The Flip Side of Self-Employment and Freedom

beach workingEntrepreneurs 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.


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  • Kevin Xiao says:

    Hey Chris,
    I’m a friend of Rachael Stovall, you took some classes at UW with her. She introduced me to this blog recently and I just wanted to say that I’ve really enjoyed all of your blogs. From your India adventures to your advices on life. Just wanted you let you know how much I appreciate your blog.

  • Chris says:

    Thanks, Kevin! I appreciate that.

    Everyone else, feel free to say hi or post your comments as well. We’ll be expanding the user participation options on the site soon.

  • Algimantas says:

    I’m not self-employed but I have very similiar freedom working at a job.

  • Allan Gardyne says:

    Hi Chris, Great stuff!

    I’ve been self-employed online for about 10 years. I reckon the toughest day working for myself is better than any day working for my old boss.

    Although I outsource and delegate, taking REAL vacations (non-working ones) has been a huge challenge.

    A big mistake I made was that I used to begin all sorts of time-consuming projects simply because they seemed a good idea at the time. It took me ages to understand that I should design my business to suit the sort of lifestyle I wanted. Lesson learned: Don’t start a high-maintenance project unless you’re sure you can delegate those tasks.

    It took us while, but we’re getting there…

    My wife, Joanna, will be off soon on a month-long vacation in Europe (sorry, not Sierra Leone!) and we’re leaving our laptops at home for the first time. I hope we don’t suffer withdrawal symptoms.

  • FreshNerd says:

    I am not self employed as of yet, but I am constantly working towards it. It is very challenging to do when my day job occupies 50 hrs per week. Some of the points in this post are helpful in regards to my situation, but I’m wondering if there are any other tips for those of us that work full time while moving towards self employment??

  • Scott Ballum says:

    Hi Chris, I am recently self-employed, and reading something like this helps so much, letting me know that I’m not alone, it’s not just me, and I’m not crazy. Everything from “your friends won’t get it” to “prepare to address the problems of too much freedom”. Found myself nodding along.

    A friend recently sent me your 279days article, also great stuff that’s come at a great time for me. I’ll be watching and reading, and love to connect some time, I really appreciate your ideals and ethos. Keep up the great work.

  • Sedick Sasman says:

    “Once you achieve initial success, it’s tempting to coast for a while” – I was guilty of this, and now I’m paying dearly! But I guess we learn from our mistakes…
    Great article, and great site! Will be visiting regularly.

    Your ideas are really inspiring. Thanks for sharing.

  • New to ANC says:

    I just quit the third office job I’ve had in five years since graduating for my PhD in order to travel and spend a couple of months of doing field work in my dream career in research and being a writer. The pattern so far has been that once I reach a certain threshold, I decide I can’t take the restrictions of office work on my life. Then I catch some glimmer of possibility of making it on my own, and I quit. So far, however, I haven’t been a financial success at being self-employed, and I think this post points out to the areas I need to work on – mainly getting things done and doing the right things.

  • Robert Jordan says:

    Great insights, Chris! You bring up good points about having freedom vs. having too much freedom.

  • Jan Bear says:

    Good advice, Chris. Sone of us who want the freedom of setting our own schedule have the flip-side trait of being challenged at designing systems and planning. Good advice to keep working on that.

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    Self-employment is the real thing if we accept it then everything fine. The also talk about it.

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    Thanks for the amazing information please check Thanks

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    I am appreciate with your opinion because when we get self-employed we have opportunity to get freedom and earn according to our needs…. thanks

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    Everyone want to be live very freely… because this life extremely expensive than money but money is also necessary to live life. I always suggest to earn independently… Thanks

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