I’m now self hosting!

June 23, 2006

I've made the move to self host my wordpress blog… so after a few trials and tribulations, you can now find it at the same old address www.blog.craigdossantos.com, but it won't redirect to this web based blog, which is now out of date. 🙂


How To Be Your Own Boss

June 20, 2006

It's a magical thing to be able to look your pals in the eye and say "I'm my own boss." You feel proud, important, and ahead of the crowd. You are not among the masses who are slave to some random, inept corporate-ladder-crawling-junkie who tell's you what to do, how to do it and when it has to be done. You are the master of your time. You are effective, decisive, flexible and efficient. You are,….aren't you?

I can't tell you the number of self-employed people I've heard quip "I could never have a boss!" and toss off the idea as if it was a ridiculous notion that only the meek and unenlightened partake in. I'm hear to tell you, as someone who has recently crossed over from corporate junkie to self-employed hero, there's more to the story.

In the past few weeks, I've noticed that I've been slowly starting to play more than one role in my work. Not only am I the employee, but I am literally his boss too. This sounds obvious at first, but take a moment to rewind that until you realize that this is actually two jobs being done by one person. Being self-employed, or 'your own boss' means that you actually have to do the job that your old boss used to do. You have to set goals. Decide whether they are in-line with the vision. You have to break up those goals into tasks and make sure they have weekly mini-goals. You have to manage your employee, and make sure he doesn't slip. You have to prioritize, and decide whether the job is being done adequately, or whether more training is needed. Oh yeah, and you have to do all the stuff you've been planning to.

Of course, I'm sure that to some of you, this still seems rather obvious, but I assure you, the time it takes to play boss is very real. It's not something that just happens because the projects you are working on seem small, or simple. It's even easier to get off course when you're self-employed than it was when you had a real boss-man, so no matter how simple, you need a plan. Who has to create it? Well your boss, of course… You.

So far, I think I've done a decent job of setting up my work-life. I have weekly goals, daily task lists, and longer term goals that I've split up into 1, 2-5, 6-10 and 11-20 year goals. I have a mission statement and a list of beliefs that I hold to be true. I try to keep all this rigid enough to hold a schedule, yet flexible enough to fit daily randomness.

It's tough. It's tough to keep it all in my head. To review it daily. To keep myself accountable. And this is just the beginning. My projects are in their infancy, and it will only get more complex from here. There are more roles that will come in… Salesperson, Secretary, Accountant, Lawyer,… As long as I'm small enough and poor enough to not afford actual other humans, I will need to fill these roles to some extent. Because life is about assuming different roles, and so is working for yourself.

So far, it's totally worth it.

Life 2.0: How to Formulate a Plan After Leaving Your Job

June 13, 2006

After 6 months of traveling, I am done with recovery from corporate life, and after a week back in seattle, I consider my new life to have started. Over the last few months, I have created a 3 phase plan in order to ease the blow on my savings as I take on this new challenge of being self-employed. I have found that creating this plan not only does the obvious in helping with its execution, but alleviates me from the mental worries of being off on my own.

A new mentality is needed in order to watch your bank account slowly go down with each payment you make. When employed, its easy to get used to seeing the account bounce back every two weeks, and think nothing of the small purchases. Having a plan on how I will generate income now, in 3 months and in the year to come has helped me adjust to this new mentality. Don’t underestimate it's power. Not having a plan for income generation can be mentally debilitating, despite the fact that you may have savings to last you for over a year
So without further ado, here's the current (but still flexible!) plan:

Phase 1: Balloon entertainment

Goal: Immediate income that allows for flexible hours, but will help pay for small expenses.

I have been twisting balloons on a volunteer basis for years, but I am now starting to earn money for it. It is easy work in that it has a very low overhead, but it naturally has a low potential upside, as I don't wish to do this full-time, nor is it physically comfortable to do so. 🙂 For those not blessed with the skill of the inflatable twist, this could easily be replaced by tutoring or teaching an instrument or academic pursuit. For any skill you have, there is an audience waiting to learn it… you just need to find them.

Phase 2: Speaking Professionally

Goal: To create an income that has a larger potential upside, while developing a skill I value.

I have been speaking sporadically on a volunteer basis, and the feedback has been overwhelmingly positive. I have taken topics that I routinely give advice about in my day-to-day life and created talks out of them, targeting students in High School and College. I will be speaking on How to Increase Your Odds When Applying to College, How to Prepare for College, Socially and Academically, (I believe success in those two areas is closely tied), and How to Use your Memory to Study More Effectively.

For others, using any skill you have to consult or teach on a one-to-many basis will enable you to practice speaking, marketing, negotiating and selling… all important parts of being an entrepreneur.

Phase 3: Web Ventures

Goal: To create long-term income by creating a high-value-add site that drives traffic and creates passive as well as active income.

My ideas for such sites was a primary reason to leave Microsoft. It's just plain more fun to work on ideas that are your own. For others, this is where your main business plan would come in. I have been working on three ideas primarily:

Greenshelf: A site to post your compensation data anonymously so others can see where they stand among their peers with respect to compensation and benefits. Never underestimate what people are willing to share anonymously on the web.

MyTeam: A site that makes it easy for orgs and teams to create a site for themselves and communicate online effectively.

This Blog: I would like to turn this blog into something that is encouraging and useful all those poor lost souls who dream of quitting their corporate gigs and doing what they love. You can do it.

All you need is a plan… 😉