So You Want To Be An Entrepreneur? 4 Challenges -- and Their Solutions

Take Charge on 02.22.12
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Photo: m.gifford/Creative Commons

I can't say that I ever wanted to work for myself. That's not for any reason except that I never really thought about it, and given my career choice (at least the one I was doing before this), unless I owned a TV station, it wasn't going to become a reality anyway. But when I was thrust into this new world of writing/brand building, there were a number of things I had to embrace -- and fast.

Don't get me wrong: There are a lot of good things about being your own boss; I just think people have a romanticized view of what it's really like. Think you're up for it? Here are 4 issues I faced and solutions I found that could help you too.

1. The issue: Working without a net. It's all on you, baby. I had a big week last week and as a result, am battling a cold this week. Aches, fever, sore throat, bad cough, I got it all. I also have a daily deadline here, have to tape a show today and write for my own site too. The harsh reality is if I don't do those things, they don't get done.  The solution: Plan for sick days. It's almost inevitable you will get sick, so what can you do in advance of that? I try to write a few posts that are evergreen and go up at anytime. Those are perfect for those days when I can't lift my feverish head off the pillow.

2. The issue: Discipline. Years ago, while interviewing a well-known author, he detailed his day for me. He told me that even though he wrote from home, he still woke up at the same time, exercised, showered, ate breakfast then started his day. The solution: Follow a routine. Like the author, adhere to a routine. Keeping a detailed diary of what your day will look like will help too. Think of it as your roadmap. I also use online tools to help me manage my productivity and see where there are gaps that need work.

3. The issue: Staying motivated. This is a big one and different from discipline, though being disciplined can help with motivation. But in true entrepreneurial fashion, there will be good days and bad, experiments that don't work, partnerships that fall through, and so on. The problem comes when you let the bad days affect your productivity or vision. The solution: Track your progress. Take a look back at where you were a year ago and compare it to where you are now. Are you as far along as you want to be? Maybe not, but moving forward -- if even in small steps -- is still growth.

4. The issue: Managing money. This is my second biggest challenge. I have a love-hate relationship with cash, stemming from my struggles with long division in the 6th grade. But I had to change that when I started making money from my brand and my writing. The solution: Track cash flow. First I learned how to use Excel (there wasn't a lot of need for that in my previous life), and then I made up a profit and loss sheet, which helped me see what was coming in and what was going out. This also makes me see myself as a business, which, in turn, keeps me motivated.

All this may sound rudimentary for those of you who are already entrenched in the world of entrepreneurship. So if you are, what else would you add to this list? What have you learned working for yourself?

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