Overheard on a Monday morning: “I wish I had my own business. If I was my own boss I could take the morning off to go fishing and start work for myself at noon.”

That’s one of the entrepreneurial dreams isn’t it? Play first and work later. Sleep in a little. Have more time for the family. It’s quite the dream and like with most dreams reality is very different. There are at least two major flaws in this way of thinking, but the good news is they aren’t completely insurmountable.

Flexible Hours - You Get to Pick Which 12 You Work

Running a business, especially when starting up (at which time you are the business) is hard work. There is everything and anything to do, and if you have run out of work then you aren’t trying very hard. To an extent you can’t really avoid this and if you are starting a company because you want to be lazy then you are doing it for the wrong reasons.

Here’s a thought though. You can get a big leg up on the competition, improve the quality of your work life, and have your business grow faster towards that point where a little time off is OK. The secret is cliche and you are welcome to go read something with a fancier answer. If you want go home earlier then read on.

Let’s say that you have to dig a hole. Would you use a shovel or dig with your hands? I’m hoping you chose shovel. But what if to use a shovel you first have to go to the department store and buy one? Unless your store is very far away, the correct answer is almost always to buy the shovel. It will provide an insane amount of value by allowing you to dig many holes quickly and whenever you want. It will also last you a very long time. You are working smart and getting the most out of your time, but while this may be obvious for digging holes, people are using their hands instead of shovels in many more complex and non-obvious tasks.

Time management and efficiency really are your keys. Time management is a concept that isn’t taught in school to any real effect and yet it makes the ultimate difference between somebody that can use their time to create $100 in value and $1000 in value. It’s not as simple as wasting less time doing nothing (although this is a good start), it’s also about knowing how to choose the most abundantly fruitful tasks and accomplishing your work in the most effective way.

Digging a hole is a simple, but how do you extend the principle to “making a business succeed”, or even “getting the promotion I want in 6 months instead of a year”? It turns out that its a complex field, like many of the softer life success topics that are convienently ignored in favor of stuffing in more trig identities. I always recommend Getting Things Done by David Allen as a start because not only is it a terrific book, it approaches the topic with a very concrete system that you can immediately begin applying. Parts of the system can be used or it can be applied as a whole. David also does a great job of identifying common flaws of time management attempts and ties the importance of goal setting and looking at the big picture back into getting things done effectively today.

It’s Too Easy to Neglect the Work When No One Breathes Down Your Neck

I have a strong suspicion that saying “you are your own boss” doesn’t really ever sink in until you are actually in this situation. Furthermore it’s only half true. When you own the business it is just as accurate to say that you don’t have a boss. There are few external deadlines to keep you on track and no fear of losing your job to keep you going. Then you give yourself flextime and decide when you work. What happens? Procrastination!

I’ve been in this situation many times, where I kept putting off the start of my work or even worst - pausing it in the middle - to do something else. The day would tick by and in the end I would be exhausted and scrambling to fit in some marginal amount of work before hitting the sack. There really is something like too much freedom and if you allow yourself to get into the position of work getting the remainder of your time then you’ll have a great time and a lousy company.

Lately I’ve been leaning towards the theory that in a situation where you are your own boss it’s actually your discipline that is the boss. There’s no external force to drive you so you must seek an internal one, and that kind of self-discipline is something that must be nurtured and cultivated over years. I propose then that when you are first starting off as your own boss you do not have flexible working hours. You should be working on your business the same amount of time every day at the same time and sticking to it. As you learn to balance this new work and life you are able to shift time around and enjoy new-found flexibility only after you have earned it and internalized the proper discipline.

Whether you’re running a business, club, or simply marking assignments it’s likely that you will have available to you some level of personal data. In the business case this may be quite a bit of data. You are hopefully aware of the importance of storing and securing such information. However you should also be cautious in how you work with it as this little tale shows.

A few years ago I piloted a new venture concept that had been rattling around my head for a couple months. It shall remain nameless only because the idea is experiencing a major overhaul. I spent quite a bit of time making updates and improving features based on the customer feedback I was receiving and often went through filling out web forms over and over to test features. Needless to say testing was tedious at times.

One lovely day I made some really cool changes to the mass mailer tool that customers would be able to use to mail their members. It had been debugged and was ready to make live. Of course I had made it a policy to test everything on the live product to make sure it had been integrated correctly. That’s just good practice.

Being an efficient developer I included a special admin-only checkbox on the mail form which when checked would go through the entire mail creation process but not actually mail anyone. I didn’t take into account user error though.

My first test didn’t work, prompting me to fix a minor detail and refresh. I then went through the entire mail send process using a quick ‘lol’ as my message text and other nonsense for subject and from. Thankfully none of it offensive as hitting send showed a peculiar result. The screen I received was the actual mail sent screen instead of the normal debug notice. My stomach tried to flip inside out.

