenue and therefore the value of your business is growing simultaneously to you having gotten paid.


Although it may take longer, a business is an investment which overtime can be worth a significant amount of money, while your job is worth nothing because it never belonged to you in the first place. If my business does 200,000 in revenue one year and I get paid 100,000, my business itself is also worth something – while my position at my old company is worth nothing to me once I no longer occupy it


These two reasons are why it is very important to not just trade time for money. Even when you are self-employed it’s important to understand the short and long term plans for your own business.


In conclusion, working for yourself has its perks and also has its disadvantages like everything else. The aspect that crushes many who attempt self-employment and fail is the mental stress you go through while you are in the building stages of your business. This stress on the mind is something that crumble many who attempt to go from employed to self-employed as the uncertainty, the perseverance needed and the lack of support and direction can be extremely difficult – especially if you are not very resourceful. Whatever you choose, just remember: that being your own boss is not easy, but it can be very rewarding and can help you realize that from the very beginning of time, the only limitation you ever had was you.

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