Last week I did it. It was under much different circumstances than I pictured 10 years ago; I originally thought I’d wait until I was a mid-40’s billionaire astronaut cowboy who flies helicopters and races sports cars. But I wanted to give the students a little different perspective. I hope I succeeded. Whatever the case, I had a lot of fun doing it.

Outsourcing starts at around the 20-minute mark. Credit is given to some of my important influences during the intro.

It was especially nice having my wife there. We’ve been married 7 years, and she’s never been able to attend any of my presentations!

#1- I’ve used it less than I thought

Ah yes, sitting on a beach somewhere while an army of personal assistants handles every less-desirable aspect of your life. And doing it for two dollars a day, no less.

In reality, even with a great assistant and a smooth workflow, it’s easy to leave your assistant with an empty queue. And it’s not for lack of things to outsource- I got over that challenge a long time ago. The simple fact is that the more you outsource, the more outsourcing you have to manage. One key technique is to set up ongoing, repeatable tasks. Right now my assistant logs less than an hour a week doing ongoing tasks. A lot of my life is already automated, but there are plenty of routine things I still need to get off my plate.

#2- It’s more rewarding than I thought

The novelty factor in Personal Outsourcing is huge, particularly when floating your tasks overseas. It just makes you feel cool. I thought that would wear off, and it did. Despite the public nature of this site, many of my friends and colleagues have no idea that we have an assistant. Those that do know, generally only find out because I try to give some background to HTD when people ask me what I’m working on these days.

And yet, there’s still something fantastic about coming back from lunch, sitting down to my computer, and seeing an update: “made that phone call and fixed that thing.” I think to myself “instead of waiting on hold during the noon hour, I just had lunch with a friend.” Or I’ll check in on ongoing task after 3 weeks of forgetting about it, and see that it’s been successfully repeated each Friday morning as requested. It’s just nice. Using outsourcing less than I thought I would doesn’t really matter. Even a couple hours a week has a noticeable impact.

#3- I’m a demanding boss

Actually, we all are. We all have these nasty little micro-managers inside us just waiting to come out. We’re quick to justify spending a few minutes (or hours…) at work surfing the web or doing otherwise “less-productive” activities. But once the tables are turned and we’re covering the payroll, it’s easy to really scrutinize the little details of how and when work gets done, how much time it’s taking, etc. It might take a little while, but eventually you learn to let go- at least if you have a solid assistant.

Those are my big 3. Feel free to share your own surprises in the comments.

Recently, Tim got to interview Michael Gerber. I’m jealous. It’s been 10 years since I read E-Myth Revisited, but I haven’t forgotten the principles that Gerber shares.

I was surprised at one of Gerber’s responses. When asked “Has the Internet really fundamentally changed the game for small business”, his response included:

“The internet era has, of course, changed the game for small business, but not as dramatically as most would profess…As many or more companies fail on the internet as anywhere else…”

It’s true; countless internet businesses fail. However, the cost of failure is so often negligible. In addition, the bar of success has been lowered. It’s why– as I’m sure you’ve heard before– SPAM continues to be the massive problem it is; it costs almost nothing to send out a few million emails.

My first web venture was created as a side project by me and my father. If you don’t include the hundreds of hours I spent teaching myself Flash, PHP, MySQL, and a slew of basic internet, server, and hosting logistics (all which was done during a time when my opportunity cost was about $7 an hour), our startup costs were negligible. We have top Google rankings for all our desired search terms and we’ve never spent a dollar on SEO*. By normal standards of business revenue, the company would not likely be considered a great success. But our margins are unheard of in the traditional business world. I have time to work on other businesses, and my pops is now retired. With just a few hours a week we can keep things rolling. I count that as success.

Back to my point: even if we did completely fail– let’s say we didn’t make enough revenue to even cover our meager hosting costs –, think of how little we’ve lost compared to a non-internet business. Imagine the overhead involved in renting retail space, offices, paying for traditional advertising, purchasing liability insurance, accounting for loss and theft of physical assets. I guess that’s why you always hear “we stated in my friend’s garage…”

The internet is the ultimate garage. Not only can you start a low-overhead business there, but you can grow and build and run keep one running there.

Yes, the internet changes everything.**

*we did shell out $600 for an ad in a printed conference proceedings once, but didn’t get a single response from it. So we’ve taken our marketing plan back to “do nothing”

** photo from Ed Fladung- his site was a great source of info and inspiration for us before our time in Mexico. I was happy we got to have lunch with he and his wife while we were in Bucerias.

We’re both pleased and overwhelmed with the number of people that have signed up to be on the waiting list. If you want in on the action, go sign up and drop a note in the “What Else?” box mentioning that you’re a loyal Newly Rich reader, and I’ll make sure your name gets bumped up higher on the list…

Here’s a quick-and-dirty rundown of the philosophies behind Having Things Done.

Part-timer

When I resigned from my job last spring, I spent several weeks working part time instead of making a clean break. This was a great opportunity to see how it felt to only show up to the office half the time. I skipped meetings (and was encouraged to do so). I took less breaks and rarely surfed the web. I found it easier to focus on work because I knew I had so little time to get my deliverables finished.

So in addition to the “hourglass” and other approaches Tim suggests for implementing 4HWW in a corporate setting, perhaps you can manage to set up a part-time arrangement for just a week or two. Both you and your boss can see how it feels to put some limits on your office time.

