How To Not Screw Up Being Your Own Boss
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How To Not Screw Up Being Your Own Boss

Career Creativity Entrepreneurship
How To Not Screw Up Being Your Own Boss

Entrepreneurs are a diverse bunch of people, but when you ask them to tell you the greatest benefit of being self-employed, you’ll usually hear the same answer over and over. That answer is FREEDOM, and rightly so. When you work for yourself, no one tells you what to do—at least not in the same way a boss would.

Even if you freelance or have clients or customers, those people don’t usually set your hours for you, tell you what to wear, approve your vacations, or any of the other hassles you deal with at a “real” job.There’s no time sheet to fill out, and no H.R. department hounding you for staff reviews. Presumably, there are a lot less useless meetings too. (If you set your own useless meetings with staff, suppliers, or clients, that’s your fault!)

It is absolutely true that freedom is the greatest thing about self-employment. Make no mistake—I personally wouldn’t trade this benefit for just about anything.

However—you’ve probably guessed this was coming—there is another side to the freedom that successful self-employment brings. Here are several problems many entrepreneurs encounter as they step out of traditional employment and into their own vision of work.

  • Your friends and family members who work at traditional jobs won’t understand. They see only the benefits of your entrepreneurial life and none of the costs and risks.They may expect you to be available all the time. If you don’t take personal calls or use Instant Messenger during the day so you can focus on your work, they may get annoyed and wonder “what else you could be doing.”
  • Once you achieve initial success, it’s tempting to coast for a while. If you freelance and just had a big project last month, you may feel worn down and need to take it easy for a while. The key lesson is not to let this down time go on forever. Business markets, especially markets dependent on Internet services, can often change rapidly. You need to find a way to keep advancing, even if the pace is slow.
  • There’s no time sheet, but there’s also no IT department to fix your computer problems. When the network stops working, it’s your problem. If your emails aren’t being sent or the web site goes down, at the very least you have to get the process in motion to fix it. In fact, virtually none of the support structure you are used to at a traditional job will not be there when you are on your own. You have to figure out health insurance, which is no small problem. Even if an accountant prepares your tax return, you usually have to think about taxes more than you would probably like to.
  • The crises are all yours for the managing. Ideally, you should minimize the crisis management and focus on important work that builds your business, but this is easier said than done. When you are responsible, there is no one else to turn to. If you’re not careful and don’t build good systems for your business, you can easily become a full-time crisis manager. Even if you’re a great crisis manager, crises don’t usually pay very well compared to the normal activities of a business. When no one else is doing the sales and marketing and you spend your time putting out fires, income will go down and stress will go up.
  • Too much flexibility in scheduling will kill your productivity. Some entrepreneurs are uncomfortable with the idea of structure because they are naturally opposed to traditional models of work. But structure that enables you to excel is a good thing. Figure out what this is—when do you do your best work, and what do you need to do it?—and set up your own time schedule. You can always adjust it to meet changing needs, but don’t throw it out entirely.

Thankfully, there are several ongoing steps you can take to offset these challenges. A few of them that I have focused on in my life and work, to varying degrees of success, are below.

1. Simply decide to stop doing stuff. It seems paradoxical, but if you keep putting something off, you may be better off to just decide not to do it at all. The mental energy you use to keep looking at it all the time will take away from other activities that may be more important. Do yourself a big favor when confronting an activity that stresses you out: either deal with it and get it done, or make an active decision not to. You may be surprised how often this works. Ask yourself, “What is the worst thing that can happen if I don’t do this?”

2. Understand what motivates you, and structure your work around those motivations. If you are doing work you are passionate about, which is usually pretty important, this should be easy. Be aware of “why” you are working each day instead of doing something else. One warning: be careful about choosing money as a primary motivation. There’s nothing wrong with earning money, but it’s more important to understand what you really want and how your work contributes to or takes away from the path to achieving your goals.

3. Improve your personal productivity skills, including planning and implementation. Both of these skill sets are critical when you are self-employed. Planning skills include both short- and long-term goal setting. What do you want to accomplish this year? How will you make divide the progress toward those goals each month, each week, and then each day? Implementation skills are often known as “getting things done” tactics, and you need these to know how you will move closer to your goals in the midst of many competing demands on your time. Making improvements in these areas will usually make a measurable difference on your work.

4. Delegate or outsource. Find others to help you and pay them for it.There’s no good excuse not to, although there are lots of bad excuses that I have used before. Delegation is the art of assigning tasks or projects to a subordinate. Outsourcing is the practice of assigning entire responsibilities to an outside contractor. Both of these practices can make self-employment life a lot easier. (There is also a flip side to outsourcing, however, and we’ll look at that later.)

5. Take a vacation. When I’m in the U.S., I usually work at least six days a week, although I don’t work the whole day on Saturday, and I include time during the week for activities that help me relax. However, from time to time I feel my energy and focus slipping, and I find that I need a longer time away from work. I travel to more than 20 countries a year, and not all of my travel is for vacation, but I do try to take at least one week of “real vacation” every year, usually in December. This also serves as a natural time of reflection on the past year and planning for the next one.

6. Build a better working environment. If you’re working from home, you need a personal, comfortable workspace. It should not be shared with anyone else whenever possible. You need a good computer, a good chair, a good printer, good lighting, and anything else that you know you need for your business. You are the best judge of what you need, so figure it out and get it.


Freedom is truly the greatest benefit of being self-employed, but don’t forget to address the challenges that go with it.

I get up at 6:00 a.m. most days, but last night I was out with some friends and didn’t get to bed until after 11:00. I slept a bit later than I had planned, and didn’t make it in to my office until 8:30. No one was waiting for me and I had no explanation to give.

At 2:00 p.m. most days this week, I’ll probably stop working and go to a coffee shop to read and journal until 4:00. This is the normal routine for me, and not a nice exception in a week of full-time work. Later in the week I’ll take off a whole day to help a friend with moving. It’s no problem at all, and as long as I structure my projects well, my income should not suffer as a result.

But to create this ideal world, I have to watch out for the flip side to self-employment freedom. The flip side involves all kinds of distractions that threaten to hinder our efficiency and effectiveness. If you’re self-employed or interested in being self-employed in the future, take care that you do the same. The rewards are too great to lose.


A version of this article originally appeared on Chris Guillebeau’s website

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