I thought I’d post what I’ve written recently to a guy who’s agreed to help me out with advice on starting my own businesses. So directly from my writing to him….

Here’s my story:

A few years ago I was making around 50K as an SDET working for a telecom and training my replacements from India. I’d been meaning to leave but was saving money and biding my time since the job market didn’t look so good after the dotcom crash and 911. The Indians where were on site were smart enough, but not equipped to manage the remote team, and then there was the corporate bureauacracy.

Back then I still though of myself as a building contractor who was taking a year (or four) stint at a desk job to pay off my last construction project failure and save up for the next. I saw an opportunity to buy land in Fiji, so I took some vacation time and went there to investigate. It wasn’t exactly what I wanted and I wasn’t quite ready, but hey, I was in Fiji, and I was expecting a round of layoffs when I got back. I’d even volunteered to be the next on the chopping block.

I got the call while in Fiji, and almost didn’t come back. Three month’s severance pay for one month’s work convinced me. I thought, I’ll be right back with an extra few grand.

As soon as I finished, I was done I got snapped up by a recruiter for a contract. When I quit that one, I got another. Finally after two years, I was ready to go back to Fiji. This time, I was more interested in developing tourism ideas than building houses. But then I ended up as crew on a sailboat heading to Australia.

I flew back to Fiji determined to get a boat of my own (for the tourism business of course.) Only one snag. I’d fallen in love right before leaving the US and promised to return. I needed money for the boat, so I did. I took another contract, but was miserable. I was about to switch but then got offered more money to stay. Finally I quit to take a full time gig for less money but hopefully more interesting work. And I was getting married.

My wife supported my dream of sailing, but she was more conservative. She took sailing lessons with me and sat through all my talk of boats and distant shores, and then sprang on me her own idea: Ecuador!

Before we got together she’d done volunteer work for a year in Ecuador with an orphanage support program. We’d been back to visit, but here was an opportunity to go back before we had kids. I still didn’t have quite enough for a boat, and I didn’t love my job, so we left for the Andes (by plane.)

She would be able to do her volunteer work with the orphans and people she loved, and I would work on starting my own business. I had some vague ideas about consulting, outsourcing, web development, and testing. I had some more vague ideas about tools and processes, and definitely strong opinions about how things could be better.

I spent 6 months there improving my ideas and skills, but not really producing anything. We came back when she got pregnant and my visa was cut short. I’d started working on a local tourism-related website with a local web developer who flaked, but I was more interested in my testing ideas.

So I’m back to work full time and chomping at the bit to get back to my business. But the baby’s due in October, and my pickup has died, and I’m shopping for cars and counting prices in fractions of a boat or months I could be working without pay.

It looks like the answer is 1/6th or 4. And I’ve been thinking… I don’t need a car if I work from home. Only we’re paying too much rent and the economy’s about to take another dive. And the baby’s due in October.

I think the car is a necessary expense, but there is some mitigation I could do. We could find a cheaper place to live (like Oklahoma — or Montana in my case) though I think strategically being in a tech center like Seattle has it’s benefits. On the other hand, people are often more interested in filling desks than results, especially with QA which managers often think is just a “due diligence” show. Being too far away to come in every day, but close enough to make it for weekly meetings might be a boon.

Being outside the USA, but not in India looks like a non-starter for most, though coincidentally my current employer has a team in Buenos Aires.

If there are large numbers of tech layoffs locally, there will be a potential pool of talent suddenly more interested in entrepeneurial ventures, either through partnerships, or as employees, without the security in the corporate world. I’ve long thought that if there was another downturn, it would be a good time to grow a small business and be poised to benefit on the next uptick, if I can survive. Having a new family complicates that, though.

Anyway, that’s my situation. I can probably save a lot of exposition later by doing it up front, though I’m told that’s no way to hold an audience.