The 5 Best Web Working Lessons I've Learned So Far


teacherfigureI’ve been working on the web — in one form or another — since 1994, and on the Internet since 1987, so I’ve had a number of years to learn some very tough lessons along the way. In trying to summarize my best advice to someone who is interested in web working, I distilled my learning into five specific tips. All these lessons were learned in the School of Hard Knocks, with a little Murphy’s Law thrown in for good measure.

Save yourself a lot of headaches; please follow this list. If you are a veteran web worker, I’d also advise reading this, printing it, and pasting it up on your wall. Why? Because I’ve made these mistakes more than once, and some of them even recently; none of us are infallible.

On with the list, in no particular order.

1. Email is imperfect. I can’t tell you how many times I’ve over-relied on email for communications with a co-worker, team member, client or vendor and nothing but disaster resulted. Miscommunication via email is rampant, and not just misunderstandings, but bad feelings too. I am trying to practice the art of in-person discussions, video conferencing or phone calls as my first options for contact, and then using email as a follow-up, to make sure everyone understands one another through a summary or recap. The more you rely on email, the more time you will spend explaining yourself, or apologizing.

2. There is not one right way to do anything. We each have our own way that we like to do things, but our way can differ vastly from the next person’s. This poses a big challenge when you are trying to get a team or clients on the same page and process as you. If you’re the boss, of course you can enforce a certain process or a particular application or tool, however, you should understand that others may have a very difficult time adjusting. I’m trying to be more accepting of the fact that as long as things get done on time, under budget and are properly documented, then all is well with the world. Just because others don’t do things exactly like me doesn’t mean the results won’t be OK.

3. It is hard to delegate, but you must. If you have someone to delegate to, do it. Learn to let go now, today, immediately. There is nothing worse than being the wrench in the process or the spanner in the works because you are hoarding work that someone else could be doing to free you up for more important things, or the things that you are good at and should be doing instead. If your time is being consumed by busy work, hire an assistant, even part-time, even virtual, even an intern to start with. Just bring on an additional person who can help you streamline processes and to whom you can unload the work that is keeping you from true productivity.

4. If you think you’ll need to access it from anywhere later, save it in the cloud. I can’t tell you how many times I’ve thought “maybe I should save this online somwhere” like my Google Docs (s goog) or 5pm, my project management system, or Dropbox. And I don’t, which ends up with me away from my computer and unable to access it when I need it. If you don’t already have one, get a secure account with a cloud storage service and use it to save those documents that you just might need later. Or make saving all archival documents part of your internal team process, as my team is now doing on 5pm.

5. Back up obsessively, like your life depends on it. If you have been reading my posts for a while, you know that I experienced a devastating computer crash over a year ago. Haven’t we all at some point? Read my lips: Back. Up. Now.

What are your biggest web working lessons?



As a web worker for the past 5 years my lessons would be…especially for telecommuters – Plan your time! It is a very important part of keeping yourself motivated and organized, since you don’t have a normal organizational context for these things.

I did a video on my day to day experiences as a remote worker –


My number one lesson: The online world is a microcosm of society in general. There are still bullies, self-starters, clingy neurotic people, preachers, helpers and all the others.

Number two: Before typing anything, ask yourself if you would say it in public, offline, and be willing to have it quoted back to you later.

Number three: Start slowly and stick with it. Many web sites that started as “the biggest collection of (fill-in-the-blank) on the internet” have disappeared within six months.


I find real value in having the same yahoo email address for almost 10 years. Other email addresses come and go and while many people recommend using a “professional” address with a personalized domain, I wish I had the emails I sent before I started being consistent with Yahoo. I appreciate Google’s ambivalence in having multiple gmail accounts simultaneously, but it does get confusing.

Barbara Ling, Virtual Coach

As someone who started online in 1989 with Netnews, I can certainly agree with your above points! Especially the ‘back it up incessantly…it will the critical document you lose when you fail that process ONCE.

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