Many people dream of being their own boss. They have romantic notions about having control and being able to do what they want, when they want. It seems like a wonderful life, being an entrepreneur. Look at Donald Trump. Look at Charles Schwab, or Richard Branson. Why can’t we all have that life, rather than the one we’re living?

Being your own boss is much harder than it looks because:

1. You are Totally Responsible for You. This means any personal strengths and talents you have can be used to full potential, but so can your weaknesses. Allegedly, a Canadian study (I haven’t been able to locate the original) found adults with ADHD were four times as likely to be entrepreneurs as those without ADHD. This rings true because so many of the people I know with ADHD, including quite a few in podcasting, are original thinkers. They are exciting, engaging people. They have great talents for getting people excited and going on projects, but often terrible at finishing things up or on total follow through.

With great strengths come great weaknesses at times. This is not a sin, or something to be embarrassed about. If you know what your weak points are and can acknowledge them, find other people to partner with and work with who are strong where you are weak. Don’t be afraid to ask for help when you need it. A friend taught me to finally understand “If you don’t ask, you won’t get”, and that there are tons of people you know who would love to help, if you’d only bother to take the time to ask.

2. Free Time Requires More, Not Less, Organization.

Transitioning from a normal workplace environment to being a full time mom was REALLY hard for me. I didn’t have to get up, get dressed and go to the office the same way I did when I was working. I was on call 24 x 7 for my baby, but the rest was up to me. Sounds blissful, but I often found myself at my wit’s end, not knowing what to do first, feeling overwhelmed. I was accountable to my husband, but no one else, really, and without a specific task sheet laid out, without routine, I was a mess.

I found out through trial and error that I work much better with some sort of schedule and routine. Without these boundaries, I was apt to get caught up in tasks, float from one to another, and nothing was truly getting finished or accomplished.  So, I decided I needed to work, at least part time, to bring order to the chaos.

I started telecommuting and working from home, I still needed a routine.  This means getting up and getting dressed, not always working in pj’s.  This means going into my office and shutting the door.  This means treating myself like an employee rather than the “boss” who profits off of the employee’s labor, but never seems to be accomplishing much on his own.

In order to be my own boss, I have to be twice as disciplined as I was when I worked for someone else.  I need top keep track of deadlines, progress on projects, and to be held accountable.  Part of this can be managed with online tools.  Taking advantage of online tools like Google Calendar, 43 Things , Don’t Forget The Milk, and other messaging/reminder services has helped keep me on track.

You might have thought life would get easier if you worked for yourself and no one was nagging you about the state of your desk or about filing.  Those problems don’t go away just because you are working on your own.  Now, you just have no one providing you a kick in the rear to do them except yourself, so the tendency can be to let things slide.  Then the problem can get to be overwhelming….

3. Being Your Own Boss Means You are In Charge of EVERYTHING. 

Until you are making enough money to pay someone to help you, you are it.  The One.  In terms of podcasting, this means you are the creator, producer, talent, IT,  PR and Marketing Department, Customer Service and everything else, all rolled up into one.  Balancing all these different roles is a huge challenge, and requires more structure, not less.

So if you thought that working on your own would make you less busy or less structured, the truth is you may have more flexibility in your schedule, but you will probably need more internal structure and organization than you ever had before.  Not to mention, in order to be successful, you will be working longer and harder than you ever were before as well.

The point of this post is not to dissuade you from trying your own thing.  Just go into any venture knowing your strengths and weaknesses, and don’t assuming you will magically become happier, richer, less busy, more organized or more relaxed working for yourself.  You take your neurology with you, and problems don’t disappear- they migrate.

By knowing your strengths and weaknesses, you can also anticipate where you might have problems and where to ask for help and guidance.  Working for yourself doesn’t always mean working alone.