1000 people were now the receivers of a completely nonsensical e-mail with my business name in the reply-to field. Even as I set about writing a paniced apology mail I had begun receiving replies ranging from confusion to anger to accusations of spam (what they thought this ’spam’ was trying to sell them I’m not too sure but I never received any of the cheques).

Needless to say this wasn’t the greatest experience for my new business and the effect it might have had on company reputation kept me worried for a good week. The story does have a happy ending though. Most people were surprisingly understanding and with no actual harm done even the most infuriated users quickly forgot. I did rewrite the test function though.

It’s a good idea to pay careful attention when a little user error could lead to embarrasing or devastating results.

As a web developer I sometimes get clients who already have websites, but are seeking to move elsewhere. For one reason or another the current provider is not filling the role properly or has possibly ceased to exist. I have been privy to all sorts of stories of anguish and frustration, and since the survival of my business depends on it, I’m very interested in not repeating the mistakes of developers named in these stories. I am now sharing some of the mistakes I hear about which the client had control over in hopes that managers looking for a site built can have a better experience.

It’s important to note that a failed project or poor results aren’t strictly the fault of the web development company. Two clients can use the same firm and have drastically different results as a result of the questions, planning, and requirements of the project. A good company will steer you in the right direction, but ultimately the creation of a website is a team effort and you are part of that team.

Here are 9 things that will help doom your project, and which you can assert proactive control over:

1) Don’t Get References

There are an incredible amount of companies out there to choose from, so feel free to scout around and find someone that you can communicate well with and is experienced in the kinds of things you are looking for. Always speak to former clients and find out what the service is like past the graphical design. There are many details involved in building a site and a great looking portfolio could be filled with duds. Find out if the work you like is that of the person or people who will actually be the ones working on your site.

2) Set Out Vague Guidelines for the Project

You may or may not know what you want on your website and what your objectives actually are. If you do know then make sure to communicate these to the company working on your project. Paint a clear picture and make sure the other party “gets it”. If you don’t know why you are getting a website or what the best features for yours are, then make sure to walk through these with your developer. Some terrifically talented people and companies make the mistake of going along with whatever the client asks for - afterall the “customer is always right”. I’ve made this mistake in the past before realizing that I have no right to expect the client to know what works and doesn’t work on the web. Make sure you and your developer both know what the end purpose of your site is so that the developer can propose a solution that can actually meet this.

3) Hire a Company Using Outdated Technology

Speaks for itself, although not always easy to avoid if you aren’t tech savy. Look for recent portfolio additions that have dated graphics, clumsy interactive elements, and generally “feel like 1997″ sites for a start. However looking at a site hardly tells the whole tale. Be sure to ask questions about the “backend” of things, such as how your website is hosted and what is done to keep it running.

4) Ignore the “You Get What You Pay For” Rule

Everyone loves to get a great deal, but a website is not the exact same gadget regardless of the store you buy it in. Figure out roughly what your budget and expectations are, then find the best company within your general price range instead of going for the lowest bid. You will get far better results and could even pay less in the long-run than a supposedly low priced competitor.

5) Assume You’ll Get What You Pay For

Pricing varies wildly in the web development industry. Add to this the complexity of the service and the different pricing models used by different firms, and it becomes very tempting to assume the higher the cost the better the quality. This is silly in general but especially dangerous here as the amount that a company charges consists largely of intangible and difficult to price qualities like talent. While there may be some bragging rights to having an expensive and amazing site, you will surely be the laughing stock if you pay a high price for poor results.

6) Assert that You’re Always Right

You definitely want to make sure that you are getting the specs you asked for and have a right within reason to expect your chosen provider to act on your requirements. However the people working on your site are professionals and a good company will provide suggestions for changes that are likely in your best interest. This is especially true for features that may make a site “cooler” but will reduce usability or search engine rankings. Do consider the suggestions and don’t feel that everything must be done your way - part of the price tag of your site is the expert advice you receive!

7) Don’t Have a Clear Timeline or Regular Meetings

It’s important to keep the project moving on both ends and communication plays a big role. Staying on top of things ensures that your project has the same priority assigned to it by the developer as it does in your head. Having regular status updates or meetings also helps steer things towards what you envision. Specific dates and milestones need to be outlined and monitored.

8) Ignore Security and Usability Issues

What the web company doesn’t mention could really hurt you. While security and user-friendliness may be wildly different issues, they are both hyper important topics that tend to get pushed off to the side or not brought-up at all. Consider the target audience of your site in terms of computer skills and likely devices that they will browse on. Consider the security requirements of your data and the consequences of a hacker break-in. Find someone that understands and can deliver.

9) Not Knowing How Your Site Will Be Updated and the Costs Involved

Many companies such as my own provide tools to allow our clients to easily update their own sites. Some companies don’t, and there are always projects and circumstances that justify having web developers do some or all of the update work. Find out what is available and what the costs involved are. If you place yourself in a position where making changes to your website is too expensive or difficult then inevitably you won’t make the updates, resulting in a stale and dead site. This is just one of the hidden costs to be wary of.