Split Personality

Another side-effect of my part-time arrangement was that it allowed me to put a hard stop on the number of hours I worked per week. I essentially shifted from a salaried employee to an hourly contractor. Don’t let the corporate man fool you into thinking salaried is better: it’s just his way of saying “you get to work overtime for free.”

When I transitioned into being completely on my own, I had two options:

1. beg, borrow, steal, and chew into our meager savings while I devoted my full effort to building up my own businesses.

2. pick up some hours doing freelance consulting (Flash and Flex development).

In my ideal world I won’t work on anything but my own projects. Until then, I think I’ve come about as close to an ideal situation as I can possibly ask for:

• I have a set and steady 20 hours a week consulting for a single client
• That client is fantastic to work with: a small company of 3 friendly, funny, professional fellas.
• I can work remotely (which will soon come in handy)
• At the rate they’re paying me, I’ll make slightly more by working 20 hours a week than I did working full-time for my previous employer
• The rest of my working hours (however many or few I choose to have) can be spent building up my own projects

I hope that doesn’t sound boastful. Rather, I’m just happy to report back a little bit of success for anybody considering trying to set up a similar arrangement. I’ve had dozens of “what if you could…” conversations with co-workers in the past several years, and most of them ended with a skeptical “yeah, but it wouldn’t really work out that way.” Well, it can.

BUT WHAT WILL YOU DO FOR HEALTH INSURANCE?!

1. Private Insurance

We thought we had a good answer. I can’t speak for the rest of the country (or world) but BCBS in Chicago (update: and now BCBS in Minnesota) has very reasonable private plans- no corporate employer required. You just fill out an application that’s about 473 pages long, wait several weeks for the initial approval, and all is well. Or so we thought.

I’ll let my wife give you the gory details in another post, but the short version is that they eventually reversed their decision and we were dropped from coverage. (as a side note, we recently watched Sicko and had a lot more empathy).

2. COBRA

COBRA is not a specific plan or company. Rather, COBRA is simply a government mandated option that allows you to continue the exact same coverage, with the exact same insurance company, that you had when you left your employer. Nice right? Well, there’s at least one major hitch: you get to pay the full premium. It’s at this point that you start wishing your employer’s coverage wasn’t quite so good. For us it means $1400+ a month. Ouch.

3. Your own company

We eventually set up a group insurance plan through the company I’ve had in place for the past few years. To be eligible, we needed to have at least two employees, so I officially hired myself and my wife. We each clock 30 hours a week at a “reasonable” rate, which pegs us as eligible full time employees. Despite the initial mountain of paper work involved in both hiring employees and applying for insurance, this arrangement has a few nice benefits. Our monthly premiums total about $450.

It’s all a write-off
There’s nothing stopping an employer from deciding to pay 100% of its employees insurance premiums, except for protecting its bottom line. Since I own the company, I get to decide how generous that company will be, and it so happens that this company pays 100%. The payback comes in the fact that insurance premiums are completely deductible for a business, but generally aren’t for employees.

Tailored to suit
My wife and I have separate plans (given the 2 employee minimum). That brought an unexpected bonus: it turns out it was cheaper for my wife to claim our daughter (guess they have less faith in a 30-year old male’s ability to manage health and well-being of a toddler). We put the two of them onto a slightly more expensive plan with better coverage and lower dedictables, given my wife’s innate ability to become pregnant, and our daughter’s accident-prone toddler-ness. Meanwhile, I’m on a high deductible plan which is cheaper and makes me eligible for an HSA.

Health Savings Account (HSA)
What do you get when you combine the benefits of a Flexible Spending Account with a Roth IRA? An HSA. I’ll save the details for another post, but for the right situation an HSA can be a great tool.

Whatever your situation, don’t let health insurance be the one thing stops you from making the jump and pursuing your own ideas!

[UPDATE] We’ve moved once and changed insurance twice since I posted this. Here are a few additional things to keep in mind.

• Private is often cheaper. At the turn of the new year, we were finally approved for private health insurance. Same insurance company, essentially the same coverage, and our monthly deductible dropped by $400 a month! In addition, we can now be on one single deductible. Being separate is advantageous if one spouse doesn’t need much and the other+kids do, but if the whole family racks up bills, it’s nice to have it level off after you’ve fulfilled just one deductible.
• Consider the timing of a switch, where possible. Switching plans mid-year wasn’t too good for us, because the deductible was reset (hence the second switch was made at year-end).
• High-deductible plans do have some potential benefits (HSA), but generally speaking if you think you’ll hit that deductible you’re probably better off keeping it low. This past year we each had separate high-deductible plans, and met both those deductibles (thanks to a debilitating pregnancy and an out-of-state hernia repair). Ouch. Thankfully we had the HSA funded enough to cover most of it.
• As per my disclaimer below, make sure you’re careful about writing premiums off as a business expense. As of right now, being a single-member LLC with tax status of S-Corp makes it possible and beneficial to count the premiums as an expense even though we’re on a private plan, but there are some very specific accounting guidelines and procedures.

Disclaimer: I am not an attorney, nor an accountant, nor a certified insurance rep. Please consult with all 3 of these about your own situation before making financial or legal decisions!